Phthalimide compounds as base oil for lubricant compositions

Abstract

The present invention relates to a lubricant composition, which contains at least one phthalimide compound as the base oil, and to the use of these phthalimide compounds, in particular as a component of a lubricant composition, for partly or completely replacing a fluorine-containing lubricant component.

Description

[0001] Phthalimide compounds as base oil for lubricant compositions

[0002] The present invention relates to a lubricant composition containing at least one phthalimide compound as a base oil and the use of these phthalimide compounds.

[0003] BACKGROUND OF THE INVENTION

[0004] Lubricants are essential components of many industrial processes in which two or more surfaces move in close contact. The range of applications for lubricating oils is very broad and includes, among others, automotive lubricants, lubricants for two-stroke and four-stroke gasoline engines, lubricants for diesel engines, gas engine oils, gas turbine oils, automatic transmission fluids, gear oils, etc.

[0005] Lubricants can be lubricating oils and greases. Industrial lubricating oils include, among others, industrial gear oils, pneumatic tool lubricants, high-temperature oils, air and gas compressor oils for all types of compressors, machine tool oils, textile oils, steam turbine oils, hydraulic fluids, paper machine oils, food machine oils, steam cylinder oils, and metalworking fluids for metal cutting, metal rolling, metal drawing, metal forging, and metal stamping. Lubricating greases contain one or more thickeners in addition to the lubricating oil.

[0006] Special requirements are placed on lubricant compositions for use at high temperatures (high-temperature lubricants). Conventional lubricants are unsuitable for use at high temperatures, especially in continuous operation, as they are destroyed, for example, by oxidation and / or thermal decomposition reactions and (de)polymerization, and lose their lubricating properties. Suitable base oils with high temperature resistance are known and include, for example, alkylated aromatics, alkyl esters of carboxylic acids or phosphorus acids, higher-molecular ester compounds such as estolides, polyphenyl ethers, silicone oils, fluorocarbons, etc.

[0007] WO 2016 / 096074 describes high-temperature lubricants containing a base oil selected from alkyl aromatics, estolides and trimellitic acid esters.

[0008] US 2015 / 0166447 A1 describes alkylated diphenyl ethers and their use as base oils for various lubricants, such as bearing oils, gear oils, engine oils, gas turbine oils, automatic transmission oils, vacuum pump oils, and greases. US 2014 / 0274836 A1 describes multiaromatic base oils consisting of naphthalene groups linked via linkers. Linkers mentioned include, among others, alkylene groups as well as linkers with ether, acyl, ester, anhydride, amino, amido, urethane, sulfur groups, and combinations thereof. However, in the examples, only naphthalenes linked via alkylene groups are used.

[0009] The subsequently published US 2023 / 0365883 A1 describes a lubricant composition which contains as lubricant a compound of formula (A) where R is a hydrocarbon group having 8 to 24 carbon atoms and m and n are an integer from 1 to 8. The preparation of the compounds (A) can be carried out via the corresponding bisphthalimides (B) as intermediates

[0010] The bisphthalimides (B) themselves are not used as lubricants.

[0011] EP 0184595 A1 describes a process for preparing N-alkylphthalimides by reacting molten phthalic anhydride with an alkylamine, particularly monomethylamine. Specifically, the reaction products of phthalic anhydride and monomethylamine, which contain residues of phthalic anhydride, are described.

[0012] GB 1377215 A describes (N-amino-hydrocarbyl)phthalimides of the general formula (C) where Y is

[0013] -(CH2CH2NH)nCH2CH2NH2,

[0014] -(CH2CH2CH2NH) n CH2CH2CH2NH2 or -(CH2CH2CH2NH) n R1 where R 1 represents a Cs-C25 alkyl group and n has a value of 1-10.

[0015] Currently, fluorine-containing compounds, such as fully or partially fluorinated alkyl compounds, are still widely used in lubricants for high-temperature applications. Perfluoropolyethers (PFPE), in particular, exhibit good lubricating properties over a very wide temperature range from approximately -70°C to over 300°C. Due to their long-chain polymer structure, PFPEs are also highly inert and suitable for applications requiring contact with reactive chemicals. Furthermore, fluorine-containing lubricants generally exhibit good compatibility with a wide range of polymer materials, are non-flammable, and exhibit low toxicity. The use of fluorinated alkyl compounds and fluoropolymers is now viewed critically due to their low degradability and the resulting environmental impact, and efforts are being made to restrict per- and polyfluorinated alkyl compounds (PFAS) throughout the EU.There is therefore a need to reduce the proportion of these compounds in lubricants or to do without them altogether in the future.

[0016] The invention is based on the object of providing a base oil for a lubricant composition that is suitable as a substitute for at least partially replacing fully or partially fluorinated lubricants, and especially fully or partially fluorinated alkyl compounds, such as perfluoropolyether oils. Despite the (partial) omission of fluorinated components, the resulting lubricant composition should possess good application properties, such as high temperature stability, good rheological properties, and good oxidation stability.

[0017] Surprisingly, it has now been found that this problem is solved by using special phthalimide compounds as base oil for lubricant compositions.

[0018] SUMMARY OF THE INVENTION

[0019] A first aspect of the invention is a lubricant composition containing a) at least one phthalimide compound of the general formula (I) wherein

[0020] R 1 , R 2 , R 3 and R 4 are independently selected from hydrogen, straight-chain or branched alkyl, straight-chain or branched alkoxy, straight-chain or branched alkanoyl, straight-chain or branched alkyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkylene, unsubstituted or substituted aryloxy, unsubstituted or substituted arylalkyleneoxy, unsubstituted or substituted arylthio, unsubstituted or substituted arylalkylenethio, unsubstituted or substituted aroyl, unsubstituted or substituted aryloxycarbonyl, unsubstituted or substituted arylcarbonyloxy,

[0021] Monoalkylaminocarbonyl, monoarylaminocarbonyl, mono(arylalkylene)aminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkylmono(arylalkylene)aminocarbonyl, monoarylmono(arylalkylene)aminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, di(arylalkylene)aminocarbonyl, monoalkanoylamino, Monoaroylamino, monoalkanoylmonoaroylamino, dialkanoylamino, diaroylamino, where the aryl radicals of monoarylaminocarbonyl, mono(arylalkylene)aminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkylmono(arylalkylene)aminocarbonyl, monoarylmono(arylalkylene)aminocarbonyl, diarylaminocarbonyl, Di(arylalkylene)aminocarbonyl, monoaroylamino, monoalkanoylmonoaroylamino and diaroylamino, respectively unsubstituted or substituted, unsubstituted or substituted aromatic hydrocarbons having 2, 3, 4 or more aromatic rings, wherein 2 of the rings are connected by a single bond or a divalent group selected from

[0022] -CH2-, -O-, -S- or -N(H)- are linked to each other, and wherein the unsubstituted or substituted aromatic hydrocarbons having 2, 3, 4 or more aromatic rings are linked via a single bond or a divalent group selected from -CH2-, -O-, -S-, -N(R a )-, -OC(=O)- or -N(R b )-C(=O)- are bonded to the benzene ring of the phthalimide group, where R a and R b are independently selected from hydrogen and Ci-C4-alkyl, carboxyl, hydroxy, nitro, NH2, alkylamino and dialkylamino, where the radicals R 1 and R 2 or R 2 and R 3 or R 3 and R 4 can also together represent a group of formula (I.1) where # denotes the binding site to the rest of the molecule, where one of the residues R 1 , R 2 , R 3 or R 4 also together with another residue R 1 , R 2 , R 3or R 4 which is bonded to another group of formula (I), can represent a divalent bridging group Y which connects the two groups of formula (I), X 1 and, if applicable, X 2 independently for straight-chain or branched C1-C 30 -alkylene, where the alkylene chain may be interrupted by 1 to 15 non-adjacent heteroatoms selected from O and S, or a group of the formula #-(CR 5 R 6 ) n -SiR 7 R 8 (O-SiR 7 R 8 ) m -(CR 9 R 10 ) p -#, where # denotes the binding site to the rest of the molecule, R 5 , R 6 , R 9 and R 10 independently of one another represent hydrogen or C1-C4-alkyl, R 7 and R 8independently of one another represent straight-chain or branched alkyl or phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4 alkyl groups, n represents an integer from 1 to 30, m represents an integer from 1 to 30, p represents an integer from 1 to 30, or a group of the formula #-(CR 11 R 12 ) q -NR 13 -(CR 14 R 15 ) r -#, where # denotes the binding site to the rest of the molecule, R 11 , R 12 , R 14 and R 15 independently of one another represent hydrogen or C1-C4 alkyl, R 13 represents hydrogen or C1-C4-alkyl, q represents an integer from 1 to 30, r represents an integer from 1 to 30, or a group of formula (I.2) where # denotes the bonding site to the rest of the molecule, Z denotes O or S, s denotes an integer from 1 to 30, Y denotes a group of the formula -(O)0,1 -(C1-C 30 -alkylene)-(O) 0,1 - or -(S) 0,1 -(C1-C 30 -Alkylene)-(S) 0,1 - or -(C=O)-(O) 0,1 -(C1-C 30 -alkylene)-(O) 0,1 -(C=O)-, where alkylene is straight-chain or branched and can be interrupted by 1 to 15 non-adjacent heteroatoms selected from O and S, or Y is a group of the formula #-(O) 0,1 -(CR 5 R 6 ) n -SiR 7 R 8 (O-SiR 7 R 8 ) m -(CR 9 R 10 ) p -(O) 0,1 -# or #-(S) 0,1 -(CR 5 R 6 ) n -SiR 7 R 8 (O-SiR 7 R 8 ) m -(CR 9 R 10 ) p -(S) 0,1 -#, where # denotes the binding site to the rest of the molecule, R 5 , R 6 , R 9 and R 10independently of one another represent hydrogen or C1-C4-alkyl, R 7 and R 8 independently of one another represent straight-chain or branched alkyl or phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4 alkyl groups, n represents an integer from 1 to 30, m represents an integer from 1 to 30, p represents an integer from 1 to 30, or Y represents a group of the formula #-(O) 0,1 -(CR 11 R 12 ) q -NR 13 -(CR 14 R 15 ) r -(O) 0,1 -# or #-(S) 0,1 -(CR 11 R 12 ) q -NR 13 -(CR 14 R 15 ) r -(S) 0,1 -#, where # denotes the binding site to the rest of the molecule, R 11 , R 12 , R 14 and R 15 independently of one another represent hydrogen or C1-C4-alkyl, R 13represents hydrogen or C1-C4-alkyl, q represents an integer from 1 to 30, r represents an integer from 1 to 30, or Y represents a group of formula (I.3) (I.3) where

[0023] # denotes the binding site to the rest of the molecule,

[0024] Z 1 , Z 2 and Z 3 independently represent O or S, t represents 0 or an integer from 1 to 30,

[0025] R A and, if applicable, R Bindependently for hydrogen, unsubstituted or substituted aryl, unsubstituted or substituted aroyl, monoalkylaminocarbonyl, monoarylaminocarbonyl, mono(arylalkylene)aminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkyl(monoarylalkylene)aminocarbonyl, monoarylmono(arylalkylene)aminocarbonyl, dialkylaminocarbonyl, Diarylaminocarbonyl, di(arylalkylene)aminocarbonyl, monoalkanoylamino, monoaroylamino, monoalkanoylmonoaroylamino, dialkanoylamino, diaroylamino, where the aryl radicals of monoarylaminocarbonyl, mono(arylalkylene)aminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkylmono(arylalkylene)aminocarbonyl, Monoarylmono(arylalkylene)aminocarbonyl, diarylaminocarbonyl, Di(arylalkylene)aminocarbonyl, monoaroylamino, monoalkanoylmonoaroylamino and diaroylamino are each unsubstituted or substituted, or a phthalimide group of the formula (1.4) stands in which

[0026] R 16 , R 17 , R 18 and R19 independently of each other the previously calculated values ​​for R 1 , R 2 , R 3 and R 4 have the meaning given, and b) at least one additive different therefrom.

[0027] In a specific embodiment, the compounds of formula (I) do not represent any of the following compounds:

[0028] N-alkylphthalimides of the formula (IA) where E is CrCrAlkyl,

[0029] (N-Amino-hydrocarbyl)phthalimides of the general formula (IB) where E is

[0030] -(CH2CH2NH)nCH2CH2NH2,

[0031] -(CH2CH2CH2NH) n CH2CH2CH2NH2 or

[0032] -(CH2CH2CH2NH) n R IB where R IB represents a Cs-C25 alkyl group and n has a value of 1-10.

[0033] A specific embodiment of the invention is a lubricant composition in the form of a lubricating oil.

[0034] A lubricating oil according to the invention preferably contains: a) 80 to 99.9% by weight, preferably 90 to 99.8% by weight, based on the total weight of the lubricant composition, of at least one compound of the general formula (I), b) 0.1 to 20% by weight, preferably 0.2 to 10% by weight, based on the total weight of the lubricant composition, of at least one additive.

[0035] Another specific embodiment of the invention is a lubricant composition in the form of a lubricating grease. Lubricating greases contain at least one thickener as an additive.

[0036] A lubricating grease according to the invention preferably contains: a1) at least one compound of the general formula (I) as base oil, a2) optionally at least one further base oil different from a1), b1) at least one thickener, b2) optionally at least one further additive.

[0037] A further object of the invention is the use of phthalimide compounds of the general formula (I), as defined above and below, as base oil of a lubricant composition for lubricating tribological systems.

[0038] A further object of the invention is the use of phthalimide compounds of the general formula (I), as defined above and below, as base oil of a high-temperature lubricating grease for lubricating plain bearings, for lubricating rolling bearings and / or for driving production plants in the chemical industry, wherein the plain bearings, the rolling bearings and / or as lubricating grease for use in production plants in the chemical industry.

