EP2123741A1 - Liquid conductive additive for non-aqueous hydraulic oils - Google Patents

Abstract

Composition comprises non-aqueous hydraulic fluids or lubricants and one or more conductive additives clearly miscible or soluble in the hydraulic fluids and optionally other usual additives.

Description

Hydraulic oils are used in machines of power transmission. In this case, oil is conveyed through a line by a pump, at the end of which a piston is moved by the hydraulic oil. Due to the lever set, large forces can be transmitted with comparatively low pumping power.

Depending on the intended use and required property hydraulic fluids are structured differently. The fluids are classified according to ISO 6743 in mineral oil-based, flame-retardant and environmentally friendly fluids.

The most commonly used hydraulic fluids, but also lubricants are based on mineral oil with appropriate additives. They are also referred to as hydraulic oils. The requirements for these hydraulic oils are defined in ISO 6743/4 with the designation HL, HM, HV. In Germany, the designations HL, HLP, HVLP according to DIN 51524 are common.

[HL: with active ingredients to increase corrosion protection and aging resistance (also HL according to DIN 51524, part 1); HM: with active ingredients to increase the corrosion protection, the aging resistance as well as to reduce the scuffing wear in the mixed friction area (also HLP according to DIN 51524, part 2); HV: with active ingredients to increase the corrosion protection, the aging resistance, to reduce scuffing in the mixed friction area and to improve the viscosity-temperature behavior (also HVLP DIN 51524, Part 3)].

• Phosphorsäureester (HFD R), die heute am häufigsten eingesetzte HFD-Flüssigkeit; hat jedoch die geringste Schwerentflammbarkeit,
• Chlorierte Kohlenwasserstoffe (HFD S); kommen aus Gründen des Umweltschutzes nur noch in geschlossenen Systemen des Steinkohlenbergbaus zur Anwendung,
• Mischungen aus HFD R und HFD S,
• Andere Zusammensetzungen (HFD U).

Furthermore important are anhydrous, synthetically produced flame-retardant liquids. They are based on the following connections:

• Phosphoric acid ester (HFD R), the most commonly used HFD fluid today; but has the lowest flame retardancy,
• Chlorinated hydrocarbons (HFD S); For reasons of environmental protection, they are only used in closed systems of the coal industry,
• Mixtures of HFD R and HFD S,
• Other compositions (HFD U).

• HETG (Basis Triglyceride = pflanzliche Öle),
• HEES (Basis synthetische Ester),
• HEPG (Basis Polyglycole)
• HEPR (andere Basisflüssigkeiten, in erster Linie Poly-alpha-olefine).

In addition, biodegradable hydraulic fluids based on vegetable oils (eg rapeseed-based) are produced and used in a biologically critical environment (construction machinery in water conservation areas, piste equipment in the mountains, etc.). These fluids are pollutants of emission class I and are abbreviated HE: Hydraulic Environmental. The individual substance classes are divided as follows:

• HETG (based triglycerides = vegetable oils),
• HEES (base synthetic esters),
• HEPG (polyglycol base)
• HEPR (other basic fluids, primarily poly-alpha-olefins).

Hydraulic equipment manufacturers mostly require products in accordance with DIN 51524 Part 2 "HLP" or Part 3 "HVLP". Oils of this quality must possess a certain water-separating capacity, filterability, seal compatibility, air-separating ability, oxidation stability, wear protection, etc. (Some parts of DIN 51524 have been revised in 2005. The revised version of DIN 51524 was published in April 2005. The main change is the new introduced purity class 21/19/16).

The general assessment of an overall hydraulic system in terms of cost-effectiveness, reliability, low maintenance costs and high machine availability is through the use of high-quality components, such. As valves, control pumps, lubricants and hydraulic media influenced.

Fine particles significantly affect the life of a hydraulic system due to abrasion and other unwanted side effects. For this reason, the manufacturers of hydraulic systems stipulate that the oil is filled into the plant via special filters.

Damage analysis of hydraulic and lubrication systems usually diagnoses damage to the components used, caused by hard and high-concentration solid particles in the operating medium.

• Material der Verschmutzung (je härter die Partikel sind, desto größer ist die Komponentenbeschädigung)
• Betriebsüberdruck (je höher der Betriebsüberdruck, desto stärker werden die Feststoffpartikel in den Schmierspalt gedrückt).

The intensity of the component damage due to the solid contamination in the lubricating and hydraulic oil depends on

• Material of contamination (the harder the particles, the greater the damage to the components)
• Operating pressure (the higher the operating pressure, the more the solid particles are pressed into the lubrication gap).

• Grobe Partikel (> 15 µm): Plötzlicher Komponentenausfall,
• Feinverschmutzung (5-15 µm): Komponentenverschleiß, Leckagen, Ventilverblockungen,
• Feinstverschmutzung (< 2-5 µm): Schlammansammlung im Öl, Schnellere Ölalterung.

The failure of hydraulic and lubrication components is mostly due to the following causes:

• Coarse particles (> 15 μm): Sudden component failure,
• Fine contamination (5-15 μm): Component wear, leaks, valve blockages,
• Very fine contamination (<2-5 μm): Mud accumulation in the oil, faster oil aging.

The filters used in lubrication and hydraulic systems have the task of complying with the specified solids contamination. To achieve this goal, these filters must be mounted as close as possible to the dirt entry point, have the necessary filter fineness, be installed in the largest volume flow, so that a high tank circulation is achieved. If possible, system filtration should be assisted by efficient tank recirculation (bypass filtration). In order to avoid damage to the filter element, and an economical, cost-optimized element replacement is possible, the filter should be provided with an active clogging indicator, which stops the system if it is ignored.

These recommendations should lead to the component life required by the operator and thus the Duration of use of the entire system can be met. The task of the hydraulic filters used in the system and their correct placement in the system is to implement and comply with these purity class requirements over the entire operating period of the system. Especially with new oils, which are delivered in barrels, tankers or minicontainers, is to be reckoned with an inadmissibly high solid contamination.

The use of high-quality filters with elements that exhibit multi-particle particle size separation in the multipass test according to ISO 16889, a high dirt pick-up, a small pressure difference on the filter element and housing, a high collapse burst pressure resistance, a high dynamic pressure and volume flow pulsation resistance, the concentration of particulate contamination in lubricating and hydraulic media is significantly reduced with the aim of preventing premature component failure. A low solids concentration in the individual particle sizes in the lubricants and hydraulic media is the prerequisite that the entire system can be operated economically and reliably.

In the filtration processes occur, especially at low ambient temperatures, such as prevail in cold stores, for example, charge separations, which lead to a static charge.

The problem of the static charge is the higher, the lower the temperature, especially at reduced humidity, or residual moisture in closed systems.

Sparking due to static charging represents a high safety risk. To prevent this problem, conductivity additives are necessary to ensure a minimum conductivity of the hydraulic fluid and thus to ensure a charge drainage. Usually, solid salts are used in conjunction with organic solvents. These are necessary to achieve at least minimum solubility. This constellation has several disadvantages. On the one hand, the organic solvents increase the flammability and combustibility of the hydraulic fluid, on the other hand, they are volatile and pose a health risk. In addition, the volatility leads to the fact that the solubility of the conductive salts decreases and these are filtered out over time and even to a Damage to the hydraulic system can result from friction. In addition, the hydraulic fluid thus loses its antistatic equipment. In combination with the still present in small quantities of organic solvents increases as a result, the flammability and thus the security risk.

The maximum concentration of conductivity improvers is therefore limited and thus also the maximum achievable conductivity of the hydraulic oils or lubricants.

In the context of this application, conductivity improvers are also referred to as conductivity additives, with both terms being considered synonymous with one another.

Object of the present invention is therefore to overcome the identified shortcomings of the prior art and to provide new conductivity improvers which are capable of providing a permanent antistatic finish of hydraulic oils and / or lubricants.

Surprisingly, liquid conductivity additives have now been found which are soluble in the non-aqueous hydraulic fluid and / or the lubricant or at least clearly miscible with the hydraulic fluid and / or the lubricant and can advantageously be used in hydraulic oils and / or lubricants.

These liquid conductivity additives contain ions with organic radicals and have very low vapor pressures and thus also low volatilities.

The invention therefore relates to compositions comprising non-aqueous hydraulic oils or lubricants and one or more liquid conductivity additives which contain organic ions and may optionally contain further customary additives.

Preference is given to compositions containing liquid ionic conductivity additives in which at least either the cation and / or the anion have organic radicals.

Particularly preferred are compositions containing ionic conductivity additives having at least one cation and / or anion with organic radicals.

The ionic conductivity additive in the cation and / or anion preferably contains at least one organic radical having at least eight carbon atoms, wherein the sum of the C atoms of all radicals is at least 14.

Particular preference is given to ionic conductivity additives having at least one radical in the cation and / or anion which contains at least 12 C atoms, the sum of the C atoms of all radicals being at least 22.

Very particular preference is given to conductivity additives having two or more organic radicals in the cation and / or anion which contain at least 12 carbon atoms and in which the sum of all radicals is at least 26.

Another object of the invention is the use of liquid organic conductivity additives in hydraulic or lubricant systems, especially in those in which the lubricant is filtered continuously or semicontinuously, especially at temperatures between +20 ° C and -75 ° C, preferably between +10 ° C and -50 ° C, more preferably between 5 ° C and -25 ° C. Suitable lubricant systems are lubricant systems in 2-stroke engines, gasoline engines and diesel engines, automatic transmissions, manual transmissions, brake circuits, hydraulic systems, air and gas compressors, transmissions, ball bearings, gas turbines, steam turbines, cooling circuits, which are e.g. used in automobiles, trucks, tractors, aircraft, ships and industrial equipment. Preferred lubricant systems are hydraulic systems, particularly preferred are hydraulic systems which are continuously filtered.

By using the compositions according to the invention, the conductivity of the hydraulic oils can be increased and so as to avoid the risk of electric charging; In addition, the required properties of the hydraulic oils with respect to vapor pressure / volatility, flammability, filtration ability, turbidity and stability of the formulation are improved, but at least not adversely affected.

It is particularly advantageous that the conductivity additive is liquid and does not separate from the formulation in crystalline form, which can lead to the described problems of conventional additives when used in hydraulic or lubrication systems.

The conductivity additives used according to the invention are preferably composed of at least one cation [A ⁺ ], corresponding to a quaternary nitrogen and / or phosphorus compound and / or sulfur compound and at least one anion, and their melting point is below approximately + 250 ° C., preferably below approximately + 150 ° C, especially below about + 100 ° C. With particular preference the conductivity additives or mixtures thereof used according to the invention are liquid at room temperature, preferably at the temperatures of use.

The formulations according to the invention also have the advantage that, owing to the increased solubility of the conductivity additives according to the invention, they can also be used at temperatures below room temperature, even well below freezing point.

Thus, even at low temperatures, the conductivity can be increased and the static charge, especially in the filtration, counteracted.

• n für 1, 2, 3 oder 4 steht,
• [A]⁺für ein quartäres Ammonium-Kation, ein Oxonium-Kation, ein Sulfonium-Kation oder ein Phosphonium-Kation und
• [Y]^n- für ein n-wertiges Anion steht und/oder gemischte Salze der allgemeinen Formeln (II)

         [A¹]⁺[A²]⁺ [Y]^2-     (IIa)

         [A¹]⁺[A²]⁺[A³]⁺ [Y]^3-     (IIb)

oder

         [A¹]⁺[A²]⁺[A³]⁺[A⁴]⁺ [Y]^4-     (IIc)

wobei

• [A¹]⁺, [A²]⁺ [A³]⁺ und [A⁴]⁺ unabhängig voneinander aus den für [A]⁺ genannten Gruppen ausgewählt sind und [Y]^n- die für Formel (I) genannte Bedeutung besitzt und/oder gemischte Salze der allgemeinen Formeln (III)

         [A¹]⁺[A²]⁺[A³]⁺[M¹]⁺ [Y]^4-     (IIIa)

         [A¹]⁺[A²]⁺[M¹]⁺[M²]⁺ [Y]^4-     (IIIb)

         [A¹]⁺[M¹]⁺[M²]⁺[M³]⁺ [Y]^4-     (IIIc)

         [A¹]⁺[A²]⁺[M¹]⁺ [Y]^3-     (IIId)

         [A¹]⁺[M¹]⁺[M²]⁺ [Y]^3-     (IIIe)

         [A¹]⁺[M¹]⁺ [Y]^2-     (IIIf)

         [A¹]⁺[A²]⁺[M⁴]²⁺ [Y]^4-     (IIIg)

         [A¹]⁺[M¹]⁺[M⁴]²⁺ [Y]^4-     (IIIh)

         [A¹] + [M⁵]³⁺ [Y]^4-     (IIIi)

oder

         [A¹]⁺[M⁴]²⁺ [Y]^3-     (IIIj)

wobei

• [A¹]⁺, [A²]⁺ und [A³]⁺ unabhängig voneinander aus den für [A]⁺ genannten Gruppen ausgewählt sind,
• [Y]^n- die für Formel (I) genannte Bedeutung besitzt und [M¹]⁺, [M²]⁺, [M³]⁺ einwertige Metallkationen,
• [M⁴]²⁺ zweiwertige Metallkationen und
• [M⁵]³⁺ dreiwertige Metallkationen bedeuten, oder Gemische aus allen Formeln (I) bis (III).

Conductivity additives in the context of the present invention are salts of the general formulas (I), (II), or (III) listed below:

[A] _n ⁺ [Y] ^n- (I)

in the

• n is 1, 2, 3 or 4,
• [A] ⁺ for a quaternary ammonium cation, an oxonium cation, a sulfonium cation or a phosphonium cation and
• [Y] ^{n- is} an n-valent anion and / or mixed salts of the general formulas (II)

[A ¹ ] ⁺ [A ² ] ⁺ [Y] ^2- (IIa)

[A ¹ ] ⁺ [A ² ] ⁺ [A ³ ] ⁺ [Y] ^3- (IIb)

or

[A ¹ ] ⁺ [A ² ] ⁺ [A ³ ] ⁺ [A ⁴ ] ⁺ [Y] ^4- (IIc)

in which

• [A ¹ ] ⁺ , [A ² ] ⁺ [A ³ ] ⁺ and [A ⁴ ] ^{+ are} independently selected from the groups mentioned for [A] ⁺ and [Y] ^{n- has} the meaning given for formula (I) and / or mixed salts of the general formulas (III)

[A ¹ ] ⁺ [A ² ] ⁺ [A ³ ] ⁺ [M ¹ ] ⁺ [Y] ^4- (IIIa)

[A ¹ ] ⁺ [A ² ] ⁺ [M ¹ ] ⁺ [M ² ] ⁺ [Y] ^4- (IIIb)

[A ¹ ] ⁺ [M ¹ ] ⁺ [M ² ] ⁺ [M ³ ] ⁺ [Y] ^4- (IIIc)

[A ¹ ] ⁺ [A ² ] ⁺ [M ¹ ] ⁺ [Y] ^3- (IIId)

[A ¹ ] ⁺ [M ¹ ] ⁺ [M ² ] ⁺ [Y] ^3- (IIIe)

[A ¹ ] ⁺ [M ¹ ] ⁺ [Y] ^2- (IIIf)

[A ¹ ] ⁺ [A ² ] ⁺ [M ⁴ ] ²⁺ [Y] ^4- (IIIg)

[A ¹ ] ⁺ [M ¹ ] ⁺ [M ⁴ ] ²⁺ [Y] ^4- (IIIh)

[A ¹ ] + [M ⁵ ] ³⁺ [Y] ^4- (IIIi)

or

[A ¹ ] ⁺ [M ⁴ ] ²⁺ [Y] ^3- (IIIj)

in which

• [A ¹ ] ⁺ , [A ² ] ⁺ and [A ³ ] ^{+ are} independently selected from the groups mentioned for [A] ⁺ ,
• [Y] ^{n- has} the meaning given for formula (I) and [M ¹ ] ⁺ , [M ² ] ⁺ , [M ³ ] ⁺ monovalent metal cations,
• [M ⁴ ] ²⁺ divalent metal cations and
• [M ⁵ ] ³⁺ mean trivalent metal cations, or mixtures of all formulas (I) to (III).

