QUATERNARY DEPOSIT CONTROL ADDITIVES

Description

[0001] This invention relates to quaternary salts of various polyether polyamines, to fuel compositions and lubricating oil compositions containing these compounds and to their use as either fuel additives or detergents or dispersancy additives in lubricating oils.

[0002] Numerous deposit-forming substances are inherent in hydrocarbon fuels. These substances when used in internal combustion engines tend to form deposits on and around areas of the engine contacted by the fuel. Typical areas commonly and sometimes seriously burdened by the formation of deposits include carburetor ports, the throttle body and venturies, engine intake valves, combustion chamber, etc.

[0003] Deposits adversely affect the operation of the vehicle. For example, deposits on the carburetor throttle body and venturies increase the fuel-to-air ratio of the gas mixture to the combustion chamber thereby increasing the amount of unburned hydrocarbon and carbon monoxide discharged from the chamber. The high fuel-air ratio also reduces the gas mileage obtainable from the vehicle.

[0004] Deposits on the engine intake valves when they get sufficiently heavy, on the other hand, restrict the gas mixture flow into the combustion chamber. This restriction starves the engine of air and fuel and results in a loss of power. Deposits on the valves also increase the probability of valve failure due to burning and improper valve seating. In addition, these deposits may break off and enter the combustion chamber, possibly resulting in mechanical damage to the piston, piston rings, engine head, etc.

[0005] The formation of these deposits can be inhibited as well as removed by incorporating an active detergent and/or dispersant into the fuel. These detergents/dispersants function to cleanse these deposit- prone areas of the harmful deposits, thereby enhancing engine performance and longevity. There are numerous detergent-type gasoline additives currently available which, to varying degrees, perform these functions.

[0006] Additionally, many corrosion problems are inherent in engine operation, particularly over time. Moisture and oxygen and petroleum fuels in contact with ferrous metals contribute to the formation of corrosion products which may significantly interfere with the smooth operation of a variety of a vehicle's fuel system and engine parts, such as the fuel storage tank, fuel lines and injectors. This corrosion can also be formed or promoted by various other agents including some fuel components, such as acids, and even some deposit control additives. This corrosion, besides interfering with the vehicle's operation which may result in a shortening of the engine life, also contributes to a reduction of the efficiency of the engine. It is therefore very desirable for a fuel composition to possess both deposit control additives which effectively control the deposits in the intake systems and corrosion inhibitors which help prevent corrosive agents from interfering with efficient engine operation. The present invention discloses a new class of compounds which seek to overcome both of these problems.

[0007] Likewise, this application also relates to lubricting oil compositions containing quaternary polyether amine additives which contribute dispersancy and detergency to the compositions.

[0008] Lubricating oil compositions, particularly for use in internal combustion engines, have long performed many functions other than simply lubricating moving parts. Modern-day, highly compounded lubricating oil compositions provide anti-wear, anti-oxidant, extreme-pressure and anti-rust protection in addition to maintaining the cleanliness of the engine by detergency and dispersancy. Many lubricating oil additives are well-known for accomplishing these functions.

[0009] Additionally, many corrosion problems are inherent in engine operation, particularly over time. Moisture and oxygen and petroleum fuels in contact with ferrous metals contribute to the formation of corrosion products which may significantly interfere with the smooth operation of the engine. This corrosion can also be formed or promoted by various other agents including some lubricating oil components, such as acids, and even some dispersant additives. This corrosion, besides interfering with the vehicle's operation which may result in a shortening of the engine life, also contributes to a reduction of the efficiency of the engine. It is therefore very desirable for a lubricating oil composition to possess both dispersant additives and corrosion inhibitors. The present invention discloses a new class of compounds which seek to overcome both of these problems.

[0010] Deposit control additives including polyether amines are disclosed in U.S. Patent No. 3,864,098 and hydrocarbyl polyoxyalkylene polyamines in U.S. Patent No. 4,247,301. U.S. Patent No. 4,160,648 discloses deposit control additives comprised of polyoxyalkylene carbamates; EP-A-0100665 discloses polyether polyamine ethanes as deposit control additives.

