DE102007058429A1 - Compounds and lubricant compositions containing these compounds - Google Patents

Abstract

An imidazoline compound comprising the reaction product of (i) a dicarbonyl, (ii) a primary amine moiety of a polyamine, and (iii) a hydrocarbylcarbonyl is disclosed. Lubricants and fuel additive compositions comprising the imidazoline compounds are also disclosed.

Description

Description of the Revelation

Area of the revelation

The The present application relates to compounds and methods of preparation compounds and in particular compounds which are and lubricant compositions can be used.

Background of the Revelation

It has already been a considerable effort on the Development of chemical products as dispersing additives for Internal combustion engines used. Oil-soluble dispersants for lubricating oil were used to control deposition and varnish and sludge and other solid substances, as oxidized base oil in suspension in the lubricating oil to keep. Dispersants reduce when added to hydrocarbon fuels, which are used in the engines, effectively the deposit formation, usually in carburettor openings, throttle bodies, Air funnels, inlet ports and intake valves occurs. The reduction of these deposit concentrations has become one increased engine efficiency and a reduction in the Concentration of hydrocarbon and carbon monoxide emissions guided.

In spite of progress in the use of dispersants as oil and fuel additives are still in need of continuous improvement in the ability of dispersants to suspend sludge and / or to disperse particulate matter. Thus, new ones Compounds which have improved dispersing properties, he wishes.

Summary of the Revelation

According to the Disclosure relates to an aspect of the present application Imidazoline compound which is the reaction product of (i) a dicarbonyl, (ii) a primary amine moiety of a polyamine and (iii) of a hydrocarbylcarbonyl.

One Another aspect of the present invention relates to an imidazoline compound, the reaction product of a dicarbonyl and a mono-hydrocarbyl polyamine wherein the mono-hydrocarbyl polyamine by reaction of a Hydrocarbylcarbonyls and a polyamine is formed.

One Another aspect of the present invention relates to a lubricant composition, which comprises a base oil and an imidazoline compound, the reaction product of (i) a dicarbonyl, (ii) a primary Amine moiety of a polyamine and (iii) a hydrocarbylcarbonyl includes.

One Another aspect of the present application relates to a method for reducing deposits on a lubricated surface, the method comprising lubricating the surface with a A lubricant composition according to the present invention Application, wherein the imidazoline compound of the present Registration in the lubricant composition in an amount is sufficient to reduce the amount of deposits on the lubricated Reduce surface area compared to the amount of Deposits on the surface, the same operating conditions and lubricated with the same lubricant composition except that the composition lacks the imidazoline compound.

One Another aspect of the present application relates to a method for improving the suspension of sludge, comprising providing for a combustion system of the lubricant composition of the present application, wherein the imidazoline compounds in a lot are present, sufficient to at least a little mud upright in suspension in the base oil for a time to get that is longer than if the base oil not containing the imidazoline compounds.

One Another aspect of the present application relates to a lubricant additive package composition, a diluent and an imidazoline compound of the present application.

Another aspect of the present application relates to a fuel composition comprising a base oil and an imidazole compound containing the reaction product of (i) a dicarbonyl, (ii) a primary amine moiety of a polyamine and (iii) a hydrocarbylcarbonyl.

One Another aspect of the present application relates to a method for reducing deposits in the fuel system of an internal combustion engine, the process being used as the fuel for the internal combustion engine the fuel composition of the present Application, wherein the imidazoline compound of the present Registration in the fuel is present in an amount that is sufficient To reduce the deposits in the fuel system, in comparison to the amount of deposits in the fuel system that on the same way and using the same fuel composition is operated except that of the fuel composition the imidazoline compound is missing.

One Another aspect of the present application relates to a method for the dispersion of carbon black, comprising the provision of Fuel composition of the present application for a combustion system, wherein the imidazoline compound of the present Registration exists in an amount that is sufficient to at least some soot in suspension in the base fuel for to hold a time longer than when the base fuel the imidazoline compound did not contain.

One Another aspect of the present application relates to a fuel additive package composition which a diluent and the imidazoline compound of This application comprises

One Another aspect of the present application relates to a method for forming an imidazoline compound comprising the reaction of (i) a dicarbonyl, (ii) a primary amine moiety a polyamine and (iii) a hydrocarbylcarbonyl.

Again Another aspect of the present application relates to a method for forming an additive compound, comprising reacting a Dicarbonyl compound and a monohydrocarbylpolyamine.

additional Aspects and advantages of the disclosure will become apparent in the part of the specification, which follows, sets out and can through the practice of the revelation be learned. It goes without saying that both the previous general description as well as the following detailed description only as an example and explanatory and do not limit the disclosure as claimed.

Description of the embodiments

One Aspect of the present application relates to the production of new ones Imidazoline compounds and their uses. The imidazoline compounds may be the reaction product of (i) a dicarbonyl, (ii) a primary amine moiety of a polyamine and (iii) of a hydrocarbylcarbonyl. The compounds of the present Registration are designed to provide localized polarity regions exhibit. These localized polar regions are said to be compounds which may have one or more advantages, such as an improved ability of the dispersant, To suspend sludge and / or soot by ionic and to disperse dipolar interactions; and / or an improved one Ability to remove injector and / or valve deposits in internal combustion engines.

In In some aspects, the compounds of the present application by preparing a polyamine intermediate comprising a hydrocarbylcarbonyl implemented. The intermediate can be through implementation of a dicarbonyl having a primary amine moiety of a Polyamines are produced. Other suitable methods for forming the compounds of the present application can be used as discussed in more detail below.

dicarbonyl

The Dicarbonyl reactant compounds used in the present application may include any dicarbonyl compound, which is suitable for forming the desired intermediate. Non-limiting examples of suitable dicarbonyl compounds include alpha-omega-dicarboxylic acids and esters thereof.

sein, wobei n von 0 bis etwa 20 reicht, wie etwa 1 bis etwa 16; und R¹, R², R' und R'' unabhängig aus einem Kohlenwasserstoffatom und einer Alkylgruppe ausgewählt sind. Geeignete Alkylgruppen können beispielsweise lineare oder verzweigte C₁- bis C₁₀-Alkylgruppen umfassen, wie Methyl, Ethyl und Butyl.In one aspect, the dicarbonyl compound may be a compound of formula I

where n ranges from 0 to about 20, such as from 1 to about 16; and R ¹ , R ² , R 'and R "are independently selected from a hydrocarbon atom and an alkyl group. Suitable alkyl groups may include, for example, linear or branched C ₁ to C ₁₀ alkyl groups, such as methyl, ethyl and butyl.

In In some aspects of the present application, it may be desirable be that n is not chosen as 2 or 3. This is based that if n is 2 or 3, an internal cyclization of the Compound of formula I may occur which in reaction with a polyamine to form a 5- or 6-atom imide ring structure, like a succinimide. This can potentially be the impede the desired reaction and the formation of an imidazoline exclude. Thus, in such cases the Dicarbonyl compound no succinic, glutaric or succinate or glutarate derivative of the formula I.