The metal cations [M ¹ ] ⁺ , [M ² ] ⁺ , [M ³ ] ⁺ , [M ⁴ ] ²⁺ and [M ⁵ ] ³⁺ mentioned in formulas (IIIa) to (IIIj) are generally Metal cations of the 1st, 2nd, 6th, 7th, 8th, 9th, 10th, 11th, 12th and 13th group of the periodic table in the IUPAC nomenclature. Suitable metal cations are, for example, Li ⁺ , Na ⁺ , K ⁺ , Cs ⁺ , Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , Cr ³⁺ , Fe ²⁺ , Fe ³⁺ , CO ²⁺ , Ni ²⁺ , Cu ^{2 +} , Ag ⁺ , Zn ²⁺ and Al ³⁺ .

The conductivity additives of the invention consist of anions such as halides, carboxylates, phosphates, thiocyanates, isothiocyanates, dicyanamides, sulfates, alkyl sulfates, sulfonates, alkyl sulfonates, tetrafluoroborate, hexafluoro-phosphate or bis (trifluoromethylsulfonyl) imide combined with, for example, substituted ammonium, phosphonium -, pyridinium or imidazolium cations, wherein the aforementioned anions and cations represent a small selection of the large number of possible anions and cations and thus no claim completeness or even a restriction should be specified.

• R¹,R²,R³,R⁴ gleich oder unterschiedlich sind und Wasserstoff, einen linearen oder verzweigten gegebenenfalls Doppelbindungen enthaltenden aliphatischen Kohlenwasserstoffrest mit 1 bis 30 Kohlenstoffatomen, mit der Vorgabe, dass mindestens einer der Reste ungleich Wasserstoff ist, einen gegebenenfalls Doppelbindungen enthaltenden cycloaliphatischen Kohlenwasserstoffrest mit 5 bis 40 Kohlenstoffatomen, einen aromatischen Kohlenwasserstoffrest mit 6 bis 40 Kohlenstoffatomen, einen Alkylarylrest mit 7 bis 40 Kohlenstoffatomen, einen durch ein oder mehrere Heteroatome (Sauerstoff, NH, NR' mit R' gleich einem gegebenenfalls Doppelbindungen enthaltenden C₁-C₃₀-Alkylrest, insbesondere -CH₃) unterbrochenen linearen oder verzweigten gegebenenfalls Doppelbindungen enthaltenden aliphatischen Kohlenwasserstoffrest mit 2 bis 30 Kohlenstoffatomen, einen durch eine oder mehrere Funktionalitäten, ausgewählt aus der Gruppe -O-C(O)-, -(O)C-O-, -NH-C(O)-, -(O)C-NH, -(CH₃)N-C(O)-, -(O)C-N(CH₃)-, -S(O₂)-O-, -O-S(O₂)-, -S(O₂)-NH-, -NH-S(O₂)-, -S(O₂)-N(CH₃)-, -N(CH₃)-S(O₂)-, unterbrochenen linearen oder verzweigten gegebenenfalls Doppelbindungen enthaltenden aliphatischen Kohlenwasserstoffrest mit 2 bis 30 Kohlenstoffatomen, einen endständig mit OH, OR', NH₂, N(H)R', N(R')₂, bei denen R' gleich einem gegebenenfalls Doppelbindungen enthaltenden C₁-C₃₀-Alkylrest ist, funktionalisierten linearen oder verzweigten gegebenenfalls Doppelbindungen enthaltenden aliphatischen oder cycloaliphatischen Kohlenwasserstoffrest mit 1 bis 30 Kohlenstoffatomen oder einen blockweise oder statistisch aufgebauten Polyether gemäß -(R⁵-O)_n-R⁶ bedeuten,

wobei

R⁵

ein 2 bis 4 Kohlenstoffatome enthaltender linearer oder verzweigter Kohlenwasserstoffrest,

n

1 bis 100, vorzugsweise 2 bis 60, ist und

R⁶

Wasserstoff, einen linearen oder verzweigten gege- benenfalls Doppelbindungen enthaltenden aliphatischen Kohlenwasserstoffrest mit 1 bis 30 Kohlenstoffatomen, einen gegebenenfalls Doppelbindungen enthaltenden cycloaliphatischen Kohlenwasserstoffrest mit 5 bis 40 Kohlenstoffatomen, einen aromatischen Kohlenwasser- stoffrest mit 6 bis 40 Kohlenstoffatomen, einen Al- kylarylrest mit 7 bis 40 Kohlenstoffatomen bedeutet oder ein Rest -C(O)-R⁷ mit

R⁷

gleich einem linearen oder verzweigten gegebenenfalls Doppelbindungen enthaltenden aliphatischen Kohlenwas- serstoffrest mit 1 bis 30 Kohlenstoffatomen, einem gegebenenfalls Doppelbindungen enthaltenden cycloali- phatischen Kohlenwasserstoffrest mit 5 bis 40 Kohlen- stoffatomen, einem aromatischen Kohlenwasserstoffrest mit 6 bis 40 Kohlenstoffatomen, einem Alkylarylrest mit 7 bis 40 Kohlenstoffatomen ist.

The conductivity additives preferably used in the context of the invention can be selected, for example, from at least one organic cation [A ⁺ ] of the general formulas

R ¹ R ² R ³ R ⁴ N ⁺ (IV)

R ¹ R ² N ⁺ = CR ³ R ⁴ (V)

R ¹ R ² R ³ R ⁴ P ⁺ (VI)

R ¹ R ² P ⁺ = CR ³ R ⁴ (VII)

R ¹ R ² R ³ S ⁺ (VIII)

exist in which

• R ¹ , R ² , R ³ , R ^{4 are the} same or different and are hydrogen, a linear or branched optionally double bonds containing aliphatic hydrocarbon radical having 1 to 30 carbon atoms, with the proviso that at least one of the radicals is not hydrogen, optionally containing double bonds cycloaliphatic hydrocarbon radical having from 5 to 40 carbon atoms, an aromatic hydrocarbon radical having from 6 to 40 carbon atoms, an alkylaryl radical having from 7 to 40 carbon atoms, a C ₁ -C radical containing one or more heteroatoms (oxygen, NH, NR 'with R' equal to an optionally double bond _30- alkyl radical, in particular -CH ₃ ) interrupted linear or branched optionally double bonds containing aliphatic hydrocarbon radical having 2 to 30 carbon atoms, one by one or more functionalities selected from the group -OC (O) -, - (O) CO-, - NH-C (O) -, - (O) C-NH, - (CH ₃ ) NC (O) -, - (O) CN (CH ₃ ) -, -S (O ₂ ) -O-, -OS (O ₂ ) -, -S (O ₂ ) -NH-, -NH-S (O ₂ ) -, - S (O ₂ ) -N (CH ₃ ) -, -N (CH ₃ ) -S (O ₂ ) -, interrupted linear or branched optionally double bonds containing aliphatic hydrocarbon radical having 2 to 30 carbon atoms, one terminal with OH, OR ', NH ₂ , N (H) R ', N (R') ₂ , in which R 'is an optionally double-bond-containing C ₁ -C ₃₀ -alkyl radical, functionalized linear or branched optionally double bonds containing aliphatic or cycloaliphatic hydrocarbon radical having 1 to 30 Carbon atoms or a block-wise or random polyether according to - (R ⁵ -O) _n -R ⁶ ,

in which

R ⁵

a linear or branched hydrocarbon radical containing 2 to 4 carbon atoms,

n

1 to 100, preferably 2 to 60, and

R ⁶

Hydrogen, a linear or branched optionally double bonds containing aliphatic hydrocarbon radical having 1 to 30 carbon atoms, an optionally double bonds containing cycloaliphatic hydrocarbon radical having 5 to 40 carbon atoms, an aromatic hydrocarbon radical having 6 to 40 carbon atoms, an al kylarylrest having 7 to 40 Carbon atoms or a radical -C (O) -R ⁷ with

R ⁷

is a linear or branched, optionally double bond-containing, aliphatic hydrocarbon radical having 1 to 30 carbon atoms, an optionally double-bond-containing cycloaliphatic hydrocarbon radical having 5 to 40 carbon atoms, an aromatic hydrocarbon radical having 6 to 40 carbon atoms, an alkylaryl radical having 7 to 40 carbon atoms is.

Preference is given to quaternary ammonium salts of alkoxylated fatty acids - also known as alkanolamine ester quats - characterized by the generic formula of the type R ¹ R ² R ³ R ⁴ N ⁺ A ^- (IV) in which R ^{1 is} an alkyl radical having 1 to 20 carbon atoms, R ^{2 is} an alkyl radical with 1 to 4 carbon atoms, R ^{3 is} a radical (CH ₂ CHRO) _n -H with n from 1 to 200 and R is H or CH ₃ , R ^{4 is} an alkyl radical having 1 to 4 carbon atoms or a radical (CH ₂ CHRO) _n -H with n from 1 to 200 and R is H or CH ₃ and A ^{- is} a monovalent anion.

1. (i) R⁶ _4-mN⁺[(CH₂)_n-Q-R⁷]_m X^-

bevorzugt, wobei
jeder Rest R⁶ unabhängig voneinander eine Alkylgruppe oder Hydroxyalkylgruppe mit 1 bis 6 Kohlenstoffatomen, oder eine Benzylgruppe und vorzugsweise eine Methylgruppe ist,

R⁷

ist unabhängig voneinander Wasserstoff, eine lineare oder verzweigte Alkylgruppe mit 11 bis 22 Kohlenstoffatomen, eine lineare oder verzweigte Alkenylgruppe mit 11 bis 22 Kohlenstoffatomen, mit der Bedingung dass mindestens ein Rest R⁷ nicht Wasserstoff ist,

Q

ist unabhängig ausgewählt aus den Gruppen der Formeln -O-C O)-, -C(O)O, -NR⁸-C(O)-, -C(O)-NR⁸-, -O-C(O)-O, -CHR⁹-O-C(O)- oder -CH(OCOR⁷)-CH₂-O-C(O)-, wobei R⁸ Wasserstoff, Methyl, Ethyl, Propyl- oder Butylrest ist und R⁹ Wasserstoff oder Methyl ist und vorzugsweise Q ist -O-C(O)- oder -NH-C(O)-;

M

ist gleich 1 bis 4 und vorzugsweise 2 oder 3;

N

ist gleich 1 bis 4 und vorzugsweise 2; und

X

ein mit Hydraulikölen kompatibles Anion, z.B. Methylsulfat, Ethylsulfat, Methylsulfonat, Butyl- sulfat, Octylsulfat, Phosphinat oder 2-(2-me- thoxyethoxy)ethylsulfat vorzugsweise Methylsulfat, 2- (2-methoxyethoxy)ethylsulfat, Octylsulfat und Phos- phinat. Die quaternäre Ammonium-Verbindung kann Gemische der Verbindungen mit unterschiedlichen Gruppen R⁷ enthalten die nicht gleich Wasserstoff sind, deren Wert von 1 bis zu m reicht. Vorzugsweise umfassen solche Gemische auf Durchschnitt von 1,2 bis 2,5 Gruppen R⁷, die nicht Wasserstoff sind. Vorzugsweise liegt der Anteil der Nicht- Wasserstoffgruppen R⁷ bei 1,4 bis 2,0 und bevorzugt bei 1,6 bis 1,9.

In these compounds are substances of the formula

1. (i) R ⁶ _4-m N ⁺ [(CH ₂ ) _n -QR ⁷ ] _m X ^-

preferred, wherein
each R ^{6 is} independently an alkyl group or hydroxyalkyl group of 1 to 6 carbon atoms, or a benzyl group and preferably a methyl group,

R ⁷

is independently hydrogen, a linear or branched alkyl group having 11 to 22 carbon atoms, a linear or branched alkenyl group having 11 to 22 carbon atoms, with the proviso that at least one radical R ^{7 is} not hydrogen,

Q

is independently selected from the groups of the formulas -OC O) -, -C (O) O, -NR ⁸ -C (O) -, -C (O) -NR ⁸ -, -OC (O) -O, - CHR ⁹ -OC (O) - or -CH (OCOR ⁷ ) -CH ₂ -OC (O) -, wherein R ^{8 is} hydrogen, methyl, ethyl, propyl or butyl and R ^{9 is} hydrogen or methyl and is preferably Q -OC (O) - or -NH-C (O) -;

M

is equal to 1 to 4 and preferably 2 or 3;

N

is equal to 1 to 4 and preferably 2; and

X

an anion compatible with hydraulic oils, for example methylsulfate, ethylsulfate, methylsulfonate, butylsulfate, octylsulfate, phosphinate or 2- (2-methoxyethoxy) ethylsulfate, preferably methylsulfate, 2- (2-methoxyethoxy) ethylsulfate, octylsulfate and phosphinate. The quaternary ammonium compound may contain mixtures of the compounds with different groups R ⁷ which are not equal to hydrogen, ranging in value from 1 to m. Preferably, such mixtures comprise on average from 1.2 to 2.5 R ⁷ non-hydrogen groups. Preferably, the proportion of non-hydrogen groups R ⁷ is 1.4 to 2.0 and preferably 1.6 to 1.9.