[0039] The invention further relates to the use of phthalimide compounds of the general formula (I), as defined above and below, as base oil of a high-temperature lubricating grease for the lubrication of plain bearings, in particular gas fittings, actuators, linear guides, regulating and control flaps in the intake manifold, couplings, screws, bolts, fittings, chains for the food industry, in particular in bread and waffle baking machines; for the lubrication of rolling bearings, in particular rolling bearings for wood pressing or corrugated cardboard systems and / or for driving production systems in the chemical industry.

[0040] Another object of the invention is the use of a phthalimide compound of formula (I), as defined above and below, as a component of a lubricant composition for partially or completely replacing a fluorine-containing lubricant component, in particular a linear or branched perfluoropolyether oil (PFPE oil).

[0041] DESCRIPTION OF THE INVENTION

[0042] A tribological system is, in general terms, a technical system that enables, influences, or prevents movement through contact. Its essential components are the pairs of active surfaces involved in a tribological load and the load collective acting on them. Typically, a tribological system comprises at least one base body that is in contact and moving relative to at least one counter-body. The load collective includes the load applied to the bodies as well as the movement conditions, the friction state, and the temperature. An intermediate substance is often located between the two bodies; this can be lubricants specifically introduced to reduce wear.

[0043] In the context of the invention, a tribological system specifically refers to a system in which friction occurs as a result of the relative movement of interacting surfaces, and lubrication is required to minimize wear caused by the stress on the surfaces resulting from friction. Lubricants reduce wear and ensure the functionality of parts subject to frictional forces. Typical tribological systems for the use of the lubricant compositions according to the invention are bearings, chains, compressors, gears, etc.

[0044] Lubricant compositions for use at high temperatures are also called high-temperature lubricants. High-temperature lubricants include high-temperature lubricating greases and high-temperature lubricating oils. The following criteria for the high-temperature performance of lubricants are given based on various standards, such as the dropping point or the FE9 rolling bearing grease tester. The lubricant compositions according to the invention for use as high-temperature lubricants have an upper operating temperature of at least 140°C, preferably at least 150°C, in particular at least 160°C.

[0045] The lubricant compositions according to the invention have the following advantages:

[0046] The lubricant compositions according to the invention and the phthalimide compounds contained therein are characterized in particular by very good oxidation stability.

[0047] The lubricant compositions and the phthalimide compounds have a property profile with regard to viscosity and temperature behavior that makes them suitable for use as high-performance lubricants.

[0048] The phthalimide compounds of formula (I) are advantageously suitable as a component of a lubricant composition for the partial or complete replacement of a fluorine-containing lubricant component, in particular a linear or branched perfluoropolyether oil (PFPE oil).

[0049] The phthalimide compounds of formula (I) are characterized by high compatibility, especially miscibility, with a variety of other base oils.

[0050] The phthalimide compounds of formula (I) are further characterized by high compatibility with a wide range of lubricant additives.

[0051] The lubricant compositions according to the invention possess very good tribological properties. In particular, they exhibit good lubricating properties at high temperatures over a long period of time. They exhibit good hydrolytic stability and are corrosion and wear resistant. The lubricant compositions according to the invention also exhibit good low-temperature behavior, especially a low pour point. Phthalimide compounds of the formula (I) In the illustrated formula drawings, a methyl group may be represented by a solid line. For example, the following formulas are two alternatives for representing the same compound: It should also be noted that hydrogen atoms are generally not shown in the illustrated formulas, as is common practice. Accordingly, the definition that an aromatic ring, e.g., a benzene ring, may be substituted by 0 to x substituents means that ring atoms that can be substituted but do not bear a substituent bear hydrogen atoms instead. The definitions of the variables given in the formulas use collective terms that are generally representative of the respective substituents. The definition C n -C m indicates the number of possible carbon atoms in the respective substituent or substituent part. The term "unbranched" as used herein is also referred to as linear or straight-chain. The term "C n -C m-Alkyl" as used herein refers to a branched or unbranched saturated hydrocarbon group having n to m carbon atoms, e.g. 1 to 4 ("C1-C4-alkyl") or 1 to 20 ("C1-C 20 -Alkyl"). These include, for example, C1-C4-alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl. Suitable longer-chain C5-C 20-Alkyls are, for example, n-pentyl, 2-pentyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 2-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,2-Dimethylbutyl, 1,3-Dimethylbutyl, 2,3-Dimethylbutyl, 1,1-Dimethylbutyl, 2,2-Dimethylbutyl, 3,3-Dimethylbutyl, 1,1,2-Trimethylpropyl, 1,2,2-Trimethylpropyl, 1-Ethylbutyl, 2-Ethylbutyl, 1-Ethyl-2-methylpropyl, n-Nonanyl and its branched isomers, n-decanyl and its branched isomers, n-Undecanyl and its branched isomers, n-Dodecanyl and its branched isomers, n-Tridecanyl and its branched isomers, n-Tetradecanyl and its branched isomers, n-Pentadecanyl and its branched isomers, n-Hexedecanyl and its branched isomers, n-Heptadecanyl and its branched isomers, n-Octadecanyl and its branched isomers, n-Nonadecanyl and its branched isomers, n-Eicosanyl and its branched isomers and the like.The same applies to the alkyl radicals in alkoxy, alkanoyl, alkyloxycarbonyl, monoalkylaminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkyl(monoarylalkenyl)aminocarbonyl, dialkylaminocarbonyl, monoalkanoylamino, monoalkanoylmonoaroylamino, dialkanoylamino, etc. The term aryl refers to monocyclic, bicyclic, tricyclic, tetracyclic or higher aromatic hydrocarbon radicals having preferably 6 to 18 ring carbon atoms, in which the rings are all fused or two of the aromatic rings can also be linked to one another by a chemical bond and a divalent radical selected from -CH2-, -O-, -S- or N(H)-. Examples are phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, 11H-benzo[b]fluorenyl, naphtho[2,3-b]benzofuryl, naphtho[2,3-b]benzothienyl and 5H-benzo[b]carbazolyl.Aryl can be substituted at one, two, three, four, more than four, or all substitutable positions. Suitable substituents are generally C1-C. 20-Alkyl, C1-C4-Alkoxy, Acyl, Dialkylamino, Arylalkylenamino, Dia- rylamino, C5-C8-Cycloalkyl, etc. Das gleiche gilt für die Arylreste in Aryloxy, Arylalkylen- oxy, Arylthio, Arylalkylenthio, Aroyl, Aryloxycarbonyl, Arylcarbonyloxy, Monoarylamino- carbonyl, Mono(arylalkylen)-aminocarbonyl, Monoalkylmonoaryl¬aminocarbonyl, Mo- noalkyl-mono(arylalkylen)¬aminocarbonyl, Monoarylmono(arylalkylen)aminocarbonyl, Diaryl-aminocarbonyl, Di(arylalkylen)aminocarbonyl, Monoaroylamino, Monoalkanoyl- monoaroylamino, Diaroylamino, etc.Specifically, the aryl radicals in aryloxy, arylalkylenoxy, arylthio, arylalkylenthio, aroyl, aryloxycarbonyl, arylcarbonyloxy, monoarylaminocarbonyl, mono(arylalkylene)aminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkylmono(arylalkylene)aminocarbonyl, monoarylmono(arylalkylene)aminocarbonyl, diarylaminocarbonyl, di(arylalkylene)aminocarbonyl, monoaroylamino, monoalkanoylmonoaroylamino and diaroylamino are unsubstituted or have 1, 2, 3 or 4 substituents, preferably independently selected from C1-C. 20-Alkyl and C1-C4-alkoxy. Specifically, the substituents of the aryl radicals are selected from C1-C4-alkyl and C1-C4-alkoxy, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, methoxy, and ethoxy. In the context of the present invention, the term "alkylene" (alkanediyl) refers to divalent hydrocarbon radicals having preferably 1 to 30, particularly preferably 2 to 20, carbon atoms. The divalent hydrocarbon radicals can be unbranched or branched. These include, for example, C1-C 30-Alkylene groups, such as methylene, ethylene, 1,2-propylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene, 1,6-hexylene, 2-methyl-1,5-pentylene, 3-methyl-1,5-pentylene, 1,7-heptylene, 2-methyl-1,6-hexylene, 3-methyl-1,6-hexylene, 1,8-octylene, 2-methyl-1,7-heptylene, 2-ethyl-1,6-hexylene, 1,9-nonylene, 2-methyl-1,8-octylene, 3-methyl-1,8-octylene, 4-methyl-1,8-octylene, 1,10-decylene, 1,11-Undecylene, 1,12-Dodecylene, 1,13-Tridecylene, 1,14-Tetradecylene, 1,15-Pentadecylene, 1,16-Hexadecylene, 1,18-Octadecylene, 1,20-Eicosanylene, 1,25-Pentacosanylene, 1,30-Triacontanylene, and the like. In a specific embodiment, the lubricant composition according to the invention is free of N-alkylphthalimides of the formula (IA) wherein E is C1-C4 alkyl. In particular, the lubricant composition according to the invention is free from N-methylphthalimide (ie the compound of formula (IA) where E is methyl). Free from N-alkylphthalimides of formula (IA) in the sense of the invention means that the lubricant composition according to the invention does not contain any added N-alkylphthalimides of formula (IA). It is preferred that the lubricant composition according to the invention is completely free from N-alkylphthalimides of formula (IA). The lubricant composition according to the invention preferably contains N-alkylphthalimides of formula (IA) in an amount in the range from 0 to 0.00005 wt.%, based on the total weight of the lubricant composition, particularly preferably from 0 to 0.00001 wt.%, based on the total weight of the lubricant composition, in particular 0 wt.%, based on the total weight of the lubricant composition.In a specific embodiment, the lubricant composition according to the invention is free from (N-amino-hydrocarbyl)phthalimides of the general formula (IB). where E is -(CH2CH2NH) n CH2CH2NH2, -(CH2CH2CH2NH) n CH2CH2CH2NH2or -(CH2CH2CH2NH) n R IB where R IB for a C5-C 25-alkyl group and n has a value of 1-10. Free of (N-amino-hydrocarbyl)phthalimides of the general formula (IB) in the sense of the invention means that the lubricant composition according to the invention does not contain any added (N-amino-hydrocarbyl)phthalimides of the general formula (IB). It is preferred that the lubricant composition according to the invention is completely free of (N-amino-hydrocarbyl)phthalimides of the general formula (IB). The lubricant composition according to the invention preferably contains (N-amino-hydrocarbyl)phthalimides of the general formula (IB) in an amount in the range from 0 to 0.00005 wt.%, based on the total weight of the lubricant composition, particularly preferably from 0 to 0.00001 wt.%, based on the total weight of the lubricant composition, in particular 0 wt.%, based on the total weight of the lubricant composition.

[0052] Preferably, in the compounds of formula (I) at least one of the radicals R 1 , R 2 , R 3 and R 4 and / or, if present, at least one of the radicals R 16 , R 17 , R 18 and R 19 for a group selected from groups (AR-1) to (AR-XXIV)

[0053] (AR-XVI 11) (AR-XIX) (AR-XXIV) where # denotes the binding site to the rest of the molecule, A is selected from the groups where ~ denotes the bonding site of group A to the benzene ring, R c represents hydrogen or C1-C4 alkyl, R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 and R 30 , if present, are independently selected from hydrogen, straight-chain or branched C1-C 20-alkyl and straight-chain or branched C1-C4-alkoxy. In a preferred embodiment, in the compounds of formula (I), at least one of the radicals R 1 , R 2 , R 3 and R 4 other than hydrogen. In a preferred embodiment, in the compounds of formula (I) at least one of the radicals R 1 , R 2 , R 3 and R 4 represents hydrogen. In a further preferred embodiment, at least two of the radicals R 1 , R 2 , R 3 and R 4 represents hydrogen. In a further preferred embodiment, at least three of the radicals R 1 , R 2 , R 3 and R 4 represents hydrogen. In particular, in the compounds of formula (I), the radicals R 1 , R 3 and R 4 represents hydrogen or the radicals R 2 , R3 and R 4 represents hydrogen or the radicals R 1 , R 2 , R 3 and R 4 represents hydrogen. In a preferred embodiment, the compounds of formula (I) have a phthalimide group of formula (I.4) and at least one of the radicals R 16 , R 17 , R 18 and R 19 represents a radical other than hydrogen. In a preferred embodiment, the compounds of formula (I) have a phthalimide group of formula (I.4) and at least one of the radicals R 16 , R 17 , R 18 and R 19 represents hydrogen. In a further preferred embodiment, the compounds of formula (I) have a phthalimide group of formula (I.4) and at least two of the radicals R 16 , R 17 , R 18 and R 19represent hydrogen. In a further preferred embodiment, the compounds of formula (I) have a phthalimide group of formula (I.4) and at least three of the radicals R 16 , R 17 , R 18 and R 19 represent hydrogen. In particular, the compounds of formula (I) have a phthalimide group of formula (I.4) and the radicals R 16 , R 18 and R 19 represents hydrogen or the radicals R 17 , R 18 and R 19 represents hydrogen or the radicals R 16 , R 17 , R 18 and R 19 is hydrogen. In the compounds of formula (I) X 1 and, if applicable, X 2 independently of each other for - straight-chain or branched C1-C 20 -alkylene, or - a group of the formula #-(CH2CH2O) 1-10 -(CH2CH2)-#, or - a group of the formula #-(CH2) 1-5 -Si(CH3)2-(O-(Si(CH3)2)) 1-5 -(CH2) 1-5-#, or - a group of the formula #-(CH2) 1-5 -NR 13 -(CH2) 1-5 -#, where R 13 represents hydrogen or C1-C4-alkyl, or - or a group of formula (I.2a) where # denotes the bonding site to the rest of the molecule. In the compounds of formula (I), the group Y preferably represents - -(O) 0,1 -(C1-C 20 -alkylene)-(O) 0,1 - or -(S) 0,1 -(C1-C 20 -Alkylene)-(S) 0,1 - or -(C=O)-(O) 0,1 -(C1-C 30 -alkylene)-(O) 0,1 -(C=O)-, where alkylene is straight-chain or branched, or - a group of the formula #-(O) 0,1 -(CH2CH2O) 1-10 -(CH2CH2)-(O) 0,1 -#, or - a group of the formula #-(O) 0,1 -(CH2) 1-5 -Si(CH3)2-(O-(Si(CH3)2)) 1-5 -(CH2) 1-5 -(O) 0,1 -#, or - a group of the formula #-(O) 0,1 -(CH2) 1-5 -NR 13 -(CH2) 1-5 -(O) 0,1 -#, where R 13represents hydrogen or C1-C4-alkyl, or - or a group of formula (I.3a) where # denotes the binding site to the rest of the molecule. In a specific embodiment, in the compounds of formula (I), at least one of the radicals R A and, if applicable, R B represents a group (AR-I) to (AR-XXIV), as defined above. In a specific embodiment, in the compounds of formula (I), at least one of the radicals R A and, if applicable, R Bfor a phthalimide group of the formula (I.4). Preference is given to the compound of formula (I) selected from the following compounds (1) to (116) and the compounds obtainable by reducing the non-amidic carbonyl group(s) of the compounds (1) - (9), (22) - (27) and (71) - (90). Furthermore, the lubricant composition according to the invention preferably comprises at least one compound of the formula (I) selected from compounds (1) to (116) and the compounds obtainable by reducing the non-amidic carbonyl group(s) of the compounds (1) - (9), (22) - (27) and (71) - (90).