[0011] Additionally, carboxylic and other acid salts, as well as the quaternary salts of basic nitrogen-containing polymers are known in the art as deposit control and/or carburetor detergent additives in fuel compositions. See, for example, U.S. Patent No. 3,468,640. These additives are also known to have improved corrosion inhibition properties relative to the pure basic nitrogen-containing polymers.

[0012] In accordance with the present invention, additives are provided which, when added to fuel or used as fuel concentrates, are effective in maintaining the cleanliness of the engine and its intake systems. The additives consist of the quaternary salts of various polyether polyamines soluble in hydrocarbon fuel boiling in the gasoline range. These quaternary salts show enhanced dispersancy and corrosion inhibition and therefore serve well as deposit control and/or carburetor dispersants. The nature of the anion in these various salts has also been found to affect their performance.

[0013] When added to lubricating oils, these additives are effective in maintaining the dispersancy of the oil and the efficiency of the engine. The additives consist of the quaternary salts of various polyether polyamines soluble in lubricating oil. These quaternary salts show enhanced dispersancy and corrosion inhibition and therefore serve well as lubricating oil dispersant agents. The nature of the anion in these varous salts has also been found to affect their performance.

[0014] The quaternary salts of the present invention are comprised of basically three moieties or components: a hydrophobic moiety at one end of the molecule comprising polyoxyalkylene polymer submoieties; a hydrophilic amine moiety at the other end, the basic nitrogen atom of which has been quaternized with an appropriate alkyl halide; and the third moiety, a connecting group serving to unite the hydrophilic and hydrophobic ends of the molecule.

[0015] The polyoxyalkylene moiety comprises at least 5 oxyalkylene units of from 2 to 4 carbon atoms and may be terminated or "capped" with a hydrocarbyl group. The hydrocarbyl terminating group of the polyoxyalkylene moiety may contain from between 5 to 30 carbon atoms. Preferably, the polyoxyalkylene chain is bonded through a terminal oxygen to the appropriate connecting group which is in turn bonded to an amino nitrogen atom in the amine or polyamine group. The polyamine preferably contains from 2 to 12 amine nitrogens and from 2 to 40 carbon atoms, with a carbon-nitrogen ratio of between 1:1 and 10:1. At least one nitrogen atom is quaternized with a hydrocarbyl halide. The compounds have a molecular weight in the range of 500 to 2500, and preferably from 800 to 1500.

[0016] The hydrocarbyl halides finding use as the quaternizing agents include alkyl groups containing from 1 to 20 carbon atoms and may be or contain aromatic groups such as phenyl or benzyl groups. The halides of the alkyl halide group ordinarily consist of chloride, bromide and iodide. Certain of the additives of the present invention are believed to be useful as dispersant additives in lubricating oils as well.

[0017] The present invention herein consists of a fuel additive, a quaternized polyoxyalkylene polyamine or polyether polyamine, and a fuel composition containing a liquid hydrocarbon fuel boiling in the gasoline range and from 30 to 10,000 rpm of said additive. The quaternized polyether polyamine has a molecular weight of from 500 to 2500, and preferably from 800 to 1500. The additive consists of three parts or moieties. The first is the polyether .or polyoxyalkylene moiety, which may or may not be hydrocarbyl terminated or "capped". The polyether moiety is bound through the second moiety, a connecting group or linkage to the nitrogen atom of the third moiety, the amine, which is quaternized by an appropriate alkyl halide.

[0018] As fuel additives, the polyoxyalkylene moiety and the quaternized amino moiety are selected to provide solubility in the fuel composition, deposit control activity, and corrosion inhibition within a vehicle's fuel system and engine. As lubricating oil additives, the moieties are selected to provide solubility in a lubricating oil composition with dispersant activity and corrosion inhibition properties.

[0019] As lubricating oil additives, the moieties are selected to provide solubility in a lubricating oil composition with dispersant activity and corrosion inhibition properties.

Polyoxyalkylene Moiety

[0020] The polyoxyalkylene moiety is ordinarily comprised of polyoxyalkylene polymers containing 5 to 30 oxyalkylene units, and most preferably 10 to 25 oxyalkylene units. When polymerized in the polymerization reaction, a single type of alkylene oxide may be employed. Copolymers, however, are equally satisfactory and random copolymers are readily prepared. Blocked copolymers of oxyalkylene units also provide satisfactory polyoxyalkylene polymers for the practice of the present invention.

