FR2911873A1 - New imidazoline compounds for use as lubricant additives or motor fuel additives, obtained by reacting dicarbonyl compounds with polyamine compounds and hydrocarbyl-carbonyl compounds - Google Patents

Abstract

Imidazoline compounds (IC) obtained by the reaction of: (i) a dicarbonyl compound, (ii) a prim. amino group of a polyamine and (iii) a hydrocarbyl-carbonyl compound, are new. Independent claims are also included for (1) imidazoline compounds (IC) comprising the reaction products of dicarbonyl compounds and monohydrocarbyl-polyamines formed by reaction of hydrocarbyl-carbonyl compounds with polyamines (2) lubricant compositions (LC) containing a base oil and an imidazoline compound (IC) (3) a method (M1) for reducing deposits on a lubricated surface by lubricating the surface with LC containing sufficient IC to reduce the amount of deposit by comparison with the same lubricant without IC (under the same conditions) (4) a method (M2) for improving the suspension of sludge by providing a combustion system with LC containing sufficient IC to keep a certain amount of sludge in suspension in the base oil for a longer time than achieved with base oil containing no IC (5) lubricant additive formulations comprising a diluent and an IC compound (6) fuel compositions (FC) containing base fuel and IC (7) a method (M3) for reducing deposits in the fuel distribution systems of internal combustion engines by using the above fuel compositions (FC) (8) a method (M4) for dispersing soot by using FC in a combustion system (9) fuel additive formulations comprising a diluent and IC (10) a method (M5) for the production of IC by the reaction of components (i), (ii) and (iii) as above (11) a method (M6) for forming compounds suitable for use as additives by reacting dicarbonyl compounds with monohydrocarbyl-polyamines .

Description

The present application relates to compounds and methods for

  preparation of compounds and, more specifically, compounds which can be used in fuel and lubricant compositions.

  Considerable effort has gone into developing chemicals as dispersant additives for internal combustion engines. Oil-soluble dispersants for lubricating oils have been developed to control the formation of deposits and gum, and to maintain sludge and other solids, such as oxidized base oil, in suspension in the oil. lubricating oil. Dispersants, when added to hydrocarbon fuels used in engines, effectively reduce the formation of deposits that usually occurs in carburetor ports, throttle bodies, venturis, intake ports and fuel valves. 'admission. The reduction in these deposition quantities has resulted in an increase in engine efficiency and a reduction in the amount of hydrocarbon and carbon monoxide emissions. Despite advances in the use of dispersants as additives for oils and fuels, there continues to be a need for continuous improvements in the ability of dispersants to suspend sludge and / or disperse particles. Thus, novel compounds with improved dispersion characteristics are desired. In accordance with the present invention, one aspect of the present invention relates to an imidazoline compound comprising the reaction product (i) of a dicarbonyl compound, (ii) a primary amine group of a polyamine and (iii) of a hydrocarbyl carbonyl compound. Another aspect of the present invention relates to an imidazoline compound comprising the reaction product of a dicarbonyl compound and a monohydrocarbyl polyamine, the monohydrocarbyl polyamine being formed by reaction of a hydrocarbyl carbonyl compound and a a polyamine. Another aspect of the present invention relates to a lubricating composition comprising a base oil, and an imidazoline compound comprising the reaction product (i) of a dicarbonyl compound, (ii) a primary amine group of a polyamine, and (iii) a hydrocarbyl carbonyl compound.

  Another aspect of the present invention relates to a method for reducing deposits on a lubricated surface, which method comprises lubricating the surface with a lubricating composition of the present invention, wherein the imidazoline compound of the present invention is present in the lubricant composition in an amount sufficient to reduce the amount of deposits on the lubricated surface, as compared to the amount of deposits on the surface subjected to the same operating conditions and lubricated with the same lubricant composition, except that the composition is free of the compound imidazoline. Another aspect of the present invention relates to a method for improving suspension sludge, comprising the step of providing a combustion system to the lubricating composition of the present invention, wherein the imidazoline compounds are present in a sufficient to maintain at least some sludge in suspension in the base oil for a period of time greater than that achieved if the base oil does not contain the imidazoline compounds. Another aspect of the present invention relates to a lubricant additive formulation composition comprising a diluent, an imidazoline compound of the present invention.

  Another aspect of the present invention relates to a fuel composition comprising a base fuel, an imidazoline compound comprising the reaction product (i) of a dicarbonyl compound, (ii) a primary amine group of a polyamine, and (iii) a hydrocarbyl carbonyl compound. Another aspect of the present invention relates to a method for reducing deposits in the fuel distribution system of an internal combustion engine, which method comprises using as a fuel for the internal combustion engine the fuel composition of the present invention. wherein the imidazoline compound of the present invention is present in the fuel in an amount sufficient to reduce deposits in the fuel delivery system, as compared to the amount of deposits in the fuel dispensing system operating in the fuel system. the same way and using the same fuel composition, except that the fuel composition is free of imidazoline compound. Another aspect of the present invention relates to a method for dispersing soot, comprising the step of providing a combustion system with the fuel composition of the present invention, wherein the imidazoline compound of the present invention is present in a an amount sufficient to maintain at least a certain amount of soot suspended in the base fuel for a period of time greater than that attained if the base fuel does not contain the imidazoline compound. Another aspect of the present invention relates to a fuel additive formulation composition comprising a diluent, and the imidazoline compound of the present invention.

  Another aspect of the present invention relates to a process for forming an imidazoline compound, comprising reacting (i) a dicarbonyl compound, (ii) a primary amine group of a polyamine, and (iii) a a hydrocarbyl carbonyl compound. A further aspect of the present invention is a process for forming an additive compound comprising reacting a dicarbonyl compound and a monohydrocarbyl polyamine. Additional aspects and advantages of the present invention will become apparent in part hereinafter and may be established by practicing the invention. It should be understood that the foregoing general description and the detailed description below are illustrative and explanatory only and are not limiting of the present invention.

  One aspect of the present invention relates to the preparation of novel imidazoline compounds and their uses. The imidazoline compounds may include the reaction product (i) of a dicarbonyl compound, (ii) a primary amine group of a polyamine, and (iii) a hydrocarbyl carbonyl compound. The compounds of the present invention are designed to have localized regions of polarity. These localized polar regions are believed to result in compounds that may have one or more advantages such as, for example, improved dispersant capacity to suspend sludge and / or disperse soot by ionic and dipolar interactions. and / or improved ability to remove deposits in injectors and / or valves in combustion materials.