• (ii) R⁶N⁺[CH₂CHR⁹OH-][CH₂CHR⁹OC(O)R⁷]₂ X^-
• (iii) R⁶N⁺[CH₂CHR⁹OC(O)R⁷]₂ X^-
• (iv) R⁶N⁺[CH₂CHR⁹OH-][CH₂CH₂NHC(O)R⁷]₂ X^-,

wobei R⁶, R⁷ und X haben die gleiche Bedeutung wie für Formel (i) oben definiert, mit der Bedingung dass R⁷ nicht Wasserstoff ist.The preferred quaternary ammonium compounds are the compounds of the type:

• (ii) R ⁶ N ⁺ [CH ₂ CHR ⁹ OH -] [CH ₂ CHR ⁹ OC (O) R ⁷ ] ₂ X ^-
• (iii) R ⁶ N ⁺ [CH ₂ CHR ⁹ OC (O) R ⁷ ] ₂ X ^-
• (iv) R ⁶ N ⁺ [CH ₂ CHR ⁹ OH -] [CH ₂ CH ₂ NHC (O) R ⁷ ] ₂ X ^- ,

wherein R ⁶ , R ⁷ and X have the same meaning as defined for formula (i) above, with the proviso that R ^{7 is} not hydrogen.

Preferably, the fragment -C (O) R ^{7 is} a fatty acyl group. Useful fatty acyl groups are derived from the natural sources of triglycerides, preferably tallow, vegetable oils, partially hydrogenated tallow, and partially hydrogenated vegetable oils. Usable sources of triglycerides are soybean oil, Sebum, partially hydrogenated tallow, palm oil, palm kernels, rapeseed, lard, coconut, rapeseed, thistle oil, corn, rice and tall oil and mixtures of these components.

It is known to those skilled in the art that the composition of the fatty acid-containing compounds is subject to certain natural variations, depending on crop to crop or of the variety of vegetable oil sources. The R ⁷ groups are usually mixtures of the linear and branched carbon chains of the saturated and unsaturated aliphatic fatty acids.

The proportion of the unsaturated groups R ⁷ in such mixtures is preferably at least 10%, particularly preferably at least 25% and very particularly preferably 40% to 70%. The proportion of the polyunsaturated groups R ⁷ in such mixtures is less than 10%, preferably less than 5% and particularly preferably less than 3%. If necessary, partial hydrogenation can be carried out to increase the saturated character and thus improve the stability (eg, odor, color, etc.) of the final product. The content of unsaturated matter expressed by the iodine number should be in a range of 5 to 150, and preferably in a range of preferably 5 to 50. The ratio of cis and trans isomers of the double bonds in the unsaturated groups R ⁷ is preferably greater than 1: 1 and more preferably in the range of 4 to 1 to 50 to 1.

• N,N-Di(tallowyloxyethyl)-N,N-dimethylammonium-chlorid;
• N,N-Di(canolyloxyethyl)-N,N-dimethylammonium-chlorid;
• N,N-Di(tallowyloxyethyl)-N-methyl,N-(2-hydroxyethyl)-ammonium-methylsulfat;
• N,N-Di(canolyloxyethyl)-N-methyl,N-(2-hydroxyethyl)-ammonium-methylsulfat;
• N,N-Di(tallowylamidoethyl)-N-methyl,N-(2-hydroxyethyl) ammonium-methylsulfat;
• N,N-Di(2-tallowyloxy-2-oxo-ethyl)-N,N-dimethylammonium-chlorid;
• N,N-Di(2-canolyloxy-2-oxo-ethyl)-N,N-dimethylammonium-chlorid;
• N,N-Di(2-tallowyloxyethylcarbonyloxyethyl)-N,N-dimethylammonium-chlorid;
• N,N-Di(2-canolyloxyethylcarbonyloxyethyl)-N,N-dimethylammonium-chlorid;
• N(2-tallowoyloxy-2-ethyl)-N-(2-tallowyloxy-2-oxo-ethyl)-N,N-dimethylammonium-chlorid;
• N(2-canolyloxy-2-ethyl)-N(2-canolyloxy-2-oxo-ethyl)-N,N-dimethylammonium-chlorid;
• N,N,N-Tri(tallowyloxyäthyl)-N-methylammonium-chlorid; N,N,N-Tri(canolyloxyäthyl)-N-methylammonium-chlorid;
• 1,2-Ditallowyloxy-3-N,N,N-trimethylammoniumpropyl-chlorid; und
• 1,2-Dicanolyloxy-3-N,N,N-trimethylammoniumpropyl-chlorid.

Preferred examples of the compounds of formula (i) are:

• N, N-di (tallowyloxyethyl) -N, N-dimethylammonium chloride;
• N, N-di (canolyloxy-ethyl) -N, N-dimethylammonium chloride;
• N, N-di (tallowyloxyethyl) -N-methyl, N- (2-hydroxyethyl) ammonium methyl sulfate;
• N, N-di (canolyloxy-ethyl) -N-methyl, N- (2-hydroxyethyl) ammonium methyl sulfate;
• N, N-di (tallowylamidoethyl) -N-methyl, N- (2-hydroxyethyl) ammonium methylsulfate;
• N, N-di (2-tallowyloxy-2-oxo-ethyl) -N, N-dimethylammonium chloride;
• N, N-di (2-canolyloxy-2-oxo-ethyl) -N, N-dimethylammonium chloride;
• N, N-di (2-tallowyloxyethylcarbonyloxyethyl) -N, N-dimethylammonium chloride;
• N, N-di (2-canolyloxyethylcarbonyloxyethyl) -N, N-dimethylammonium chloride;
• N (2-tallowoyloxy-2-ethyl) -N- (2-tallowyloxy-2-oxo-ethyl) -N, N-dimethylammonium chloride;
• N (2-canolyloxy-2-ethyl) -N- (2-canolyloxy-2-oxo-ethyl) -N, N-dimethylammonium chloride;
• N, N, N-tri (tallowyloxyäthyl) -N-methyl ammonium chloride; N, N, N-tri (canolyloxyäthyl) -N-methyl ammonium chloride;
• 1,2-Ditallowyloxy-3-N, N, N-trimethylammonium propyl chloride; and
• 1,2-dicanolyloxy-3-N, N, N-trimethylammonium propyl chloride.

Further preferred quaternary ammonium salts are ditallowdimethylammonium chloride, ditallowdimethylammonium methylsulfate, dimethylammonium chloride, di (hydrogenated estallow) distearyldimethylammonium chloride and dibehenyldimethylammonium chloride.

R¹ und R²

besitzen dabei die vorgenannte Bedeutung,

R

ist ein Wasserstoff, ein linearer oder verzweigter gegebenenfalls Doppelbindungen enthaltender aliphati- scher Kohlenwasserstoffrest mit 1 bis 30 Kohlenstoff- atomen, ein cycloaliphatischer gegebenenfalls Doppel- bindungen enthaltender Kohlenwasserstoffrest mit 5 bis 40 Kohlenstoffatomen, ein aromatischer Kohlen- wasserstoffrest mit 6 bis 40 Kohlenstoffatomen oder ein Alkylarylrest mit 7 bis 40 Kohlenstoffatomen,

X

ist ein Sauerstoffatom, ein Schwefelatom oder ein substituiertes Stickstoffatom (X = O, S, NR¹).

Also suitable as cations are ions derived from saturated or unsaturated cyclic compounds and from aromatic compounds each having at least one trivalent nitrogen atom in a 4- to 10-, preferably 5- to 6-membered heterocyclic ring which may optionally be substituted , Such cations can be simplified (ie without specifying exact location and number of double bonds in the molecule) by the general formulas (IX), (X) and (XI) described below, wherein the heterocyclic rings optionally also a plurality of heteroatoms such as nitrogen, oxygen or May contain sulfur

R ¹ and R ²

have the aforementioned meaning,

R

is a hydrogen, a linear or branched optionally double bonds containing aliphatic hydrocarbon radical having 1 to 30 carbon atoms, a cycloaliphatic optionally double bonds containing hydrocarbon radical having 5 to 40 carbon atoms, an aromatic hydrocarbon radical having 6 to 40 carbon atoms or an alkylaryl radical with 7 to 40 carbon atoms,

X

is an oxygen atom, a sulfur atom or a substituted nitrogen atom (X = O, S, NR ¹ ).

Examples of cyclic nitrogen compounds of the aforementioned type are pyrrolidine, dihydropyrrole, pyrrole, imidazoline, oxazoline, oxazole, thiazoline, thiazole, isoxazole, isothiazole, indole, carbazole, piperidine, pyridine, the isomeric picolines and lutidines, quinoline and iso-quinoline. The cyclic nitrogen compounds of the general formulas (IX), (X) and (XI) can be unsubstituted (R =H), monosubstituted or polysubstituted by the radical R, where in the case of multiple substitution by R the individual radicals R are the same or different can.

Further suitable cations are ions which are derived from saturated acyclic, saturated or unsaturated cyclic compounds and from aromatic compounds each having more than one trivalent nitrogen atom in a 4- to 10-, preferably 5- to 6-membered heterocyclic ring. These compounds may be substituted on both the carbon atoms and the nitrogen atoms. They may also be annelated by, optionally substituted, benzene rings and / or cyclohexane rings to form polynuclear structures. Examples of such compounds are pyrazole, 3,5-dimethylpyrazole, imidazole, benzimidazole, N-methylimidazole, dihydropyrazole, pyrazolidine, pyridazine, pyrimidine, pyrazine, 2,3-, 2,5- and 2,6-dimethylpyrazine, cinnoline, phthalazine , Quinazoline, phenazine and piperazine. In particular, cations derived from imidazole and its alkyl and phenyl derivatives can be used.

in denen

R⁸,R⁹,R¹⁰,R¹¹,R¹²

gleich oder unterschiedlich sind und Wasserstoff, einen linearen oder verzweigten gegebenenfalls Doppelbindungen enthaltenden aliphatischen Kohlenwasserstoffrest mit 1 bis 30 Kohlenstoffatomen, einen cycloaliphatischen gegeben- enfalls Doppelbindungen enthaltenden Kohlenwasser- stoffrest mit 5 bis 40 Kohlenstoffatomen, einen aro- matischen Kohlenwasserstoffrest mit 6 bis 40 Kohlen- stoffatomen, einen Alkylarylrest mit 7 bis 40 Kohlen- stoffatomen, einen durch ein oder mehrere Heteroatome (Sauerstoff, NH, NR' mit R' gleich einem gegebenenfalls Doppelbindungen enthaltenden C₁-C₃₀- Alkylrest), unterbrochenen linearen oder verzweigten gegebenenfalls Doppelbindungen enthaltenden aliphatischen Kohlenwasserstoffrest mit 1 bis 30 Kohlenstoffatomen, einen durch ein oder mehrere Funk- tionalitäten, ausgewählt aus der Gruppe -O-C(O)-, -(O)C-O-, -NH-C(O)-, -(O)C-NH, -(CH₃)N-C(O)-, -(O)C-N(CH₃)-, -S(O₂)-O-, -O-S(O₂)-, -S(O₂)-NH-, -NH-S(O₂)-, -S(O₂)-N(CH₃)-, -N(CH₃)-S(O₂)-, unterbrochenen linearen oder verzweigten gegebenenfalls Doppelbindungen enthaltenden aliphati- schen Kohlenwasserstoffrest mit 1 bis 30 Kohlen- stoffatomen, einen endständig OH, OR', NH₂, N(H)R', N(R')₂ mit R' gleich einem gegebenenfalls Doppelbindungen enthaltenden C₁-C₃₀-Alkylrest, funktionalisierten linearen oder verzweigten gegebenenfalls Doppelbindungen enthaltenden aliphatischen oder cycloaliphatischen Kohlen- wasserstoffrest mit 1 bis 30 Kohlenstoffatomen oder einen blockweise oder statistisch aufgebauten Polyether aufgebaut aus -(R⁵-O)_n-R⁶ bedeuten,

wobei

R⁵

ein 2 bis 4 Kohlenstoffatome enthaltender Kohlenwas- serstoffrest,

n

1 bis 100 ist und

R⁶

Wasserstoff, einen linearen oder verzweigten gege- benenfalls Doppelbindungen enthaltenden aliphatischen Kohlenwasserstoffrest mit 1 bis 30 Kohlenstoffatomen einen cycloaliphatischen gegebenenfalls Doppelbindun- gen enthaltenden Kohlenwasserstoffrest mit 5 bis 40 Kohlenstoffatomen, einen aromatischen Kohlenwasser- stoffrest mit 6 bis 40 Kohlenstoffatomen, einen Al- kylarylrest mit 7 bis 40 Kohlenstoffatomen bedeutet oder ein Rest -C(O)-R⁷ mit

R⁷

gleich einem linearen oder verzweigten gegebenenfalls Doppelbindungen enthaltenden aliphatischen Kohlen- wasserstoffrest mit 1 bis 30 Kohlenstoffatomen, einem gegebenenfalls Doppelbindungen enthaltenden cycloali- phatischen Kohlenwasserstoffrest mit 5 bis 40 Kohlen- stoffatomen, einem aromatischen Kohlenwasserstoffrest mit 6 bis 40 Kohlenstoffatomen, einem Alkylarylrest mit 7 bis 40 Kohlenstoffatomen ist.

Also suitable as cations are ions which contain two nitrogen atoms and are represented by the general formula (XII)

in which

R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹²

are the same or different and are hydrogen, a linear or branched optionally double bonds containing aliphatic hydrocarbon radical having 1 to 30 carbon atoms, a cycloaliphatic optionally double bonds containing hydrocarbon radical having 5 to 40 carbon atoms, an aromatic hydrocarbon radical having 6 to 40 carbon atoms , an alkylaryl radical having 7 to 40 carbon atoms, an aliphatic hydrocarbon radical interrupted by one or more heteroatoms (oxygen, NH, NR 'with R' equal to an optionally double bond-containing C ₁ -C ₃₀ -alkyl radical), interrupted linear or branched optionally double bonds having 1 to 30 carbon atoms, one by one or more functionalities selected from the group -OC (O) -, - (O) CO-, -NH-C (O) -, - (O) C-NH, - (CH ₃ ) NC (O) -, - (O) CN (CH ₃ ) -, -S (O ₂ ) -O-, -OS (O ₂ ) -, -S (O ₂ ) -NH-, -NH-S (O ₂ ) -, -S (O ₂ ) -N (CH ₃ ) -, -N (CH ₃ ) -S (O ₂ ) -, interrupted linear or branched optionally double bonds containing aliphatic hydrocarbon radical having 1 to 30 carbon atoms, one terminal OH, OR ', NH ₂ , N (H) R', N (R ') ₂ with R' equal to an optionally double bonds containing C ₁ -C ₃₀ -alkyl radical, functionalized linear or branched, optionally double bond-containing, aliphatic or cycloaliphatic hydrocarbon radical having 1 to 30 carbon atoms or a block-wise or randomly structured polyether composed of - (R ⁵ -O) _n -R ⁶ ,

in which

R ⁵

a hydrocarbon radical containing from 2 to 4 carbon atoms,

n

1 to 100 is and

R ⁶

Hydrogen, a linear or branched, optionally double bond-containing, aliphatic hydrocarbon radical having 1 to 30 carbon atoms, a cycloaliphatic hydrocarbon radical optionally containing double bonds with 5 to 40 carbon atoms, an aromatic hydrocarbon radical having 6 to 40 carbon atoms, an alkylaryl radical having 7 to 40 carbon atoms or a radical -C (O) -R ⁷ with

R ⁷

is a linear or branched optionally double bond-containing aliphatic hydrocarbon radical having 1 to 30 carbon atoms, an optionally double bonds containing cycloaliphatic hydrocarbon radical having 5 to 40 carbon atoms, an aromatic hydrocarbon radical having 6 to 40 carbon atoms, an alkylaryl radical having 7 to 40 carbon atoms is.