[0021] The polyoxyalkylene moiety may also be terminated or "capped" by a hydrocarbyl terminating group. This terminating group may be comprised of an alkyl group of from 5 to 30 carbon atoms, an aryl group of from 6 to 30 carbon atoms, an alkaryl group of from 7 to 30 carbon atoms, an aralkyl group of from 7 to 30 carbon atoms, or a methylol-substituted alkyl group of from 5 to 30 carbon atoms.

[0022] The polyoxyalkylene moiety may ordinarily be prepared in a variety of ways, the most common for the practice of the present invention being by the reaction of an appropriate lower alkylene oxide containing from 2 to 4 carbon atoms with an appropriate initiator; for example, chlorohydrin or an alkyl phenol. In the preferred embodiment, ethylene chlorohydrin is used. Copolymers may be readily prepared by contacting the initiator compound with a mixture of alkylene oxides, while the blocked copolymers may be prepared by reacting the initiator first with one alkylene oxide and then another in any order or repetitively under polymerization conditions.

[0023] As an example, the polyoxyalkylene moiety derived from an alkyl phenol initiated polymerization detailed above is prepared as an alcohol containing a terminal hydroxyl group. The polyether moiety is then attached through the appropriate connecting group to the polyamine moiety by a variety of ways, one of which includes reacting the hydroxyl group of the polyoxyalkylene unit with phosgene to form a polyoxyalkylene chloroformate and then reacting the polyoxyalkylene chloroformate with an amine. Alternatively, the hydroxyl group may be reacted with epichlorohydrin to give a methylol-substituted ethyl chloride end group. The resulting polyoxyalkylene alkyl chloride is then reacted with an amine or polyamine to produce the composition to be quaternized, resulting in the composition of the present invention.

The Connecting Group

[0024] The connecting group joining the poloxyalkylene moiety with the amine moiety may be any relatively small diradical containing at least one hydrogen, carbon, oxygen, sulfur and/or nitrogen atom.

[0025] The connecting group which results and is used in the present composition is ordinarily a function of the method by which the compositions are formed and/or by which components of the polyoxyalkylene moiety and the polyamine moiety are joined together. Suitable connecting groups include:





where Z and Z' independently = H, or an alkyl group of from 1 to 2 carbon atoms.

The Amine Moiety

[0026] The amine moiety of the quaternized polyether amine is derived from ammonia or, more preferably, from a polyamine having from 2 to 12 amine nitrogen atoms and from 2 to 40 carbon atoms. The polyamine preferably has a carbon to nitrogen ratio of from about 1:1 to about 10:1. The polyamine may be substituted with a substituent group selected from (A) hydrogen; (B) hydrocarbyl groups from 1 to 10 carbon atoms; (C) acyl groups from 2 to 10 carbon atoms; and (D) monoketo, monocyano, lower alkyl and lower alkoxy derivatives of (B), (C). "Lower", as used in lower alkyl and lower alkoxy, means a group containing 1 to 6 carbon atoms. "Hydrocarbyl" denotes an organic radical composed of carbon and hydrogen which may be aliphatic, alicyclic, aromatic or combinations thereof, e.g. aralkyl. The substituted polyamines of the present invention are generally, but not necessarily, N-substituted polyamines. The acyl groups falling within the definition of the aforementioned (C) substituents are such as propionyl, acetyl, etc. The more preferred substituents are hydrogen, C₁ to C₆ alkyls, and C_l-C_e hydroxyalkyls.

[0027] The more preferred polyamines finding use within the scope of the present invention are polyalkylene polyamines, including alkylene diamine and substituted polyamines, e.g. alkyl and hydroxyalkyl- substituted polyalkylene polyamines. Preferably the alkylene groups contain from 2 to 6 carbon atoms, there being preferably from 2 to 3 carbon atoms between the nitrogen atoms. Such groups are exemplified by ethyleneamines and include ethylene diamine, diethylene triamine, di(trimethylene)triamine, dipropylenetriamine, triethylenetetramine, etc. Such amines encompass isomers which are the branched- chain polyamines and the previously mentioned substituted polyamines, including hydroxy and hydrocarbyl-substituted polyamines. Among the polyalkylene polyamines, those containing 2 to 12 amine nitrogen atoms and 2 to 24 carbon atoms, are especially preferred and the C₂ to C₃ alkylene polyamines are most preferred, in particular, the lower polyalkylene polyamines, e.g. ethylene diamine, tetraethylenepentamine, etc.