  In some aspects, the compounds of the present invention are produced by preparing a polyamine intermediate, which is reacted with a hydrocarbyl carbonyl compound. The intermediate can be prepared by reacting a dicarbonyl compound with a primary amine group of a polyamine. Other suitable methods for forming the compounds of the present invention may be used, as described in more detail below. Dicarbonyl Compounds The reaction dicarbonyl compounds used in the present invention may comprise any dicarbonyl compound suitable for forming the desired intermediate. Non-limiting examples of suitable dicarbonyl compounds include alpha-omega dicarboxylic acids and their esters.

  In one aspect, the dicarbonyl compound may be a compound of formula I wherein n is from 0 to about 20, e.g. from about 1 to about 16; and R2, R 'and R "are independently selected from a hydrogen atom and an alkyl group. Suitable alkyl groups may include, for example, linear or branched C1 to C10 alkyl groups, such as methyl, ethyl In some aspects of the present invention, it may be desirable that the value chosen for n is not equal to 2 or 3. This is because, when n is 2 or 3, an internal cyclization of the Formula compound can occur which can result in formation of an imide ring structure of 5 or 6 atoms, such as succinimide, by reaction with a polyamine which can potentially hinder the desired reaction and prevent Thus, in such cases, the dicarbonyl compound is not succinic acid, glutaric acid or succinate or glutarate derivatives of formula I.

  Non-limiting examples of the dicarbonyl compound include dicarboxylic acids selected from oxalic acid, malonic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and the like. undecanedioic acid, dodecanedioic acid, hexadecanedioic acid and isophthalic acid, and esters of any of these dicarboxylic acids, such as, for example, methyl, ethyl and butyl esters. In one aspect of the present invention, the dicarbonyl compound may be an alkylated diester. For example, R 1 and R 2 in formula I may be methyl, R 'and R "may be ethyl and n may be 1, thereby forming the alkylated diester dimethyl diethyl malonate. of the present invention, the polyamine reactant used to form the polyamine intermediate of the present invention may be a linear, branched or cyclic polyalkylene amine having at least one primary amine moiety In some aspects, the polyamine may have at least three For example, the polyamine may be a polyalkylene amine having the following formula II: NH 2 ((CH 2) qCHNH), wherein R 6 may represent a hydrogen atom or a lower alkyl group molecular weight having about 1 to about 6 carbon atoms, q may be an integer of about 1 to about 3 and m may be an integer of about 2 to about Iron 10, e.g. from about 3 to about 8. Non-limiting examples of R 6 alkyl groups include methyl, ethyl, propyl and butyl. Non-limiting examples of suitable polyamines include propylenediamine, butylenediamine, diethylenediamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TETA), pentaethylenehexamine (PEHA), hexaethyleneheptamine ( HEHA), dipropylenetriamine and tripropylenetetramine. The polyamines may comprise branched or cyclic linear compounds or mixtures thereof. In one aspect, the polyamine is a polyethylene amine, such as DETA, TETA, TEPA, PEHA, and HEHA. In one aspect, the polyamine may be a copolymer of any of the foregoing polyethylene amines, having a molecular weight in the range of about 100 to about 600. In some aspects, the polyamines may comprise mixtures of two or more than two polyamines, for example mixtures of two or more compounds selected from TEPA, PEHA, HEHA and higher molecular weight polyethylene amine products. In some aspects, a mixture may comprise heavy polyamines. A heavy polyamine is a mixture of polyalkylene amines comprising small amounts of lower amine oligomers, for example TEPA and PEHA, but mainly comprising oligomers having 7 or more than 7 nitrogen atoms, 2 or more groups primary amines per molecule and more extensive branching than conventional amine mixtures. The dicarbonyl and polyamine reactants can be combined under any suitable reaction conditions resulting in the desired imidazoline intermediate compound. In one aspect, the dicarbonyl and polyamine may be combined and heated to a reaction temperature in the range of about 150 ° C to about 250 ° C under a nitrogen atmosphere, or other relatively inert atmosphere, such as under vacuum until the alcohol and / or water are removed, and the imidazoline product is formed. This reaction time can range, for example, from about 2 hours to about 6 hours. At this point, the imidazoline product can be isolated to form a polyamine intermediate of the present invention. The reaction can be carried out in pure form or with solvents. Optionally, any amount of water or solvent may be removed during or after the reaction to provide the desired polyamine intermediate. In one aspect of the present invention, the ratio of dicarbonyl to polyamine may be any suitable ratio so that at least two unreacted primary amine groups persist in the intermediate. For example, the molar ratio of dicarbonyl compounds to primary amine compounds may range from about 1: 1.1 to about 1: 2.

  The resulting intermediate compound comprises one or more polyamine groups attached to one or more imidazoline-amine groups and / or one or more bisimidazoline groups. For example, the intermediate compound may be a polyamine-imidazoline-amide compound of formula IIIa, or polyamine-bis-imidazoline of formula Ilib or mixtures thereof: ## STR2 ## where x has a value of from about 1 to about 11 and n, R 'and R "are as defined above with respect to Formula I, and m is as defined above with respect to Formula II: hydrocarbyl carbonyl compound hydrocarbyl compound The reaction carbonyl of the present invention may be any suitable compound having a hydrocarbyl group and a carbonyl group, and which is capable of binding to the polyamine intermediates to form the compounds of the present invention. Suitable hydrocarbyl carbonyls include, but are not limited to, hydrocarbyl substituted succinic anhydrides, hydrocarbyl substituted succinic acids, and sugar acid esters. hydrocarbyl substituted cinics. Specific examples include compounds such as dodecenylsuccinic anhydrides, C16-Cm alkenylsuccinic anhydride and polyisobutenyl succinic anhydride (PIBSA). In some embodiments, the PIBSA may comprise 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 groups in the hydrocarbyl carbonyl compound can be in the range of about 1: 1 to about 6: 1. In the present invention, the term hydrocarbyl group or the term hydrocarbyl is used in its usual sense, which is well known to those skilled in the art. More specifically, it denotes a group having a carbon atom directly attached to the remainder of the molecule having a hydrocarbon main character. Examples of hydrocarbyl groups include: (1) hydrocarbon substituents, i.e., aliphatic (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl or cycloalkenyl) substituents, and aromatic, aliphatic and alicyclic substituted aromatic substituents; as well as cyclic substituents in which the ring is supplemented by another part of the molecule (for example two substituents together form an alicyclic radical). (2) substituted hydrocarbon substituents, i.e., substituents containing non-hydrocarbon groups which, in the context of the present invention, do not modify the main hydrocarbon substituent (for example halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso and sulfoxy); (3) heterosubstituents, i.e., substituents which, while having a hydrocarbon principal character, in the context of the present invention, contain atoms other than carbon atoms in a ring or chain formed by elsewhere of carbon atoms. The heteroatoms include sulfur, oxygen and nitrogen and include substituents such as pyridyl, furyl, thienyl and imidazolyl substituents. In general, a number no greater than two, or, as a further example, no greater than 1 non-hydrocarbon substituent will be present for each number of carbon atoms in the hydrocarbyl group; in some embodiments, there will be no non-hydrocarbon substituent in the hydrocarbyl group. In certain aspects, the hydrocarbylcarbonyl compound may be a polyalkylene succinic anhydride reactant having the following formula IV: wherein R14 is a hydrocarbyl group such as, for example, a polyolefinic radical having a number average molecular weight of about 350 to about 10,000 daltons. For example, the number average molecular weight of R14 may be in the range of about 1000 to about 5000 daltons as measured by GPC. Unless otherwise indicated, the molecular weights in the present invention are number average molecular weights. In some aspects, R14 may represent a polyolefinic radical comprising one or more polymeric units selected from linear alkenyl units and branched alkenyl units. In some aspects, the alkenyl units may have from about 2 to about 10 carbon atoms. For example, the polyolefinic radical may comprise one or more linear or branched polymer units chosen from ethylene radicals, propylene radicals, butylene radicals, pentene radicals, hexene radicals, octene radicals and decene radicals. In some aspects, R 14 may be a polyolefinic radical in the form of, for example, a homopolymer, copolymer or terpolymer. For example, the polyolefinic radical may be a copolymer of ethylene and propylene. In another example, the polyolefinic radical is a polyisobutylene homopolymer. The polyolefinic compounds used to form the R14 polyolefin radicals can be formed by any suitable methods, such as by conventional catalytic oligomerization of alkenes.