Non-limiting examples of the dicarbonyl compounds include dicarboxylic acids selected from oxalic acid, malonic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, hexadecanedioic acid and isophthalic acid, and esters of any one of these dicarboxylic acids such as methyl, ethyl and butyl ester. In one aspect of the present application, the dicarbonyl compound may be an alkylated diester. For example, R ¹ and R ² of Formula I may be methyl groups, R 'and R "may be ethyl groups, and n may be 1; thereby forming the alkylated diester, dimethyl diethyl malonate.

polyamine

In In some aspects of the present application, the formation the polyamine intermediate used in the present application Polyamine reactant linear, branched or cyclic polyalkyleneamine with at least one primary amine moiety. In In some aspects, the polyamine may have at least three nitrogen atoms exhibit.

sein, wobei R⁶ ein Wasserstoffatom oder eine niedermolekulare Alkylgruppe mit etwa 1 bis etwa 6 Kohlenstoffatomen sein kann, q eine ganze Zahl im Bereich von etwa 1 bis etwa 3 sein kann und m eine ganze Zahl im Bereich von etwa 2 bis etwa 10 sein kann, wie etwa 3 bis etwa 8. Nicht einschränkende Beispiele für R⁶-Alkylgruppen umfassen Methyl, Ethyl, Propyl oder Butyl.For example, the polyamine may be a polyalkyleneamine of the following formula II

wherein R ^{6 may be} a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms, q may be an integer ranging from about 1 to about 3, and m may be an integer ranging from about 2 to about 10 such as 3 to about 8. Non-limiting examples of R ⁶ alkyl groups include methyl, ethyl, propyl or butyl.

Not limiting examples of suitable polyamines include propylenediamine, butylenediamine, diethylenetriamine (DETA), Triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), Hexaethyleneheptamine (HEHA), dipropylenetriamine and tripropylenetetramine. The polyamines can be linear, branched or cyclic Include compounds or mixtures thereof. In one Aspect, the polyamine is a polyethyleneamine, such as DETA, TETA, TEPA, PEHA and HEHA. In one aspect, the polyamine may be a copolymer of one of the aforementioned polyethyleneamines, which in molecular weight range from about 100 to about 600.

In In some aspects, the polyamines may be mixtures of two or more polyamine compounds, such as mixtures of two or more Compounds selected from TEPA, PEHA, HEHA, and higher molecular weight polyethylene amine products. In some aspects, the mixture may include heavy polyamines. A heavy polyamine is a mixture of polyalkyleneamines which include small amounts of lower amine oligomers, like TEPA and PEHA, which are mainly oligomers with 7 or more nitrogen atoms, 2 or more primary amines per molecule and a stronger branching than conventional ones Include amine mixtures.

The dicarbonyl and polyamine reactants may be combined under any suitable reaction conditions which result in the desired intermediate imidazoline compound. In one aspect the dicarbonyl and the polyamine are combined and heated to a reaction temperature in the range of from about 150 ° C to about 250 ° C under nitrogen or other relatively inert atmosphere, such as under vacuum, until alcohol and / or water are removed and the imidazoline product is formed is. This reaction time may be, for example, about 2 to about 6 hours. At this time, the imidazoline product can be isolated to form a polyamine intermediate of the present application.

The Reaction can be carried out neat or with solvents become. Optionally, water or solvents be removed during or after the reaction to the to provide the desired polyamine intermediate.

at In one aspect of the present application, the dicarbonyl may be in polyamine ratio be any suitable ratio such that at least two unreacted primary amine groups in the Lag behind. For example, the molar ratio the dicarbonyl compounds to the primary amine compounds from about 1: 1.1 to about 1: 2.

wobei x von etwa 1 bis etwa 11 reicht und n, R' und R'' wie zuvor hinsichtlich Formel I definiert sind, und m wie vorstehend bezüglich Formel II definiert ist.The resulting intermediate compound comprises one or more polyamine groups attached to one or more imidazoline amide groups and / or one or more bisimidazoline groups. For example, the intermediate compound may be a polyamine-imidazoline amide compound of the formula IIIa or a polyamine-bis-imidazoline of the formula IIIb or mixtures thereof.

wherein x ranges from about 1 to about 11 and n, R 'and R "are as previously defined with respect to formula I, and m is as defined above with respect to formula II.

Hydrocarbylcarbonylverbindung

The hydrocarbylcarbonyl reactant compound of the present application may be any suitable compound having a hydrocarbyl group and a carbonyl moiety and capable of bonding with the intermediate polyamine compounds to form the compounds of the present application. Non-limiting examples of suitable hydrocarbylcarbonyl compounds include, but are not limited to, hydrocarbyl-substituted succinic anhydrides, hydrocarbyl-substituted succinic acids, and esters of hydrocarbyl-substituted succinic acids. Specific examples include such compounds as dodecenyl succinic anhydride, C _16-18 alkenyl succinic anhydride and polyisobutenyl succinic anhydride (PIBSA). In some embodiments, the PIBSA may have a polyisobutylene moiety having a molecular weight in the range of about 200 to about 6000 daltons and a vinylidene content in the range of about 4% to about 100%. In some embodiments, the ratio of the number of carbonyl groups to the number of hydrocarbyl moieties in the hydrocarbylcarbonyl compound may range from about 1: 1 to about 6: 1.

• (1) Kohlenwasserstoffsubstituenten, d. h. aliphatische (z. B. Alkyl oder Alkenyl), alicyclische (z. B. Cycloalkyl, Cycloalkenyl) Substituenten und aromatisch-, aliphatisch- und alicyclisch-substituierte aromatische Substituenten sowie cyclische Substituenten, wobei der Ring durch einen anderen Teil des Moleküls vervollständigt ist (z. B. zwei Substituenten bilden miteinander einen alicyclischen Rest);
• (2) substituierte Kohlenwasserstoffsubstituenten, d. h. Substituenten, die Nicht-Kohlenwasserstoffgruppen enthalten, die in dem Zusammenhang der Beschreibung hier nicht den überwiegend Kohlenwasserstoffsubstituent andern (z. B. Halogen, insbesondere Chlor und Fluor), Hydroxy, Alkoxy, Mercapto, Alkylmercapto, Nitro, Nitroso und Sulfoxy);
• (3) Hetero-Substituenten, d. h. Substituenten, die obgleich sie einen überwiegend Kohlenwasserstoffcharakter besitzen, in dem Zusammenhang dieser Beschreibung in einem Ring oder einer Kette, die ansonsten aus Kohlenstoffatomen besteht, etwas anderes als Kohlenstoff enthalten. Heteroatome umfassen Schwefel, Sauerstoff, Stickstoff und schließen Substituenten ein, wie Pyridyl, Furyl, Thienyl und Imidazolyl. Im Allgemeinen sind nicht mehr als zwei, oder als ein weiteres Beispiel, nicht mehr als ein Nicht-Kohlenwasserstoffsubstituent auf jeweils zehn Kohlenstoffatome in der Hydrocarbylgruppe vorhanden; bei einigen Ausführungsformen ist kein Nicht-Kohlenwasserstoffsubstituent in der Hydrocarbylgruppe vorhanden.