[0028] In many instances a single compound will not be used as reactant in the preparation of the compositions of this invention, in particular the polyamine component. That is, mixtures will be used in which one or two compounds will predominate with the average composition indicated.

The Quaternized Composition

[0029] The final compositions of the present invention are prepared by the quaternization of the polyether polyamines using alkyl halides. Quaternary ammonium compounds are generally prepared by the reaction of amines with alkyl halides. These compounds have 4 carbon atoms linked directly to a nitrogen atom through covalent bonding. The anion in the original alkylating agent is therefore linked to the nitrogen through an electrovalent bond. The compositions are prepared by reacting the appropriate polyether polyamine with an alkyl halide containing from 1 to 20 carbon atoms. The alkyl halide may also contain aromatics such as benzyl, etc. The halides utilized in the alkyl halides of the present invention ordinarily consist of chloride, bromide and iodide. The anion portion of the quaternized ammonium compounds may also be exchanged for other anions such as acetate, trimethylacetate, alkylphenoxide, or hydroxide. These may be generalized as C₂ to C₁₂ carboxylate anions, C₆ to C₃₀ phenoxides, or alkyl-substituted phenoxides. The polyether polyamines are quaternized by standard quaternizing reactions; that is, mixing appropriate amounts of the amine and the alkyl halide and applying heat.

[0030] A generalized, preferred formula for the quaternized polyether polyamines finding utility in this invention is as follows:

wherein

R = an alkyl group of 5 to 30 carbon atoms, aryl group of 6 to 30 carbon atoms, alkaryl group of 7 to 30 carbon atoms, aralkyl group of 7 to 30 carbon atoms, or methylol-substituted alkyl group of 5 to 30 carbon atoms;

R' and R" independently = hydrogen, methyl or ethyl;

n = 5 to 30, preferably 10 to 25;

X = the connecting group as defined above;

Rⁱⁱⁱ = a chemical bond, an alkylene or hydroxy substituted alkylene group of 2 to 12 carbon atoms, or (̵NH―CH₂―CH₂)̵_x, where x = 0 to 5;

R^ivand R^v independently = alkyl groups of 1 to 20 carbon atoms, aralkyl group of 7 to 20 carbon atoms, alkaryl group of 7 to 20 carbon atoms, or phenyl;

R" = alkyl groups of 1 to 20 carbon atoms, aralkyl groups of 7 to 20 carbon atoms, alkaryl groups of 7 to 20 carbon atoms, phenyl, or

where x = 1 to 5; and

Y = a halide, a C₂ to C₁₂ carboxylate anion, or a C₆ to C₃₀ phenoxide or alkyl-substituted phenoxide.

[0031] The proper concentration of the additive in fuel necessary in order to achieve the desired deposit control effect or carburetor detergency is dependent upon a variety of factors, including type of fuel used, the presence of other detergents or dispersants, or other additives, etc. Generally, however, and in the preferred embodiment, the range of concentration of the additive in the base fuel is from 30 to 10,000 weight ppm, preferably from 30 to 2,000 weight ppm, and most preferably from 100 to 700 ppm of quaternized polyether polyamine per part of base fuel. If other detergents are present, a lesser amount of quaternized polyether polyamine may be used.

[0032] The oils which find use in this invention are oils of lubricating oil viscosity derived from petroleum or synthetic sources. Oils of lubricating viscosity normally have viscosities in the range of 35 to 50,000 Saybolt Universal Seconds (SUS) at 37.8°C, and more usually from about 50 to 10,000 SUS at 37.8°C. Examples of such base oils are naphthenic bases; paraffin bases; mixed-base mineral oils; and synthetic oils, for example, alkylene polymers such as polymers of propyiene, butylene, etc.; and mixtures thereof.