  In some aspects, high reactivity polyisobutenes comprising relatively high proportions of polymer molecules with a terminal vinylidene group can be used to form the hydrocarbyl substituent. In one example, a proportion of at least 4% of the total terminal olefinic double bonds in these high reactivity polyisobutenes may be methylvinylidene isomer. In other examples, a proportion equal to or greater than 50%, for example equal to at least 70%, of the total terminal olefinic double bonds may consist of methylvinylidene isomers. Well known high reactivity polyisobutenes are described, for example, in U.S. Patent No. 4,152,499, incorporated by reference in its entirety in the present invention. The hydrocarbonylcarbonyl compounds can be prepared using any suitable method. Methods for forming hydrocarbyl carbonyl compounds are well known in the art.

  An example of a known method for forming a hydrocarbyl carbonyl compound comprises mixing a polyolefin and maleic anhydride. The polyolefin and maleic anhydride reactants are heated to temperatures in the range of, for example, from about 150 ° C to about 250 ° C, optionally using a catalyst such as chlorine or peroxide. The hydrocarbyl carbonyl compound may be combined with the desired polyamine intermediate under any suitable reaction condition which will result in the desired imidazoline derivative of the present invention. For example, a mixture of the hydrocarbyl carbonyl derivative and the polyamine intermediate may be heated at a temperature in the range of about 100 ° C to about 200 ° C, for example, about 140 ° C to about 180 ° C. in a nitrogen atmosphere or other relatively inert atmosphere, for example under vacuum. The reaction mixture can be heated to the reaction temperature until the desired succinimide product is formed, optionally with complete removal of the water. Suitable reaction times may range, for example, from about 2 hours to about 4 hours. The reaction can be carried out in pure form or with solvents and / or diluents, such as a diluent oil. Once the reaction is complete, the mixture can be filtered to obtain the desired dispersant. In another embodiment, the reaction of the dicarbonyl compound, the polyamine and the hydrocarbyl carbonyl compound can be carried out in a different order than that described above. For example, instead of reacting a dicarbonyl compound and a polyamine to form the polyamine intermediate described above, the hydrocarbyl carbonyl compounds described above can be reacted with the polyamines described above for form a monohydrocarbylpolyamine intermediate. The monohydrocarbylpolyamine intermediate can then be reacted with the dicarbonyl compounds described above to form the desired compounds of the present invention.

  In one aspect of the present invention, the monohydrocarbylamines used may have from about 3 to about 10 nitrogen atoms, and the amine moiety may have at least one primary amine moiety. Examples of these monohydrocarbylpolyamine intermediate compounds can be represented by the following formula: embedded image in which R 16, R '4, q and m are as defined above with respect to Formulas II and IV. Non-limiting examples of these monohydrocarbylpolyamines include polyamine succinimides such as propylenediamine succinimide, butylenediamine succinimide, diethylenetriamine (DETA) -succinimide, triethylene tetramine (TETA) -succinimide, tetraethylenepentamine (TEPA) -succinimide, pentaethylene hexamine (PEHA) -succinimide, hexaethyleneheptamine (HEHA) -succinimide, dipropylenetriamide succinimide and tripropylene tetramine succinimide, all of which are substituted with a hydrocarbyl group R14. The monohydrocarbylamines of the present invention can be formed by reacting the hydrocarbyl carbonyl compound and the polyamine under any conditions resulting in the desired monohydrocarbyl polyamine compounds. For example, a hydrocarbyl carbonyl compound and a polyamine in a molar ratio of 1: 1 equivalents can be mixed and heated to temperatures of, for example, from about 120 ° C to about 250 ° C.