As used herein, the term "hydrocarbyl group" or "hydrocarbyl" is used in its usual sense, which is well known to those skilled in the art. Specifically, it relates to a group in which a carbon atom is bonded directly to the remainder of a molecule and which has a predominantly hydrocarbon character. Examples of hydrocarbyl groups include:

• (1) Hydrocarbon substituents, that is, aliphatic (eg, alkyl or alkenyl), alicyclic (eg, cycloalkyl, cycloalkenyl) substituents, and aromatic, aliphatic, and alicyclic-substituted aromatic substituents, as well as cyclic substituents, wherein the ring is substituted by another Part of the molecule is completed (for example, two substituents together form an alicyclic radical);
• (2) substituted hydrocarbyl substituents, ie, substituents containing non-hydrocarbon groups which in the context of the description herein do not change the predominantly hydrocarbon substituent (eg, halogen, especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, Nitroso and sulfoxy);
• (3) Hetero-substituents, that is, substituents which, although predominantly hydrocarbon in character, in the context of this description in a ring or chain otherwise composed of carbon atoms, contain anything other than carbon. Heteroatoms include sulfur, oxygen, nitrogen and include substituents such as pyridyl, furyl, thienyl and imidazolyl. Generally, not more than two, or as another example, no more than one non-hydrocarbon substituent is present for every ten carbon atoms in the hydrocarbyl group; in some embodiments, no non-hydrocarbon substituent is present in the hydrocarbyl group.

wobei R¹⁴ eine Hydrocarbylgruppe ist, wie beispielsweise ein Polyolefinrest mit einem Zahlenmittel des Molekulargewichts von etwa 350 bis etwa 10.000 Dalton. Beispielsweise kann das Zahlenmittel des Molekulargewichts von R¹⁴ von etwa 1000 bis etwa 5000 Dalton reichen, wie gemessen durch GPC. Wenn nicht anderweitig angegeben, sind die Molekulargewichte in der vorliegenden Beschreibung Zahlenmittelmolekulargewichte.In some aspects, the hydrocarbylcarbonyl compound may be a polyalkylene succinic anhydride reactant having the following formula IV:

wherein R ^{14 is} a hydrocarbyl group, such as a polyolefin residue having a number average molecular weight of from about 350 to about 10,000 daltons. For example, the number average molecular weight of R ^{14 can range} from about 1000 to about 5000 daltons, as measured by GPC. Unless otherwise stated, molecular weights in the present specification are number average molecular weights.

In some aspects, R ¹⁴ may be a polyolefin moiety comprising one or more polymer units selected from linear or branched alkenyl moieties. In some aspects, the alkenyl units may have from about 2 to about 10 carbon atoms. For example, the polyolefin radical may comprise one or more linear or branched polymer units selected from ethylene radicals, propylene radicals, butylene radicals, pentene radicals, hexene radicals, octene radicals and decene radicals. In some aspects, R ¹⁴ may be a polyolefin moiety in the form of, for example, a homopolymer, copolymer or terpolymer. For example, the polyolefin residue may be a copolymer of ethylene and propylene. In another example, the polyolefin residue is a homopolymer of polyisobutylene. The polyolefin compounds used to form the R ¹⁴ polyolefin moieties can be formed by any suitable method, such as by conventional catalytic oligomerization of alkenes.

In some aspects, highly reactive polyisobutenes having relatively high levels of polymer molecules having a terminal vinylidene group can be used to form the hydrocarbyl substituent. In one example, at least 4% of the total terminal olefinic double bonds in such highly reactive polyisobutenes may be a methylvinylidene isomer. In other examples, 50% or more of the total terminal olefinic double bonds may be methylvinylidene isomers, such as at least 70%. Well-known highly reactive polyisobutenes are for example in the U.S. Patent No. 4,152,499 , the disclosure of which is incorporated herein by reference in its entirety.

The hydrocarbylcarbonyl compounds can be prepared using any suitable method. Methods of forming hydrocarbylcarbonyl compounds are well known in the art. An example of a known process for forming a hydrocarbylcarbonyl compound summarizes the mixing of a polyolefin and maleic anhydride. The polyolefin and maleic anhydride reactants are heated to temperatures of, for example, about 150 ° C to about 250 ° C, optionally using a catalyst such as chlorine or peroxide.

The Hydrocarbonylcarbonyl compound may be combined with the desired Polyamine intermediate under all suitable reaction conditions which are combined to give the desired imidazoline compound lead the present application. For example, can a mixture of the hydrocarbylcarbonyl compound and the polyamine intermediate to a temperature in the range of about 100 ° C to about 200 ° C, such as 140 ° C to about 180 ° C, under nitrogen or other relatively inert atmosphere, like vacuum, are heated. The reactant mixture can are heated at the reaction temperature until the desired Succinimide product is formed and optionally the complete Distance from water is reached. Suitable reaction times can for example, from about 2 hours to about 4 hours. The Reaction can be pure or with solvents and / or diluents, like process oil, to be driven. After completion of the reaction can The mixture is filtered to the desired dispersant to surrender.

at In an alternative embodiment, the reaction of the Dicarbonyl, polyamine and hydrocarbylcarbonyl compound in one different order than as described above. For example, instead of the Reaction of a dicarbonyl compound and a polyamine compound forming the above-described polyamine intermediate, the hydrocarbylcarbonyl compounds, which are described above, with those described above Polyamine compounds to form a monohydrocarbylpolyamine intermediate be implemented. The monohydrocarbylpolyamine intermediate can subsequently with the dicarbonyl compounds described above to form the desired compounds of the present invention Registration will be implemented.

wobei R⁶, R¹⁴, q und m wie vorstehend bezüglich der Formeln II und IV definiert sind. Nicht einschränkende Beispiele für solche Monohydrocarbylpolyaminverbindungen umfassen Polyaminsuccinimidverbindungen, wie Propylendiaminsuccinimid, Butylendiaminsuccinimid, Diethylentriamin(DETA)-succinimid, Triethylentetramin(TETA)-succinimid, Tetraethylenpentamin(TEPA)-succinimid, Pentaethylenhexamin(PEHA)-succinimid, Hexaethylenheptamin(HEHA)-succinimid, Dipropylentriaminsuccinimid und Tripropylentetraminsuccinimid, wovon alle mit einer R¹⁴-Hydrocarbylgruppe substituiert sind.In one aspect of the present application, the monohydrocarbylamine compounds employed may have from about 3 to about 10 nitrogen atoms, and the amine moiety may have at least one primary amine moiety. Examples of such monohydrocarbylpolyamine intermediate compounds may have the following formula V,

wherein R ⁶ , R ¹⁴ , q and m are as defined above with respect to formulas II and IV. Non-limiting examples of such monohydrocarbylpolyamine compounds include polyamine succinimide compounds such as propylenediamine succinimide, butylenediamine succinimide, diethylenetriamine (DETA) succinimide, triethylenetetramine (TETA) succinimide, tetraethylenepentamine (TEPA) succinimide, pentaethylenehexamine (PEHA) succinimide, hexaethyleneheptamine (HEHA) succinimide, dipropylenetriamine succinimide and tripropylenetetramine succinimide, all of which are substituted with an R ¹⁴ hydrocarbyl group.

The Monohydrocarbylamine compounds of the present application can by reacting the hydrocarbylcarbonyl and polyamine compounds under all reaction conditions leading to the desired Monohydrocarbylpolyaminverbindungen lead, are formed. For example, a 1: 1 molar equivalent of a Hydrocarbonylcarbonylverbindung and a polyamine mixed and on Temperatures in the range, for example, from about 120 ° C to heated to about 250 ° C.