[0033] Usually included in the oils besides the subject additives are such additives as dispersants/detergents, rust inhibitors, anti-oxidants, oiliness agents, foam inhibitors, viscosity index improvers, pour point depressants, etc. Usually, these other additives will be present in amounts of from about 0.5 to 15.0 weight percent of the total composition. Generally, each of the additives will be present in the range from about 0.01 to 5.0 weight percent of the total composition.

[0034] It is also contemplated that the quaternized polyether polyamines may be used as concentrates, and could be used as additives to fuels or lubricating oils subsequent to their preparation. In concentrates, the weight percent of these additives will usually range from 10 to 50 weight percent. The concentrate would ordinarily comprise an inert, stable oleophilic, organic solvent and the carrier of said solvent, boiling in the range of from about 65.6°C to 204.4°C.

[0035] The following examples are presented to illustrate a specific embodiment of the practice of this invention and should not be interpreted as a limitation upon the scope of that invention.

Examples

Example 1

Preparation of

[0036] 

[0037] To an ice-cold solution of 55 mls (0.724 moles) dimethyl hydrazine in 100 mls methylene chloride was added a solution of 600 gms (0.360 equivalents)

in 600 mls methylene chloride at a rate of approximately 1 drop/second with vigorous stirring under an atmosphere of nitrogen.

[0038] After the addition was complete, the reaction was warmed to room temperature and concentrated in vacuo to afford a slurry. This slurry was dissolved in approximately 600 mls of toluene and extracted once with 100 mls of water, once with 100 mls saturated aqueous NaHC0₃ and then with water until the washings were neutral (pH paper). The organic layer was dried over anh. MgS0₄, filtered and stripped in vacuo to afford 634 gms of a golden oil: Basic nitrogen = 0.67%; total nitrogen = 1.39%; IR (cm^-1) 1730 (C=O), 3310 (N-H).

Example 2

Preparation of

[0039] 

The procedure of M. S. Brown [J. Chem. and Eng. Data, 12 (4) 612 (1967)] was followed. To 570 gms (0.326 equivalents) of the polyether dimethyl hydrazine carbamate prepared in Example 1 was added 41 mls (0.658 moles) of methyl iodide dropwise over approximately 10 minutes under an atmosphere of nitrogen with vigorous stirring. The reaction was stirred at room temperature and monitored by IR until all the starting material had reacted (approximatley 18 hours). The reaction was then stripped in vacuo to afford an oil: IR 1750 cm^-1 (C=O).

Example 3

Preparation of

[0040] 

To an ice-cold solution of 300 gms (0.166 moles)

in 50 mls of dimethylformamide and 80 mls tributylamine was added 11 mls (0.166 moles) methyl iodide dropwise with vigorous stirring under an atmosphere of nitrogen. After the addition, the reaction was heated to 60°C for 1 hour and then allowed to cool to room temperature with stirring overnight. The reaction was then extracted with water until the washings were neutral (pH dried over Na2S04 and stripped to afford an oil: Basic nitrogen = 0%; IR (cm-¹) 1710 (carbamate C=O), 3320 (N-H).

Example 4

Preparation of

[0041] 

Claims

1. Quaternized polyoxyalkylene amine salts of molecular weight in the range from 500 to 2500 and comprising a polyoxyalkylene moiety attached by a connecting group to an amine moiety, said polyoxyalkylene moiety comprising 5 to 30 oxyalkylene units selected from oxyalkylene units having from 2 to 4 carbon atoms; said connecting group being a diradical containing one or more atoms selected from hydrogen, carbon, oxygen, sulfur and nitrogen atoms, and said amine moiety being derived from ammonia or a polyamine having from 2 to 12 amine nitrogen atoms and from 2 to 40 carbon atoms and being quaternized with hydrocarbyl groups selected from alkyl groups containing from 1 to 20 carbon atoms, aralkyl groups containing from 7 to 20 carbon atoms, alkaryl groups containing from 7 to 20 carbon atoms and phenyl.

2. Quaternized polyoxyalkylene amine salts as claimed in Claim 1, wherein the amine moiety is quaternized with alkyl groups.