  In a further embodiment, the monohydrocarbyl polyamines used may be any suitable polyamines obtained from any suitable source. For example, fatty amines, such as TETRAMEEN OV, available from Akzo Nobel, or ADOGEN 670 and ADOGEN 770 available from Degussa, can be used as monohydrocarbyl-polyamines of the present invention. Other examples of fatty amines include fatty acid amides such as those of the formula: R 16 C (O) -NH 2 (CH 2) n- [NH (CH 2) r] t -NH 2 where R 16 is a group of at linear or branched, saturated or unsaturated C30, r is 2 or 3 and ta is 0-10. These fatty acid amides can be formed by any suitable method known in the art, for example by reaction of fatty acids with polyamines. The monohydrocarbyl polyamines can be reacted with any of the dicarbonyl compounds described above, such as the dicarbonyl compounds of formula I, to form the desired compounds of the present invention. The reaction can be conducted by mixing any suitable amounts of the monohydrocarbyl polyamines and dicarbonyl compounds under suitable process conditions. For example, a molar ratio of the dicarbonyl compounds to the monohydrocarbyl polyamide may range from about 1: 2 to about 4: 2, for example from 1: 1 to about 3: 4. in the pure state or in a diluent oil at a temperature in the range of about 80 ° C. to about 200 ° C. The particular reaction temperature used may have an effect on the distribution of the reaction products. For example, linear diamides and arrays of amides or polyamides can be formed at low temperatures in the range of about 80 ° C to about 150 ° C, while cyclic products such as imidazolines, can be formed by heating at higher temperatures such as, for example, temperatures in the range of about 160 ° C. to about 200 ° C. Thus, to form the imidazoline derivatives of the present invention, the Higher reaction temperatures can be used. However, it may also be desirable to use this process to form additive compounds at lower temperatures if compounds comprising the diamide groups are desired. Accordingly, the compounds formed by this process may comprise a central polyamine chain of one or more polyamine groups linked to one another with one or more groups selected from diamide groups, imidazolinamide groups and bis-imidazoline groups, a hydrocarbyl carbonyl group being attached to at least one end of the polyamine chain. Imidazolines are described in more detail below. The diamides may comprise compounds of formula X, also as shown below in the description of the compounds obtained as products, where Y is, for example, as defined in formula XIa: wherein R ', R "and n are to the above definitions with respect to formula I. In an illustrative aspect of the present invention, a monohydrocarbyl polyamine may be heated at a temperature in the range of about 160 ° C to about 250 ° C under a nitrogen atmosphere, or in another relatively inert atmosphere, eg under vacuum A dicarbonyl compound can then be added The reaction mixture can be stirred and heated to the desired reaction temperature until the desired reaction product is formed and, optionally, the reaction product Water and / or alcohol are removed from the mixture, for example, suitable reaction times may range from about 1 hour to about 5 hours. The reaction can be carried out in pure form or with solvents and / or diluents, such as a diluent oil. Once the reaction is complete, the mixture can be diluted with, for example, a diluent oil and filtered to obtain the desired dispersant. Compounds Obtained as Products In some aspects, the compounds of the present invention may comprise a central polyamine chain of one or more polyamine groups linked to one another with one or more diamine groups, imidazolin-amide groups and / or one or more groups. bisimidazoline, a hydrocarbyl carbonyl group being attached to one or both ends of the chain of the polyamine. In aspects of the present invention, the compounds obtained as reaction products may have at least one titratable nitrogen atom. Non-limiting examples of the polyamide-succinimides include compounds of the formula X: ## STR2 ##

  wherein z has a value of from 0 to about 10, x has a value of about i to about 10, R14 is as defined above with respect to formula IV and Y is chosen to represent one or more groups of formula XIb and Wherein n, R ', R "are as defined above with respect to formula I. The compounds of formula X are illustrative only and other compounds may be formed, for example, ethylene units. Amine XIc or of formulas X, XIa, XIb and XIc could be replaced by other amine units corresponding to the more general formulas: and - ((CH2) gCHNH) - R6 - ((CH2) gCHN) - R6 wherein q and R6 are as defined above with respect to formula II In further embodiments, the imidazole derivatives of the present invention may also include other Y moieties in addition to the imidazole moieties. of formulas XIb and XIc, such as the diamide groups of formula XIa described above. As noted above, the compounds of the present invention are designed to have localized regions of polarity. These localized polar regions are believed to result in compounds that may exhibit one or more advantages, such as, for example, improved dispersant dispersibility to suspend sludge and / or disperse soot through ionic and dipoles; and / or improved ability to remove deposits in injectors and / or valves in combustion materials. In some aspects of the present invention, it may be possible for the imidazolineamides to have a unique network of hydrogen bonds in a non-polar medium, as illustrated by Formula XII below, for example when the compounds are combined with a lubricating oil. The broken lines in formula XII represent potential hydrogen bonds. Wherein R 1 represents a hydrocarbyl group such as, for example, a polyolefinic radical having a number average molecular weight of about 350 to about 10,000 daltons. When the compounds of the present invention are used as dispersants in lubricant compositions, they may be present in any suitable amount. In one example, the compounds may be present in an amount of from about 0.1 to about 20 percent by weight of the total composition, for example from about 0.5 to about 15 percent by weight, and in another example, from about 1 to about 7% by weight. The lubricating compositions described in the present invention may comprise a base oil. Base oils which can be suitably used in the formulation of the disclosed compositions can be selected, for example, from synthetic oils, mineral oils and mixtures thereof. The base oil may be present in a dominant amount, it being understood that the term "dominant amount" refers to an amount greater than or equal to 50% by weight of the lubricant composition, for example from about 80% to about 98% by weight. weight of the lubricant composition. The base oil usually has a viscosity of, for example, in the range of from about 2 to about 15 cSt, and by way of further example from about 2 to about 10 cSt at 100 C. Examples not mineral oils suitable as base oils include animal oils and vegetable oils (eg castor oil, lard oil) as well as other mineral lubricating oils such as liquid oils derived from petroleum and solvent-treated or acid-treated mineral lubricating oils of paraffinic type, naphthenic type or mixed paraffinic-naphthenic type. Oils derived from coal or shale are also suitable. In addition, oils derived from a gas to liquid process are also suitable. Non-limiting examples of synthetic oils include hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, etc.); poly-alpha-olefins such as poly- (1-hexenes), poly (1-octenes), poly (1-decenes), etc. and their mixtures; alkylbenzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di- (2-ethylhexyl) benzenes, etc.); polyphenyls (eg biphenyls, terphenyl, alkylpolyphenyls, etc.); alkylated diphenyl ethers and alkylated diphenyl sulfides as well as their derivatives, analogs and homologs and the like. Alkylene oxide interpolymer polymers and derivatives thereof wherein the terminal hydroxyl groups have been modified by esterification, etherification, or the like, represent another class of known synthetic oils that can be used. These oils are illustrated by the oils prepared by polymerization of ethylene oxide or propylene oxide, the alkyl ethers and aryl ethers of these polymers of the polyoxyalkylene type (for example polyisopropylene glycol methyl ether having a mean molecular weight of about 1000, polyethylene glycol diphenyl ether having a molecular weight of about 500 to 1000, polypropylene glycol diethyl ether having a molecular weight of about 1000 to 1500, etc.) or their mono- and polycarboxylic esters, by Examples are acetic acid esters, C3 to C8 mixed fatty acid esters or the C13 oxy acid diester of tetraethylene glycol. Another class of synthetic oils that can be used include dicarboxylic acid esters (eg, phthalic acid, succinic acid, alkyl succinic acids, alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, and the like). , linoleic acid dimer, malonic acid, alkylmalonic acids, alkenylmalonic acids, etc.) with various 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, di-eicosyl sebacate, linoleic acid dimer 2-ethylhexyl diester, the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid and similar compounds. Esters useful as synthetic oils also include those prepared from C 5 -C 11 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol, tripentaerythritol, and the like. . Accordingly, the base oil used to prepare the compositions described in the present invention can be selected from any of the Group I to IV base oils specified in the Americal Petroleum Institute's Base Oil Interchangeability Guidelines (API). ). These groups of base oils are as follows: Group I contains less than 90% saturated compounds and / or more than 0.03% sulfur and has a viscosity index greater than or equal to 80 and less than 120; group II contains an amount greater than or equal to 90% of saturated compounds and an amount less than or equal to 0.03% of sulfur and has a viscosity index greater than or equal to 80 and less than 120; group III contains an amount greater than or equal to 90% of saturated compounds and an amount less than or equal to 0.03% of sulfur and a viscosity index greater than or equal to 120; group IV consists of poly-alpha-olefins (PAO); group V includes all other basic lubricating oils not included in groups I, II, III and IV. The test methods used in the definition of the above groups are ASTM D2007 for saturated compounds; ASTM D2270 method for viscosity index; and one of ASTM methods D2622, 4294, 4927 and 3120 for sulfur. Group IV lubricating oils, i.e. poly-alpha-olefins (PAOs), comprise hydrogenated oligomers of an alpha-olefin, the most important oligomerization processes being free radical processes, Ziegler catalysis and Friedel-Crafts cation catalysis. The poly-alpha-olefins usually have viscosities in the range of from 2 to 100 cSt at 100 ° C, for example from 4 to 8 cSt at 100 ° C. They may be, for example, oligomers of alpha-olefins with branched or straight chain chain having from about 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. Homopolymers of the interpolymers and mixtures thereof are included. With respect to the remainder of the above-mentioned basic lubricating oils, a Group I lubricating oil also includes a Group I lubricating oil with which one or more lubricating base oils of one or more several other groups, provided that the resulting blends have characteristics corresponding to those specified above for Group I lubricating oils. Examples of basic lubricating oils include Group I lubricating oils and blends. of Group II lubricating oils with a Group I base lubricating oil.