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[0057] 

[0058]

[0059] where n is an integer from 1 to 30, m is an integer from 1 to 30, p is an integer from 1 to 30, u is an integer from 1 to 15, v is 1 or 2, R 2 and R 17are independently selected from hydrogen, straight-chain or branched alkyl, straight-chain or branched alkoxy, straight-chain or branched alkanoyl, straight-chain or branched alkyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylalkyleneoxy, unsubstituted or substituted arylthio, unsubstituted or substituted arylalkylenethio, unsubstituted or substituted aroyl, unsubstituted or substituted aryloxycarbonyl, unsubstituted or substituted arylcarbonyloxy, monoalkylaminocarbonyl, monoarylaminocarbonyl, mono(arylalkylene)aminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkylmono(arylalkylene)aminocarbonyl, Monoarylmono(arylalkylene)aminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, di(arylalkylene)aminocarbonyl, monoalkanoylamino, monoaroylamino, monoalkanoylmonoaroylamino, dialkanoylamino, diaroylamino,where the aryl radicals of monoarylaminocarbonyl, mono(arylalkylene)aminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkylmono(arylalkylene)aminocarbonyl, monoarylmono(arylalkylene)aminocarbonyl, diarylaminocarbonyl, di(arylalkylene)aminocarbonyl, monoaroylamino, monoalkanoylmonoaroylamino and diaroylamino are each unsubstituted or substituted, R, 7 and R 8 independently of one another represent straight-chain or branched C1-C4 alkyl, R 13 represents hydrogen or C1-C4 alkyl, R c for hydrogen or C1 -C 4-Alkyl,R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 and R 30 , if present, are independently selected from hydrogen, straight-chain or branched C1-C 20-Alkyl and straight-chain or branched C1-C4-alkoxy. Preparation of the phthalimide compounds The compounds of formula (I) can in principle be prepared according to the schemes described below and by synthetic methods of organic chemistry known to those skilled in the art. Substituents, variables and indices correspond to the definitions given above for the compounds (I), unless stated otherwise in individual cases. Specific conditions for the reactions can be found in the working examples. Specific compounds of formula (I) can be prepared according to the schemes shown by suitable selection of reagents with suitable substitution. Suitable solvents, temperatures, pressures and other reaction conditions can be readily selected by a person skilled in the art. The starting materials are commercially available or can be readily prepared by a person skilled in the art.Scheme 1 generally describes the preparation of compounds (I) by condensation of phthalic anhydride and its derivatives with primary amines. As an example, the reaction of phthalic anhydride and its derivatives with an alkylamine (X) is used. 1 = C1-C 30 -alkylene, R A = H). where R 1 , R 2 , R 3 , R 4 , X 1 and R A have the meanings given above. Depending on the molar ratios of the products, monoamino group-containing intermediates or condensates with two identical terminal phthalimide groups are obtained with diamines. Monoamino group-containing intermediates can, for example, be converted into condensates with two different terminal phthalimide groups. Scheme 2 shows these syntheses using the example of a diaminoalkyl-terminated polysiloxane. Scheme 2 2 eq. eq. where R1 , R 2 , R 3 , R 4 , R 7 , R 8 , X 1 , n, m and p have the meanings given above.

[0060] Alternatively, the formation of N-substituted phthalimides is achieved by reaction of potassium phthalimides with corresponding halogen compounds, such as in the simplest case with alkyl halides, as shown in Scheme 3.

[0061] Scheme 3 where Hal is Cl, Br or I and R 1 , R 2 , R 3 , R 4 , X 1 and R A have the meanings given above. The synthesis of compounds of general formula (I) with certain substituents R 1 , R 2 , R 3 and R 4 can be carried out starting from appropriately substituted phthalic anhydride derivatives. A large number of these compounds are commercially available. For example, compounds of formula (I) in which R2 represents methyl, starting from 4-methylphthalic anhydride (CAS number: 19438-61-0). Alternatively, corresponding phthalic anhydride derivatives or corresponding phthalimide derivatives can be prepared using conventional synthetic methods. Scheme 4 shows an example of the synthesis of compounds of formula (I) with amide groups R 3 starting from trimellitic anhydride (CAS number: 552-30-7) or trimellitic anhydride chloride (CAS number: 1204-28-0). Scheme 4 where X 1 and R A have the meanings given above, R c represents C1-C4-alkyl and AR represents an aryl group-containing radical, preferably selected from groups (AR-I) to (AR-XII), as defined above. The synthesis of compounds of general formula (I) with certain substituents R Acan be carried out starting from appropriately substituted phthalimide derivatives. Scheme 5 shows an example of the synthesis of compounds of formula (I) with amide groups R A starting from a phthalimide compound as intermediate, wherein X 1 for C1-C 30 -alkylene. Scheme 5

[0062] where R 1 , R 2 , R 3 and R 4 have the meanings given above, R c represents C1-C4 alkyl and AR represents an aryl group-containing radical, preferably selected from groups (AR-I) to (AR-XI I), as previously defined.

[0063] Hydrosilanes such as triethylsilane can be used to hydrogenate the non-amidic carbonyl groups of compounds (1) - (9), (22) - (27), and (71) - (90). The reaction is preferably carried out in the presence of a strong acid, such as trifluoroacetic acid. Such reactions are described in A. Winter et al., J. Biol. Chem. (2010), 285, 28883, as well as in WO 2010 / 107909 and WO 2008 / 036755. Non-amidic carbonyl groups are not present in the form of an amide group (-C(=O)-NH-) or an imide group (-NH-C(=O)-NH-).

[0064] Lubricant compositions

[0065] Another object of the invention is a lubricant composition which contains a) at least one phthalimide compound of the general formula (I) as base oil and b) at least one lubricant additive.

[0066] A specific embodiment is a lubricant composition comprising a1) at least one compound of the general formula (I) as base oil, a2) optionally at least one further base oil different from a1), b) at least one additive, preferably selected from thickeners, corrosion inhibitors, antioxidants, metal deactivators, inorganic or organic solid lubricants, viscosity index improvers, wear protection additives, radical scavengers, UV stabilizers, pour point improvers, friction value modifiers, additives for improving the high-pressure properties, adhesion improvers, further surface-active compounds and mixtures thereof.

[0067] The lubricant composition according to the invention preferably contains at least one phthalimide compound of the general formula (I) in an amount of 10.0 wt.% to 99.9 wt.%, particularly preferably 20.0 wt.% to 99.0 wt.%, even more preferably 25.0 wt.% to 95.0 wt.% and in particular 30.0 wt.% to 90.0 wt.%, in each case based on the total weight of the lubricant composition.

[0068] In addition to at least one phthalimide compound of the general formula (I), the lubricant composition may contain at least one further base oil different therefrom (= component a2).

[0069] If the lubricant composition contains at least one further base oil a2), this is preferably selected from esters, ethers, linear or branched perfluoropolyether oils (PFPE oils), synthetic hydrocarbons, mineral oils, untreated and chemically modified vegetable oils, Group III oils, gas to liquid (GTL) oils, reraffinates and recyclates, polyalphaolefins (PAO), silicone oils, polyisobutenes and mixtures thereof.

[0070] Preferably, the further base oil a2) is selected from esters of an aliphatic or aromatic di-, tri- or tetracarboxylic acid with one or more Cybis 022 alcohols present in admixture, esters of trimethylolpropane, pentaerythritol or dipentaerythritol with aliphatic Cybis 022 carboxylic acids, Cw-dimer acid esters with Cybis 022 alcohols, as well as complex esters and estolides.

[0071] In a specific embodiment, the lubricant composition according to the invention contains as further base oil a2) at least one ester selected from pentaerythritol esters, dipentaerythritol esters, trimellitic acid esters, hemimellitic acid esters, pyromellitic acid esters, estolides, dimer acid esters, trimer acid esters, trimethylolpropane esters (TMP esters), neopentyl glycol esters, dicarboxylic acid esters and mixtures thereof.

[0072] The additional base oil a2) is preferably selected from ethers, preferably polyphenyl ethers, diaryl ethers, triaryl ethers, polyglycols, preferably homopolymers and / or copolymers of ethylene oxide, propylene oxide, 1,2-butylene oxide, and / or tetrahydrofuran (THF), preferably initiated with monoalcohols, dialcohols, trialcohols, and higher-hydric alcohols having 4, 5, or more alcoholic OH groups. Suitable higher-hydric alcohols include, for example, pentaerythritol and dipentaerythritol.

[0073] In a specific embodiment, the lubricant composition according to the invention contains, as a further base oil a2), at least one ether selected from polyalkylene glycols (PAG). Suitable poly(alkylene) glycols a2) (PAG) are homopolymers, copolymers, and mixtures (blends) thereof. For the purposes of the invention, the term copolymer also refers to polymers composed of three, four, or more different monomers (terpolymers, quaterpolymers, etc.). Suitable poly(alkylene) glycols a2) are polyethylene glycols, polypropylene glycols, polybutylene glycols, polytetrahydrofurans, and copolymers of two or more different alkylene oxide copolymers. Suitable alkylene oxides for producing poly(alkylene) glycols a2) are, for example, ethylene oxide, propylene oxide, epichlorohydrin, 1,2- and 2,3-butylene oxide.Suitable examples of copolymers are copolymers of ethylene oxide and propylene oxide, copolymers of ethylene oxide and butylene oxide, and copolymers of ethylene oxide, propylene oxide, and at least one butylene oxide. The alkylene oxide copolymers may contain the copolymerized alkylene oxide units in randomly distributed form or in block form.

[0074] Linear or branched perfluoropolyether oils (PFPE oils) are also advantageously suitable as additional base oils a2). Suitable examples include perfluoropolyethers (PFPE) with the formula:

[0075] R A -(O-CF2)v-(O-C2F4)w-(O-C3F6)x-(O-CFCF3)y-(O-CF2CF(CF3))zOR B where R A and R B are identical or different and are selected from -CF3, -C2F5 and -C3F7, and v, w, x, y, z are integers from > 0 to 500. PFPE oils are marketed, for example, under the brand names Aflunox®, Krytox®, Fomblin® and Demnum®.

[0076] Synthetic hydrocarbons, mineral oils and mixtures thereof are also advantageously suitable as further base oils a2).

[0077] Group III oils are also advantageously suitable as additional base oils a2). Group III oils (hydrocracked synthetic oils) are synthetic hydrocarbons derived from petroleum base oils, produced entirely by hydrocracking, hydroisomerization, and hydrodesulfurization. They contain at least 90 percent saturates and a maximum of 0.03 percent sulfur, as well as a viscosity index of at least 120.

[0078] GTL oils (gas to liquids oils) are also particularly suitable as additional base oils a2). GTL oils are based on synthesis gas from hydrogen and carbon monoxide, from which longer-chain hydrocarbons are produced using Fischer-Tropsch synthesis. Polyalphaolefins (PAO) are also particularly suitable as additional base oils a2). Polyalphaolefins are also known as Group IV oils and generally have a viscosity index in the range of 125 to 200. Polyalphaolefins can be produced catalytically from ethylene using known processes, with alphaolefins with longer chain lengths initially resulting as intermediate products. From these, the polyalphaolefins are essentially synthesized by oligomerization, usually producing isoparaffins with a varying number of side chains of equal length. The synthesis can be carried out by acid-catalyzed (conventional) or metallocene-catalyzed olefin polymerization (mPAO).Conventional PAOs exhibit a high degree of isomerization, whereas metallocene oligomerization results in products that are essentially free of isomerization. Suitable polyalphaolefins include, for example, the oligomers, preferably the dimers, trimers, tetramers, pentamers, and higher oligomers with more than 5 repeating units of alpha-olefins, and mixtures of these oligomers. The alpha-olefins used to prepare the polyalphaolefins are preferably selected from Cs-Cu alpha-olefins, in particular 1-octene, 1-decene, 1-dodecene, and mixtures thereof.