3. Quaternized polyoxyalkylene amine salts as claimed in Claim 1 represented by the general formula:

where R represents an alkyl group of 5 to 30 carbon atoms, aryl group of 6 to 30 carbon atoms, alkaryl group of 7 to 30 carbon atoms, aralkyl group of 7 to 30 carbon atoms, or methylol-substituted alkyl group of 5 to 30 carbon atoms;

R¹ and Rⁱⁱ independently represent hydrogen, methyl or ethyl; n is 5 to 30;

X represents a connecting group selected from:

where Z and Z' are H or a methyl or ethyl group;

Rill represents a chemical bond, an alkylene or hydroxy-substituted alkylene group of 2 to 12 carbon atoms, or (̵NH―CH₂―CH₂)̵_x, where x is 0 to 5;

R'" and R" independently represent an alkyl group of 1 to 20 carbon atoms, aralkyl group of 7 to 20 carbon atoms, alkaryl group of 7 to 20 carbon atoms, or phenyl;

R^vi represents an alkyl group of 1 to 20 carbon atoms, an aralkyl group of 7 to 20 carbon atoms, an alkary group of 7 to 20 carbon atoms, phenyl, or

+CH₂ CH₂ N^H)̵_xH, where x is 1 to 5; and

Y represents a halide, a C₂ to C₁₂ carboxylate anion, or a C₆ to C₃₀ phenoxide or alkyl-substituted phenoxide.

4. Quaternized polyoxyalkylene amine salts as claimed in Claim 3, wherein R'", R^v and R"' are all alkyl groups.

5. A quaternized amine salt in accordance with Claim 1 represented by the formula:

6. A quaternized amine salt in accordance with Claim 1 represented by the formula:

7. A quaternized amine salt in accordance with Claim 1 represented by the formula:

8. A fuel composition comprising a liquid hydrocarbon fuel boiling in the gasoline range and from 30 to 10,000 weight ppm of a quaternized amine salt as claimed in any one of Claims 1 to 7.

9. A fuel composition as claimed in Claim 8, wherein the quaternized amine salt is present in a concentration of from 100 to 700 weight ppm.

10. A lubricating oil composition comprising an oil of lubricating viscosity and from 0.01 to 10.0 percent by weight of the total composition of a quaternized amine salt as claimed in any one of Claims 1 to 7.

11. A concentrate comprising an inert, stable oleophilic organic solvent boiling in the range from 65.6°C to 204.4°C and from 10 to 50 weight percent of a quaternized amine salt as claimed in any one of Claims 1 to 7.

12. Use as a deposit control additive in a hydrocarbon fuel composition or lubricating oil composition for use in an internal combustion engine of a quaternized polyoxyalkylene amine salt as claimed in any one of Claims 1 to 7.

Ansprüche

1. Quaternisierte Polyoxyalkylenaminsalze mit einem Molekulargewicht im Bereich von 500 bis 2500 aus einem Polyoxyalkylenanteil, der über eine verbindende Gruppe mit einem Aminanteil verknüpft ist, wobei der Polyoxyalkylenanteil 5 bis 30 Oxyalkyleneinheiten aufweist, ausgewählt aus Oxyalkyleneinheiten mit 2 bis 4 Kohlenstoffatomen, die verbindende Gruppe ein Diradikal ist, der 1 oder mehr Atome enthält, ausgewählt aus Wasserstoff-, Kohlenstoff-, Sauerstoff-, Schwefel- und Stickstoffatomen, und wobei der Aminanteil auf Ammoniak oder ein Polyamin mit 2 bis 12 Aminstickstoffatomen und 2 bis 40 Kohlenstoffatomen zurückgeht und mit Hydrocarbylgruppen quaternisiert ist, ausgewählt aus Alkylgruppen, die 1 bis 20 Kohlenstoffatome enthalten, Aralkylgruppen, die 7 bis 20 Kohlenstoffatome enthalten, Alkarylgruppen, die 7 bis 20 Kohlenstoffatome enthalten und Phenyl.