  Basic lubricating oils suitable for use in the present invention can be prepared using a variety of different processes including, but not limited to, distillation, solvent refining, hydrogen treatment, oligomerization, esterification and regeneration. The base oil can be an oil derived from hydrocarbons synthesized by the Fischer-Tropsch process. Hydrocarbons synthesized by the Fischer-Tropsch process can be produced from a synthesis gas containing H 2 and CO using a Fischer Tropsch catalyst. These hydrocarbons usually require additional processing in order to be useful as the base oil. For example, the hydrocarbons can be hydroisomerized using the methods described in U.S. Patent No. 6,103,099 or 6,180,575; hydrocracked and hydroisomerized using the methods described in U.S. Patent No. 4,943,672 or 6,096,940; dewaxed using the methods described in U.S. Patent No. 5,882,505; or hydroisomerized and dewaxed using the methods described in U.S. Patent Nos. 6,013,171, 6,080,301 or 6,165,949. These patents are incorporated by reference in their entirety in the present invention. Unrefined oils, refined oils and regenerated, mineral or synthetic oils (as well as mixtures of two or more of any of these oils) of the type described above may be used in base oils . Unrefined oils are those obtained directly from a mineral or synthetic source without additional purification treatment. For example, a shale oil obtained directly from pyrogenation operations, a petroleum oil obtained directly from primary distillation or an ester oil obtained directly by an esterification process used without further processing will be an unrefined oil. Refined oils are similar to unrefined oils except that they have been further processed in one or more purification steps to improve one or more properties. Most of these purification techniques are known to those skilled in the art, examples being solvent extraction, secondary distillation, acid or base extraction, filtration, percolation, etc. The regenerated oils are obtained by methods similar to those used to obtain refined oils, the processes being applied to refined oils that have already been used. These regenerated oils are also known as reprocessed or reprocessed oils and are often further processed by techniques for the removal of spent additives, contaminants and oil degradation products.

  The lubricant compositions of the present invention can be used in any engine or other combustion systems or mechanical devices that can take advantage of it. For example, the lubricant compositions can be suitably used in the housing of an internal combustion engine. In some embodiments, the compounds of the present invention may be added to the lubricant composition as a lubricant additive formulation. Lubricant additive formulations include concentrates dissolved in a diluent, such as mineral oil, synthetic hydrocarbon oils, and mixtures thereof. When blended with the base oil, these concentrated additive compositions can provide an effective concentration of the additives in the base oil. The amount of the compounds of the present invention in the lubricant additive formulations may vary from about 5% by weight to about 75% by weight of the concentrated additive composition, for example from about 5% by weight to about 50% by weight.

  The lubricant additive formulation compositions and the finished lubricants of the present invention may contain additional additives. Examples of such additional additives include additional dispersants other than the dispersants of the present invention, detergents, antiwear agents, additional antioxidants, viscosity index improvers, pour point depressants, inhibitors, and the like. corrosion inhibitors, rust inhibitors, foaming inhibitors and friction modifiers. These additives are well known in the art, and the selection of effective amounts of additional additives in the lubricant compositions is within the skill of the art. Representative non-limiting amounts of these additional additives are shown in range 1 and range 2 of Table 1 below: Additive% by weight% by weight Interval 1 Interval 2 Antioxidant system 0 - 5 0.01 - 3 Detergents 0.1 - 15 0.2 - 8 Corrosion inhibitor 0 - 5 0 - 2 Dihydrocarbyl dithiophosphate metal 0.1 - 6 0.1 - 4 Antifoaming agent 0 - 5 0.001 - 0.15 Friction modifier 0 - 5 0 - 2 Additional anti-wear agents 0 - 1.0 0 - 0.8 Pour point depressant 0.01 - 5 0.01 - 1.5 Viscosity modifier 0.01 - 10 0.25 - 7 In one aspect, the present invention relates to a method for reducing deposits on a lubricated surface, said method comprising using as a lubricating oil for said surface a lubricating oil containing the lubricating oil derivative. imidazoline of the present invention. The imidazoline derivative can be present in an amount sufficient to reduce the amount of deposits on the surface, compared to the amount of deposits that would be formed on the surface in the case of using the same operating conditions and the same lubricating oil, except that the oil is devoid of the imidazoline derivative. Representative examples of deposits that can be reduced using the compositions of the present invention include piston deposits, piston ring span deposits, piston head bearing deposits, fire pistons. In another aspect, the present invention relates to a method for improving the suspension of sludge in a lubricating oil. The method comprises the step of providing to a combustion system the lubricating oils of the present invention, wherein the imidazoline derivative is present in an amount sufficient to maintain at least a certain amount of sludge in suspension in the oil. for a period of time greater than that obtained if the oil does not contain the imidazoline derivative. The compounds of the present invention are also useful as dispersants in fuels.