[0079] Silicone oils are also advantageously suitable as additional base oils a2). Dimethyl silicone oils are preferred as additional base oils a2).

[0080] In a specific embodiment of the invention, the further base oil a2) is a fluorine-free base oil, preferably selected from pentaerythritol esters, dipentaerythritol esters, trimellitic acid esters, hemimellitic acid esters, pyromellitic acid esters, estolides, dimer acid esters, trimer acid esters, dicarboxylic acid esters, diaryl ethers, polyglycols, synthetic hydrocarbons, conventional polyalphaolefins (PAO), metallocene-catalyzed polyalphaolefins (mPAO); mineral oils, untreated and chemically modified vegetable oils, Group III oils, dimethylsilicone oils and mixtures. Preferred ethers are homo- and / or copolymers of ethylene oxide, propylene oxide, 1,2-butylene oxide and / or tetrahydrofuran (THF), preferably initiated with monoalcohols, dialcohols and trialcohols. Preferred synthetic hydrocarbons are alkylated naphthalenes.

[0081] In a further preferred embodiment, the base oil or base oil mixture (ie phthalimide compounds (I) and, if present, at least one further base oil a2) has a kinematic viscosity, determined according to ASTM-D-7042, September 2014 edition, at 40°C of 30 mm 2 / s up to 6000 mm 2 / s, more preferably at 40°C of 50 mm 2 / s up to 1200 mm 2 / s, especially at 40°C of 50 mm 2 / s up to 800 mm 2 / s. In a further preferred embodiment of the invention, the base oil is selected from the group consisting of esters, preferably dipentaerythritol esters, trimellitic acid esters, hemimellitic acid esters, pyromellitic acid esters, estolides, pentaerythritol esters, dimer acid esters, trimer acid esters, TMP esters, dicarboxylic acid esters, each with a kinematic viscosity at 40°C determined according to ASTM-D-7042, September 2014 edition of 100 mm 2 / s up to 1200 mm 2 / s; ethers, preferably polyphenyl ethers, diaryl ethers, triaryl ethers, linear or branched perfluoropolyether oils, each with a kinematic viscosity at 40°C determined according to ASTM-D-7042 - September 2014 edition of 20 mm 2 / s up to 1200 mm 2 / s; polyglycols, preferably homo- and / or copolymers of ethylene oxide, propylene oxide, 1,2-butylene oxide and / or tetrahydrofuran (THF), preferably initiated with monoalcohols, dialcohols and trialcohols, each with a kinematic viscosity at 40°C determined according to ASTM-D-7042, September 2014 edition, of 20 mm 2 / s up to 46000 mm 2 / s; synthetic hydrocarbons, preferably alkylated naphthalenes, polyalphaolefins (PAOs), metallocene polyalphaolefins (mPAOs), each with a kinematic viscosity at 40°C determined according to ASTM-D-7042, September 2014 edition, of 10 mm 2 / s up to 20000 mm 2 / s; Group III oils with a kinematic viscosity at 40°C determined according to ASTM-D-7042, September 2014 edition, of 10 mm 2 / s up to 100 mm 2 / s, dimethyl silicone oils, arylated silicone oils, preferably alkylaryl silicone oils, in particular methyl / aryl silicone oils and fully arylated silicone oils, each with a kinematic viscosity at 40°C determined according to ASTM-D-7042, September 2014 edition of 10 mm 2 / s up to 1200 mm 2 / s and / or each with a kinematic viscosity at 25°C determined according to DIN 53019, edition 2008.09 of 20 to 2000000 mm 2 / s, which can be used individually or in combination.

[0082] Lubricating oils and greases

[0083] The lubricant compositions according to the invention can be present as either a lubricating oil or a lubricating grease. In contrast to lubricating oils, lubricating greases contain at least one thickener as an additive. Thickeners are solid substances that are almost or completely insoluble in the base oils (insoluble solids) and have a thickening effect. For the purposes of this invention, all solids that are insoluble in the base oil are considered thickeners, regardless of whether they influence friction and wear. A specific embodiment is inorganic and organic solid lubricants.

[0084] Lubricating greases are compositions that contain a liquid phase (at room temperature) and solids. The consistency of lubricating greases can be determined using a standardized measuring method in the form of worked penetration according to DIN ISO 2137. Worked penetration is measured after the lubricating grease has been worked in a grease kneader or grease walker using a penetrometer. It is the penetration depth of a standard cone under defined conditions. The measured cone penetration is then assigned to a defined NLGI class (NLGI = National Lubricating Grease Institute) according to DIN 51818. Lubricating greases according to the invention specifically exhibit a worked penetration of 85 - 475 cone penetration in 0.1 mm when measured according to DIN 51818.

[0085] If a component used as an additive in the lubricant compositions according to the invention has several effects, e.g. as a thickener and friction coefficient modifier, and is accordingly also referred to in this application as an additive for several purposes, it is fully attributed in terms of quantity to each of these additive components.

[0086] A first specific embodiment of the invention is a lubricant composition in the form of a lubricating oil, comprising a) 80 to 99.9 wt.%, based on the total weight of the lubricant composition, of at least one compound of the general formula (I) as defined above, b) 0.1 to 20 wt.%, based on the total weight of the lubricant composition, of at least one additive.

[0087] The lubricant composition in the form of a lubricating oil preferably contains 90 to 99.8 wt.% of at least one compound of the general formula (I) (component a).

[0088] The lubricant composition in the form of a lubricating oil preferably contains 0.2 to 10 wt.% of at least one additive (component b).

[0089] In a specific embodiment, the lubricant composition in the form of a lubricating oil contains at least one base oil a2) in an amount of up to 50 wt.%, preferably up to 30 wt.%, in particular up to 15 wt.%, based on the total weight of the lubricant composition.

[0090] A second specific embodiment of the invention is a lubricant composition in the form of a lubricating grease, comprising a1) at least one compound of the general formula (I) as base oil, a2) optionally at least one further base oil different from a1), b1) at least one thickener, b2) optionally at least one further additive. In a specific embodiment, the lubricant composition in the form of a lubricating grease contains at least one base oil selected from base oils a1) and a2), in an amount of 40.0 to 95.0 wt.%, preferably 50.0 to 90 wt.%, based on the total weight of the lubricant composition.

[0091] Thickener b1)

[0092] The lubricant composition in the form of a lubricating grease preferably contains at least one thickener b1) in an amount of 0.2 to 60.0 wt.%, particularly preferably 3.0 to 55 wt.%, in particular 5.0 to 50 wt.%, based on the total weight of the lubricant composition.

[0093] The thickener b1) is preferably selected from metal simple soaps, metal complex soaps, urea thickeners, metal sulfonate thickeners, waxes, boron nitride, carbon black, graphite, metal chalcogenides, highly fluorinated polymeric substances, and fluorine-free substances. The fluorine-free substances are preferably selected from fluorine-free polymers containing aromatic, heteroaromatic, and / or heterocyclic groups and having a melting or decomposition point, measured according to DIN EN ISO 11357-1, edition 2008.04, of greater than 200°C, fluorine-free phthalocyanines, silicone resins, lignins, inorganic phyllosilicates, which may be functionalized with organic groups, phosphorus compounds, melamine derivatives, and mixtures of two or more of these thickeners.

[0094] Metal single soaps suitable as thickeners b1) are preferably metal single soaps of the elements of the first and second main groups of the periodic table, in particular lithium soaps. The metal single soaps are preferably derived from at least one saturated or unsaturated C5-22 fatty acid, preferably at least one C14-20 fatty acid, or a derivative thereof. This includes, for example, hydrogenated castor oil, ie, the glyceride of 12-hydroxystearic acid. In a preferred embodiment, thickener b1) comprises at least one lithium soap. Particularly preferred lithium soaps are lithium salts of stearic acid.

[0095] Metal complex soaps suitable as thickeners b1) are preferably metal complex soaps of the elements of the first and second main groups of the periodic table, such as lithium complex soaps, sodium complex soaps, calcium complex soaps, and aluminum complex soaps. Lithium complex soaps are preferred.

[0096] Suitable metal complex soaps can be obtained by reacting a metal base (such as a hydroxide, oxide or carbonate) with b11) at least one carboxylic acid component having 10 to 32 carbon atoms, preferably selected from unsaturated or saturated C10-C32 monocarboxylic acids or unsaturated or saturated C10-C32 hydroxy monocarboxylic acids and derivatives of said C10-C32 monocarboxylic acids and C10-C32 hydroxy monocarboxylic acids and b12) at least one complexing agent.

[0097] Component b11) is preferably selected from saturated or unsaturated C12-C22 monocarboxylic acids, saturated or unsaturated C12-C22 hydroxymonocarboxylic acids, and their esters and mixtures. In particular, the monocarboxylic acids and hydroxymonocarboxylic acids b11) are selected from lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, arachidonic acid, behenic acid, 12-hydroxystearic acid, 17-hydroxystearic acid, 2-hydroxytetradecanoic acid, 3-hydroxytetradecanoic acid, 2-hydroxyhexadecanoic acid, 3-hydroxyhexadecanoic acid, and mixtures thereof.

[0098] The complexing agent b12) is preferably selected from saturated or unsaturated C2-C16 dicarboxylic acids, saturated or unsaturated C2-C5 hydroxymonocarboxylic acids, derivatives, and mixtures thereof. Particularly suitable dicarboxylic acids b2) are adipic acid, sebacic acid, azelaic acid, 3-tert-butyladipic acid, and their esters and mixtures. Hydroxybenzoic acids, e.g., salicylic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2-hydroxy-4-hexylbenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 4-hydroxy-4-methoxybenzoic acid, and mixtures thereof.

[0099] Most preferably, the lithium complex soap comprises lithium salts of 12-hydroxystearic acid combined with azelaic acid or sebacic acid, in particular 12-hydroxystearic acid combined with azelaic acid.

[0100] In a preferred embodiment, the thickener b1) is a urea thickener, in particular an alkylated and / or arylated (oligo)urea. Preferred urea thickeners are the reaction products of at least one diisocyanate with at least one amine, selected from monoamines, polyamines, and mixtures thereof. The diisocyanate is preferably selected from 2,4-diisocyanatotoluene, 2,6-diisocyanatotoluene, 4,4'-diisocyanatodiphenylmethane, 2,4'-diisocyanatophenylmethane, 4,4'-diisocyanatodiphenyl, 4,4'-diisocyanato-3,3'-dimethylphenyl, 4,4'-diisocyanato-3,3'-dimethylphenyl, and mixtures thereof.

[0101] Preferably, the amine is selected from monoamines of the formula R a 2N-R b , diamines of the formula R a 2N-R c -NR a 2and mixtures thereof, where R a is independently selected from hydrogen, linear or branched C1-C 22 - Alkyl and C6-C 14 -Aryl, R bis independently selected from linear or branched C1-C 22 -alkyl and C6- C 14 -aryl residues, R c a divalent bridging group, preferably consisting of C1-C 22 -alkylene and C6-C 14-arylene is selected. Metal sulfonate thickeners suitable as thickener b1) are in particular calcium sulfonate thickeners. Calcium sulfonate thickeners specifically contain crystalline calcium carbonate in the form of calcite and calcium salts of acids, in particular aromatic sulfonic acids, very particularly preferably alkylbenzenesulfonic acids, carboxylic acids, in particular stearic acid, 12-hydroxystearic acid, acetic acid, boric acid and mixtures thereof. Waxes suitable as thickener b1) are in particular polyethylene (PE), polypropylene (PP) and polyamide (PA) wax. The wax preferably has a melting or decomposition point, measured according to DIN EN ISO 11357-1 edition 2008.04, of higher than 100°C. Metal chalcogenides suitable as thickener b1) are in particular molybdenum disulfide, tungsten disulfide and metal selenides. Highly fluorinated polymeric substances suitable as thickeners b1) are, in particular, PTFE.However, this is not a preferred embodiment of the invention. Fluorine-free components that differ from the previously mentioned thickeners b1) are also suitable as thickeners b1). The fluorine-free components preferably have an average particle size (D50) of less than 80 μm, for example 1 μm to 80 μm, more preferably from 1 μm to 50 μm, even more preferably from 1 μm to 20 μm, in particular from 1 μm to 15 μm, in each case measured according to ISO 13320-1, edition 2020-01. Preferred further fluorine-free components are boron nitride, carbon black, graphite, graphene, tin(IV) sulfide, zinc(II) sulfide, tungsten sulfide. Preferred other fluorine-free components are talc, bentonite, mica, and fumed silica, which can be functionalized with organic groups. A special type of bentonite is montmorillonite, whose sodium ions can be partially or completely exchanged for ammonium ions.Other suitable fluorine-free thickeners b1) are aluminosilicates, aluminum oxide, and silica (e.g., Aerosil). Other suitable fluorine-free thickeners b1) are nanoparticulate silicon dioxide functionalized with organic groups, zinc pyrophosphate, calcium (pyro)phosphate, and zirconium hydrogen phosphate. Other suitable fluorine-free thickeners b1) are melamine derivatives selected from melamine cyanurate, melamine phosphate, and 1,3,5-triazine-2,4,6(1H,3H,5H)-trithione. In a further preferred embodiment, the thickener b1) is a combination of two or more of the aforementioned other thickeners.

[0102] Other additives:

[0103] The lubricant composition according to the invention may comprise at least one additive b2) different from the thickeners b1). The additives are preferably selected from corrosion inhibitors, antioxidants, metal deactivators, inorganic or organic solid lubricants, viscosity index improvers, antiwear additives, free radical scavengers, UV stabilizers, pour point improvers, friction modifiers, additives for improving high-pressure properties, adhesion improvers, other surface-active compounds, and mixtures thereof.