In yet another embodiment, the monohydrocarbyl polyamine compounds employed may be any suitable polyamine obtained from a suitable source. For example, fatty acid compounds, such as TETRAMEEN OV, available from Akzo Nobel, or ADOGEN 670 and ADOGEN 770, available from Degussa, may be employed as the monohydrocarbyl polyamine compounds of the present application. Other examples of fatty acid amine compounds include fatty acid amides, such as those of the formula R ¹⁶ C (O) -NH ₂ (CH ₂ ) _r - [NH (CH ₂ ) _r -T-NH ₂ wherein R ^{16 is} a linear or branched, saturated or unsaturated C ₈ to C ₃₀ group, r = 2 or 3 and t is 0 to 10 means. Such fatty acid amides can be formed by any suitable method known in the art, such as by the reaction of fatty acids with polyamine compounds.

ist, wobei R', R'' und n wie vorstehend bezüglich Formel I definiert sind, umfassen.The monohydrocarbyl polyamine compounds can be reacted with any of the above-described dicarbonyl compounds, such as the dicarbonyl compounds of the formula I, to form the desired compounds of the present application. The reaction can be carried out by mixing all suitable amounts of the monohydrocarbyl polyamine compounds and the dicarbonyl compounds under suitable process conditions. For example, the molar ratio of the dicarbonyl compounds to the monohydrocarbyl polyamine compounds may range from about 1: 2 to about 4: 2, such as from 1: 2 to about 3: 4. The reaction may be carried out neat or in a process oil at a temperature in the range of about 80 ° C to about 200 ° C. The particular reaction temperature employed may effect the distribution of the reaction products. For example, diamides and linear amide series or polyamides may form at low temperatures ranging from about 80 ° C to about 150 ° C, while cyclic products such as imidazolines may be formed by heating to higher temperatures, such as from about 160 ° C to about 200 ° C, can form. Thus, to form the imidazoline compounds of the present application, the higher reaction temperatures can be employed. However, it may also be desirable to use this process to form the additive compounds at the lower temperatures when the compounds including the diamide groups are desired. Thus, the compounds formed by this process can be a central polyamine chain of one or more polyamine groups linked together with one or more groups selected from diamide groups, imidazoline amide groups and bisimidazoline groups, and a hydrocarbylcarbonyl group attached to at least one end the polyamine chain is attached include. The imidazolines are described in more detail below. The diamides can be compounds of formula X, as also shown below in the discussion of the product compounds, where Y is, for example, XIa

wherein R ', R "and n are as defined above with respect to formula I.

In An exemplary aspect of the present application may include Monohydrocarbylpolyamine compound at a temperature in the range from about 160 ° C to about 250 ° C under nitrogen or another relatively inert atmosphere, such as vacuum, to be heated. A dicarbonyl compound may then be added. The reactant mixture can be stirred and the selected Reaction temperature are heated until the desired Reaction product is formed, and optionally, the water and / or alcohol removed from the mixture. For example, you can suitable reaction times of about 1 hour to about 5 hours. The reaction can be pure or with solvents and / or Diluents, such as process oil, to be driven. Upon completion of the reaction, the mixture may be reacted with, for example Diluted process oil and filtered to the to provide desired dispersants.

Attaching products

worin z von 0 bis etwa 10 reicht, x von etwa 1 bis etwa 10 reicht, R¹⁴ wie vorstehend bezüglich der Formel IV definiert ist und Y aus einer oder mehreren Gruppierungen der Formeln XIb und XIc gewählt ist:

wobei n, R' und R'' wie zuvor bezüglich Formel I ausgeführt definiert sind. Die Verbindungen der Formel X sind nur beispielhaft, und andere Verbindungen können gebildet werden. Beispielsweise könnten die Ethylenamineinheiten:

der Formeln X, XIa, XIb bzw. XIc durch andere Amineinheiten ersetzt werden, die unter die allgemeineren Formeln:

fallen, wobei q und R⁶ wie vorstehend bezüglich der Formel II definiert sind. Bei wieder anderen Ausführungsformen können die Imidazolverbindungen der vorliegenden Anmeldung auch andere Y-Gruppierungen zusätzlich zu den Imidazolgruppierungen der Formeln XIb und XIc einschließen, wie die Diamidgruppierungen der Formeln XIa, die vorstehend beschrieben sind.In some aspects, the compounds of the present application may comprise a central polyamine chain of one or more polyamine groups linked together with one or more diamine groups, imidazolinamide groups, and / or one or more bisimidazoline groups, and a hydrocarbylcarbonyl group attached to one or both ends of the polyamine chain is linked. In aspects of the present application, the reaction product compounds may comprise at least one titratable nitrogen. Non-limiting examples of the polyamine succinimide compounds include compounds of the formula X:

wherein z ranges from 0 to about 10, x ranges from about 1 to about 10, R ^{14 is} as defined above with respect to formula IV and Y is selected from one or more moieties of formulas XIb and XIc:

where n, R 'and R "are defined as above with regard to formula I. The compounds of formula X are exemplary only, and other compounds can be formed. For example, the ethylenamine units could:

of the formulas X, XIa, XIb or XIc are replaced by other amine units which are classified under the more general formulas:

wherein q and R ^{6 are} as defined above with respect to formula II. In still other embodiments, the imidazole compounds of the present application may also include other Y groups in addition to the imidazole moieties of formulas XIb and XIc, such as the diamide moieties of formulas XIa described above.

wobei R¹⁴ eine Hydrocarbylgruppe wie beispielsweise ein Polyolefinrest mit einem Zahlenmittel des Molekulargewichts von etwa 350 bis etwa 10.000 Dalton ist.As mentioned above, the compounds of the present application are designed to have localized polarity regions. It is believed that these localized polar regions result in compounds that may have one or more benefits, such as an improved ability of the dispersant to suspend sludge and / or disperse soot through ionic and dipolar interactions; and / or improved ability to remove injector and / or valve deposits in internal combustion engines. In some aspects of the invention, it may be possible for the imidazoline amide compounds to have a unique hydrogen bonding network in a non-polar medium, as illustrated by Formula XII below, such as when the compounds are combined with a lubricating oil. The dashed lines in Formula XII represent potential hydrogen bonds,

wherein R ^{14 is} a hydrocarbyl group such as a polyolefin residue having a number average molecular weight of about 350 to about 10,000 daltons.

If the compounds of this application are used as dispersants in lubricating compositions They can be present in any suitable quantity be. In one example, the connections may be in one Amount of from about 0.1% to about 20% by weight of the total composition be present, such as from about 0.5 to about 15 wt .-%, and in one Another example is from about 1 to about 7% by weight.

The Lubricating compositions disclosed herein may be a base oil include. Base oils for use in the formulation of the disclosed compositions from, for example, synthetic or mineral oils and mixtures thereof.

The Base oil can be in a larger quantity be present, with "greater amount" being understood as meaning greater than or equal to 50% by weight of the lubricant composition, such as from about 80% to about 98% by weight of the lubricant composition is meant. The base oil typically has a viscosity from, for example, about 2 to about 15 cSt, and as another example from about 2 to about 10 cSt at 100 ° C.

Not limiting examples of mineral oils, which are suitable as base oils include animal oils and vegetable oils (eg castor oil, bacon oil) and other mineral lubricating oils, such as liquid Petroleum oils and solvents treated or Acid treated mineral lubricating oils of the paraffinic, naphthenic or mixed paraffinic-naphthenic types. oils which come from coal or shale, are also suitable. Farther are also oils that are from a gas-to-liquid process come, suitable.

Not limiting examples of synthetic oils include hydrocarbon oils such as polymerized and interpolymerized Olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, etc.); Polyalphaolefins such as poly (1-hexenes), poly (1-octenes), poly (1-decenes) etc. and mixtures thereof; Alkylbenzenes (eg dodecylbenzenes, tetradecylbenzenes, Dinonylbenzenes, di (2-ethylhexyl) benzenes, etc.); Polyphenyls (e.g. Biphenyls, terphenyl, alkylated polyphenyls, etc.); alkylated Diphenyl ethers and alkylated diphenyl sulfides and derivatives, analogs and homologs thereof and the like.

Alkylene oxide polymers and interpolymers and derivatives thereof, wherein the terminal hydroxyl groups have been modified by esterification, etherification, etc., constitute another class of known synthetic oils that can be used. Such oils are exemplified by the oils formed by polymerization of ethylene oxide or propylene oxide, the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methylpolyisopropylene glycol ethers having an average molecular weight of about 1000, diphenyl ethers of polyethylene glycol having a molecular weight of about 500-1000, diethyl ethers of polypropylene glycol having a molecular weight of 1000-1500, etc.) or Mono- and polycarboxylic acid esters thereof, for example the acetic acid esters, the mixed C _3-8 fatty acid esters or the C ₁₃ -oxoic acid diesters of tetraethylene glycol are prepared.