2. Quaternisierte Polyoxyalkylenaminsalze gemäß Anspruch 1, wobei der Aminanteil mit Alkylgruppen quaternisiert ist.

3. Quaternisierte Polyoxyalkylenaminsalze nach Anspruch 1, der allgemeinen Formel

worin R eine Alkylgrupe mit 5 bis 30 Kohlenstoffatomen, eine Arylgruppe mit 6 bis 30 Kohlenstoffatomen, eine Alkarylgruppe mit 7 bis 30 Kohlenstoffatomen, eine Aralkylgruppe mit 7 bis 30 Kohlenstoffatomen oder methylolsubstituierte Alkylgruppe mit 5 bis 30 Kohlenstoffatomen ist, R' und R" unabhängig voneinander für Wasserstoff, Methyl oder Ethyl stehen, N 5 bis 30 ist, X eine verbindende Gruppe ist, ausgewählt aus





worin Z und Z' für H oder eine Methyl- oder Ethylgruppe steht, Rⁱⁱⁱ eine chemische Bindung, eine Alkylen-oder Hydroxy-substituierte Alkylengruppe mit 2 bis 12 Kohlenstoffatomen oder (̵NH―CH₂―CH₂)̵_x bedeutet, worin X 0 bis 5 ist, R'" und R" unabhängig voneinander eine Alkylgruppe mit 1 bis 20 Kohlenstoffatomen, Aralkylgruppe mit 7 bis 20 Kohlenstoffatomen, Alkarylgruppe mit 7 bis 20 Kohlenstoffatomen oder Phenyl darstellen,

R^vi eine Alkylgruppe mit 1 bis 20 Kohlenstoffatomen, eine Aralkylgruppe mit 7 bis 20 Kohlenstoffatomen, eine Alkarylgruppe mit 7 bis 20 Kohlenstoffatomen, Phenyl, oder (̵CH₂ CH₂ N^H)̵_xH bedeutet, wobei x 1 bis 5 ist, und Y ein Halogenid, eine C₂- bis C₁₂-Carboxylatanion oder ein C₆- bis C₃₀-Phenoxid oder ein Alkyl-substituiertes Phenoxid ist.

4. Quaternisierte Polyoxyalkylenaminsalze nach Anspruch 3, wobei R^iv, R^v und R^vi jeweils Alkylgruppen sind.

5. Quaternisiertes Aminsalz gemäß Anspruch 1 der Formel:

6. Quaternisiertes Aminsalz gemäß Anspruch 1 der Formel:

7. Quaternisiertes Aminsalz gemäß Anspruch 1 der Formel:

8. Treibstoffzubereitung aus einem flüssigen Kohlenwasserstofftreibstoff, der im Benzinbereich siedet, und 30 bis 10000 Gewicht-ppm eines quaternisierten Aminsalzes gemäß einem der Ansprüche 1 bis 7.

9. Treibstoffzusammensetzung nach Anspruch 8, wobei das quaternisierte Aminsalz in einer Konzentration von 100 bis 700 Gewicht-ppm vorliegt.

10. Schmierölzubereitung aus einem Öl mit Schmierviskosität und 0,01 bis 10 Gewichtsprozent, bezogen auf das Gesamtgewicht der Zubereitung, eines quaternisierten Aminsalzes gemäß einem der Ansprüche 1 bis 7.

11. Konzentrat aus einem inerten, stabilen oleofinen organischen Lösungsmittel, das im Bereich von 65,6°C bis 204,4°C siedet, und 10 bis 50 Gewichtsprozent eines quaternisierten Aminsalzes gemäß einem der Ansprüche 1 bis 7.

12. Verwendung eines quaternisierten Polyoxyalkylenaminsalzes gemäß einem der Ansprüche 1 bis 7 als Ablagerungen steuerndes Additiv in einer Kohlenwasserstofftreibstoffzubereitung oder in einer Schmierölzubereitung für eine Verwendung in einem Verbrennungsmotor.