[0104] If present, the lubricant composition preferably contains each of the additives in an amount of 0.1 to 20 wt.%, particularly preferably 0.5 to 10 wt.%, even more preferably 1 to 8 wt.%, and especially 1 to 5 wt.%, in each case based on the total weight of the lubricant composition.

[0105] Corrosion inhibitors

[0106] The lubricant composition according to the invention may contain at least one corrosion inhibitor as an additive.

[0107] Corrosion inhibitors neutralize acidic reaction products, e.g., from the oxidation of the base oil or additive degradation. This reduces or prevents corrosive attack. Suitable corrosion inhibitors are the salts of various acids, such as sulfonates, naphthenates, carboxylates, amine phosphates, succinic acid semiesters, or partial polyol esters. The corrosion inhibitor is preferably selected from calcium sulfonates, preferably "overbased" calcium sulfonates with a base number (TBN) of 100 to 500 mg KOH / g, amine-neutralized phosphates, alkylated Ca-naphthalenesulfonates, oxazoline derivatives, imidazole derivatives, succinic acid semiesters, benzotriazole, N-alkylated benzotriazoles, and mixtures thereof.

[0108] The lubricant composition according to the invention preferably contains at least one corrosion inhibitor in an amount of at least 0.1 wt.%, particularly preferably at least 0.5 wt.%, in particular at least 1.0 wt.%, based on the total weight of the lubricant composition. Antioxidants

[0109] The lubricant composition according to the invention may contain at least one antioxidant as an additive.

[0110] Antioxidants increase resistance to aging caused by oxidative and / or thermal stress at the lubrication point. Oxidation can produce acids and oil-insoluble components, which form contaminants that can settle on the lubrication point.

[0111] Suitable antioxidants are aromatic amine antioxidants such as alkylated phenyl-alpha-naphthylamine, dialkyldiphenylamine, aralkylated diphenylamine, sterically hindered phenols such as butylhydroxytoluene (BHT), bis-2,6-di-t-butylphenol derivatives, sulfur-containing hindered phenols, sulfur-containing hindered bisphenol and mixtures thereof.

[0112] The lubricant composition according to the invention preferably contains at least one antioxidant in an amount of at least 0.1% by weight, particularly preferably at least 0.5% by weight, in particular at least 1.0% by weight, based on the total weight of the lubricant composition.

[0113] Metal deactivators

[0114] The lubricant composition according to the invention may contain at least one metal deactivator (additive for protection against metal influences) as an additive.

[0115] Various metals, such as copper and its compounds, are catalysts for the formation of peroxides and thus contribute to oxidation. Suitable metal deactivators are chelating agents that passivate the metal surface. Non-limiting examples of metal deactivators are triazoles or thiadiazoles, especially aryltriazoles such as benzotriazole and tolyltriazole, alkyl derivatives of such triazoles, and benzothiadiazoles such as R(CeH3)N2S, where R is H or C1 to C8-alkyl.

[0116] The lubricant composition according to the invention preferably contains at least one metal deactivator in an amount of at least 0.1% by weight, particularly preferably at least 0.5% by weight, in particular at least 1.0% by weight, based on the total weight of the lubricant composition.

[0117] Wear protection agent The lubricant composition according to the invention can contain at least one wear protection agent as an additive.

[0118] Wear protection agents are used to prevent wear caused by tribological processes, such as fluid and mixed friction

[0119] The anti-wear agent is preferably selected from amine-neutralized phosphates, alkylated and non-alkylated triaryl phosphates, alkylated and non-alkylated triaryl thiophosphates, Zn, Mo or W dialkyl dithiophosphates, Zn, Mo or W diaryl dithiophosphates, carbamates, thiocarbamates, Zn, Mo or W dithiocarbamates, dimercaptothiadiazole, organoborates, organophosphites and mixtures thereof.

[0120] The lubricant composition according to the invention preferably contains at least one wear protection agent in an amount of at least 0.1% by weight, particularly preferably at least 0.5% by weight, in particular at least 1.0% by weight, based on the total weight of the lubricant composition.

[0121] Viscosity index improver

[0122] The lubricant composition according to the invention may contain at least one viscosity index improver (VI improver) as an additive.

[0123] Examples of VI improvers are olefin copolymers, polyalkyl methacrylates and dispersing olefin copolymers.

[0124] The lubricant composition according to the invention preferably contains at least one VI improver in an amount of at least 0.1% by weight, particularly preferably at least 0.5% by weight, in particular at least 1.0% by weight, based on the total weight of the lubricant composition.

[0125] Extreme pressure additives

[0126] The lubricant composition according to the invention may contain at least one extreme pressure additive as an additive.

[0127] High-pressure additives act as coating agents and / or surface-active substances. Preferred high-pressure additives are selected from thiophosphates, such as zinc dithiophosphate, molybdenum oxide sulfide dithiophosphate, molybdenum amine compounds, sulfur compounds, such as sulfurized oils and fats, sulfurized fatty acids, sulfurized fatty acid esters, alkylated polysulfides, and mixtures thereof. The lubricant composition according to the invention preferably contains at least one high-pressure additive in an amount of at least 0.1 wt.%, more preferably at least 0.5 wt.%, in particular at least 1.0 wt.%, based on the total weight of the lubricant composition.

[0128] Pour point improvers

[0129] The lubricant composition according to the invention may contain at least one power point improver as an additive.

[0130] Preferred additives for improving the pour point are selected from linear or branched, alkylated, acrylated, and / or aliphatic polymers and copolymers, which can be used individually or in combination. A specific example of a pour point depressant is polyalkyl methacrylate.

[0131] The lubricant composition according to the invention preferably contains at least one pour point improver in an amount of at least 0.1% by weight, particularly preferably at least 0.5% by weight, in particular at least 1.0% by weight, based on the total weight of the lubricant composition.

[0132] Adhesion improver

[0133] The lubricant composition according to the invention may contain at least one adhesion improver as an additive.

[0134] Preferred additives for improving adhesion are selected from long-chain polar polymers that give the oil or grease increased adhesion to the surface to be lubricated.

[0135] The lubricant composition according to the invention preferably contains at least one adhesion improver in an amount of at least 0.1% by weight, particularly preferably at least 0.5% by weight, in particular at least 1.0% by weight, based on the total weight of the lubricant composition.

[0136] The following examples serve to illustrate the invention without limiting it in any way.