Another class of synthetic oils that can be used includes the esters of dicarboxylic acids (eg, phthalic, succinic, alkylsuccinic, alkenylsuccinic, maleic, azelaic, suberic, sebacic, fumaric, adipic, linoleic, malonic, alkyl malonic acids, alkenylmalonic acids, etc.) with a variety of alcohols (eg, butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol, etc.). Specific examples of these esters include dibutyl adipate, di (2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diesters of linoleic acid dimer, the complex ester prepared by reacting one mole of Sebacic acid is formed with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid, and the like.

Esters useful as synthetic oils also include those made from C _5-12 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol, tripentaerythritol, etc.

Therefore the base oil used to make the compositions, as described herein, from one of the base oils in Groups I-V, as in the American Petroleum Institute (API) Base Oil Interchangeability Guidelines become. Such base oil groups are as follows: Group I contains less than 90% saturated and / or more than 0.03% sulfur and has a viscosity index of greater or equal to 80 and less than 120; Group II contains more than or equal to 90% Saturated and less or equal 0.03% sulfur and has a viscosity index of greater or equal to 80 and less than 120; Group III contains more than or equal to 90% Saturated and less than or equal to 0.03% sulfur and has a viscosity index greater than or equal to 120; Group IV are polyalphaolefins (PAO); and group V does not include all others in group I, II, III or IV included stocks.

The Test methods used to define the above groups ASTM D2007 are for saturated; ASTM D2270 for the viscosity index and one of ASTM D2622, 4294, 4927 and 3120 for sulfur.

Group IV stocks d. H. Polyalphaolefins (PAO) include hydrogenated oligomers of a Alphaolefins, with the main methods of oligomerization radical methods, Ziegler catalysis and cationic Friedel-Crafts catalysis are.

The Polyalphaolefins typically have viscosities in the Range from 2 to 100 cSt at 100 ° C, for example 4 to 8 cSt at 100 ° C. You can, for example, oligomers branched or straight-chain alpha olefins of 2 to about 30 carbon atoms, non-limiting examples include polypropenes, polyisobutenes, poly-1-butenes, poly-1-hexenes, Poly-1-octenes and poly-1-decene. Included are homopolymers, Interpolymers and mixtures.

Regarding of the remainder of the stock referred to above a "Group I stock" also has a Group I stock, with the one Stock (stocks) of one or more other groups can be mixed, with the proviso that the resulting mixture has characteristics below those fall for group I stocks above are executed.

exemplary Stocks include Group I stocks and mixtures Group II holdings with a Group I holdings.

stocks which are suitable for use herein may be used a variety of different processes are manufactured, including, but not limited to distillation, solvent refining, Hydrogen processing, oligomerization, esterification and re-refining.

The base oil may be an oil derived from Fischer-Tropsch synthesized hydrocarbons. Fischer-Tropsch synthesized hydrocarbons can be produced using a Fischer-Tropsch catalyst from synthesis gas containing H ₂ and CO. Such hydrocarbons typically require further processing to be suitable as a base oil. For example, the hydrocarbons may be prepared using methods that are described in the U.S. Patent No. 6,103,099 or 6,180,575 disclosed are hydroisomerized; hydrocracked and hydroisomerized using methods disclosed in U.S. Pat U.S. Patent No. 4,943,672 or 6,096,940 are disclosed; are dewaxed using methods that in the U.S. Patent No. 5,882,505 are disclosed or hydroisomerized and dewaxed using methods described in U.S. Pat U.S. Patent No. 6,013,171 ; 6,080,301 or 6,165,949 are disclosed. The disclosures of each of these patents are incorporated herein by reference in their entirety as though fully set forth herein.

Unrefined, refined and refined oils, either mineral or synthetic (and gemi two or more of these) of the type disclosed hereinabove may be used in the base oils. Unrefined oils are those obtained directly from a mineral or synthetic source without further purification treatment. For example, a shale oil obtained directly from retort operations, a kerosene obtained directly from the primary distillation or an ester oil obtained directly from an esterification process and used without further treatment would be an unrefined oil. Refined oils are similar to unrefined oils except that they have been treated in one or more purification steps to improve one or more properties. Many such purification techniques are known to those skilled in the art, such as solvent extraction, secondary distillation, acid or base extraction, filtration, percolation, etc. Refined oils are obtained by methods similar to those used to obtain refined oils, which methods apply to refined oils be used already in use. Such refined oils are also known as reclaimed or re-processed oils and are often additionally processed by processes directed to the removal of spent additives, contaminants and oil degradation products.

The Lubricating compositions of the present application may in any engine or in other combustion or mechanical systems Devices are used, which can benefit from it. For example, the lubricant compositions for use in the crankcase of an internal combustion engine be suitable.

at In some embodiments, the compounds may be the present application of the lubricant composition in the Form of a lubricant additive package can be added. Lubricant additive packages include concentrates dissolved in a diluent, like mineral oil, synthetic hydrocarbon oils and mixtures thereof. When mixing with the base oil can these concentrate additive compositions are an effective concentration provide the additives in the base oil. The amount of Compounds of the present application in the lubricant additive packages may be from about 5% to about 75% by weight of the concentrate additive composition vary, such as from about 5% to about 50% by weight.

The lubricant additive package compositions and finished lubricants of the present application may contain other additional additives. Examples of such additional additives include additional dispersants other than the dispersants of the present application, detergents, antiwear agents, supplemental antioxidants, viscosity index improvers, pour point depressants, corrosion inhibitors, rust inhibitors, foam inhibitors, and friction modifiers. Such additives are well known in the art and the selection of effective amounts of additional additives in lubricant compositions is within the ordinary skill in the art. Non-limiting representative amounts of these additional additives are shown in the range 1 and in the range 2 of Table 1 below. additives Weight% range 1 Weight% range 2 Antioxidant system 0-5 0.01-3 metal detergents 0.1-15 0.2-8 corrosion inhibitor 0-5 0-2 Metal dihydrocarbyl dithiophosphate 0.1-6 0.1-4 Anti-foaming agents 0-5 0.001 to 0.15 friction 0-5 0-2 Complementary anti-wear agents 0-1.0 0-0.8 Pour-point depressants 0.01-5 0.01-1.5 viscosity modifiers 0.01-10 0.25 to 7 support material rest rest

at In one aspect, the present application relates to a method for Reduction of deposits on a lubricated surface, the method being used as the lubricating oil for includes the surface of a lubricating oil that the Imidazoline compound of the present invention. The imidazoline compound may be present in an amount that sufficient to reduce the amount of deposits on the surface to reduce compared to the amount of deposits on the surface would be formed if they would be subject to the same operating conditions and using the same lubricating oil, except that the oil lacks the imidazoline compound. Representative Examples of deposits that can be reduced using the compositions of the invention include piston deposits, ring land deposits, crown surface deposits and headface deposition.

In In another aspect, the present application relates to a method to improve the suspension of sludge in a lubricating oil. The method includes providing for a combustion system the lubricating oils of the present application, wherein the imidazoline compound is present in an amount that is sufficient to at least something Mud in suspension in the oil for a time to hold, which is longer, than if the oil the Imidazoline compound did not contain.