Very particularly preferred imidazolium ions (XII) which may be mentioned are 1- (1-octyl) -imidazolium, 1- (1-dodecyl) -imidazolium, 1- (1-tetradecyl) -imidazolium, 1- (1-hexadecyl) -imidazolium, 1- (1-butyl) -3-methylimidazolium, 1- (1-butyl) -3-ethylimidazolium, 1- (1-hexyl) -3-methylimidazolium, 1- (1-hexyl) -3-ethyl imidazolium, 1- (1-hexyl) -3-butylimidazolium, 1- (1-octyl) -3-methylimidazolium, 1- (1-octyl) -3-ethylimidazolium, 1- (1-octyl) -3- butyl imidazolium, 1- (1-dodecyl) -3-methylimidazolium, 1- (1-dodecyl) -3-ethylimidazolium, 1- (1-dodecyl) -3-butylimidazolium, 1- (1-dodecyl) -3- octylimidazolium, 1- (1-tetradecyl) -3-methylimidazolium, 1- (1-tetradecyl) -3-ethylimidazolium, 1- (1-tetradecyl) -3-butylimidazolium, 1- (1-tetradecyl) -3-octylimidazolium, 1- (1-hexadecyl) -3-methylimidazolium, 1- (1-hexadecyl) -3-ethylimidazolium, 1- (1-hexadecyl) -3-butylimidazolium, 1- (1-hexadecyl) -3-octylimidazolium, 1- (1-butyl) -2,3-dimethylimidazolium, 1- (1-hexyl) -2,3-dimethylimidazolium, 1- (1-octyl) -2,3-dimethylimidazolium, 3-butylimidazole to, 1,4-dimethyl-3-octylimidazolium, 1,4,5-trimethyl-3-butylimidazolium and 1,4,5-trimethyl-3-octylimidazolium.

Also suitable as cations are ions which in particular are composed of the abovementioned cations which form dications, trications or polycations due to dimerization, trimerization or polymerization. These also include such dications, trications and polycations which have a polymeric backbone, for example based on siloxanes, polyethers, polyesters, polyamides or polyacrylates, in particular branched and hyperbranched polymers.

einer oder mehrere der Reste

R¹ bis R⁵

unabhängig voneinander 1-Butyl, 2-Butyl, 2- Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.- Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1- butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl- 2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3- Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4- Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2- pentyl, 4-Methyl-2- pentyl, 2-Methyl-3-pentyl, 3- Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl- 1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3- Dimethyl-2-butyl, 3,3-Dimethyl-2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenylmethyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclopentylmethyl, 2-Cyclopentylethyl, 3- Cyclopentylpropyl, Cyclohexylmethyl, 2- Cyclohexylethyl, 3-Cyclohexylpropyl ist und die verbleibenden Reste R¹ bis R⁵ Wasserstoff oder Methyl oder Ethyl sind, R³ Dimethylamino ist und die verbleibenden Reste R¹, R², R⁴ und R⁵ Wasserstoff sind, alle Reste R¹ bis R⁵ Wasserstoff sind, R² Carboxy oder Carboxamid ist und die verbleibenden Reste R¹, R², R⁴ und R⁵ Wasserstoff sind, oder R¹ und R² oder R² und R³ 1,4-Buta-1,3-dienylen ist und die verbleibenden Reste R¹, R², R⁴ und R⁵ Wasserstoff sind,

und insbesondere ein solches, bei dem

R¹ bis R⁵

Wasserstoff sind, oder einer der Reste R¹ bis R⁵ Methyl oder Ethyl ist und die verbleibenden Reste R¹ bis R⁵ Wasserstoff sind.

Conductivity additives are also contemplated in which the cation [A] ^{+ is} a pyridinium ion (XIIIa) in which

one or more of the radicals

R ¹ to R ⁵

independently of one another 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl 1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl , 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2 -Methyl 3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1 -butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl , Henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3 Cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl and the remaining radicals R ¹ to R ^{5 are} hydrogen or methyl or ethyl, R ^{3 is} dimethylamino and the remaining radicals R ¹ , R ² , R ⁴ and R ^{5 are} hydrogen, all radicals R ¹ to R ^{5 are} hydrogen, R ^{2 is} carboxy or carboxamide and the remaining radicals R ¹ , R ² , R ⁴ and R ^{5 are} hydrogen, or R ¹ and R ² or R ² and R ^{3 are} 1,4- Is buta-1,3-dienylene and the remaining radicals R ¹ , R ² , R ⁴ and R ^{5 are} hydrogen,

and in particular one in which

R ¹ to R ⁵

Are hydrogen, or one of R ¹ to R ^{5 is} methyl or ethyl and the remaining R ¹ to R ^{5 are} hydrogen.

As very particularly preferred pyridinium ions (XIIIa) may be mentioned 1- (1-hexyl) pyridinium, 1- (1-octyl) -pyridinium, 1- (1-hexyl) -pyridinium, 1- (1-octyl) -pyridinium, 1 - (1-dodecyl) -pyridinium, 1- (1-tetradecyl) -pyridinium, 1- (1-hexadecyl) -pyridinium, 1- (1-hexyl) -2-methyl-pyridinium, 1- (1-octyl) 2-methylpyridinium, 1- (1-dodecyl) -2-methylpyridinium, 1- (1-tetradecyl) -2-methylpyridinium, 1- (1-hexadecyl) -2-methylpyridinium, 1- (1-hexyl) -2 -ethylpyridinium, 1- (1-octyl) -2-ethylpyridinium, 1- (1-dodecyl) -2-ethylpyridinium, 1- (1-tetradecyl) -2-ethylpyridinium, 1- (1-hexadecyl) -2-ethylpyridinium , 1- (1-Hexyl) -2-methyl-3-ethylpyridinium and 1- (1-octyl) -2-methyl-3-ethyl-pyridinium, 1- (1-dodecyl) -2-methyl-3 ethyl-pyridinium, 1- (1-tetradecyl) -2-methyl-3-ethyl-pyridinium and 1- (1-hexadecyl) -2-methyl-3-ethyl-pyridinium.

bei dem

R₁ bis R₄

Wasserstoff sind, oder einer oder mehrere der Reste R₁ bis R₄ unabhängig voneinander 1-Butyl, 2- Butyl, 2-Methyl-1-propyl (Isobutyl), 2-Methyl-2- propyl (tert.-Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1-butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl-2-butyl, 2,2- Dimethyl-1-propyl, 1-Hexyl, 2- Hexyl, 3-Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4-Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2- pentyl, 4-Methyl-2- pentyl, 2-Methyl-3-pentyl, 3- Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl- 1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3- Dimethyl-2-butyl, 3,3-Dimethyl-2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenylmethyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclopentylmethyl, 2-Cyclopentylethyl, 3- Cyclopentylpropyl, Cyclohexylmethyl, 2- Cyclohexylethyl, 3-Cyclohexylpropyl ist und die verbleibenden Reste R₁ bis R₄ Wasserstoff oder Methyl oder Ethyl sind.

In addition, conductivity additives are contemplated in which the cation [A] ^{+ is} a pyridazinium ion (XIIIb),

in which

R ₁ to R ₄

Are hydrogen, or one or more of R ₁ to R _{4 are} independently 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1 Pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1 -propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl -2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3 , 3-Dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl , Tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3 Phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl , Cyclohexylmethyl, 2- Cyclohexylethyl, 3-cyclohexylpropyl and the remaining radicals R ₁ to R _{4 are} hydrogen or methyl or ethyl.

bei dem

R₁

Wasserstoff, Methyl oder Ethyl ist und R₂ bis R₄ unabhängig voneinander Wasserstoff oder Methyl sind, oder einer oder mehrere der Reste R₁ bis R₄ unabhängig voneinander 1-Butyl, 2-Butyl, 2-Methyl-1- propyl (Isobutyl), 2-Methyl-2-propyl (tert.-Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1-butyl, 3- Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl-2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3-Hexyl, 2- Methyl-1-pentyl, 3-Methyl-1-pentyl, 4-Methyl-1- pentyl, 2-Methyl-2-pentyl, 3-Methyl-2-pentyl, 4- Methyl-2- pentyl, 2-Methyl-3-pentyl, 3-Methyl-3- pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl- 1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3-Dimethyl- 2-butyl, 3,3-Dimethyl-2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenylmethyl, 2- Phenylethyl , 3-Phenylpropyl, Cyclopentylmethyl, 2- Cyclopentylethyl, 3-Cyclopentylpropyl, Cyclohexyl- methyl, 2-Cyclohexylethyl, 3-Cyclohexylpropyl ist und die verbleibenden Reste R₁ bis R₄ Wasserstoff oder Methyl oder Ethyl sind.

Conductivity additives in which the cation [A] ^{+ is} a pyrimidinium ion (XIIIc) are also very particularly preferred .

in which

R ₁

Is hydrogen, methyl or ethyl and R ₂ to R ₄ independently of one another are hydrogen or methyl, or one or more of the radicals R ₁ to R ₄ independently of one another are 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl) , 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl , 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl 1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl 1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2 butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, Tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3 -Cyclohexylpropyl and the remaining radicals R ₁ to R _{4 are} hydrogen or methyl or ethyl.

bei dem
einer oder mehrere der Reste

R₁ bis R₄

unabhängig voneinander 1-Butyl, 2-Butyl, 2- Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.- Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1- butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl- 2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3- Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4- Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2- pentyl, 4-Methyl-2- pentyl, 2-Methyl-3-pentyl, 3- Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl- 1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3- Dimethyl-2-butyl, 3,3-Dimethyl-2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, P e ntadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenylmethyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclopentylmethyl, 2-Cyclopentylethyl, 3-Cyclopentyl- propyl, Cyclohexylmethyl, 2-Cyclohexylethyl, 3-Cyclo- hexylpropyl ist und die verbleibenden Reste R₁ bis R₄ Wasserstoff oder Methyl oder Ethyl sind, R₁ Wasserstoff, Methyl oder Ethyl ist, R₂ und R₄ Methyl sind und R₃ Wasserstoff ist, R₁ bis R₄ Methyl sind, oder R₁ bis R₄ Methyl oder Wasserstoff sind.

Also contemplated are conductivity additives in which the cation [A] ^{+ is} a pyrazinium ion (XIIId),

in which
one or more of the radicals

R ₁ to R ₄

independently of one another 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl 1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl , 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2 -Methyl 3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1 butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, Tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3 -Phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl and the remaining radicals R ₁ to R _{4 are} hydrogen or methyl or ethyl, R _{1 is} hydrogen, methyl or ethyl R ₂ and R _{4 are} methyl and R _{3 is} hydrogen, R ₁ to R _{4 are} methyl, or R ₁ to R _{4 are} methyl or hydrogen.

R₁

Wasserstoff, Methyl oder Ethyl ist und

R₂ bis R₄

unabhängig voneinander Wasserstoff oder Methyl sind, einer oder mehrere der Reste R₁ bis R₄ unabhängig voneinander 1-Butyl, 2-Butyl, 2-Methyl-1- propyl (Isobutyl), 2-Methyl-2-propyl (tert.-Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1-butyl, 3- Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl-2-butyl, 2,2- Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3-Hexyl, 2- Methyl-1-pentyl, 3-Methyl-1-pentyl, 4-Methyl-1- pentyl, 2-Methyl-2-pentyl, 3-Methyl-2-pentyl, 4- Methyl-2- pentyl, 2-Methyl-3-pentyl, 3-Methyl-3- pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl- 1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3-Dimethyl- 2-butyl, 3,3-Dimethyl-2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenylmethyl, 2- Phenylethyl, 3-Phenylpropyl, Cyclopentylmethyl, 2- Cyclopentylethyl, 3-Cyclopentylpropyl, Cyclohexyl- methyl, 2-Cyclohexylethyl, 3-Cyclohexylpropyl ist und die verbleibenden Reste R₁ bis R₄ Wasserstoff oder Methyl oder Ethyl sind.

Conductivity additives in which the cation [A] ^{+ is} a pyrazolium ion (XIIIf), (XIIIg) or (XIIIg '), in which

R ₁

Is hydrogen, methyl or ethyl and

R ₂ to R ₄

independently of one another are hydrogen or methyl, one or more of the radicals R ₁ to R ₄ independently of one another are 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl ), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl 2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3- Dimethyl 1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, Decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl , 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl and the remaining radicals R ₁ to R _{4 are} hydrogen or methyl or ethyl.

bei dem
einer oder mehrere der Reste

R₁ bis R₄

unabhängig voneinander 1-Butyl, 2-Butyl, 2- Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.- Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1- butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl- 2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3- Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4- Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2- pentyl, 4-Methyl-2- pentyl, 2-Methyl-3-pentyl, 3- Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl- 1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3- Dimethyl-2-butyl, 3,3-Dimethyl- 2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenyl- methyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclopentyl- methyl, 2-Cyclopentylethyl, 3-Cyclopentylpropyl, Cyclohexylmethyl, 2-Cyclohexylethyl, 3-Cyclohexyl- propyl ist und die verbleibenden Reste R₁ bis R₄ Wasserstoff oder Methyl oder Ethyl sind.

In addition, conductivity additives in which the cation [A] ^{+ is} a pyrazolium ion (XIIIh) are also suitable,

in which
one or more of the radicals

R ₁ to R ₄

independently of each other 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert. Butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2.2 Dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl , 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1 -butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl , Dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl and the remaining radicals R ₁ to R _{4 are} hydrogen or methyl or ethyl.

bei dem
einer oder mehrere der Reste

R₁ bis R₄

unabhängig voneinander 1-Butyl, 2-Butyl, 2- Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.- Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1- butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl- 2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3- Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4- Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2- pentyl, 4-Methyl-2- pentyl, 2-Methyl-3-pentyl, 3- Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl- 1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3- Dimethyl-2-butyl, 3,3-Dimethyl-2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nona- cosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenyl- methyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclopentyl- methyl, 2-Cyclopentylethyl, 3-Cyclopentylpropyl, Cyclohexylmethyl, 2-Cyclohexylethyl, 3-Cyclo- hexylpropyl ist und die verbleibenden Reste R₁ bis R₄ Wasserstoff oder Methyl oder Ethyl sind.