[0137] EXAMPLES

[0138] I.) Synthesis examples Example 1: Synthesis of compound A) Step 1a: N-(2-Ethylhexyl)-trimellitic acid imide. 35.0 g (0.27 mol) of 2-ethylhexylamine and 52.0 g (0.27 mol) of trimellitic anhydride were initially charged in 131.0 g of acetic acid. The mixture was stirred under reflux for eight hours. During the synthesis, a gentle stream of nitrogen was passed through the apparatus. After the solution cooled, a white solid crystallized. The solid was filtered off with suction, washed five times with 0.4 L of water, and then dried at 60°C under vacuum (0.2 mbar). A white solid was obtained with a yield of 63.8 g (78%). 1 H NMR (CDCl3): G = 0.80-1.00 (m, 6H), 1.32 (m, 8H), 1.86 (m, 1H), 3.63 (d, 2H), 7.98 (d, 1H), 8.49 (dd, 1H), 8.58 (s, 1H) ppm. Stage 1b: N-(2-ethylhexyl)-trimellitic imide-4-chloride 71.3 g (0.24 mol) of the compound from step 1a, 164.2 g (1.38 mol) of thionyl chloride, and 4 drops of N,N-dimethylformamide were initially charged, and the mixture was stirred at reflux under nitrogen for 6.3 hours. The resulting solution was cooled, thionyl chloride was distilled off under membrane pump vacuum (150 mbar), and finally dried at 65°C under vacuum (0.3 mbar). A light yellow solid was obtained with a yield of 74.7 g (99%). 1H-NMR (CDCl3): G = 0.80-1.00 (m, 6 H), 1.16-1.42 (m, 8 H), 1.85 (m, 1 H), 3.63 (d, 2 H), 7.99 (d, 1 H), 8.47 (dd, 1 H), 8.58 (dd, 1 H) ppm. Step 1c: Compound A) 14.0 g (0.04 mol) of the compound from Step 1b was dissolved in 70.0 g of anhydrous toluene. The solution was cooled to 0°C. 4.2 g (0.05 mol) of anhydrous pyridine was added to this solution. Subsequently, a solution of 14.9 g (0.09 mol) of N-methyl-1-naphthylmethylamine in 17.0 g of anhydrous toluene was added dropwise over a period of 25 minutes at a maximum internal temperature of 5°C. A yellowish solid formed. After the addition was complete, the mixture was warmed to room temperature within one hour and stirred for a further 15 hours. During the synthesis, a gentle stream of nitrogen was passed through the apparatus. The solid formed was filtered off with suction, and the resulting solution was dried on a rotary evaporator.The residue was dissolved in 50 mL of ethyl acetate, extracted three times with 50 mL of aqueous HCl (1N) and then four times with 50 mL of semisaturated aqueous NaCl solution. The organic phase was dried over Na2SO4, filtered off with suction, the solvent was removed on a rotary evaporator, and then dried at 60°C under vacuum (0.2 mbar). A viscous, yellow-orange oil was obtained with a yield of 15.4 g (67%). 1 H-NMR (CDCl3): G = 0.89 (m, 6 H), 1.29 (m, 8 H), 1.82 (m, 1 H), 2.76 (s, 2 H), 3.19 (s, 1 H), 3.58 (m, 2 H), 4.97 & 5.26 (2 xs, 2 H), 7.40-8.30 (m, 10H) ppm. DSC (10 K / min.): T g = 5°C Dynamic viscosity (90.6 s -1 @ 100°C): 730 mPas Example 2: Synthesis of compound B) Step 2a: 4-Methyl-N-(5-carboxypentyl)phthalimide 40.0 g (0.31 mol) of 6-aminohexanoic acid and 49.5 g (0.31 mol) of 4-methylphthalic anhydride were initially dissolved in 76.0 g of acetic acid. The mixture was stirred under reflux for eight hours. During the synthesis, a gentle stream of nitrogen was passed through the apparatus. After the solution cooled, a yellowish solid crystallized. The solid was filtered off with suction, washed five times with 0.4 L of water, and then dried at 60°C under vacuum (0.2 mbar). A yellowish solid was obtained with a yield of 81.8 g (97%). 1H-NMR (CDCl3): G = 1.30-1.50 (m, 2 H), 1.60-1.78 (m, 4 H), 2.35 (t, 2 H), 2.51 (s, 3 H), 2.90 (t, 2 H), 3.67 (t, 3 H), 7.51 (d, 1 H), 7.64 (m, 1 H), 7.72 (d, 1 H) ppm. Step 2b: Acid chloride of 4-methyl-N-(5-carboxypentyl)phthalimide. 81.5 g (0.30 mol) of the compound from step 1a, 187.1 g (1.57 mol) of thionyl chloride, and 5 drops of N,N-dimethylformamide were initially charged, and the mixture was stirred under nitrogen for 6.6 hours under reflux. The resulting solution was cooled, thionyl chloride was distilled off under membrane pump vacuum (190 mbar), and finally dried at 60°C under vacuum (0.2 mbar). A light yellow solid was obtained with a yield of 63.5 g (95%). 1H-NMR (CDCl3): G = 1.32-1.50 (m, 2 H), 1.62-1.83 (m, 4 H), 2.51 (s, 3 H), 3.63 (d, 2 H), 7.99 (d, 1 H), 8.47 (dd, 1 H), 8.58 (dd, 1 H) ppm. Step 2c: Compound B) 15.0 g (0.05 mol) of the compound from step 2b was initially dissolved in 90.0 g of anhydrous toluene, and the solution was cooled to 0°C. 4.9 g (0.06 mol) of anhydrous pyridine was added to this solution. A solution of 17.5 g (0.10 mol) of N-methyl-1-naphthylmethylamine in 22.0 g of anhydrous toluene was then added dropwise over a period of 20 minutes at a maximum internal temperature of 5°C. A yellowish solid formed. After the addition was complete, the mixture was warmed to room temperature within one hour and stirred for a further 21 hours. A gentle stream of nitrogen was passed through the apparatus during the synthesis. The solid formed was filtered off with suction, and the resulting solution was dried on a rotary evaporator.The residue was taken up in 50 mL of ethyl acetate and extracted with 50 mL of aqueous HCl (1N). 50 mL of tetrahydrofuran was then added to the organic phase, and the solution was extracted twice more with 50 mL of aqueous HCl (1N). The organic phase was then extracted four times with 50 mL of semisaturated aqueous NaCl solution and separated. The organic phase was dried over Na2SO4, filtered off with suction, the solvent was removed using a rotary evaporator, and then dried at 60°C under vacuum (0.1 mbar). A viscous, yellow-orange oil was obtained with a yield of 15.5 g (71%). 1 H NMR (CDCl3): G = 1.20-1.50 (m, 2H), 1.55-1.85 (m, 4H), 2.25-2.45 (m, 2H), 2.48 & 2.50 (2xs, 3H), 2.83 (s, 2H), 3.06 (s, 1H), 3.55-3.75 (m, 2H), 5.01 & 5.06 (2xs, 2H), 7.10-8.15 (m, 10H) ppm. DSC (10 K / min.): T g = 10°C Dynamic viscosity (90.6 s -1 @ 100°C): 300 mPas Example 3: Synthesis of compound C) Step 3a: N-(6-Bromohexyl)phthalimide 40.0 g (0.22 mol) of potassium phthalimide, 211.0 g (0.86 mol) of 1,6-dibromohexane, and 3.0 g (0.02 mol) of anhydrous K2CO3 were initially charged in 711.0 g of anhydrous acetonitrile under a gentle nitrogen stream. The reaction mixture was stirred under reflux for 20 hours. During the synthesis, a gentle nitrogen stream was passed through the apparatus. The reaction mixture was cooled and filtered off with suction. Acetonitrile and excess 1,6-dibromohexane were distilled from the resulting solution. The residue was taken up in 100 mL of ethanol and heated to reflux of the ethanol. The crystalline solid formed after cooling was filtered off with suction and dried at 160°C under vacuum (0.5 mbar). A slightly yellowish solid was obtained with a yield of 54.9 g (82%). 1H-NMR (DMSO-d6): G = 1.30 (m, 2 H), 1.41 (m, 2 H), 1.60 (q, 2 H), 1.79 (q, 2 H), 3.50 (t, 2 H), 3.57 (t, 2 H), 7.78-7.91 (m, 4 H) ppm. Step 3b: Compound C) 25.0 g (0.08 mol) of the compound from step 3a and 16.7 g (0.12 mol) of anhydrous K2CO3 were initially charged to 195.0 g of anhydrous acetonitrile under a gentle nitrogen stream. Then, 23.5 g (0.14 mol) of N-methyl-1-naphthylmethylamine was added portionwise over 5 minutes. The nitrogen stream was stopped, and the reaction mixture was stirred under reflux for 2 hours. After cooling the reaction mixture, the solid formed was filtered off with suction, and the resulting solution was dried on a rotary evaporator. The residue was taken up in 0.15 L of ethyl acetate and washed with 0.1 L of water. The organic phase was separated, and 0.14 L of tetrahydrofuran was added to the organic phase. The mixture was washed twice with 80 mL of water.The organic phase was dried over Na2SO4, filtered off with suction, the solvent was removed on a rotary evaporator, and then dried at 190°C under vacuum (0.3 mbar). A viscous, orange oil was obtained with a yield of 29.0 g (90%). After approximately five days, the product slowly began to crystallize. 1 H NMR (DMSO-d6): G = 1.22 (m, 4 H), 1.35-1.65 (m, 4 H), 2.25-2.45 (m, 2 H), 2.10 (s, 3 H), 2.37 (t, 2 H), 3.51 (t, 2 H), 3.81 (s, 2 H), 7.35-7.55 (m, 4H), 7.75-7.90 (m, 6H), 8.26 (dd, 1H) ppm. DSC (10 K / min.): T g = -19°C; after complete crystallization, the product also has a T m from 72°C to dynamic viscosity (90.6 s -1 @ 100°C): 40 mPas Example 4: Synthesis of compound D) 93.1 g (0.57 mol) of 4-methylphthalic anhydride and 85.0 g (0.57 mol) of phthalic anhydride were initially charged in 1047.0 g of acetic acid. The mixture was heated to 50°C. After the anhydrides had completely dissolved, 520.0 g (0.57 mol) of diaminopropyl-terminated polydimethylsiloxane (viscosity: 10-15 cSt) were added dropwise over a period of 60 minutes at a maximum internal temperature of 60°C. After the addition was complete, the solution was heated to reflux and stirred under reflux for a further eight hours. A gentle stream of nitrogen was passed through the apparatus during the synthesis. After cooling to room temperature, the reaction solution was poured into 1.5 L of water, and 1.8 L of ethyl acetate was added. The aqueous phase was separated and the organic phase was washed five times with 0.5 L of semi-saturated aqueous NaCl solution, twice with 0.5 L of aqueous NaHCO3 solution (5%) and once with 0.75 L of water.The organic phase was dried over Na2SO4, filtered off with suction, the solvent was removed using a rotary evaporator, and then dried at 100°C under vacuum (0.1 mbar). A low-viscosity, yellow-orange liquid was obtained with a yield of 617.0 g. 1 H-NMR (CDCl3): G = 0.05 (m, 72 H), 0.53 (m, 4 H), 1.65 (m, 4 H), 2.47 (s, 3 H), 3.63 (m, 4 H), 7.45 (2, 1 H), 7.61 (s, 1 H), 7.63-7.73 (m, 3 H), 7.76-7.86 (m, 2H) ppm. DSC (10 K / min.): T g = -81°C Dynamic viscosity (90.6 s -1 @ 100°C): 14 mPas Dynamic viscosity (90.6 s -1 @ 40°C): 81 mPas Example 5: Synthesis of compound E) Step 5a: N-(n-Octyl)-trimellitic acid imide. 178.4 g (0.93 mol) of trimellitic anhydride was initially dissolved in 254.0 g of acetic acid. 120.0 g (0.93 mol) of 1-octylamine was added over a period of 14 minutes. The mixture was stirred under reflux for eight hours. During the synthesis, a gentle nitrogen stream was passed through the apparatus. The cooled reaction mixture was precipitated into 2.0 L of ice water, the solid was washed six times with 1.8 L of water, and then dried at 60°C under vacuum (0.4 mbar). A white solid was obtained with a yield of 273.6 g (97%). 1H-NMR (CDCl3): G = 0.87 (t, 3 H), 1.15-1.49 (m, 10 H), 1.69 (q, 2 H), 3.72 (t, 2 H), 7.98 (d, 1 H), 8.50 (dd, 1 H), 8.58 (s, 1 H) ppm. Step 5b: N-(n-octyl)-trimellitic acid imide-4-chloride. 240.3 g (0.79 mol) of the compound from Example 5a, 440.5 g (3.70 mol) of thionyl chloride, and 10 drops of N,N-dimethylformamide were initially charged, and the mixture was stirred under reflux under nitrogen for 6.5 hours. The resulting solution was cooled, thionyl chloride was distilled off under membrane pump vacuum (170 mbar), and finally dried at 60°C under vacuum (0.2 mbar). A light yellow solid was obtained with a yield of 246.6 g (97%). 1H-NMR (CDCl3): G = 0.87 (t, 3 H), 1.17-1.42 (m, 10 H), 1.69 (q, 2 H), 3.73 (t, 2 H), 8.00 (d, 1 H), 8.48 (dd, 1 H), 8.58 (d, 1 H) ppm. Step 5c: Compound E) 258.6 g (1.94 mol) of anhydrous aluminum chloride was initially dissolved in 1662.0 g of anhydrous dichloromethane. The internal temperature of the mixture was lowered to 5°C. Subsequently, a solution of 195.0 g (0.61 mol) of the compound from step 5b) in 324.0 g of anhydrous dichloromethane was added over a period of 16 minutes at a maximum internal temperature of 11°C. After a further five minutes, 531.0 g of a mixture of alkylated naphthalenes (NA-LUBE KR-015 from King Industries, kinematic viscosity of 114 cSt at 40°C and 13.5 cSt at 100°C) in 400.0 g of anhydrous dichloromethane was added over a period of 24 minutes at a maximum internal temperature of 11°C. The mixture was stirred for 110 minutes at 5°C, warmed to room temperature within 50 minutes, and then refluxed for 21 hours.During the synthesis, a gentle stream of nitrogen was passed through the apparatus. The cooled reaction mixture was poured into 3.0 L of ice water and stirred for one hour. The organic phase was separated and washed four times with 0.8 L of aqueous Na2CO3 solution (5%). In the first wash step, 0.6 L of tetrahydrofuran was added to the organic phase, followed by 0.4 L of tetrahydrofuran after the first wash step, and in the final wash step, 0.4 L of an ethyl acetate / tetrahydrofuran mixture in a ratio of 1:1. Finally, the organic phase was washed twice with 0.7 L of water, dried over Na2SO4, filtered off with suction, freed from the solvent on a rotary evaporator, and then dried at 120°C under vacuum (0.3 mbar). A viscous, brown oil with a yield of 475.3 g was obtained. DSC (10 K / min.): T. g = -40°C Dynamic viscosity (90.6 s -1 @ 100°C): 90 mPas Example 6: Synthesis of compound F) Step 6a: 4-Methyl-N-(5-carboxypentyl)phthalimide 345.0 g (2.63 mol) of 6-aminohexanoic acid and 426.4 g (2.63 mol) of 4-methylphthalic anhydride were initially dissolved in 657.0 g of acetic acid. The mixture was stirred under reflux for eight hours. During the synthesis, a gentle nitrogen stream was passed through the apparatus. The cooled reaction mixture was precipitated into 3.0 L of ice water, and the solid was washed four times with 3.0 L of water and then dried at 100°C under vacuum (0.8 mbar). A pale yellow solid was obtained with a yield of 709.6 g (98%). 1H-NMR (CDCl3): G = 1.32-1.54 (m, 2 H), 1.60-1.82 (m, 4 H), 2.35 (t, 2 H), 2.51 (s, 3 H), 3.67 (t, 2 H), 7.50 (d, 1 H), 7.64 (s, 1 H), 7.72 (d, 1 H) ppm. Step 6b: Acid chloride of 4-methyl-N-(5-carboxypentyl)phthalimide. 330.8 g (1.20 mol) of the compound from Step 6a, 574.2 g (4.83 mol) of thionyl chloride, and 12 drops of N,N-dimethylformamide were initially charged, and the mixture was stirred under nitrogen for 6.7 hours at reflux. The resulting solution was cooled, thionyl chloride was distilled off under membrane pump vacuum (140 mbar), and finally dried at 60°C under vacuum (0.2 mbar). A light yellow solid was obtained with a yield of 345.5 g (98%). 1 H NMR (CDCl3): G = 1.32-1.50 (m, 2 H), 1.62-1.83 (m, 4 H), 2.51 (s, 3 H), 2.90 (t, 2 H), 3.67 (t, 2 H), 7.51 (d, 1 H), 7.64 (s, 1 H), 7.72 (d, 1 H) ppm. Stage 6c: Connection F)

[0139] 290.5 g (2.18 mol) of anhydrous aluminum chloride was initially charged in 1661.0 g of anhydrous dichloromethane. The internal temperature of the mixture was lowered to 5°C. Subsequently, a solution of 200.0 g (0.68 mol) of WTA2047 in 288.0 g of anhydrous dichloromethane was added over a period of 12 minutes at a maximum internal temperature of 11°C. After a further five minutes, a solution of 600.0 g of NA-LUBE KR-015 in 400.0 g of anhydrous dichloromethane was added over a period of 7 minutes at a maximum internal temperature of 10°C. The mixture was stirred for 53 minutes at 5°C, warmed to room temperature within 50 minutes, and then refluxed for 22 hours. A gentle nitrogen stream was passed through the apparatus during the synthesis.

[0140] The cooled reaction mixture was precipitated into 3.0 L of ice-water and stirred for one hour. The organic phase was separated and washed three times with 0.8 L of 5% aqueous Na2CO3 solution. Finally, the organic phase was washed twice with 0.8 L of water. The organic phase was dried over Na2SO4, filtered off with suction, concentrated in a rotary evaporator, and dried at 120°C under vacuum (0.5 mbar). A viscous, brown oil was obtained with a yield of 605.1 g.

[0141] Analytics:

[0142] DSC (10 K / min.): T g = -44°C

[0143] Dynamic viscosity (29.0 s -1 @ 100°C): 45 mPas

[0144] Example 7: Synthesis of compound G)

[0145] 290.5 g (2.18 mol) of anhydrous aluminum chloride was initially dissolved in 1661.0 g of anhydrous dichloromethane. The internal temperature of the mixture was then lowered to 5°C. Subsequently, a solution of 200.0 g (0.68 mol) of the compound from step 6b in 287.0 g of anhydrous dichloromethane was added over a period of 21 minutes at a maximum internal temperature of 11°C. After a further five minutes, a mixture of 510.2 g of alkylated diphenyl ethers (HILUBE LB-15, dynamic viscosity 15.8 mm 2 / s at 40°C, Moresco, JP) in 404.0 g of anhydrous dichloromethane was added over a period of 16 minutes at a maximum internal temperature of 10°C. The mixture was stirred at 5°C for 66 minutes, warmed to room temperature within 40 minutes, and then refluxed for 20 hours. During the synthesis, a gentle nitrogen stream was passed through the apparatus. The cooled reaction mixture was precipitated into 3.0 L of ice-water and stirred for one hour. The organic phase was separated and washed three times with 0.6 L of aqueous Na2CO3 solution (5%). After the first washing step, 0.5 L of ethyl acetate was added to the organic phase. Finally, the organic phase was washed twice with 0.6 L of water, dried over Na2SO4, filtered off with suction, and the solvent was removed on a rotary evaporator. The excess Hl-LUBE LB-15 was removed at 220°C under vacuum (0.2 mbar).A viscous, dark brown oil was obtained with a yield of 375.1 g.