Revendications

1. Sels quaternisés de polyoxyalkylène-amines de poids moléculaire compris dans la plage de 500 à 2500 et comprenant un groupement polyoxyalkylène attaché par un groupe de jonction à un groupement amine, ledit groupement polyoxyalkylène comportant 5 à 30 motifs oxyalkylène choisis entre des motifs oxyalkylène ayant 2 à 4 atomes de carbone; ledit groupe de jonction étant un diradical contenant un ou plusieurs atomes choisis entre des atomes d'hydrogène, de carbone, d'oxygène, de soufre et d'azote, et ledit groupement amine étant dérivé d'ammoniac ou d'une polyamine ayant 2 à 12 atomes d'azote d'amine et 2 à 40 atomes de carbone, et étant quaternisé avec des groupes hydrocarbyle choisis parmi des groupes alkyle contenant 1 à 20 atomes de carbone, des groupes aralkyle contenant 7 à 20 atomes de carbone, des groupes alkaryle contenant 7 à 20 atomes de carbone et le groupe phényle.

2. Sels quaternisés de polyoxyalkylène-amines suivant la revendication 1, dans lesquels le groupement amine est quaternisé avec des groupes alkyle.

3. Sels quaternisés de polyoxyalkylène-amines suivant la revendication 1, représentés par la formule générale:

dans laquelle R représente un groupe alkyle de 5 à 30 atomes de carbone, un groupe aryle de 6 à 30 atomes de carbone, un groupe alkaryle de 7 à 30 atomes de carbone, un groupe aralkyle de 7 à 30 atomes de carbone ou un groupe alkyle à substituant méthylol de 5 à 30 atomes de carbone;

R' et R" représentent indépendamment l'hydrogène, un groupe méthyle ou éthyle; n a une valeur de 5 à 30;

X représente un groupe de jonction choisi entre:

où Z et Z' représentent l'hydrogène ou un groupe méthyle ou éthyle; Rⁱⁱⁱ représente une liaison chimique, un groupe alkylène ou alkylène à substituant hydroxy ayant 2 à 12 atomes de carbone, ou un groupe (NH-CH₂CH₂)_x, dans lequel x a une valeur de 0 à 5;

R^iv et R" représentent indépendamment un groupe alkyle de 1 a 20 atomes de carbone, un groupe aralkyle de 7 à 20 atomes de carbone, un groupe alkaryle de 7 à 20 atomes de carbone ou un groupe phényle;

R" représente un groupe alkyle de 1 à 20 atomes de carbone, un groupe aralkyle de 7 à 20 atomes de carbone, un groupe alkaryle de 7 à 20 atomes de carbone, un groupe phényle ou un groupe (CH₂ CH₂ N^H)_xH, dans lequel x a une valeur de 1 à 5; et

Y représente un halogénure, un anion carboxylate en C₂ à C₁₂, ou un phénate en C₆ à C₃₀ ou phénate à substituant alkyle.

4. Sels quaternisés de polyoxyaikylène-amines suivant la revendication 3, dans lesquels R^iv, R^v et R^vi sont tous des groupes alkyle.

5. Sel d'amine quaternisé suivant la revendication 1, représenté par la formule:

6. Sel d'amine quaternisé suivant la revendication 1, représenté par la formule:

7. Sel d'amine quaternisé suivant la revendication 1, représenté par la formule:

8. Composition de carburant, comprenant un carburant hydrocarboné liquide bouillant dans la plage de l'essence ét 30 à 10 000 ppm en poids d'un sel d'amine quaternisé l'une quelconque des revendications 1 à 7.

9. Composition de carburant suivant la revendication 8, dans laquelle le sel d'amine quaternisé est présent à une concentration de 100 à 700 ppm en poids.

10. Composition d'huile lubrifiante comprenant une huile de viscosité propre à la lubrification et 0,01 à 10,0 pour cent en poids de la composition totale, d'un sel d'amine quaternisé suivant l'une quelconque des revendications 1 à 7.

11. Concentré comprenant un solvant organique oléophile stable, inerte, bouillant dans la plage de 65,6°C à 204,4°C et 10 à 50 pour cent en poids d'un sel d'amine quaternisé suivant l'une quelconque des revendications 1 à 7.

12. Utilisation comme additif inhibant la formation de dépôts dans une composition de carburant hydrocarboné ou dans une composition d'huile lubrifiante destinée à être utilisée dans un moteur à combustion interne, d'un sel quaternisé d'amine polyoxyalkylénique suivant l'une quelconque des revendications 1 à 7.