Also contemplated are conductivity additives in which the cation [A] ^{+ is} a 1-pyrazolinium ion (XIIII),

in which
one or more of the radicals

R ₁ to R ₄

independently of one another 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl 1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl , 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2 -Methyl 3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1 -butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl , Henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylprop yl and the remaining radicals R ₁ to R _{4 are} hydrogen or methyl or ethyl.

bei dem
einer oder mehrere der Reste

R₁ bis R₄

unabhängig voneinander 1-Butyl, 2-Butyl, 2- Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.- Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1- butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl- 2-butyl, 2,2- Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3- Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4- Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2- pentyl, 4-Methyl-2- pentyl, 2-Methyl-3-pentyl, 3- Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl- 1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3- Dimethyl-2-butyl, 3,3-Dimethyl-2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenylmethyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclopentylmethyl, 2-Cyclopentylethyl, 3- Cyclopentylpropyl, Cyclohexylmethyl, 2- Cyclohexylethyl, 3-Cyclohexylpropyl ist und die verbleibenden Reste R₁ bis R₄ Wasserstoff oder Methyl oder Ethyl sind.

Also contemplated are conductivity additives in which the cation [A] ^{+ is} a 2-pyrazolinium ion (XIIIj),

in which
one or more of the radicals

R ₁ to R ₄

independently of one another 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl 1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl , 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2 -Methyl 3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1 -butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl , Henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl is t and the remaining radicals R ₁ to R _{4 are} hydrogen or methyl or ethyl.

bei dem
einer oder mehrere der Reste

R₁ bis R₄

unabhängig voneinander 1-Butyl, 2-Butyl, 2- Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.- Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1- butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl- 2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3- Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4- Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2- pentyl, 4-Methyl-2- pentyl, 2-Methyl-3-pentyl, 3- Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl- 1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3- Dimethyl-2-butyl, 3,3-Dimethyl- 2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenyl- methyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclopentyl- methyl, 2-Cyclopentylethyl, 3-Cyclopentylpropyl, Cyclohexylmethyl, 2-Cyclohexylethyl, 3-Cyclohexyl- propyl ist und die verbleibenden Reste R₁ bis R₄ Wasserstoff oder Methyl oder Ethyl sind.

Also contemplated are conductivity additives in which the cation [A] ^{+ is} a 3-pyrazolinium ion (XIIIk) or (XIIIk '),

in which
one or more of the radicals

R ₁ to R ₄

independently of one another 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl 1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl , 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2 -Methyl 3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1 -butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl , Henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3 cyclopentylpropyl, Cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexyl propyl and the remaining radicals R ₁ to R _{4 are} hydrogen or methyl or ethyl.

bei dem

R für H

oder Methyl steht,

R₁ und R₂

unabhängig voneinander Wasserstoff, Methyl oder Ethyl, oder ein linearer gesättigter oder ungesättigter Acylrest mit 14 bis 22, vorzugsweise 16 bis 18 Kohlenstoffatomen sind und R₃ bis R₆ unabhängig voneinander für Wasserstoff, einen linearen gesättigten, gegebenenfalls OH-Gruppen enthaltenden Alkylrest mit 1 bis 4 Kohlenstoffatomen stehen, bevorzugt Methyl oder ein Fettsäurerest ist, insbesondere bevorzugt sind R₁ und R₂ Fettsäureacylreste, sowie R oder R₂ und R₃ Fettsäureacylreste. Von besonderer Bedeutung sind die Substanzen entsprechend Formel (XIIIm). Teilweise sind in der Literatur hierfür auch irreführende Formeln (analog Formel XIIIm' oder XIIIl) eingeführt.

In addition, conductivity additives in which the cation [A] ^{+ is} an imidazolinium ion (XIIIl) are also suitable,

in which

R for H

or methyl stands,

R ₁ and R ₂

are independently hydrogen, methyl or ethyl, or a linear saturated or unsaturated acyl radical having 14 to 22, preferably 16 to 18 carbon atoms and R ₃ to R _{6 are} independently hydrogen, a linear saturated, optionally OH-containing alkyl radical having 1 to 4 carbon atoms, preferably methyl or a fatty acid radical, more preferably R ₁ and R _{2 are} fatty acid acyl radicals, and R or R ₂ and R ₃ fatty acid acyl radicals. Of particular importance are the substances according to formula (XIIIm). In part, misleading formulas (analogous to formula XIIIm 'or XIIIl) have been introduced in the literature for this purpose.

bei dem

R für H

oder Methyl steht,

R₁ und R₂

unabhängig voneinander Wasserstoff, Methyl oder Ethyl, oder ein linearer gesättigter oder ungesättigter Acylrest mit 14 bis 22, vorzugsweise 16 bis 18 Kohlenstoffatomen sind und R₃ bis R₆ unabhängig voneinander für Wasserstoff, einen linearen gesättigten, gegebenenfalls OH-Gruppen enthaltenden Alkylrest mit 1 bis 4 Kohlenstoffatomen stehen, bevorzugt Methyl oder ein Fettsäurerest ist, insbesondere bevorzugt sind R₁ und R₂ Fettsäureacylreste, sowie R oder R₂ und R₃ Fettsäureacylreste. Von besonderer Bedeutung sind die Substanzen entsprechend Formel (XIIIm). Teilweise sind in der Literatur hierfür auch irreführende Formeln (analog Formel XIIIm' oder XIIIl) eingeführt.

Also contemplated are conductivity additives in which the cation [A] ^{+ is} an imidazolinium ion (XIIIm) or (XIIIm '),

in which

R for H

or methyl stands,

R ₁ and R ₂

are independently hydrogen, methyl or ethyl, or a linear saturated or unsaturated acyl radical having 14 to 22, preferably 16 to 18 carbon atoms and R ₃ to R _{6 are} independently hydrogen, a linear saturated, optionally OH-containing alkyl radical having 1 to 4 carbon atoms, preferably methyl or a fatty acid radical, more preferably R ₁ and R _{2 are} fatty acid acyl radicals, and R or R ₂ and R ₃ fatty acid acyl radicals. Of particular importance are the substances according to formula (XIIIm). In part, misleading formulas (analogous to formula XIIIm 'or XIIIl) have been introduced in the literature for this purpose.

bei dem
einer oder mehrere der Reste

• R₁ bis R₃ unabhängig voneinander 1-Butyl, 2-Butyl, 2-Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.-Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1-butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl-2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3-Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4-Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2-pentyl, 4-Methyl-2- pentyl, 2-Methyl-3-pentyl, 3-Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl-1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3-Dimethyl-2-butyl, 3,3-Dimethyl- 2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenylmethyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclopentylmethyl, 2-Cyclopentylethyl, 3-Cyclopentylpropyl, Cyclohexylmethyl, 2-Cyclohexylethyl, 3-Cyclohexylpropyl ist und die verbleibenden Reste R₁ bis R₄ Wasserstoff oder Methyl oder Ethyl sind. In Betracht kommen auch Leitfähigkeitsadditive, bei denen das Kation [A]⁺ ein 1,2,4-Triazoliumion (XIIIq), (XIIIq') beziehungsweise (XIIIq") ist,

bei dem
einer oder mehrere der Reste

• R₁ bis R₃ unabhängig voneinander 1-Butyl, 2-Butyl, 2-Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.-Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1-butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl-2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3-Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4-Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2-pentyl, 4-Methyl-2- pentyl, 2-Methyl-3-pentyl, 3-Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl-1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2, 3-Dimethyl-2-butyl, 3,3-Dimethyl- 2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenylmethyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclopentylmethyl, 2-Cyclopentylethyl, 3-Cyclopentylpropyl, Cyclohexylmethyl, 2-Cyclohexylethyl, 3-Cyclohexylpropyl ist und die verbleibenden Reste R₁ bis R₄ Wasserstoff oder Methyl oder Ethyl sind. In Betracht kommen weiterhin Leitfähigkeitsadditive, bei denen das Kation [A]⁺ ein 1,2,3-Triazoliumion (XIIIr), (XIIIr') beziehungsweise (XIIIr") ist,

bei dem

R₁

Wasserstoff, Methyl oder Ethyl ist und

R₂ und R₃

unabhängig voneinander Wasserstoff oder Methyl sind, oder R₂ und R₃ zusammen 1,4-Buta-1,3-dienylen ist, einer oder mehrere der Reste R₁ bis R₃ unabhängig voneinander 1-Butyl, 2-Butyl, 2-Methyl-1- propyl (Isobutyl), 2-Methyl-2-propyl (tert.-Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1-butyl, 3- Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl-2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3-Hexyl, 2- Methyl-1-pentyl, 3-Methyl-1-pentyl, 4-Methyl-1- pentyl, 2-Methyl-2-pentyl, 3-Methyl-2-pentyl, 4- Methyl-2- pentyl, 2-Methyl-3-pentyl, 3-Methyl-3- pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl-1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3-Dimethyl- 2-butyl, 3,3-Dimethyl-2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenylmethyl, 2- Phenylethyl, 3-Phenylpropyl, Cyclopentylmethyl, 2- Cyclopentylethyl, 3-Cyclopentylpropyl, Cyclohexyl- methyl, 2-Cyclohexylethyl, 3-Cyclohexylpropyl ist und die verbleibenden Reste R₁ bis R₃ Wasserstoff oder Methyl oder Ethyl sind.

In addition, conductivity additives in which the cation [A] ^{+ is} a thiazolium ion (XIIIo) or (XIIIo ') and an oxazolium ion (XIIIp) are also suitable,

in which
one or more of the radicals

• R ₁ to R ₃ independently of one another are 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3 Pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2 Hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl 2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, Octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3 Cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl and the remaining radicals R ₁ to R _{4 are} hydrogen or methyl or ethyl. Also contemplated are conductivity additives in which the cation [A] ^{+ is} a 1,2,4-triazolium ion (XIIIq), (XIIIq ') or (XIIIq "),

in which
one or more of the radicals

• R ₁ to R ₃ independently of one another are 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3 Pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2 Hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl 2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2, 3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, Octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3 Cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl and the remaining radicals R ₁ to R _{4 are} hydrogen or methyl or ethyl. Also contemplated are conductivity additives in which the cation [A] ^{+ is} a 1,2,3-triazolium ion (XIIIr), (XIIIr ') or (XIIIr "),

in which

R ₁

Is hydrogen, methyl or ethyl and

R ₂ and R ₃

independently of one another are hydrogen or methyl, or R ₂ and R ₃ together are 1,4-buta-1,3-dienylene, one or more of the radicals R ₁ to R ₃ independently of one another are 1-butyl, 2-butyl, 2-methyl 1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl 1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3 pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, Tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3 Cyclohexylpropyl and the remaining radicals R ₁ to R _{3 are} hydrogen or methyl or ethyl.

bei dem

R₁

Wasserstoff, Methyl, Ethyl oder Phenyl ist und

R₂ bis R₉

unabhängig voneinander Wasserstoff oder Methyl sind einer oder mehrere der Reste R₁ bis R₃ unabhängig voneinander 1-Butyl, 2-Butyl, 2-Methyl-1- propyl (Isobutyl), 2-Methyl-2-propyl (tert.-Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1-butyl, 3- Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl-2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3-Hexyl, 2- Methyl-1-pentyl, 3-Methyl-1-pentyl, 4-Methyl-1- pentyl, 2-Methyl-2-pentyl, 3-Methyl-2-pentyl, 4- Methyl-2- pentyl, 2-Methyl-3-pentyl, 3-Methyl-3- pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl-1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3-Dimethyl- 2-butyl, 3,3-Dimethyl- 2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenylmethyl, 2- Phenylethyl, 3-Phenylpropyl, Cyclopentylmethyl, 2- Cyclopentylethyl, 3-Cyclopentylpropyl, Cyclohexyl- methyl, 2-Cyclohexylethyl, 3-Cyclohexylpropyl ist und die verbleibenden Reste R₁ bis R₃ Wasserstoff oder Methyl oder Ethyl sind.

Also contemplated are conductivity additives in which the cation [A] ^{+ is} a pyrrolidinium ion (XIIIs),

in which

R ₁

Is hydrogen, methyl, ethyl or phenyl and

R ₂ to R ₉

independently of one another hydrogen or methyl are one or more of the radicals R ₁ to R _3, independently of one another, 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl) , 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl 1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3 Methyl 2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl , 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl 2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, Pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl and the remaining radicals R ₁ to R _{3 are} hydrogen or methyl or ethyl.

bei dem
einer oder mehrere der Reste

R₁ bis R₈

unabhängig voneinander 1-Butyl, 2-Butyl, 2- Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.- Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1- butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl- 2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3- Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4- Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2- pentyl, 4-Methyl-2- pentyl, 2-Methyl-3-pentyl, 3- Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl- 1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3- Dimethyl-2-butyl, 3,3-Dimethyl-2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Tri- phenylmethyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclopentylmethyl, 2-Cyclopentylethyl, 3-Cyclo- pentylpropyl, Cyclohexylmethyl, 2-Cyclohexylethyl, 3- Cyclohexylpropyl ist und die verbleibenden Reste R₁ bis R₈ Wasserstoff oder Methyl oder Ethyl sind.

In addition, conductivity additives in which the cation [A] ^{+ is} an imidazolidinium ion (XIIIt) are also suitable,

in which
one or more of the radicals

R ₁ to R ₈

independently of one another 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl 1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl , 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2 Methyl 3-pentyl, 3 Methyl 3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl 2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, Pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3 - Cyclohexylpropyl and the remaining radicals R ₁ to R _{8 is} hydrogen or methyl or ethyl.

bei dem
einer oder mehrere der Reste

R₁ bis R₃

unabhängig voneinander 1-Butyl, 2-Butyl, 2- Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.- Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1- butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl- 2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3- Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4- Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2- pentyl, 4-Methyl-2-pentyl, 2-Methyl-3-pentyl, 3- Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl- 1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3- Dimethyl-2-butyl, 3,3-Dimethyl-2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenylmethyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclopentylmethyl, 2-Cyclopentylethyl, 3-Cyclopentyl- propyl, Cyclohexylmethyl, 2-Cyclohexylethyl, 3-Cyclo- hexylpropyl ist und die verbleibenden Reste R₁ bis R₄ Wasserstoff oder Methyl oder Ethyl sind; oder R₁ bis R₃ unabhängig voneinander Wasserstoff oder C C₁-C₁₈- Alkyl sind und R₄ 2-Hydroxyethyl ist; oder R₁ und R₂ zusammen 1,5-Pentylen oder 3-Oxa-1,5-pentylen sind und R₃ C₁-C₁₈-Alkyl, 2-Hydroxyethyl oder 2-Cyanoethyl ist.