[0146] DSC (10 K / min.): T g = -33°C

[0147] Dynamic viscosity (90.6 s _1 @ 100°C): 72 mPas

[0148] Example 8: Synthesis of compound H)

[0149] Stage 8.1: Diaminopropyl-terminated poly(co-diphenylsiloxane-dimethylsiloxane)

[0150] 1,3-Bis(aminopropyl)tetramethyldisiloxane (28.0 g, 0.113 mol), octamethylcyclotetrasiloxane (17.0 g, 57.3 mmol), octaphenylcyclotetrasiloxane (8.56 g, 10.8 mmol), and tetramethylammonium 3-aminopropyldimethylsilanolate (71 mg, 0.34 mmol) were placed in a 100 mL flask equipped with a reflux condenser. The apparatus was continuously purged with a gentle stream of N2. The reaction mixture was heated to an internal temperature of 110°C and stirred at this temperature for approximately 23 h. The reaction mixture was then heated to an internal temperature of 150°C and stirred at this temperature for 2 h to deactivate the catalyst. The colorless reaction mixture was cooled. The reaction mixture was then purified by distillation. At a heat transfer medium temperature of 125°C, a colorless substance was removed (approx. 1 mbar, fraction 1, 18.45 g). The product was obtained as a residue (colorless substance, 32.67 g). Product analysis: 1H-NMR (CDCl3): δ = -0.05-0.17 (m), 0.40-0.60 (m), 1.00-1.53 ​​(m), 2.53-2.71 (m), 7.23- 7.45 (m), 7.52-7.71 (m) ppm. Step 8.2: Compound H 4-Methylphthalic anhydride (6.95 g, 42.9 mmol), phthalic anhydride (6.35 g, 42.9 mmol), and acetic acid (65 g) were placed in a three-necked flask. The apparatus was continuously purged with a gentle stream of N2. The reaction mixture was heated to an internal temperature of 46°C so that the reactants were completely dissolved. The product from Step 8.1 (30.1 g, 42.7 mmol) was added dropwise over a period of 1 h 12 min. The reaction mixture warmed by approximately 10°C. The dropping funnel was rinsed with acetic acid (3.3 g). The reaction mixture was heated to reflux (internal temperature approximately 116°C), stirred under these conditions for 8 h, and then cooled. The reaction mixture was then precipitated into ice-water (200 mL). Partial phase separation was observed. The organic phase was separated.The aqueous-organic phase was treated with ethyl acetate (200 mL) and aqueous NaCl (half-saturated, 50 mL) to accelerate phase separation. The organic phase was separated. The combined organic phases were then washed with aqueous NaCl (half-saturated, 3 x 100 mL), aqueous NaHCO3 (5%, 2 x 150 mL), and water (200 mL). The organic phase was dried over Na2SO4 and the solvent was removed under reduced pressure (up to approximately 1 mbar and 120 °C). Compound H was obtained as a light yellow liquid (37.19 g). Analysis: 1H-NMR (CDCl3): į = -0.13-0.18 (m), 0.43-0.65 (m), 1.52-1.78 (m), 2.50 (s), 3.52-3.72 (m), 7.16-7.66 (m), 7.68-7.76 (m), 7.79-7.89 (m,) ppm. II.) Application examples Measurement methods Determination of kinematic viscosity The kinematic viscosity at 40°C (KV40) and at 100°C (KV100) is determined according to ASTM D7042, July 2016 edition. The viscosity measurement is carried out using a Stabinger SVM 3000 viscometer (Anton Paar GmbH, Germany). Determination of shear viscosity The shear viscosity is determined using a Rheometer MCR 300 (Anton Paar GmbH, DE) according to DIN 53019-1:2008-09 at a test temperature of 25°C and a shear rate of 300 s -1determined. The values ​​determined after a measurement duration of 90 s correspond to the shear viscosity. Viscosity index The viscosity index (VI) can be calculated from the kinematic viscosity, as specified, for example, in DIN ISO 2909:2004-08. Density The densities are determined at 20°C (^20), 40°C (^40), and 100°C (^100) according to DIN 51757:2011-01 using a Stabinger rheometer. Determination of oxidation stability: The oxidation stability was determined according to DIN 51830-1, 2022-10 using a RapidOxy measuring device (Anton Paar GmbH, DE). The time until a pressure loss of 30% of the initial pressure at the measuring temperature occurs, starting from an initial pressure of 700 kPa oxygen at room temperature, is measured. Pour point The pour point was determined according to DIN ISO 3016-2017-11. Evaporation loss aluminum cup test: 1.50 g of the oil to be tested is weighed into a round aluminum cup with a diameter of 2.3 cm and a depth of 1 cm.The weight of the oil-filled bowl is recorded. A circulating air drying cabinet (Binder, type FD 56) is heated to 200°C. Once the test temperature has stabilized for 30 minutes, the oil-filled bowl is placed in the drying cabinet's test chamber. The bowl is removed from the drying cabinet after 24 or 100 hours and weighed. The difference between the weight before and after the test is divided by the initial weight of oil to determine the evaporation loss.

[0151] 1 H-NMR spectroscopy

[0152] A 300 MHz device of the type Mercury 300 (manufacturer Varian) was used.

[0153] The glass transition temperatures (Tg) were determined by DSC (differential scanning calorimetry) using a DSC measuring instrument from Netzsch-Gerätebau, Germany, type DSC 214 Polyma. The sample weight was 15 mg, the heating rate was 1 K / min, the first temperature ramp was from -150°C to 100°C for thermal calibration, the sample was cooled to -150°C, and the temperature ramp was repeated from -150°C to 100°C. The second temperature run was evaluated.

[0154] The grease's continuous operating temperature was determined on an FAG FE-9 testing machine with installation variant B based on DIN 51825:2004-06. The FAG FE-9 test rig is used to assess the service life and determine the upper operating temperature of greases for rolling bearing lubrication. The rolling bearings operate at medium speeds and moderate axial loads. Specifically, the measurements were taken at an axial load of 1500 N and a speed of 3000 rpm. 1The test temperatures are specified in the test examples.

[0155] The consistency of lubricating greases can be determined using a standardized measuring method with a penetrometer in the form of cone penetration. A standardized cone penetrates a specific amount of grease. The penetration depth achieved in 5 seconds, measured in 0.1 mm, determines the penetration number. The rest penetration (also referred to simply as penetration) and the worked penetration after 60 double strokes were determined according to ISO 2137:2020. For the worked penetration, the sample was additionally processed (mechanically loaded) in a grease kneader or grease roller with 60 double strokes prior to measurement. The measured cone penetration can then be assigned to a defined NLGI class (NLGI = National Lubricating Grease Institute) according to DIN 51818.

[0156] 11.1) Determination of the oxidation stability of different samples

[0157] The samples were measured at 140°C, the sample weight was 4.0 g.

[0158] II.2) Determination of the viscosity-temperature behavior, the pour point and the oxidation resistance of various samples The determination of the oxidation resistance was carried out using a sample weight of 5.0 ml of lubricating oil at a measuring temperature of 160°C.

[0159] II.3) Determination of the kinematic viscosity, the viscosity index and the density of various samples. The measurements were carried out on mixtures of various compounds according to the invention with trimellitic acid ester A (TMA = reaction product of trimellitic acid with a 1:1 molar mixture of n-octanol and n-decanol) in a weight ratio of 1:1. The mixtures were prepared by stirring with a magnetic stirrer at 80°C for 2 h.

[0160] II.4) Determination of kinematic viscosity, viscosity index and density of different samples

[0161] The measurements were carried out on mixtures of various compounds according to the invention with trimellitic acid ester A (TMA = reaction product of trimellitic acid with a 1:1 molar mixture of n-octanol and n-decanol), varying the weight ratios. The mixtures were prepared by stirring with a magnetic stirrer at 80°C for 2 hours.

[0162] II.5) Tests on the additivity of compound D) in comparison to a standard dimethyl silicone oil. As a reference silicone oil (Si Ref), a dimethyl silicone oil with a KV40 of 75 mm is used. 2 / s is used.

[0163] Compound D) or Si Ref are each mixed with 1 wt.% of a lubricant additive according to the following table, and the mixture is stirred at 60°C for 30 minutes (magnetic stirrer, beaker, stir bar). After cooling, the samples are examined. Mixtures that form precipitates or emulsions are considered immiscible.

[0164] II.6) Effect of antioxidants on the oxidative stability of compound D)

[0165] Compound D) is mixed with 1 wt.% or 3 wt.% of the respective antioxidant and stirred at 60°C for 30 min (magnetic stirrer, beaker, stir bar). After cooling, clear solutions are obtained. Oxidation stability is tested using the RapidOxy test as described under "Measurement Methods."

[0166] Aminic antioxidant: p,p'-dinonyldiphenylamine

[0167] Phenolic antioxidant: Tetrakis(methylene(3,5-di-tert-butyl-4-hydroxyhydrocinnamate))methane

[0168] Ionic liquid: Trihexyltetradecylphosphonium bis(trifluoromethylsulfonyl)imide 11.7) Mixing tests of compound D) with compound E) compared to Si Ref with compound E)

[0169] The mixtures are prepared in the weight ratios specified in the following tables by stirring with a magnetic stirrer at 80°C for 2 hours. Mixtures that exhibit two phases after cooling are designated as immiscible.

[0170] Comparison mixtures mixtures according to the invention

[0171] 11.8: Application tests for the production of fats

[0172] Greases were prepared using compound D. A Speedmixer DAO 700.1 FVZ from Hauschild was used to prepare the greases described below. The components were mixed for 5 minutes at 1000 µm in each case. 1mixed and homogenized twice on a three-roll mill. All fat components were added simultaneously.

[0173] Table II.8

[0174] PPS = polyphenylene sulfide micropowder: melting point 280°C, average particle size

[0175] D50 = 5 pm

[0176] DSS = Disodium sebacate: average particle size approx. 5 pm PTFE (micropowder): average particle size approx. 8 pm

[0177] Tricalcium phosphate: average particle size approx. 6 pm

[0178] Using compound D according to the invention as base oil, lubricating greases can be produced which meet the service life requirements at 200°C and 220°C.

[0179] II.9 Application data compound H

[0180] Table II.9: Data Compound H

Claims

Patent claims 1. Lubricant composition containing a) a base oil containing or consisting of at least one phthalimide compound of the general formula (I) wherein R 1 , R 2 , R 3 and R 4 are independently selected from hydrogen, straight-chain or branched alkyl, straight-chain or branched alkoxy, straight-chain or branched alkanoyl, straight-chain or branched alkyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkylene, unsubstituted or substituted aryloxy, unsubstituted or substituted arylalkyleneoxy, unsubstituted or substituted arylthio, unsubstituted or substituted arylalkylenethio, unsubstituted or substituted aroyl, unsubstituted or substituted aryloxycarbonyl, unsubstituted or substituted arylcarbonyloxy, Monoalkylaminocarbonyl, Monoarylaminocarbonyl, Mono(arylalkylene)-aminocarbonyl, Monoalkylmonoarylaminocarbonyl, Monoalkylmono-(arylalkylene)aminocarbonyl, Monoarylmono(arylalkylene)aminocarbonyl, Dialkylaminocarbonyl, Diarylaminocarbonyl, Di(arylalkylene)aminocarbonyl, Monoalkanoylamino, Monoaroylamino, Monoalkanoylmonoaroylamino, dialkanoylamino, diaroylamino, where the aryl radicals of monoarylaminocarbonyl, mono(arylalkylene)aminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkylmono(arylalkylene)-aminocarbonyl, monoarylmono(arylalkylene)aminocarbonyl, diaryl-aminocarbonyl, di(arylalkylene)aminocarbonyl, monoaroylamino, Monoalkanoylmonoaroylamino and diaroylamino are each unsubstituted or substituted, unsubstituted or substituted aromatic hydrocarbons having 2, 3, 4 or more aromatic rings, wherein 2 of the rings are each linked by a single bond or a divalent group selected from -CH2-, -O-, -S- or -N(H)- are linked to each other, and wherein the unsubstituted or substituted aromatic hydrocarbons having 2, 3, 4 or more aromatic rings are linked via a single bond or a divalent group selected from -CH2-, -O-, -S-, -N(R a )-, -OC(=O)- or -N(R b )-C(=O)- are bonded to the benzene ring of the phthalimide group, where R a and R b are independently selected from hydrogen and C1-C4 alkyl, carboxyl, hydroxy, nitro, NH2, alkylamino and dialkylamino, where the radicals R 1 and R 2 or R 2 and R 3 or R 3 and R 4 can also together represent a group of formula (I.1) where # denotes the binding site to the rest of the molecule, where one of the residues R 1 , R 2 , R 3 or R 4 also together with another residue R 1 , R 2 , R3 or R 4 which is bonded to another group of formula (I), can represent a divalent bridging group Y which connects the two groups of formula (I), X 1 and, if applicable, X 2 independently for straight-chain or branched C1-C 30 -alkylene, where the alkylene chain may be interrupted by 1 to 15 non-adjacent heteroatoms selected from O and S, or a group of the formula #-(CR 5 R 6 ) n -SiR 7 R 8 (O-SiR 7 R 8 ) m -(CR 9 R 10 ) p -#, where # denotes the binding site to the rest of the molecule, R 5 , R 6 , R 9 and R 10 independently of one another represent hydrogen or C1-C4-alkyl, R 7 and R 8independently of one another represent straight-chain or branched alkyl or phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4 alkyl groups, n stands for an integer from 1 to 30, m stands for an integer from 1 to 30, p stands for an integer from 1 to 30, or a group of the formula #-(CR 11 R 12 ) q -NR 13 -(CR 14 R 15 ) r -#, where # denotes the binding site to the rest of the molecule, R 11 , R 12 , R 14 and R 15 independently of one another represent hydrogen or C1-C4-alkyl, R 13 represents hydrogen or C1-C4-alkyl, q represents an integer from 1 to 30, r represents an integer from 1 to 30, or a group of formula (I.2) where # denotes the bonding site to the rest of the molecule, Z denotes O or S, s denotes an integer from 1 to 30, Y denotes a group of the formula -(O) 0,1 -(C1-C 30 -alkylene)-(O) 0,1 - or -(S) 0,1 -(C1-C 30 -Alkylene)-(S) 0,1 - or -(C=O)-(O) 0,1 -(C1-C 30 -alkylene)-(O) 0,1 -(C=O)-, where alkylene is straight-chain or branched and may be interrupted by 1 to 15 non-adjacent heteroatoms selected from O and S, or Y for a group of the formula #-(O) 0,1 -(CR 5 R 6 ) n -SiR 7 R 8 (O-SiR 7 R 8 ) m -(CR 9 R 10 ) p -(O) 0,1 -# or #-(S) 0,1 -(CR 5 R 6 ) n -SiR 7 R 8 (O-SiR 7 R 8 ) m -(CR 9 R 10 ) p -(S) 0,1-#, where # denotes the binding site to the rest of the molecule, R 5 , R 6 , R 9 and R 10 independently of one another represent hydrogen or C1-C4 alkyl, R 7 and R 8 independently of one another represent straight-chain or branched alkyl or phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4 alkyl groups, n represents an integer from 1 to 30, m represents an integer from 1 to 30, p represents an integer from 1 to 30, or Y represents a group of the formula #-(O) 0,1 -(CR 11 R 12 ) q -NR 13 -(CR 14 R 15 ) r -(O) 0,1 -# or #-(S) 0,1 -(CR 11 R 12 ) q -NR 13 -(CR 14 R 15 ) r -(S) 0,1 -#, where # denotes the binding site to the rest of the molecule, R 11 , R 12 , R 14 and R 15independently of one another represent hydrogen or C1-C4 alkyl, R 13 represents hydrogen or C1-C4-alkyl, q represents an integer from 1 to 30, r represents an integer from 1 to 30, or Y represents a group of formula (I.3) (1-3) where # denotes the binding site to the rest of the molecule, Z 1 , Z 2 and Z 3 independently represent O or S, t represents 0 or an integer from 1 to 30, R A and, if applicable, R Bindependently for hydrogen, unsubstituted or substituted aryl, unsubstituted or substituted aroyl, monoalkylaminocarbonyl, monoarylaminocarbonyl, mono-(arylalkylene)aminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkyl-(monoarylalkylene)aminocarbonyl, monoarylmono(arylalkylene)-aminocarbonyl, dialkylaminocarbonyl, Diarylaminocarbonyl, di(arylalkylene)aminocarbonyl, monoalkanoylamino, monoaroylamino, monoalkanoylmonoaroylamino, dialkanoylamino, diaroylamino, where the aryl radicals of monoarylaminocarbonyl, mono(arylalkylene)aminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkylmono(arylalkylene)-aminocarbonyl, Monoarylmono(arylalkylene)aminocarbonyl, diarylaminocarbonyl, di(arylalkylene)aminocarbonyl, monoaroylamino, Monoalkanoylmonoaroylamino and diaroylamino are each unsubstituted or substituted, or a phthalimide group of formula (1.4) stands in which R 16 , R 17 , R 18 and R19 independently of each other the previously calculated values ​​for R 1 , R 2 , R 3 and R 4 have the meaning given, and b) at least one additive different therefrom.