The Compounds of the present application are also useful as dispersants suitable in fuels. Thus, another aspect of the present invention Sign a fuel composition containing a larger amount of a fuel and a smaller amount of compounds present application, which is sufficient to a desired To provide dispersibility. The term "smaller Amount "is understood that less than 50 wt .-% of the lubricant composition are meant. The concentration of the additive in a fuel depends on a variety of factors including of the type of fuel used, the presence of other dispersants or other additives and the like. Non-limiting Exemplary concentrations may range from about 10 to about 10,000 ppm or from about 30 to about 5,000 ppm.

The base fuels used in formulating the fuel compositions of the present invention include all basic fuels suitable for use in the operation of gasoline engines or diesel engines, such as diesel fuel, jet fuel, kerosene, leaded or unleaded gasoline and aviation gasoline, and so-called reformulated gasolines which are both hydrocarbons the gasoline boiling range as well as fuel-soluble oxygenates, such as alcohols, ethers and other suitable oxygen-containing organic compounds. Examples of oxygenates suitable for use in the present application include methanol, ethanol, isopropanol, t-butanol, C ₁ to C ₅ alcohol mixtures, methyl tertiary butyl ether, tertiary amyl methyl ether, ethyl tertiary butyl ether, and mixtures of ethers. Oxygenates, when used, may be used in the base fuel in an amount below, for example, about 25% by volume. In some embodiments, the oxygenates may be present in an amount that provides an oxygen content in the total fuel in the range of about 0.5 to about 5% by volume.

The Basic fuels used in the formulation of the invention For example, fuel compositions may be used Diesel fuels with a sulfur content of up to about 0.2% by weight, such as up to about 0.05% by weight as specified by ASTM D 2622-98 Testing procedure. In some embodiments are suitable diesel fuels for use in the present Invention low sulfur diesel fuels.

In In another aspect of the present application are the Compounds of the present application as a dispersant in Fuel additive concentrates suitable. The fuel concentrates may be an inert stable organic solvent for a diluent and about 5 to 50% by weight an imidazoline compound of the present application. Non-limiting examples of suitable diluents include benzene, toluene, xylene or higher boiling aromatics.

In In one aspect, the present application relates to a method for Reduction of deposits in the fuel system of an internal combustion engine, the process being used as the fuel for the internal combustion engine of the fuel compositions described above includes. The compounds of the present application may be present in the fuel in an amount that is sufficient to reduce the deposits in the fuel system. The deposits can be reduced compared to the amount of deposits that would occur in the same fuel system in the same way and using the same fuel composition is operated when the fuel composition, the imidazoline compound would be missing.

In In one aspect, the present application relates to a method for Cleaning inlet valve deposits in a motor. The procedure includes the provision for a combustion system of the Fuel compositions of the present application, wherein the Imidazoline compound present in the fuel in an amount which is sufficient to purer inlet valve deposits for to maintain a period longer than if the fuel did not contain the imidazoline compound.

The The following examples are used for a specific explanation of the Invention cited. These examples and explanations should by no means limit the scope of the invention be interpreted.

EXAMPLES

example 1

In a 3 liter resin kettle equipped with an overhead stirrer 1087 g of alkylenyl succinic anhydride (acid number = 0.552) submitted. The PIBSA was heated to 180 ° C and stirred under a nitrogen atmosphere. 113.4 g TEPA were added via a dropping funnel. The reaction mixture was heated to 180 ° C under reduced pressure for 3 hours. 771.1 g of process oil was added. The reaction mixture was then heated to 180 ° C, and then 48.1 g of diethyl malonate was added. The reaction mixture was allowed to stand under reduced pressure for 3 hours Heated to 180 ° C. Subsequently, the Reaction mixture filtered, giving 1863 g of the desired Reaction product supplied.

Example 2

In a 3 liter resin kettle equipped with an overhead stirrer 1087 g of alkylenyl succinic anhydride (acid number = 0.552) submitted. The PIBSA was heated to 180 ° C and stirred under a nitrogen atmosphere. 113.4 g TEPA were added via a dropping funnel. The reaction mixture was heated under reduced pressure at 180 ° C for 3 hours. 781.6 g of process oil were added. Subsequently the reaction mixture was heated to 180 ° C, on which 52.3 g of dimethyl adipate were added. The reaction mixture was heated under reduced pressure to 180 ° C for 3 hours. Subsequently, the reaction mixture was filtered, giving 1853 g of the desired reaction product.

Example 3

In a 3 liter resin kettle equipped with an overhead stirrer 1087 g of alkylenyl succinic anhydride (acid number = 0.552) submitted. The PIBSA was heated to 180 ° C and stirred under a nitrogen atmosphere. 113.4 g TEPA were added via a dropping funnel. The reaction mixture was heated under reduced pressure at 180 ° C for 3 hours. 807.7 g of process oil was added. Subsequently the reaction mixture was heated to 180 ° C, and then 78.4 g of dimethyl adipate was added. The reaction mixture was added under reduced pressure for 3 hours Heated to 180 ° C. Subsequently, the Reaction mixture filtered, giving 1748 g of the desired Reaction product gave.

Example 4

In a 3 liter resin kettle equipped with an overhead stirrer 1087 g of alkylenyl succinic anhydride (acid number = 0.552) submitted. The PIBSA was heated to 180 ° C and stirred under a nitrogen atmosphere. 113.4 g TEPA were added via a dropping funnel. The reaction mixture was heated under reduced pressure to 180 ° C for 3 hours. 801.4 g of process oil was added. Subsequently the reaction mixture was heated to 180 ° C, whereupon 72.1 g of diethyl malonate was added. The reaction mixture was Heated under reduced pressure to 180 ° C for 3 hours. Subsequently, the reaction mixture was filtered, giving 1027 g of the desired reaction product.

Example 5

In a 3 liter resin kettle equipped with an overhead stirrer 1087 g of alkylenyl succinic anhydride (acid number = 0.552) submitted. The PIBSA was heated to 180 ° C and stirred under a nitrogen atmosphere. 113.4 g TEPA were added via a dropping funnel. The reaction mixture was heated under reduced pressure to 180 ° C for 3 hours. 787.6 g of process oil were added. The reaction mixture was then heated to 180 ° C, to which 58.3 g of dimethyl isophthalate was added. The reaction mixture was heated under reduced pressure at 180 ° C for 3 hours. Subsequently, the reaction mixture was filtered, giving 1840 g of the desired reaction product.

The dispersant additives of Examples 1 to 3 were each used in a passenger car motor oil formulation using other components, including metal-containing sulfonates, zinc dithiophosphate wear inhibitors, sulfur-containing antioxidants, diarylamine and phenol antioxidants, oleate and molybdenum friction modifiers, a pour point depressant, a viscosity index improver (HiTEC ^® 5751) and a lubricating base oil. These other components occurred in concentrations typically found in fully formulated multigrade passenger car engine oils.

The kinematic viscosity at 100 ° C (KV100) (mm ² / s) and the cold cranking simulator viscosity at 30 ° C (CCS-30) (centipoise) were determined and the results are shown in Table 2 below. Table 2 5W 30 mixed results dispersants PIB Mn solids KV100 CCS-30 example 1 2100 2.5 10.62 6010 Example 2 2100 2.5 11.28 6005 Example 3 2100 2.5 12.07 5990

In Table 3 below shows the slurry-containing properties of lubricants containing the dispersants of Examples 1, 2, 3 and 5, as described above, and a comparative lubricant, the one commercially available lubricant using the Sequence VG engine test (an industrial dispersant sludge test) compared to determine the average engine sludge ("AES"). The lubricants used were fully formulated Lubricant. In each example, the ingredients of the lubricant were exactly the same, with the exception of the dispersant.