Also contemplated are conductivity additives in which the cation [A] ^{+ is} an ammonium ion (IV),

in which
one or more of the radicals

R ₁ to R ₃

independently of one another 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl 1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl , 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2 Methyl 3-pentyl, 3 Methyl 3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl 2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, Pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclo - is hexylpropyl and the remaining radicals R ₁ to R _{4 are} hydrogen or methyl or ethyl; or R ₁ to R _{3 are} independently hydrogen or CC ₁ -C ₁₈ alkyl and R _{4 is} 2-hydroxyethyl; or R ₁ and R ₂ together are 1,5-pentylene or 3-oxa-1,5-pentylene and R _{3 is} C ₁ -C ₁₈ alkyl, 2-hydroxyethyl or 2-cyanoethyl.

bei dem
einer oder mehrere der Reste

R₁ bis R₅

unabhängig voneinander 1-Butyl, 2-Butyl, 2- Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.- Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1- butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl- 2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3- Hexyl, 2-Methyl-l-pentyl, 3-Methyl-1-pentyl, 4- Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2- pentyl, 4-Methyl-2- pentyl, 2-Methyl-3-pentyl, 3- Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl- 1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3- Dimethyl-2-butyl, 3,3-Dimethyl- 2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Docosyl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenyl- methyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclo- pentylmethyl, 2-Cyclopentylethyl, 3-Cyclopentyl- propyl, Cyclohexylmethyl, 2-Cyclohexylethyl, 3- Cyclohexylpropyl ist und die verbleibenden Reste R₁ bis R₄ Wasserstoff oder Methyl oder Ethyl sind; R₁ bis R₅ unabhängig voneinander C₁-C₁₈-Alkyl sind; oder R₁ bis R₅ unabhängig voneinander Wasserstoff oder C₁- C₁₈-Alkyl oder 2-Hydroxyethyl sind.

In addition, conductivity additives are contemplated in which the cation [A] ^{+ is} a guanidinium ion (IVv),

in which
one or more of the radicals

R ₁ to R ₅

independently of one another 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl 1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl , 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2 -Methyl 3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1 -butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl , Henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3 Cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylprop yl and the remaining radicals R ₁ to R _{4 are} hydrogen or methyl or ethyl; R ₁ to R _{5 are} independently C ₁ -C ₁₈ alkyl; or R ₁ to R ₅ independently of one another are hydrogen or C ₁ -C ₁₈ -alkyl or 2-hydroxyethyl.

R₁ und R₂

unabhängig voneinander Methyl, Ethyl, 1-Butyl oder 1-Octyl sind und R₃ Wasserstoff, Methyl, Ethyl, Acetyl, -SO₂OH oder -PO(OH)₂ ist; R₁ Methyl, Ethyl, 1- Butyl oder 1-Octyl ist, R₂ eine -CH₂-CH₂-OR₄-Gruppe ist und R₃ und R₄ unabhängig voneinander Wasserstoff, Methyl, Ethyl, Acetyl, -SO₂OH oder -PO(OH)₂ sind; oder R₁ eine -CH₂-CH₂-OR₄-Gruppe ist, R₂ eine -CH₂-CH₂- OR₅-Gruppe ist und R₃ bis R₅ unabhängig voneinander Wasserstoff, Methyl, Ethyl, Acetyl, -SO₂OH oder -PO(OH)₂ sind; R₁ Methyl, Ethyl, 1-Butyl, 1-Octyl, Acetyl, -SO₂OH, oder -PO(OH)₂ ist und R₃ bis R₅ unabhängig voneinander Wasserstoff, Methyl, Ethyl, Acetyl, -SO₂OH, -PO(OH)₂, oder -(C_nH_2nO)_mR₁ mit n = 1 bis 5 und m = 1 bis 100 sind.

Also suitable are conductivity additives in which the cation [A] ^{+ is} a derivative of an ethanolamine, for example a cholinium ion (XIIIw), or a diethanolamine (XIIIw '), or a triethanolamine (XIIIw "),

R ₁ and R ₂

independently of one another are methyl, ethyl, 1-butyl or 1-octyl and R _{3 is} hydrogen, methyl, ethyl, acetyl, -SO ₂ OH or -PO (OH) ₂ ; R _{1 is} methyl, ethyl, 1-butyl or 1-octyl, R _{2 is} a -CH ₂ -CH ₂ -OR ₄ group and R ₃ and R _{4 are} independently hydrogen, methyl, ethyl, acetyl, -SO ₂ OH or -PO (OH) ₂ ; or R ₁ is a -CH ₂ -CH ₂ -OR ₄ group, R ₂ is a -CH ₂ -CH ₂ - OR ₅ group and R ₃ to R ₅ are independently hydrogen, methyl, ethyl, acetyl, -SO _{2 are} OH or -PO (OH) ₂ ; R _{1 is} methyl, ethyl, 1-butyl, 1-octyl, acetyl, -SO ₂ OH, or -PO (OH) ₂ and R ₃ to R ₅ independently of one another are hydrogen, methyl, ethyl, acetyl, -SO ₂ OH, -PO (OH) ₂ , or - (C _n H _2n O) _m R ₁ where n = 1 to 5 and m = 1 to 100.

Preference is furthermore given to compounds in which R, R ₁ and R _{2 are} alkyl groups having 1 to 4 carbon atoms, more preferably a methyl group, and R ₃ and / or R _{4 are} saturated or unsaturated fatty acid or acyl radicals having 8 to 22 carbon atoms 12 to 18 carbon atoms. There may also be mixtures of the acyl or fatty acid residues (especially, for example, in naturally occurring proportions).

Most preferably, the formula (XIIIw ") with R, R ₁ , R ₂ is an alkyl radical having 1 to 4 carbon atoms, in particular methyl groups and R ₃ is a fatty acid radical and R ₄ and R ₅ is a fatty acid radical or hydrogen.

Conductivity additives in which the cation [A] ^{+ is} a phosphonium ion (VI) in which R ₁ to R ₃ independently of one another are C ₁ -C ₁₈ -alkyl, in particular butyl, isobutyl, 1-hexyl or 1-octyl, are suitable ,

Particular preference is given to tributyloctylphosphonium, triisobutyloctylphosphonium, trioctylethylphosphonium, trioctylbutylphosphonium, tributylhexylphosphonium, tetraoctylphosphonium, tributyltetradecylphosphonium, trihexyloctylphosphonium, trihexyltetradecylphosphonium and the tetra-tetradecylphosphonium cation.

The conductivity additives according to the invention are composed of at least one of the abovementioned cations combined with at least one anion each. As anions are in principle all anions into consideration, which lead in conjunction with the cation to a non-aqueous hydraulic oil clearly soluble liquid.

• der Gruppe der Halogenide und halogenhaltigen Verbindungen der Formeln: F^- Cl^-, Br^-, I^-, BF₄ ^-, PF₆ ^-, AlCl₄ ^-, Al₂Cl₇ ^-, Al₃Cl₁₀ ^-, AlBr₄ ^-, FeCI₄ ^-, BCl₄ ^- SbF₆ ^-, AsF₆ ^-, ZnCl₃ ^-, SnCl₃ ^-, CuCl₂ ^-, CF₃SO₃ ^-, (CF₃SO₃)₂N^-, CF₃CO₂ ^-, CCl₃CO₂ ^-, CN^-, SCN^-, OCN^-, NO₂ ^-, NO₃ ^-, N(CN)^-; der Gruppe der Sulfate, Sulfite und Sulfonate der allgemeinen Formeln: SO₄ ^2-, HSO₄ ^-, SO₃ ^2", HSO₃ ^-, R^aOSO₃ ^-, R^aSO₃ ^-;
• der Gruppe der Phosphate der allgemeinen Formeln: PO₄ ^3-, HPO₄ ^2-, H₂PO^4-, R^aPO₄ ^2-, HR^aPO₄ ^-, R^aR^bPO₄ ^-;
• der Gruppe der Phosphonate und Phosphinate der allgemeinen Formel: R^aHPO₃ ^-, R^aR^bPO₂ ^-, R^aR^bPO₃ ^-;
• der Gruppe der Phosphite der allgemeinen Formeln: PO₃ ^3-, HPO₃ ^2-, H₂PO₃ ^-, R^aPO₃ ^2-, R^aHPO₃ ^-, R^aR^bPO₃ ^-;
• der Gruppe der Phosphonite und Phosphinite der allgemeinen Formel: R^aR^bPO₂ ^-, R^aHPO₂ ^-, R^aR^bPO^-, R^aHPO^-; der Gruppe der Carboxylate der allgemeinen Formeln: R^aCOO^-;
• der Gruppe der Borate der allgemeinen Formeln: BO₃ ^3-, HBO₃ ^2-, H₂BO₃ ^-, R^aR^bBO₃ ^-, R^aHBO₃ ^-, R^aBO₃ ^2-, B(OR^a)(OR^b)(OR^c)(OR^d)^-, B(HSO₄)^-, B(R^aSO₄)- ;
• der Gruppe der Boronate der allgemeinen Formeln: R^aBO₂ ^2-, R^aR^bBO^-;
• der Gruppe der Carbonate und Kohlensäureester der allgemeinen Formeln: HCO₃ ^-, CO₃ ^2-, R^aCO^3-;
• der Gruppe der Silikate und Kieselsäuresäureester der allgemeinen Formeln: SiO₄ ^4-, HSiO₄ ^3-, H₂SiO₄ ^2-, H₃SiO₄ ^-, R^aSiO₄ ^3-, R^aR^bSiO₄ ^2-, R^aR^bR^cSiO₄ ^-, HR^aSiO₄ ^2-, H₂R^aSiO₄ ^-, HR^aR^bSiO₄ ^-;
• der Gruppe der Alkyl- bzw. Arylsilan-Salze der allgemeinen Formeln: R^aSiO₃ ^3-, R^aR^bSiO₂ ^2-, R^aR^bR^cSiO^-, R^aR^bR^cSi0₃ ^-, R^aR^bR^cSi0₂ ^-, R^aR^bSi0₃ ^2-;
• der Gruppe der Carbonsäureimide, Bis(sulfonyl)imide und Sulfonylimide der allgemeinen Formeln:
  
• der Gruppe der Methide der allgemeinen Formel:
  
• der Gruppe der Alkoxide und Aryloxide der allgemeinen Formeln: R^aO^-;
• der Gruppe der Halometallate der allgemeinen Formel [M_rHal_t]^s-, wobei M für ein Metall und Hal für Fluor, Chlor, Brom oder lod steht, r und t ganze positive Zahlen sind und die Stöchiometrie des Komplexes angeben und s eine ganze positive Zahl ist und die Ladung des Komplexes angibt;
• der Gruppe der Sulfide, Hydrogensulfide, Polysulfide, Hydrogenpolysulfide und Thiolate der allgemeinen Formeln:
• S^2-, HS^-, [S_v]^2-, [HS_v]^-, [R^aS]^-, wobei v eine ganze positive Zahl von 2 bis 10 ist;
• der Gruppe der komplexen Metallionen wie Fe(CN)₆ ^3-, Fe(CN)₆ ^4-, MnO₄ ^-, Fe(CO)₄ ^-.
• Darin bedeuten R^a, R^b, R^c und R^d unabhängig voneinander jeweils Wasserstoff;
• C₁-C₃₀-Alkyl und deren aryl-, heteroaryl-, cycloalkyl, halogen-, hydroxy-, amino-, carboxy-, formyl-, -O-, - CO-, -CO-O- oder -CO-N< substituierte Komponenten, wie beispielsweise Methyl, Ethyl, 1-Propyl, 2-Propyl, 1-Butyl, 2-Butyl, 2-Methyl-1-propyl (Isobutyl), 2-Methyl-2-propyl (tert.-Butyl), 1-Pentyl, 2-Pentyl, 3-Pentyl, 2-Methyl-1-butyl, 3-Methyl-1-butyl, 2-Methyl-2-butyl, 3-Methyl-2-butyl, 2,2-Dimethyl-1-propyl, 1-Hexyl, 2-Hexyl, 3-Hexyl, 2-Methyl-1-pentyl, 3-Methyl-1-pentyl, 4-Methyl-1-pentyl, 2-Methyl-2-pentyl, 3-Methyl-2-pentyl, 4-Methyl-2-pentyl, 2-Methyl-3-pentyl, 3-Methyl-3-pentyl, 2,2-Dimethyl-1-butyl, 2,3-Dimethyl-1-butyl, 3,3-Dimethyl-1-butyl, 2-Ethyl-1-butyl, 2,3-Dimethyl-2-butyl, 3,3-Dimethyl-2-butyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Icosyl, Henicosyl, Doco- syl, Tricosyl, Tetracosyl, Pentacosyl, Hexacosyl, Heptacosyl, Octacosyl, Nonacosyl, Triacontyl, Phenylmethyl (Benzyl), Diphenylmethyl, Triphenylmethyl, 2-Phenylethyl, 3-Phenylpropyl, Cyclopentylmethyl, 2-Cyclopentylethyl, 3-Cyclopentylpropyl, Cyclohexylmethyl, 2-Cyclohexylethyl, 3-Cyclohexylpropyl, Methoxy, Ethoxy, Formyl, Acetyl oder C_qF_2(q-a)+(1-b)H_2a+b mit q < 30, 0 ≤ a ≤ q und b = 0 oder 1 (beispielsweise CF₃, C₂F₅, CH₂CH₂-C_(q-2)F_2(q-2)+1, C₆F₁₃, C₈F₁₇, C₁₀F₂₁, C₁₂F₂₅);
• C₃-C₁₂-Cycloalkyl und deren aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -O-, -CO- oder -CO-O-substituierte Komponenten, wie beispielsweise Cyclopentyl, 2-Methyl-1-cyclopentyl, 3-Methyl-1-cyclopentyl, Cyclohexyl, 2-Methyl-1-cyclohexyl, 3-Methyl-1-cyclohexyl, 4-Methyl-1-cyclohexyl oder C_qF_2(q-a)-(1-b)H_2a-b mit q ≤ 30, 0 ≤ a ≤ q und b = 0 oder 1 ; C₂-C₃₀-Alkenyl und deren aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -O-, -CO- oder -CO-O-substituierte Komponenten, wie beispielsweise 2-Propenyl, 3-Butenyl, cis-2-Butenyl, trans-2-Butenyl oder C_qF_2(q-a)-(1-b)H_2a-b mit q ≤ 30, 0 ≤ a ≤ q und b = 0 oder 1;
• C₃-C₁₂-Cycloalkenyl und deren aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -O-, -CO- oder -CO-O-substituierte Komponenten, wie beispielsweise 3-Cyclopentenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, 2,5- Cyclohexadienyl oder C_qF_{2(q-a)-3(1-b)}H_2a-3b mit q ≤ 30, 0 ≤ a ≤ q und b = 0 oder 1;
• Aryl oder Heteroaryl mit 2 bis 30 Kohlenstoffatomen und deren alkyl-, aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -O-, - CO- oder -CO-O-substituierte Komponenten, wie beispielsweise Phenyl, 2-Methyl-phenyl (2-Tolyl), 3-Methyl-phenyl (3-Tolyl), 4-Methyl-phenyl, 2-Ethyl-phenyl, 3-Ethyl-phenyl, 4-Ethyl-phenyl, 2,3-Dimethyl-phenyl, 2, 4-Dimethyl-phenyl, 2,5-Dimethyl-phenyl, 2,6-Dimethyl-phenyl, 3,4-Dimethyl-phenyl, 3,5-Dimethyl-phenyl, 4-Phenyl-phenyl, 1-Naphthyl, 2-Naphthyl, 1-Pyrrolyl, 2-Pyrrolyl, 3-Pyrrolyl, 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl oder C₆F_(5-a)H_a mit 0 ≤ a ≤ 5; oder
• zwei Reste einen ungesättigten, gesättigten oder aromatischen, gegebenenfalls durch funktionelle Gruppen, Aryl, Alkyl, Aryloxy, Alkyloxy, Halogen, Heteroatome und/oder Heterocyclen substituierten und gegebenenfalls durch ein oder mehrere Sauerstoff-und/oder Schwefelatome und/oder ein oder mehrere substituierte oder unsubstituierte Iminogruppen unterbrochenen Ring.