  Thus, another aspect of the present invention is a fuel composition comprising a major amount of a fuel and a small amount of compounds of the present invention sufficient to provide a desired dispersancy. It is understood that the term "minor amount" refers to less than 50% by weight of the lubricant composition. The concentration of the additive in a fuel depends on various factors, including the type of fuel used, the presence of other dispersants and other additives and similar factors. Nonlimiting examples of concentrations may range from about 10 to about 10,000 millionths, or from about 30 to about 5,000 millionths. The basic fuels used in formulating the fuel compositions of the present invention include any of the basic fuels that can be suitably used in the operation of spark ignition or compression ignition engines, such as diesel fuel, jet fuel, kerosene, lead-free or lead-free gasoline for engines and aviation, and gasoline known as reformulated gasolines that may contain both hydrocarbons in the boiling range of gasoline and oxygen compounds that are soluble in fuels such as alcohols, ethers and other suitable oxygenated organic compounds. Examples of oxygenates which can be suitably used in the present invention include methanol, ethanol, isopropanol, t-butanol, mixed C 1 to C 5 alcohols, tert-butyl methyl ether, tert-amyl methyl ether, tert-butyl ethyl ether and mixed ethers. Oxygen compounds, when used, may be present in the base fuel in a less than, for example, about 25% by volume. In some embodiments, the oxygenated compounds may be present in an amount that provides an amount of oxygen in the total fuel in the range of about 0.5 to about 5 volume percent. The basic fuels used in formulating the fuel compositions of the present invention may include, for example, fuels for compression ignition engines having a sulfur content of up to about 0.2 wt. Example up to about 0.05% by weight, as determined by the test method specified in ASTM D 2622-98. In some embodiments, suitable fuels for compression ignition engines for use in the present invention are low sulfur diesel fuels. In a further aspect of the present invention, the compounds of the present invention are useful as dispersants in fuel additive concentrates. The fuel concentrates may comprise a stable inert organic solvent as a diluent and about 5 to 50% by weight of an imidazoline derivative of the present invention. Non-limiting examples of suitable diluents include benzene, toluene, xylene or higher boiling aromatic compounds. In one aspect, the present invention relates to a method for reducing deposits in the fuel distribution system of an internal combustion engine, which method comprises using as fuel for the internal combustion engine fuel compositions described above. . The compounds of the present invention may be present in the fuel in an amount sufficient to reduce deposits in the fuel delivery system. The deposits can be reduced by comparison with the amount of deposits that would appear in the same fuel distribution system operating in the same manner and using the same fuel composition, in the case where the fuel composition is devoid of the imidazoline derivative. . In one aspect, the present invention relates to a method for removing deposits on intake valves in an engine. The method comprises the step of supplying the fuel compositions of the present invention to a combustion system, wherein the imidazoline derivative is present in the fuel in an amount sufficient to maintain the absence of deposits on the intake valve. for a period of time greater than that obtained if the fuel does not contain the imidazoline derivative. The following examples are provided to specifically illustrate the present invention. These examples and illustrations should not be considered in any way as limiting the scope of the present invention. EXAMPLES Example 1 1087 g of alkylenylsuccinic anhydride (acid number = 0.552) were introduced into a plastic 3-liter flask equipped with an overhead stirrer. The PIBSA was heated to 180 ° C. and stirred under a nitrogen atmosphere. 113.4 g of TEPA was added via a separatory funnel. The reaction mixture was heated at 180C under reduced pressure for 3 hours; 777.1 g of diluent oil was added. The reaction mixture was then heated to 180 ° C. and 48.1 g of diethyl malonate was then added. The reaction mixture was heated at 180C under reduced pressure for 3 hours. Then, the reaction mixture was filtered to give 1863 g of the desired reaction product. EXAMPLE 2 1087 g of alkylenylsuccinic anhydride (acid number = 0.552) were introduced into a plastic 3-liter flask equipped with an overhead stirrer. The PIBSA was heated to 180 ° C. and stirred under a nitrogen atmosphere. 113.4 g of TEPA was added via a separatory funnel. The reaction mixture was heated at 180C under reduced pressure for 3 hours; 781.6 g of diluent oil was added. The reaction mixture was then heated to 180 ° C. and 52.3 g of dimethyl adipate was then added. The reaction mixture was heated at 180C under reduced pressure for 3 hours. Then, the reaction mixture was filtered to give 1853 g of the desired reaction product. Example 3 1087 g of alkylenylsuccinic anhydride (acid number = 0.552) were introduced into a plastic 3-liter flask equipped with an overhead stirrer. The PIBSA was heated to 180 ° C. and stirred under a nitrogen atmosphere. 113.4 g of TEPA was added via a separatory funnel. The reaction mixture was heated at 180C under reduced pressure for 3 hours; 807.7 g of diluent oil was added. The reaction mixture was then heated to 180 ° C. and 78.4 g of dimethyl adipate was then added. The reaction mixture was heated at 180C under reduced pressure for 3 hours. Then, the reaction mixture was filtered to give 1748 g of the desired reaction product. EXAMPLE 4 1087 g of alkylenylsuccinic anhydride (acid number = 0.552) were introduced into a plastic 3-liter flask equipped with an overhead stirrer. The PIBSA was heated to 180 ° C. and stirred under a nitrogen atmosphere. 113.4 g of TEPA was added via a separatory funnel. The reaction mixture was heated at 180C under reduced pressure for 3 hours; 801.4 g of diluent oil was added. The reaction mixture was then heated to 180 ° C and 72.1 g of diethyl malonate was added. The reaction mixture was heated at 180C under reduced pressure for 3 hours.

  Then, the reaction mixture was filtered to give 1027 g of the desired reaction product. EXAMPLE 5 1087 g of alkylenylsuccinic anhydride (acid number = 0.552) were introduced into a plastic 3-liter flask equipped with an overhead stirrer. The PIBSA was heated to 180 ° C. and stirred under a nitrogen atmosphere. 113.4 g of TEPA was added via a separatory funnel. The reaction mixture was heated at 180C under reduced pressure for 3 hours; 787.6 g of diluent oil was added. The reaction mixture was then heated to 180 ° C. and 58.3 g of dimethyl isophthalate was then added. The reaction mixture was heated at 180C under reduced pressure for 3 hours. Then, the reaction mixture was filtered to give 1840 g of the desired reaction product. The dispersant additives of Examples 1 to 3 were each blended with a particular vehicle engine oil formulation using other components, including metal sulfonates of zinc dithiophosphate wear inhibitors, sulfur containing antioxidants. , diarylamine-type antioxidants and phenolic antioxidants, oleate friction modifiers, molybdenum-containing friction modifiers, pour point depressant, viscosity index improver (HiTEC 5751), and lubricating base oil. These other constituents were present at the concentrations usually found in fully formulated multigrade oils for passenger car engines. Kinematic washes at 100 C (KV100) (mm2 / s) and viscosity in a cold start simulator at 30 C (CCS-30) (mPa. $) Were determined and the results are shown in Table 2 below. below.