Of the Sequence VG engine sludge and paint deposit test is a dynamometer test with ignited engine, the ability of a Lubricant rated, the formation of sludge and varnish deposits too minimize. The test procedure was a cyclic test with a Total running time of 216 hours, consisting of 54 cycles of each 4 hours. The test engine was a Ford 4.6 l, 4-stroke, 8-cylinder "V" -configured Otto engine. The features of this engine included dual overhead camshafts, a cross flow rapid fire cylinder head construction, two valves per Cylinder and electronic fuel injection. A 90-minute Interruption schedule was performed before each test, because a new engine design was used for each test. After completion of the test, the engine was disassembled and evaluated for sludge. The average engine mud was for each sample calculated.

The results of this testing are shown in Table 3. The pass rates for each power measurement are also given in the table. Table 3 Sequence VG engine test data Dispersants Code AES example 1 9.24 Example 2 8.90 Example 3 9.53 Example 5 9.48 Comparative example 7.91 Best Hung limits 7.80

As shown in Table 3 above, there was the lubricant the dispersants of Examples 1, 2, 3 and 5 did not just any performance measurement, but also gave higher AES test scores as Comparative Example A. The results of this test show the improved performance of the dispersant of the present invention Registration.

The Disclosure of each patent cited in the foregoing disclosure or publication are incorporated herein by reference, as if they were fully executed here.

For the purposes of this specification and the appended claims, unless otherwise indicated given any numbers which express quantities, percentages or proportions and other numerical values used in the specification and claims are to be understood as being modified in all circumstances by the term "about". Thus, unless indicated otherwise, the numerical parameters set forth in the following description and appended claims are approximations that may vary depending upon the desired properties sought to be obtained by the present disclosure. Finally, and not as an attempt to limit the application to the doctrine of equivalents of the scope of the claims, each numerical parameter should be construed at least in light of the number of significant digits indicated and by applying the usual rounding techniques.

It is determined as described in this description and the attached Claims that the singular forms "one", "one" and "the" plural references include, if not expressly stated and unequivocally confined to a reference. Thus includes For example, the reference to "one acid" two or several different acids. As used here is the Term "includes" and does not limit its grammatical variants be such, that the performance of points in one Do not list the exclusion of other equivalent points that replaced or added to the listed items be limited.

Even though certain embodiments have been described Alternatives, modifications, variations, improvements and essential equivalents, which are currently unforeseen or not currently foreseen can be with the applicants or other professionals occur. Accordingly, the appended claims, as submitted and how they can be changed all such alternatives, modifications, variations, improvements and essential equivalents.

QUOTES INCLUDE IN THE DESCRIPTION

This list The documents listed by the applicant have been automated generated and is solely for better information recorded by the reader. The list is not part of the German Patent or utility model application. The DPMA takes over no liability for any errors or omissions.

Cited patent literature

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• US 6103099 [0061]
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• - US 6096940 [0061]
• US 5882505 [0061]
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Claims (66)

Imidazoline compound, which is the reaction product of (i) a dicarbonyl, (ii) a primary amine moiety a polyamine and (iii) a hydrocarbylcarbonyl. A compound according to claim 1, wherein the dicarbonyl selected from alpha omega dicarboxylic acids and esters thereof is. A compound according to claim 1 wherein the dicarbonyl is a compound of formula I

where n ranges from 0 to about 20; and R ¹ , R ² , R 'and R "are independently selected from a hydrogen atom and an alkyl group. A compound according to claim 3, wherein at least one R 'and R "is an alkyl group. A compound according to claim 3 or 4, wherein n is not 2 or 3 is. A compound according to claim 1, wherein the dicarbonyl a dicarboxylic acid selected from oxalic acid, malonic acid, Adipic acid, pimelic acid, suberic acid, Azelaic acid, sebacic acid, undecanedioic acid, Dodecanedioic acid, hexadecanedioic acid and isophthalic acid and esters of one of these dicarboxylic acids. A compound according to claim 1, wherein the dicarbonyl Dimethyldiethylmalonat is. A compound according to any one of claims 1 to 7, wherein the polyamine is a linear, branched or cyclic Polyalkyleneamine having at least one primary amine moiety is. A compound according to any one of claims 1 to 8, wherein the polyamine is a compound of formula II

wherein R ^{6 is} a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms, q is an integer ranging from about 1 to about 3, and m is an integer ranging from about 2 to about 10. A compound according to any one of claims 1 to 9, wherein the polyamine is selected from the group consisting from propylenediamine, butylenediamine, diethylenetriamine, triethylenetetramine, Tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, Dipropylenetriamine and tripropylenetetramine. A compound according to any one of claims 1 to 10, wherein the polyamine has at least three nitrogen atoms and the compound is a reaction product of the hydrocarbylcarbonyl and a polyamine intermediate obtained by reacting the dicarbonyl is formed with the polyamine. A compound according to claim 11, wherein the polyamine intermediate by reacting the dicarbonyl with two equivalents of Polyamine is formed. A compound according to any one of claims 11 or 12, wherein the polyamine intermediate is at least two unreacted includes primary amine groups. A compound according to any one of claims 11 to 13, wherein the polyamine intermediate comprises a compound selected from

wherein n ranges from 0 to 20, m ranges from 2 to 10, x ranges from 1 to 11, and R 'and R "are independently selected from a hydrogen atom and an alkyl group. A compound according to claim 14, wherein the hydrocarbylcarbonyl is a compound of the following formula IV:

wherein R ^{14 is} a hydrocarbyl group. The compound of claim 15, wherein R ^{14 is} a polyolefin residue having a number average molecular weight in the range of about 350 to about 10,000 daltons. The compound of claim 15, wherein R ^{14 is} polyisobutene. A compound according to any one of claims 11 to 17, wherein the hydrocarbylcarbonyl is hydrocarbyl-substituted Succinic anhydrides, hydrocarbyl-substituted succinic acids and esters of hydrocarbyl-substituted succinic acids is selected. A compound according to any one of claims 1 to 18, wherein the hydrocarbylcarbonyl is a compound of the following formula IV:

wherein R ^{14 is} a hydrocarbyl group. The compound of claim 19, wherein R ^{14 is} a polyolefin residue having a number average molecular weight in the range of about 350 to about 10,000 daltons. A compound according to claim 19 or 20, wherein R ^{14 is} polyisobutene. A compound according to any one of claims 1 to 21, wherein the compound is a reaction product of dicarbonyl and a monohydrocarbylpolyamine intermediate, by reaction of the hydrocarbylcarbonyl is formed with the polyamine. Imidazoline compound which is the reaction product of a Dicarbonyls and a monohydrocarbylpolyamine, wherein the Monohydrocarbylpolyamine by reaction of a hydrocarbylcarbonyl and a polyamine is formed. A compound according to claim 22 or 23, wherein the dicarbonyl is a compound of formula I:

where n ranges from 0 to about 20, with the proviso that n is not 2 or 3; and R ¹ , R ² , R 'and R "are independently selected from a hydrogen atom and an alkyl group. A compound according to claim 24, wherein at least one R 'and R "is an alkyl group. A compound according to any one of claims 22 to 25, wherein the dicarbonyl is a dicarboxylic acid from oxalic acid, malonic acid, adipic acid, Pimelic acid, suberic acid, azelaic acid, Sebacic acid, undecanedioic acid, dodecanedioic acid, Hexadecanedioic acid and isophthalic acid and from Esters of one of these dicarboxylic acids. A compound according to any one of claims 22 to 26, wherein the monohydrocarbyl polyamine is a compound of formula V:

wherein R ^{14 is} a hydrocarbyl group; R ^{6 is} a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms; m is an integer ranging from about 2 to about 10; and q is an integer in the range of about 1 to 3. A compound according to any one of claims 22 to 27, wherein the monohydrocarbylpolyamine is a fatty acid amine with at least one primary nitrogen atom. A compound according to any one of claims 22 to 28, wherein the hydrocarbylcarbonyl is a compound of the following formula IV:

wherein R ^{14 is} a hydrocarbyl group. The compound of claim 29, wherein R ^{14 is} a polyolefin residue having a number average molecular weight in the range of about 350 to about 10,000 daltons. A compound according to any one of claims 22 to 30, wherein the hydrocarbylcarbonyl is selected from dodecenyl succinic anhydride, C _16-18 alkenyl succinic anhydride and polyisobutenyl succinic anhydride. A compound according to any one of claims 22 to 31, wherein the polyamine is a linear, branched or cyclic Polyalkyleneamine having at least one primary amine moiety is. A compound according to any one of claims 22 to 32, wherein the polyamine is the compound of formula II:

wherein R ^{6 is} a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms, q is an integer ranging from about 1 to about 3, and m is an integer ranging from about 2 to about 10. A compound according to any one of claims 22 to 33, wherein the polyamine is selected from the group consisting from propylenediamine, butylenediamine, diethylenetriamine, triethylenetetramine, Tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, Dipropylenetriamine and tripropylenetetramine. A lubricant composition comprising: one Base oil; and an imidazoline compound which is the reaction product of (i) a dicarbonyl, (ii) a primary amine moiety a polyamine and (iii) a hydrocarbylcarbonyl or an imidazoline compound according to one of claims 1 to 34. A lubricant composition according to claim 35, wherein the concentration of imidazoline compound from about 0.1% by weight to about 20% by weight relative to the total weight of the composition enough. A lubricant composition according to claim 35 or 36 wherein the dicarbonyl is a compound of formula I:

where n ranges from 0 to about 20; and R ¹ , R ² , R 'and R "are independently selected from a hydrogen atom and an alkyl group. A lubricating composition according to claim 37, wherein at least one of R 'and R "is an alkyl group. A lubricating composition according to claim 37 or 38, wherein the polyamine is a compound of formula II:

wherein R ^{6 is} a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms, q is an integer ranging from about 1 to about 3, and m is an integer ranging from about 2 to about 10. A lubricating composition according to any one of claims 35 to 39, wherein the hydrocarbylcarbonyl is a compound of the following formula IV:

wherein R ^{14 is} a hydrocarbyl group. The lubricating composition of claim 40, wherein R ^{14 is} polyisobutene. Process for the reduction of deposits on one lubricated surface, the process being the lubrication the surface with the lubricating composition after a of claims 35 to 41, wherein the imidazoline compound is present in an amount sufficient to reduce the amount of deposits on the lubricated surface compared to the amount of deposits on the surface, the same operating conditions is subjected and with the same lubricant composition is lubricated, except that the composition of the imidazoline compound lacking, belittle. Method for improving the suspension of sludge, comprising providing the lubricating composition according to one of claims 35 to 41 for a combustion system, wherein the imidazoline compound is present in an amount is sufficient to at least some sludge in suspension in the base oil for a period that is longer, as if the base oil did not contain the imidazoline compound. Lubricant additive package composition comprising: one Diluent; and the imidazoline compound according to one of claims 1 to 34. The additive package of claim 44, wherein the concentration the imidazoline compound of from about 5 to about 75% by weight relative to the total weight of the additive package composition. The additive package of claim 44 or 45, further one or more additional additives selected from additional dispersants, detergents, anti-wear agents, supplemental antioxidants, viscosity index improvers, Pour Point suppressants, corrosion inhibitors, rust inhibitors, Foam inhibitors and friction modifiers. A fuel composition comprising: a fuel base; and an imidazoline compound which is the reaction product of (i) a dicarbonyl, (ii) a primary amine moiety of a polyamine, and (iii) a hydrocarbylcarbonyl; or the imidazoline compound according to any one of claims 1 to 34. A fuel composition according to claim 47, wherein the concentration of the imidazoline compound of about 10 to 10,000 ppm is enough. A fuel composition according to claim 47 or 48, wherein the dicarbonyl is a compound of formula I:

where n ranges from 0 to about 20; and R ¹ , R ² , R 'and R "are independently selected from a hydrogen atom and an alkyl group. A fuel composition according to any one of claims 47 to 49, wherein the polyamine is a compound of formula II:

wherein R ^{6 is} a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms, q is an integer ranging from about 1 to about 3, and m is an integer ranging from about 2 to about 10. A fuel composition according to any one of claims 47 to 50, wherein the hydrocarbylcarbonyl is a compound of the following formula IV:

wherein R ^{14 is} a hydrocarbyl group. A fuel composition according to claim 51, wherein R ^{14 is} polyisobutene. Process for the reduction of deposits in the Fuel system of an internal combustion engine, wherein the method Use of the fuel composition of any of the claims 47 to 52 as the fuel for the internal combustion engine wherein the imidazoline compound in the fuel in an amount is present, which is sufficient for the deposits in the fuel system compared to the amount of deposits in the fuel system, in the same way and using the same fuel composition is operated except that of the fuel composition the imidazoline compound is lacking. A method of dispersing carbon black comprising providing the fuel composition of any of the claims 47 to 52 for a combustion system, wherein the imidazoline compound is present in an amount that is sufficient to at least something Soot in suspension in the fuel base for to hold a period that is longer than when the Fuel base the imidazoline compound did not contain. A fuel additive package composition comprising: a diluent; and the imidazoline compound according to any one of claims 1 to 34. Fuel additive package composition 55, wherein the concentration of the imidazoline compound of about 5% by weight to about 50% by weight of the total fuel additive package composition enough. Process for forming an imidazoline compound, comprising reacting (i) a dicarbonyl, (ii) a primary Amine moiety of a polyamine and (iii) a hydrocarbylcarbonyl, or for forming the imidazoline compound according to any one of the claims 1 to 34. The method of claim 57, wherein the method includes: (i) reacting the dicarbonyl with the polyamine below Reaction conditions sufficient to form a polyamine-imidazoline intermediate to build; and (ii) reacting the polyamine-imidazoline intermediate with the hydrocarbylcarbonyl. The method of claim 58, wherein the reaction conditions heating to form the polyamine-imidazoline intermediate at reaction temperatures ranging from about 150 ° C to about 250 ° C. Process for forming an additive compound or a compound for use in an additive package after a of claims 44 to 46, comprising reacting a dicarbonyl compound and a monohydrocarbyl polyamine. The method of claim 60, wherein the dicarbonyl is a compound of formula I:

where n ranges from 0 to about 20; and R ¹ , R ² , R 'and R "are independently selected from a hydrogen atom and an alkyl group. The method of claim 60 or 61, wherein the monohydrocarbylpolyamine is a fatty acid amine. Method according to one of claims 60 to 62, wherein the monohydrocarbyl polyamine by reacting a Hydrocarbonylcarbonyls is formed with a polyamine. The method of claim 63, wherein the polyamine is a compound of formula II:

wherein R ^{6 is} a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms, q is an integer ranging from about 1 to about 3, and m is an integer ranging from about 2 to about 10. A process according to claim 63 or 64, wherein the hydrocarbylcarbonyl is a compound of the following formula IV:

wherein R ^{14 is} a hydrocarbyl group. Method according to one of claims 60 to 65, wherein the additive compound is a central polyamine chain of one or more polyamine groups linked together with one or more are grouped together, selected from Diamide groups, imidazoline amide groups and bisimidazoline groups, and a hydrocarbylcarbonyl group attached to at least one end the polyamine chain is attached.