The anion [Y] ^{n of} the conductivity additives is for example selected from:

• the group of halides and halogen ^- containing compounds of the formulas: F ^- Cl ^- , Br ^- , I ^- , BF ₄ ^- , PF ₆ ^- , AlCl ₄ ^- , Al ₂ Cl ₇ ^- , Al ₃ Cl ₁₀ ^- , AlBr ₄ ^- , FeCl ₄ ^- , BCl ₄ ^- SbF ₆ ^- , AsF ₆ ^- , ZnCl ₃ ^- , SnCl ₃ ^- , CuCl ₂ ^- , CF ₃ SO ₃ ^- , (CF ₃ SO ₃ ) ₂ N ^- , CF ₃ CO ₂ ^- , CCl ₃ CO ₂ ^- , CN ^- , SCN ^- , OCN ^- , NO ₂ ^- , NO ₃ ^- , N (CN) ^- ; the group of sulfates, sulfites and sulfonates of the general formulas: SO ₄ ^2- , HSO ₄ ^- , SO ₃ ^{2 "} , HSO ₃ ^- , R ^a OSO ₃ ^- , R ^a SO ₃ ^- ;
• the group of phosphates of the general formulas: PO ₄ ^3- , HPO ₄ ^2- , H ₂ PO ^4- , R ^a PO ₄ ^2- , HR ^a PO ₄ ^- , R ^a R ^b PO ₄ ^- ;
• the group of phosphonates and phosphinates of the general formula: R ^a HPO ₃ ^- , R ^a R ^b PO ₂ ^- , R ^a R ^b PO ₃ ^- ;
• the group of phosphites of the general formulas: PO ₃ ^3- , HPO ₃ ^2- , H ₂ PO ₃ ^- , R ^a PO ₃ ^2- , R ^a HPO ₃ ^- , R ^a R ^b PO ₃ ^- ;
• the group of phosphonites and phosphinites of the general formula: R ^a R ^b PO ₂ ^- , R ^a HPO ₂ ^- , R ^a R ^b PO ^- , R ^a HPO ^- ; the group of carboxylates of the general formulas: R ^a COO ^- ;
• the group of borates of the general formulas: BO ₃ ^3- , HBO ₃ ^2- , H ₂ BO ₃ ^- , R ^a R ^b BO ₃ ^- , R ^a HBO ₃ ^- , R ^a BO ₃ ^2- , B (OR ^a ) (OR ^b ) (OR ^c ) (OR ^d ) ^- , B (HSO ₄ ) ^- , B (R ^a SO ₄ ) -;
• the group of boronates of the general formulas: R ^a BO ₂ ^2- , R ^a R ^b BO ^- ;
• the group of carbonates and carbonic esters of the general formulas: HCO ₃ ^- , CO ₃ ^2- , R ^a CO ^3- ;
• the group of silicates and silicic acid esters of the general formulas: SiO ₄ ^4- , HSiO ₄ ^3- , H ₂ SiO ₄ ^2- , H ₃ SiO ₄ ^- , R ^a SiO ₄ ^3- , R ^a R ^b SiO ₄ ^2- , R ^a R ^b R ^c SiO ₄ ^- , HR ^a SiO ₄ ^2- , H ₂ R ^a SiO ₄ ^- , HR ^a R ^b SiO ₄ ^- ;
• the group of alkylsilane and arylsilane salts of the general formulas: R ^a SiO ₃ ^3-, R ^a R ^b SiO ₂ ^2-, R ^a R ^b R ^c SiO ^-, R ^a R ^b R ^c Si0 ₃ ^-, R ^a R ^b R ^c Si0 ₂ ^- , R ^a R ^b Si0 ₃ ^2- ;
• the group of carboximides, bis (sulfonyl) imides and sulfonylimides of the general formulas:
  
• the group of methides of the general formula:
  
• the group of alkoxides and aryloxides of the general formulas: R ^a O ^- ;
• the group of halometalates of the general formula [M _r Hal _t ] ^s- , where M is a metal and Hal is fluorine, chlorine, bromine or iodine, r and t are integers positive and indicate the stoichiometry of the complex and s is a whole is positive number and indicates the charge of the complex;
• the group of sulfides, hydrogen sulfides, polysulfides, hydrogen polysulfides and thiolates of the general formulas:
• S ² , HS ^- , [S _v ] ² , [HS _v ] ^- , [R ^a S] ^- , where v is a whole positive number from 2 to 10;
• the group of complex metal ions such as Fe (CN) ₆ ^3- , Fe (CN) ₆ ^4- , MnO ₄ ^- , Fe (CO) ₄ ^- .
• Wherein R ^a , R ^b , R ^c and R ^d are each independently hydrogen;
• C ₁ -C ₃₀ -alkyl and their aryl, heteroaryl, cycloalkyl, halogeno, hydroxy, amino, carboxy, formyl, -O-, - CO-, -CO-O- or -CO-N <substituted components, such as, for example, methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl 1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl 1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2 butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, Triacontyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentene tylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, methoxy, ethoxy, formyl, acetyl or C _q F _{2 (qa) + (1-b)} H _{2a + b} with q <30, 0 ≤ a ≤ q and b = 0 or 1 (e.g. CF ₃ , C ₂ F ₅ , CH ₂ CH ₂ -C _(q-2) F _{2 (q-2) +1} , C ₆ F ₁₃ , C ₈ F ₁₇ , C ₁₀ F ₂₁ , C ₁₂ F ₂₅ );
• C ₃ -C ₁₂ cycloalkyl and their aryl, heteroaryl, cycloalkyl, halogen, hydroxy, amino, carboxy, formyl, -O-, -CO- or -CO-O-substituted components, such as for example cyclopentyl, 2-methyl-1-cyclopentyl, 3-methyl-1-cyclopentyl, cyclohexyl, 2-methyl-1-cyclohexyl, 3-methyl-1-cyclohexyl, 4-methyl-1-cyclohexyl or C _q F _{2 ( qa) - (1-b)} H _2a-b with q ≤ 30, 0 ≤ a ≤ q and b = 0 or 1; C ₂ -C ₃₀ alkenyl and their aryl, heteroaryl, cycloalkyl, halogen, hydroxy, amino, carboxy, formyl, -O-, -CO- or -CO-O-substituted components, such as For example, 2-propenyl, 3-butenyl, cis-2-butenyl, trans-2-butenyl or C _q F _{2 (qa) - (1-b)} H _2a-b with q ≤ 30, 0 ≤ a ≤ q and b = 0 or 1;
• C ₃ -C ₁₂ cycloalkenyl and their aryl, heteroaryl, cycloalkyl, halogen, hydroxy, amino, carboxy, formyl, -O-, -CO- or -CO-O-substituted components, such as For example, 3-cyclopentenyl, 2-cyclohexenyl, 3-cyclohexenyl, 2,5-cyclohexadienyl or C _q F _{2 (qa) -3 (1-b)} H _2a-3b with q ≤ 30, 0 ≤ a ≤ q and b = 0 or 1;
• Aryl or heteroaryl having 2 to 30 carbon atoms and their alkyl, aryl, heteroaryl, cycloalkyl, halogen, hydroxy, amino, carboxy, formyl, -O-, -CO- or -CO-O- substituted components such as phenyl, 2-methylphenyl (2-tolyl), 3-methylphenyl (3-tolyl), 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethyl -phenyl, 2,3-dimethyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl , 4-phenyl-phenyl, 1-naphthyl, 2-naphthyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl or C ₆ F _(5-a) H _a with 0 ≤ a ≤ 5; or
• two radicals are an unsaturated, saturated or aromatic, optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles and optionally substituted by one or more oxygen and / or sulfur atoms and / or one or more substituted or unsubstituted imino groups interrupted ring.

Suitable anions are, for example, chloride; Bromide; iodide; thiocyanate; hexafluorophosphate; trifluoromethanesulfonate; methane; formate; Acetate; glycolate; lactate; oxalate; citrate; maleate; maleate; tartrate; mandelate; Nitrate; Nitrite; trifluoroacetate; Sulfate; Bisulfate; Methyl sulfate; ethyl sulfate; 1-propyl sulfate; 1-butyl sulfate; 1-hexyl sulfate; 1-octyl sulfate; Phosphate; dihydrogen phosphate; Hydrogen phosphate; C ₁ -C ₄ dialkyl phosphates; propionate; tetrachloroaluminate; Al ₂ Cl ₇ ^- ; chlorozincate; Chloroferrat; imide, bis (trifluoromethylsulfonyl); Bis (pentafluoroethylsulfonyl) imide; Bis (methylsulfonyl) imide; Bis (p-tolylsulfonyl) imide; Tris (trifluoromethylsulfonyl) methide; Bis (pentafluoroethylsulfonyl) methide; p-tolylsulfonate; tetracarbonylcobaltate; Dimethylenglykolmonomethylethersulfat; oleate; stearate; acrylate; methacrylate; maleate; hydrogen citrate; vinylphosphonate; Bis (pentafluoroethyl) phosphinate; Borates such as bis [salicylato (2 -)] borate, bis [oxalato (2 -)] borate, bis [1,2-benzenediolato (2 -) - 0,0 '] borate, tetracyano borate, tetrafluoroborate; dicyanamide; Tris (pentafluoroethyl) trifluorophosphate; Tris (heptafluoropropyl) trifluorophosphate, cyclic aryl phosphates such as Brenzcatecholphosphat (C ₆ H ₄ O ₂₎ P (O) O ^- and Chlorocobaltat.

Preferred anions are selected from the group - without being exhaustive - the halides, bis (perfluoroalkylsulfonyl) amides or imides such as bis (trifluoromethylylsulfonyl) imide, alkyl and aryl tosylates, perfluoroalkyl tosylates, nitrate, sulfate, hydrogen sulfate, Alkyl and aryl sulfates, polyether sulfates and sulfonates, perfluoroalkyl sulfates, sulfonate, alkyl and aryl sulfonates, perfluorinated alkyl and aryl sulfonates, alkyl and aryl carboxylates, perfluoroalkyl carboxylates, perchlorate, tetrarchloroaluminate, saccharinate. Furthermore, dicyanamide, thiocyanate, isothiocyanate, tetraphenylborate, tetrakis (pentafluorophenyl) borate, tetrafluoroborate, hexafluorophosphate, polyether phosphates, dialkyl phosphates, isostearates, alkylbenzenesulfonates, bis (alkyl) phosphinates, phosphatides, decanoates and phosphate are preferred.

Very particularly preferred anions are: chloride, bromide, hydrogensulfate, tetrachloroaluminate, thiocyanate, methylsulfate, ethylsulfate, methanesulfonate, formate, acetate, glycolate, lactate, dimethyl phosphate, diethyl phosphate, p-toluenesulfonate, tetrafluoroborate, hexafluorophosphate, diethyl phosphate, isostearate, dodecylbenzyl sulfonate, bis (2, 4, 4-trimethylpentyl) -phosphinate, phosphatide, decanoate, and tosylate.

According to the invention in a further preferred embodiment, such conductivity additives or mixtures thereof are used, which is a combination of a 1,3-dialkylimidazolium, 1,2,3-Trialkylimidazolium-, 1,3-Dialkylimidazolinium- and 1,2,3-Trialkylimidazoliniumkations with an anion selected from the group of halides, bis (trifluoromethylsulfonyl) imide, perfluoroalkyl tosylates, alkyl sulfates and sulfonates, perfluorinated alkyl sulfonates and sulfates, perfluoroalkyl carboxylates, perchlorate, dicyanamide, thiocyanate, isothiocyanate, tetraphenylborate, tetrakis (pentafluorophenyl) borate, Tetrafluoroborate, hexafluorophosphate, acetate, glycolate, lactate included.

The mixing ratios of hydraulic oil and conductivity additive are between 100,000: 1 and 10: 1, preferably between 10,000: 1 and 20: 1, more preferably 5,000: 1 and 25: 1, very particularly preferably between 1,000: 1 and 50: 1.

The composition of hydraulic oil and conductivity additive may contain other conventional additives. These include, for example, viscosity index improvers, defoamers, pour point depressants, extreme pressure additives, anti-wear additives, corrosion inhibitors, friction modifier additives, demulsifying additives, antioxidants or detergents.

The required minimum conductivity is, for example, at least 1,000 pS / m for applications in cold store hydraulic fluids. The desired conductivity is much higher, but can not be permanently achieved by the previously known conductivity improvers, as it comes to evaporation of the volatile solvent and associated with precipitations or salting out. A limitation of the conductivity upwards is certainly not necessary, since the desired effect, the tendency to static charge, with increasing conductivity continues to decrease. The ionic conductivity additives according to the invention with organic radicals in the ions no longer have these disadvantages.

In other application areas, the minimum conductivities and desired conductivities may differ and also maximum conductivities may be relevant.

The inventive conductivity additives and their use are described below by way of example, without the invention being considered to be limited to these exemplary embodiments. Given below, ranges, general formulas, or classes of compounds are intended to encompass not only the corresponding regions or groups of compounds explicitly mentioned, but also all sub-regions and sub-groups of compounds obtained by removing individual values (ranges) or compounds can be.

EXAMPLES

In the examples given below, the present invention is described by way of example, without the invention, the scope of application of which is apparent from the entire description and the claims, being able to be read as limited to the embodiments mentioned in the examples.

Experimental procedure:

100 g cold storage hydraulic oil 50468783 (Jungheinrich) was presented and added in each case 1 g or 5 g of the conductivity additive. The sample was stirred until homogeneous and then the electrical rest conductivity and turbidity FNU (Formazine Nephelometric Units) were determined.

The static conductivity was determined according to DIN 51412 Part 1 (2005-06).

To determine the turbidity, a laboratory haze photometer NEPHLA type LPG239 (manufacturer Dr. Bruno Lange GmbH, Dusseldorf) was used. The comparison was made against DIN standard formazine.