  Table 2 Results of the study with the 5W mixture Dispersant Mn of PIB Material KV100 CCS-30 solids Example 1 2100 2.5 10.62 6010 Example 2 2100 2.5 11.28 6005 Example 3 2100 2.5 12, In Table 3 below, the sludge containment properties of the lubricants containing the dispersants of Examples 1, 2, 3 and 5, as described above, and a comparative lubricant containing a dispersant available from The trade was compared using the VG Sequence Engine Test (an industrial dispersant test for sludge limitation) to determine the average amount of sludge in the engine (AES). The lubricants used were fully formulated lubricants. In each sample, the lubricant ingredients were exactly the same, with the exception of the dispersant. VG Sequence Engine Sludge and Gum-like Deposition Experiment is a power-driven dynamometer test that assesses the ability of a lubricant to minimize the formation of sludge and gum deposits. . The test method was a cyclic test with a total run time of 216 hours consisting of 54 cycles of 4 hours each. The test engine was a four-stroke, spark-ignition 4.6-liter Ford V-8 engine. The characteristics of this engine included double overhead camshafts, a cross-flow, fast-flowing cylinder head configuration with two valves per cylinder, and an electronic injection of fuel into the intake port. A 90-minute break-in schedule was implemented before each test because a new engine is used for each test. After the test was completed, the engine was disassembled and evaluated for sludge. The amount of sludge in the engine was calculated for each sample. The results of this test are shown in Table 3. The success limits for each performance measure are also shown in the table.

  Table 3 Results of Engine Test VG Sequence AES Dispersant Code Example 1 9.24 Example 2 8.90 Example 3 9.53 Example 5 9, 48 Comparative 7.91 Success Limits 7.80 As shown in Table 3 above, the lubricant containing the dispersants of Examples 1, 2, 3 and 5, not only successfully underwent each performance measure, but resulted in higher numerical ESA values than of Comparative Example A. The results of this test indicate the improved performance of the dispersant of the present invention. The various patents or publications mentioned in the present invention are all cited by reference. For purposes of the present invention, unless otherwise indicated, all numerical values expressing quantities, percentages or proportions, and other numerical values used in the present invention are intended to be modified in any case by the term about . Accordingly, unless otherwise indicated, the numerical parameters indicated in the present invention are approximations which may vary depending on the desired properties sought to be achieved in the present invention. Each numerical parameter should be considered at least in the light of the number of significant digits indicated and by applying the usual rounding techniques.

It will be appreciated that, as used in the present invention, forms one, one, and the include the plural references, unless otherwise specified and unequivocal to a reference. Thus, for example, the reference to an acid includes reference to two or more different acids. As used in the present invention, the term includes or includes and its grammatical variants are intended to be non-limiting, so that the indication of elements in a list is not made to the exclusion of other elements. similar ones that can be used in place of or added to the items listed. It goes without saying that the present invention has been described for explanatory purposes, and in no way limiting, and that many modifications can be made without departing from its scope.

Claims (57)