2. Lubricant composition according to claim 1, with the proviso that the compounds of formula (I) do not represent one of the following compounds: - N-alkylphthalimides of the formula (IA) where E is C1-C4-alkyl, - (N-amino-hydrocarbyl)phthalimides of the general formula (IB) where E is -(CH2CH2NH) n CH2CH2NH2, -(CH2CH2CH2NH) n CH2CH2CH2NH2or -(CH2CH2CH2NH) n R IB where R IB for a C5-C 25 -alkyl group and n has a value of 1-10.

3. Lubricant composition according to claim 1 or 2, wherein in the compounds of formula (I) at least one of the radicals R 1 , R 2 , R 3 and R 4and / or, if present, at least one of the radicals R 16 , R 17 , R 18 and R 19 represents a radical other than hydrogen.

4. Lubricant composition according to one of the preceding claims, wherein in the compounds of formula (I) at least one of the radicals R 1 , R 2 , R 3 and R 4 and / or, if present, at least one of the radicals R 16 , R 17 , R 18 and R 19 represents a group selected from the groups (AR-I) to (AR-XXIV) (AR-XXIV) where # denotes the binding site to the rest of the molecule, A is selected from the groups where ~ denotes the bonding site of group A to the benzene ring, R c represents hydrogen or C1-C4 alkyl, R 21 , R 22 , R 23 , R 24 , R25 , R 26 , R 27 , R 28 , R 29 and R 30 , if present, are independently selected from hydrogen, straight-chain or branched C1-C 20 -alkyl and straight-chain or branched C1-C4-alkoxy.

5. Lubricant composition according to one of claims 1 to 4, wherein in the compounds of formula (I) at least one of the radicals R 1 , R 2 , R 3 and R 4 represents hydrogen, preferably at least two of the radicals R 1 , R 2 , R 3 and R 4 represent hydrogen, preferably at least three of the radicals R 1 , R 2 , R 3 and R 4 represent hydrogen, in particular the radicals R 1 , R 3 and R 4 represent hydrogen or the radicals R 2 , R 3 and R 4 represent hydrogen or the radicals R 1 , R 2 , R 3 and R 4represent hydrogen, and / or if present, in the groups of formula (I.4) at least one of the radicals R 16 , R 17 , R 18 and R 19 represents hydrogen, preferably at least two of the radicals R 16 , R 17 , R 18 and R 19 represent hydrogen, preferably at least three of the radicals R 16 , R 17 , R 18 and R 19 represent hydrogen, in particular the radicals R 16 , R 18 and R 19 represent hydrogen or the radicals R 17 , R 18 and R 19 represent hydrogen or the radicals R 16 , R 17 , R 18 and R 19 stand for hydrogen.

6. Lubricant composition according to one of the preceding claims, wherein in the compounds of formula (I) X 1 and, if applicable, X 2 independently for straight-chain or branched C1-C 20-alkylene, or a group of the formula #-(CH2CH2O) 1-10 -(CH2CH2)-#, or a group of the formula #-(CH2) 1-5 -Si(CH3)2-(O-(Si(CH3)2)) 1-5 -(CH2) 1-5 -#, or a group of the formula #-(CH2) 1-5 -NR 13 -(CH2) 1-5 -# stands, where R 13 represents hydrogen or C1-C4-alkyl, or a group of formula (I.2a) where # denotes the bonding site to the rest of the molecule.

7. Lubricant composition according to one of the preceding claims, wherein in the compounds of formula (I) Y is -(O) 0,1 -(C1-C 20 -alkylene)-(O) 0,1 - or -(S) 0,1 -(C1-C 20 -Alkylene)-(S) 0,1 - or -(C=O)-(O) 0,1 -(C1-C 30 -alkylene)-(O) 0,1 -(C=O)-, where alkylene is straight-chain or branched, or a group of the formula #-(O) 0,1 -(CH2CH2O) 1-10 -(CH2CH2)-(O) 0,1-#, or a group of the formula #-(O) 0,1 -(CH2) 1-5 -Si(CH3)2-(O-(Si(CH3)2)) 1-5 -(CH2) 1-5 -(O) 0,1 -#, or a group of the formula #-(O) 0,1 -(CH2) 1-5 -NR 13 -(CH2) 1-5 -(O) 0,1 -# stands, where R 13 represents hydrogen or C1-C4-alkyl, or a group of formula (I.3a) stands in which # denotes the binding site to the rest of the molecule.

8. Lubricant composition according to one of the preceding claims, wherein in the compounds of formula (I) at least one of the radicals R A and, if applicable, R B represent a group (AR-I) to (AR-XXIV) as defined in claim 2.

9. Lubricant composition according to one of the preceding claims, wherein in the compounds of formula (I) at least one of the radicals R A and, if applicable, R Brepresent a phthalimide group of formula (1.4).

10. Lubricant composition according to one of the preceding claims, comprising a compound of formula (I) selected from compounds (1) to (116) and the compounds obtainable by reduction of the non-amidic carbonyl group(s) of compounds (1) - (9), (22) - (27) and (71) - (90)  5 where n is an integer from 1 to 30, m is an integer from 1 to 30, p is an integer from 1 to 30, u stands for an integer from 1 to 15, v stands for 1 or 2, R 2 and R 17are independently selected from hydrogen, straight-chain or branched alkyl, straight-chain or branched alkoxy, straight-chain or branched alkanoyl, straight-chain or branched alkyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylalkyleneoxy, unsubstituted or substituted arylthio, unsubstituted or substituted arylalkylenethio, unsubstituted or substituted aroyl, unsubstituted or substituted aryloxycarbonyl, unsubstituted or substituted arylcarbonyloxy, monoalkylaminocarbonyl, monoarylaminocarbonyl, mono(arylalkylene)aminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkylmono(arylalkylene)aminocarbonyl, Monoarylmono(arylalkylene)aminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, di(arylalkylene)aminocarbonyl, monoalkanoylamino, monoaroylamino, monoalkanoylmonoaroylamino, dialkanoylamino, diaroylamino,where the aryl radicals of monoarylaminocarbonyl, mono(arylalkylene)aminocarbonyl, monoalkylmonoarylaminocarbonyl, monoalkylmono(arylalkylene)aminocarbonyl, monoarylmono(arylalkylene)aminocarbonyl, diarylaminocarbonyl, di(arylalkylene)aminocarbonyl, monoaroylamino, monoalkanoylmonoaroylamino and diaroylamino are each unsubstituted or substituted, R, 7 and R 8 independently of one another represent straight-chain or branched C1-C4 alkyl, R 13 represents hydrogen or C1-C4 alkyl, R c represents hydrogen or C1-C4 alkyl, R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 and R 30 , if present, are independently selected from hydrogen, straight-chain or branched C1-C 20 -alkyl and straight-chain or branched C1-C4-alkoxy.

11. Lubricant composition according to one of the preceding claims, containing a1) at least one compound of the general formula (I) as base oil, a2) optionally at least one further base oil different from a1), b) at least one additive, preferably selected from thickeners, corrosion inhibitors, antioxidants, wear protection additives, radical scavengers, UV stabilizers, inorganic or organic solid lubricants, pour point improvers, friction modifiers, additives for improving high-pressure properties, viscosity index improvers, adhesion improvers, further surface-active compounds and mixtures thereof.

12. Lubricant composition according to one of the preceding claims, containing at least one phthalimide compound of the general formula (I) in an amount of 10.0 wt.% to 99.9 wt.%, preferably 20.0 wt.% to 99.0 wt.%, more preferably 25.0 wt.% to 95.0 wt.% and in particular 30.0 wt.% to 90.0 wt.%, in each case based on the total weight of the lubricant composition.

13. Lubricant composition according to one of the preceding claims, containing at least one base oil a2) selected from esters, preferably dipentaerythritol esters, trimellitic acid esters, hemimellitic acid esters, pyromellitic acid esters, estolides, pentaerythritol esters, dimer acid esters, trimer acid esters, trimethylolpropane esters (TMP esters), neopentyl glycol esters, dicarboxylic acid esters; ethers, preferably polyphenyl ethers, diaryl ethers, triaryl ethers, polyglycols, preferably homo- and / or copolymers of ethylene oxide, propylene oxide, 1,2-butylene oxide and / or tetrahydrofuran (THF), preferably initiated with monoalcohols, dialcohols, trialcohols and higher-hydric alcohols having 4, 5 or more alcoholic OH groups, linear or branched perfluoropolyether oils (PFPE oils); synthetic hydrocarbons, preferably alkylated naphthalenes, polyalphaolefins (PAOs), metallocene polyalphaolefins (mPAOs); mineral oils, untreated and chemically modified vegetable oils, Group III oils;Gas to Liquid (GTL) oils; Re-refined and recycled materials, preferably obtained from mineral oils, Group III oils, GTL oils and / or PAO, dimethyl silicone oils; arylated silicone oils, alkylaryl silicone oils, polyisobutenes and mixtures thereof.

14. Lubricant composition in the form of a lubricating oil according to one of claims 1 to 13, containing a) 80 to 99.9% by weight, preferably 90 to 99.8% by weight, based on the total weight of the lubricant composition, of at least one compound of the general formula (I), b) 0.1 to 20 wt.%, preferably 0.2 to 10 wt.%, based on the total weight of the lubricant composition, of at least one additive.

15. Lubricant composition in the form of a lubricating oil according to claim 14, comprising at least one base oil a2) in an amount of up to 50 wt.%, preferably up to 30 wt.%, in particular up to 15 wt.%, based on the total weight of the lubricant composition.

16. Lubricant composition according to one of claims 1 to 13 in the form of a lubricating grease, comprising a1) at least one compound of the general formula (I) as base oil, a2) optionally at least one further base oil different from a1), b1) at least one thickener, b2) optionally at least one further additive.

17. Lubricant composition in the form of a lubricating grease according to claim 16, comprising at least one base oil selected from base oils a1) and a2), in an amount of 40.0 to 95.0 wt.%, preferably 50.0 to 90 wt.%, based on the total weight of the lubricant composition.

18. Lubricant composition in the form of a lubricating grease according to claim 16 or 17, containing at least one thickener b1) in an amount of 0.2 to 60.0 wt.%, preferably 3.0 to 55 wt.%, in particular 5.0 to 50 wt.%, based on the total weight of the lubricant composition.

19. Use of phthalimide compounds of the general formula (I) as defined in any one of claims 1 to 10 as base oil of a lubricant composition for lubricating tribological systems, in particular tribological systems in applications where an upper service temperature of at least 160°C is necessary.

20. Use of phthalimide compounds of the general formula (I), as defined in any one of claims 1 to 10, as base oil of a high-temperature lubricating grease for lubricating plain bearings, in particular chains, rolling bearings and / or for driving production plants in the chemical industry, wherein the plain bearings, the rolling bearings and / or the production plants in the chemical industry are operated, preferably at least temporarily, at temperatures of at least 160°C.

21. Use of phthalimide compounds of the general formula (I), as defined in any one of claims 1 to 10, as a base oil of a high-temperature lubricating grease for the lubrication of plain bearings, in particular gas fittings, actuators, linear guides, regulating and control flaps in the intake manifold, clutches, screws, bolts, fittings, chains for the food industry, in particular in bread and waffle baking machines; of rolling bearings, in particular rolling bearings for wood pressing or corrugated cardboard systems and / or for driving production systems in the chemical industry.

22. Use of a phthalimide compound of the formula (I), as defined in any one of Claims 1 to 10 defined as a component of a lubricant composition for the partial or complete replacement of a fluorine-containing lubricant component, in particular a linear or branched perfluoropolyether oil (PFPE oil).

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