The turbidity value quantifies the qualitative phenomenon of turbidity. The aim of the turbidity measurement is to obtain information about the content of scattering particles. FNU (also FTU: formazin turbidity unit) is a unit of measurement of turbidity, which was measured with stray light, used according to the standard ISO 7027. To make scattered light measurements comparable, be these measuring instruments are calibrated with a suspension, eg formazine, in order to be able to reduce the measurements to a common standard.

Carrying out the turbidity measurement:

The cuvette was filled with the respective sample to the black ring and conditioned to the appropriate temperature (in each case 0 ° C and room temperature). Thereafter, the cuvette was inserted into the apparatus. At least 3 measurements were carried out in different cuvette positions and the mean was calculated. In order to avoid condensation of atmospheric moisture, working was carried out at 0 ° C. in a protective gas atmosphere. Table 1: Turbidity and static conductivity at room temperature of additized hydraulic oil (Kühlhaus Hydrauliköl 50468783 (Jungheinrich) rest conductivity haze value pS / m FNU Blank value pure hydraulic oil 50 0.24 1% addition Trihexyltetradecylphosphonium bis (2,4,4-trimethylpentyl) phosphinate 38520 2.7 5% addition trihexyltetradecylphosphonium bis (2,4,4-trimethylpentyl) phosphinate 210000 1% additive TEGO ^® IL ZTO 50,000 0.24 5% additive TEGO ^® IL ZTO 281700 0.24

Not only with TEGO ^® IL ZTO, a Fettsäureaminpolyglykolether-diesterquat, CAS-No. 217813-30-4, but also with TEGO ^® IL ZTI, a Talloylaminpolyglykolether-diester quat, and with TEGO ^® IL IM36, a 2- (C ₁₇ and C ₁₇ -unsaturatedalkyl) -1- [2- (C ₁₈ and C ₁₈ -unsatd.amido) -ethyl] -4,5-dihydro-1-methyl, imidazolium methylsulfate and Trihexyltetradecylphosphonium bis (2,4,4-trimethylpentyl) phosphinate comparatively high conductivities associated with very low turbidity levels are achieved (TEGO ^® is a trademark Evonik Goldschmidt GmbH Even at temperatures around the freezing point (0 ° C), the organic conductivity improver remains in solution and so that the high relative conductivity is obtained. These conductivities are significantly higher in comparison to an inorganic conducting salt in maximum concentration (ie with sediment).

The results clearly show that the formulations according to the invention can be equipped with a much higher proportion of conductivity additive than technical solutions used hitherto. Thus, even with respect to the prior art, absolutely higher conductivity values can be achieved and set.

Claims (17)

A composition comprising nonaqueous hydraulic oils or lubricants and one or more conductivity additives which are clearly miscible or soluble with the hydraulic oil and optionally further customary additives. A composition according to claim 1, characterized in that the conductivity additive is liquid and of ionic structure and contains ions with organic radicals. Composition according to at least one of claims 1 or 2, characterized in that the ionic conductivity additive comprises at least one cation and / or an anion with organic radicals. A composition according to at least one of claims 1 to 3, characterized in that the ionic conductivity additive in the cation and / or anion contains at least one organic radical having at least 8 C atoms, wherein the sum of the C atoms of all radicals is at least 14. Composition according to any one of Claims 1 to 4, comprising as the conductivity additive a compound of the formulas (I), (II) or (III)

[A] _n ⁺ [Y] ^n- (I)

in the n is 1, 2, 3 or 4, [A] ⁺ for a quaternary ammonium cation, an oxonium cation, a sulfonium cation or a phosphonium cation and [Y] ^{n- stands} for an n-valent anion and / or
mixed salts of the general formulas (II)

[A ¹ ] ⁺ [A ² ] ⁺ [Y] ^2- (IIa),

[A ¹ ] ⁺ [A ² ] ⁺ [A ³ ] ⁺ [Y] ^3- (IIb),

or

[A ¹ ] ⁺ [A ² ] ⁺ [A ³ ] ⁺ [A ⁴ ] ⁺ [Y] ^4- (IIc)

in which [A ¹ ] ⁺ , [A ² ] ⁺ [A ³ ] ⁺ and [A ⁴ ] ^{+ are} independently selected from the groups mentioned for [A] ⁺ , [Y] ^{n- has} the meaning given for formula (I) and / or
mixed salts of the general formulas (III)

[A ¹ ] ⁺ [A ² ] ⁺ [A ³ ] ⁺ [M ¹ ] ⁺ [Y] ^4- (IIIa),

[A ¹ ] ⁺ [A ² ] ⁺ [M ¹ ] ⁺ [M ² ] ⁺ [Y] ^4- (IIIb)

A ¹ ] ⁺ [M ¹ ] ⁺ [M ² ] ⁺ [M ³ ] ⁺ [ _Y ] ^4- (IIIc),

[A ¹ ] ⁺ [A ² ] ⁺ [M ¹ ] ⁺ [Y] ^3- (IIId),

[A ¹ ] ⁺ [M ¹ ] ⁺ [M ² ] ⁺ [Y] ^3- (IIIe),

[A ¹ ] ⁺ [M ¹ ] ⁺ [Y] ^2- (IIIf),

[A ¹ ] ⁺ [A ² ] ⁺ [M ⁴ ] ²⁺ [Y] ^4- (IIIg),

[A ¹ ] ⁺ [M ¹ ] ⁺ [M ⁴ ] ²⁺ [Y] ^4- (IIIh),

[A ¹ ] ⁺ [M ⁵ ] ³⁺ [Y] ^4- (IIIi),

or

[A ¹ ] ⁺ [M ⁴ ] ²⁺ [Y] ^3- (IIIj),

in which [A ¹ ] ⁺ , [A ² ] ⁺ or [A ³ ] ^{+ are} independently selected from the groups mentioned for [A] ⁺ , [Y] ^{n- has} the meaning given for formula (I) and [M ¹ ] ⁺ , [M ² ] ⁺ , [M ³ ] ⁺ monovalent metal cations, [M ⁴ ] ²⁺ divalent metal cations and [M ⁵ ] ³⁺ mean trivalent metal cations or mixtures of all formulas (I) to (III). Composition according to Claim 5, containing as cation [A ⁺ ] structural elements of the general formulas (IV) to (VIII)

R ¹ R ² R ³ R ⁴ N ⁺ (IV)

R ¹ R ² N ⁺ = CR ³ R ⁴ (V)

R ¹ R ² R ³ R ⁴ P ⁺ (VI)

R ¹ R ² P ⁺ = CR ³ R ⁴ (VII)

R ¹ R ² R ³ S ⁺ (VIII)

in which R ¹ , R ² , R ³ , R ^{4 are the} same or different and are hydrogen, a linear or branched optionally double bonds containing aliphatic hydrocarbon radical having 1 to 30 carbon atoms, with the proviso that at least one radical is not hydrogen, a cycloaliphatic optionally containing double bonds Hydrocarbon radical having 5 to 40 carbon atoms, an aromatic hydrocarbon radical having 6 to 40 carbon atoms, an alkylaryl radical having 7 to 40 carbon atoms, one by one or more heteroatoms such as oxygen, NH, NR 'with R' is an optionally double bonds containing C ₁ -C ₃₀ alkyl, interrupted linear or branched optionally double bonds containing aliphatic hydrocarbon radical having 2 to 30 carbon atoms, one by a or several functionalities selected from the group -OC (O) -, - (O) CO-, -NH-C (O) -, - (O) C-NH, - (CH ₃ ) NC (O) -, - (O) CN (CH ₃ ) -, -S (O ₂ ) -O-, -OS (O ₂ ) -, -S (O ₂ ) -NH-, -NH-S (O ₂ ) -, - S (O ₂ ) -N (CH ₃ ) -, -N (CH ₃ ) -S (O ₂ ) -, interrupted linear or branched optionally double bonds containing aliphatic hydrocarbon radical having 2 to 30 carbon atoms, one terminal with OH, OR ', NH ₂ , N (H) R', N (R ') ₂ , in which R' is an optionally double-bond-containing C ₁ -C ₃₀ -alkyl radical, or functionalized linear or branched optionally double bonds containing aliphatic or cycloaliphatic is a hydrocarbon radical having 1 to 30 carbon atoms or a blockwise or random polyether according to - (R ⁵ -O) _n -R ⁶ , in which R ^{5 is} a linear or branched hydrocarbon radical containing 2 to 4 carbon atoms, n is 1 to 100 and R ^{6 is} hydrogen, a linear or branched optionally double bond-containing aliphatic hydrocarbon radical having 1 to 30 carbon atoms, an optionally Double-bond-containing cycloaliphatic hydrocarbon radical having 5 to 40 carbon atoms, an aromatic hydrocarbon radical having 6 to 40 carbon atoms, an alkylaryl radical having 7 to 40 carbon atoms or a radical -C (O) -R ⁷ with R ⁷ is a linear or branched, optionally double bond-containing aliphatic hydrocarbon radical having 1 to 30 carbon atoms, an optionally double bonds containing cycloaliphatic hydrocarbon radical having 5 to 40 carbon atoms, an aromatic hydrocarbon radical having 6 to 40 carbon atoms, a Alkylaryl radical having 7 to 40 carbon atoms. Composition according to at least one of claims 5 or 6, characterized in that the metal cations [M ¹ ] ⁺ , [M ² ] ⁺ , [M ³ ] ⁺ , [M ⁴ ] ²⁺ and [M ⁵ ] ^{3+ are} selected from the metal cations of the 1st, 2nd, 6th, 7th, 8th, 9th, 10th, 11th, 12th and 13th group of the periodic table in the IUPAC nomenclature. Composition according to at least one of claims 5 to 7, characterized in that the anions [Y] ^{n- are} selected from the group of halides, carboxylates, phosphates, thiocyanates, isothiocyanates, dicyanamides, sulfates, alkyl sulfates, sulfonates, alkyl sulfonates, tetrafluoroborate, hexafluorophosphate , Bis (trifluoromethylsulfonyl) imide, dialkyl phosphates, isostearates, alkylbenzylsulfonates, bis (alkyl) phosphinates, phosphatides, decanoates. Composition according to Claim 5, characterized in that the anions [Y] ^n- with cations [A ¹ ] ⁺ , [A ² ] ⁺ [A ³ ] ⁺ and [A ⁴ ] ⁺ in the form of substituted ammonium, phosphonium, Pyridinium or imidazolium cations are combined. Composition according to at least one of claims 5 to 9, characterized in that the conductivity additive or the mixture of the conductivity additives of at least one quaternary nitrogen and / or phosphorus compound and / or sulfur compound and at least one anion [Y] ^n- composed and the melting point of Composition is below about + 250 ° C. A composition according to claim 10, characterized in that the conductivity additive or its mixtures are liquid at room temperature. Use of compositions according to at least one of claims 1 to 11 in hydraulic and / or lubricant systems. Use of compositions according to any one of claims 1 to 11, containing one or more hydraulic oils or lubricants and one or more compounds selected from N, N-di (tallowyloxyethyl) -N, N-dimethylammonium chloride; N, N-di (canolyloxy-ethyl) -N, N-dimethylammonium chloride; N, N-di (tallowyloxyethyl) -N-methyl, N- (2-hydroxyethyl) ammonium methyl sulfate; N, N-di (canolyloxy-ethyl) -N-methyl, N- (2-hydroxyethyl) ammonium methyl sulfate; N, N-di (tallowylamidoethyl) -N-methyl, N- (2-hydroxyethyl) ammonium methyl sulfate; N, N-di (2-tallowyloxy-2-oxo-ethyl) -N, N-dimethylammonium chloride; N, N-di (2-canolyloxy-2-oxo-ethyl) -N, N-dimethylammonium chloride; N, N-di (2-tallowyloxyethylcarbonyloxyethyl) -N, N-dimethylammonium chloride; N, N-di (2-canolyloxyethylcarbonyloxyethyl) -N, N-dimethylammonium chloride; N (2-tallowoyloxy-2-ethyl) -N- (2-tallowyloxy-2-oxo-ethyl) -N, N-dimethylammonium chloride; N (2-canolyloxy-2-ethyl) -N- (2-canolyloxy-2-oxo-ethyl) -N, N-dimethylammonium chloride; N, N, N-tri (tallowyloxyäthyl) -N-methyl ammonium chloride; N, N, N-tri (canolyloxyäthyl) -N-methyl ammonium chloride; 1,2-Ditallowyloxy-3-N, N, N-trimethylammoniumpropyl chloride, 1,2-Dicanolyloxy-3-N, N, N-trimethylammonium propyl chloride, ditallowdimethylammonium chloride, ditallowdimethylammonium methylsulfate, dimethylammonium chloride Di (hydrogenated-tallow) distearyl-dimethylammonium chloride and / or dibehenyldimethylammonium chloride as a conductivity additive in hydraulic systems or lubricant systems. Use of compositions according to one of claims 1 to 11, containing as conductivity additive compounds which contain structural fragments as cations, which consist of saturated or unsaturated cyclic compounds and of aromatic compounds each having at least one trivalent nitrogen atom in a 4- to 10-, preferably 5- to derive 6-membered heterocyclic ring, which may optionally be substituted, in hydraulic systems or lubricant systems. Use of compositions according to claim 14, wherein the cation of the conductivity additive has the structure of formulas (IX), (X) and (XI), which heterocyclic rings may optionally also contain a plurality of heteroatoms such as nitrogen, oxygen or sulfur, and

R ¹ and R ² are defined according to claim 2, R is a hydrogen, a linear or branched optionally double bonds containing aliphatic hydrocarbon radical having 1 to 30 carbon atoms, a cycloaliphatic optionally double bonds containing hydrocarbon radical having 5 to 40 carbon atoms, an aromatic hydrocarbon radical having 6 to 40 carbon atoms or an alkylaryl radical 7 to 40 carbon atoms and X is an oxygen atom, a sulfur atom or a substituted nitrogen atom (X = O, S, NR ¹ ) and the cyclic nitrogen compounds unsubstituted (R = H), may be monosubstituted or polysubstituted by the radical R, wherein in a multiple substitution by R, the individual radicals R may be the same or different, in hydraulic systems or lubricant systems. Use of compositions according to claim 14, wherein the cations of the conductivity additive of saturated acyclic, saturated or unsaturated cyclic compounds and of aromatic compounds each having more than one trivalent nitrogen atom in a 4- to 10, preferably 5 to 6-membered heterocyclic ring can be derived and substituted both on the carbon atoms and on the nitrogen atoms and may optionally be fused by substituted benzene rings and / or cyclohexane rings to form polynuclear structures, in hydraulic systems or lubricant systems. Use of compositions according to any one of claims 1 to 11, characterized in that the electrical conductivity of hydraulic oils or lubricants can be increased by the addition of miscible or soluble conductivity additives.