  An imidazoline compound, characterized in that it comprises the reaction product (i) of a dicarbonyl compound, (ii) a primary amine group of a polyamine and (iii) a compound of 'hydrocarbyl carbonyl.   2. Compound according to claim 1, characterized in that the dicarbonyl compound is selected from alpha-omega-dicarboxylic acids and their esters.   3. A compound according to claim 1, characterized in that the dicarbonyl compound is a compound of the formula: ## STR1 ## wherein n is from 0 to 20; and R2, R 'and R "are independently selected from a hydrogen atom and an alkyl group, preferably wherein at least one of R' and R" is an alkyl group.   4. Compound according to claim 3, characterized in that n is not 2 or 3.   The compound according to claim 1, wherein the dicarbonyl compound is 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, isophthalic acid and esters of any of these dicarboxylic acids, the dicarbonyl compound being preferably dimethyl diethylmalonate.   6. Compound according to claim 1, characterized in that the polyamine is a linear, branched or cyclic polyalkylene amine having at least one primary amine group.   7. A compound according to claim 1, characterized in that the polyamine is a compound of the formula II NH2 ((CH2) qCHNH) n, wherein R6 is a hydrogen atom or a low molecular weight alkyl group having 1 to 6 carbon atoms, q is an integer of 1 to 3 and m is an integer of 2 to 10.   A compound according to claim 1, characterized in that the polyamine is selected from the group consisting of propylenediamine, butylene diamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, dipropylenetriamine and tripropylenetetramine .   A compound according to claim 1, characterized in that the polyamine has at least three nitrogen atoms and the compound is a reaction product of the hydrocarbyl carbonyl compound and a polyamine intermediate formed by reacting the polyamine compound. dicarbonyl with polyamine.   10. A compound according to claim 9, characterized in that the polyamine intermediate is formed by reacting the dicarbonyl compound with two equivalents of the polyamine.   11. A compound according to claim 9, characterized in that the polyamine intermediate comprises at least two unreacted primary amine groups.   12. A compound according to claim 9 characterized in that the polyamine intermediate comprises a compound selected from a value of from 0 to 20, preferably from 0 to 20, wherein a value of 2 to 10, x has a value of 1 to 11 and R 'and R "are independently selected from hydrogen and alkyl.   13. A compound according to claim 12, characterized in that the hydrocarbyl carbonyl compound is a compound of the following Formula IV wherein R14 is a hydrocarbyl group.   A compound according to claim 13, wherein R 14 is a polyolefinic radical having a number average of the ivmolecular weight in the range of 350 to 10,000 daltons, R 14 preferably being a polyisobutene group.   A compound according to claim 9, characterized in that the hydrocarbyl carbonyl compound is selected from hydrocarbyl-substituted succinic anhydrides, hydrocarbyl-substituted succinic acids and hydrocarbyl-substituted succinic acid esters.   16. A compound according to claim 1, characterized in that the hydrocarbyl carbonyl compound is a compound of the following Formula IV: wherein R14 is a hydrocarbyl group.   17. A compound according to claim 16 wherein R14 is a polyolefinic radical having a number average molecular weight of 350 to 10,000 daltons, R14 preferably being a polyisobutene group.   A compound according to claim 1, which is a reaction product of the dicarbonyl compound and a mono-hydrocarbyl polyamine amine intermediate formed by reacting the hydrocarbyl carbonyl compound with the polyamine. .   19. An imidazoline compound, characterized in that it comprises the reaction product of a dicarbonyl compound and a mono-hydrocarbyl polyamine, wherein the mono-hydrocarbyl polyamine is formed by reaction of a hydrocarbyl carbonyl compound and a polyamine.   20. A compound according to claim 19, characterized in that the dicarbonyl compound is a compound of the formula I: wherein n is 0-20, provided that n is not 2 or 3; and R 1, R 2, R 'and R "are independently selected from hydrogen and alkyl, preferably wherein at least one of R' and R" is alkyl.   The compound according to claim 19, wherein the dicarbonyl compound is 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 any of these dicarboxylic acids.   22. A compound according to claim 19, characterized in that the monohydrocarbyl polyamine is a compound of the formula V: ## STR5 ## wherein hydrocarbyl group; R6 represents a hydrogen atom or a low molecular weight alkyl group having 1 to 6 carbon atoms; m represents an integer from 2 to 10; and q represents an integer of 1 to 3.   23. A compound according to claim 19, characterized in that the monohydrocarbyl polyamine is a fatty amine having at least one primary nitrogen atom.   24. A compound according to claim 19, characterized in that the hydrocarbyl carbonyl compound is a compound having the following formula IV: wherein R14 is a hydrocarbyl group, preferably a polyolefinic group having a number average of molecular weight of 350 to 10,000 daltons.   25. A compound according to claim 19, characterized in that the hydrocarbyl carbonyl compound is selected from dodecenylsuccinic anhydride, C16-6 alkenylsuccinic anhydride and polyisobutenyl succinic anhydride.   26. A compound according to claim 19, characterized in that the polyamine is a branched or cyclic linear polyalkyleneamine having at least one primary amine group.   27. The compound according to claim 19, wherein the polyamine is a compound of the formula II: wherein R6 is a hydrogen atom or a lower alkyl group; molecular weight having 1 to 6 carbon atoms, q represents an integer of 1 to 3 and m represents an integer of 2 to 10. 5   28. A compound according to claim 19, characterized in that the polyamine is selected from the group consisting of propylenediamine, butylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, dipropylenetriamine and tripropylene.   29. Lubricating composition, characterized in that it comprises: a base oil; and an imidazoline compound comprising the reaction product (i) of a dicarbonyl compound, (ii) a primary amine group of a polyamine, and (iii) a hydrocarbyl carbonyl compound.   30. Lubricating composition according to claim 29, characterized in that the concentration of the imidazoline compound is in the range of 0.1% by weight to 20% by weight relative to the total weight of the composition.   31. Lubricating composition according to claim 29, characterized in that the dicarbonyl compound is a compound of the formula I: ## STR2 ## wherein n is 0 to 20 and R 2, R 2 and R "are independently selected from hydrogen and alkyl; preferably wherein at least one of R 'and R "is an alkyl group.   32. A lubricating composition according to claim 31, wherein the polyamine is a compound of formula II: 1 to 6 carbon atoms, q is an integer of 1 to 3 and m is an integer of 2 to 10.   33. Lubricating composition according to claim 29, characterized in that the hydrocarbyl carbonyl compound is a compound corresponding to the following formula IV: wherein R 14 is a hydrocarbyl group, preferably a polyisobutene group.   A method for reducing deposits on a lubricated surface, characterized in that it comprises lubricating the surface with the lubricating composition of claim 29, wherein the imidazoline compound is present in an amount sufficient to reduce the amount of deposition on the lubricated surface, as compared to the amount of deposits on the surface subjected to the same operating conditions and lubricated with the same lubricant composition, except that the composition is free of the imidazoline compound.   A process for improving the suspension of sludge, characterized in that it comprises the step of providing a combustion system to the lubricating composition of claim 29, wherein the imidazoline compound is present in an amount sufficient to maintaining at least a certain amount of sludge in suspension in the base oil for a period of time greater than that reached if the base oil does not contain the imidazoline compound.   36. Lubricant additive formulation composition, characterized in that it comprises: a diluent; and the imidazoline compound of claim 1.   37. An additive formulation according to claim 36, characterized in that the concentration of the imidazoline compound is in the range of 5 to 75% by weight based on the total weight of the additive formulation composition.   38. An additive formulation according to claim 36, characterized in that it further comprises one or more additional additives selected from additional dispersants, detergents, anti-wear agents, additional antioxidants, index improvers of viscosity, pour point depressants, corrosion inhibitors, rust inhibitors, foaming inhibitors and friction modifiers.   39. Fuel composition, characterized in that it comprises: a base fuel; and an imidazoline compound comprising the reaction product (i) of a dicarbonyl compound, (ii) a primary amine group of a polyamine and (iii) a hydrocarbyl carbonyl compound.   40. Fuel composition according to claim 39, characterized in that the concentration of the imidazoline compound is in the range of 10 to 10 000 millionths.   41. Fuel composition according to claim 39, characterized in that the dicarbonyl compound is a compound of the formula I: wherein n is 0 to 20; and R2, R 'and R "are independently selected from hydrogen and alkyl.   42. Fuel composition according to Claim 39, characterized in that the polyamine is a compound of the formula II: NH2 ((CH2) qCHNH) mH R6 in which R6 represents a hydrogen atom or a low molecular weight alkyl group having 1 to 6 carbon atoms, q is an integer of 1 to 3 and m is an integer of 2 to 10.   43. Fuel composition according to claim 39, characterized in that the hydrocarbyl carbonyl compound is a compound of the following formula IV: wherein R 14 is a hydrocarbyl group, preferably a polyisobutene group.   A method for reducing deposits in the fuel distribution system of an internal combustion engine, characterized in that it comprises the use as fuel for the internal combustion engine of the fuel composition according to claim 39, the imidazoline compound being present in the fuel in an amount sufficient to reduce deposits in the fuel dispensing system, as compared to the amount of deposits in the fuel system operating in the same manner and using the same composition of fuel, except that the fuel composition is free of the imidazoline compound.   45. Process for dispersing soot, characterized in that it comprises the step of supplying to a combustion system the fuel composition according to claim 39, the imidazoline compound being present in an amount sufficient to maintain at least a certain amount of soot suspended in the base fuel for a longer period of time than if the base fuel does not contain the imidazoline compound.   46. Fuel additive formulation composition, characterized in that it comprises: a diluent; and the imidazoline compound of claim 1.   47. A fuel additive formulation composition according to claim 46, characterized in that the concentration of the imidazoline compound is in the range of 5% by weight to 50% by weight of the formulation formulation composition. total additive for fuel.   48. Process for forming an imidazoline compound, characterized in that it comprises the reaction (i) of a dicarbonyl compound, (ii) a primary amine group of a polyamine and (iii) a hydrocarbyl carbonyl compound.   49. A process according to claim 48, which comprises: (i) reacting the dicarbonyl compound with the polyamine under reaction conditions sufficient to form a polyamine-imidazoline intermediate; and (ii) reacting the polyamine imidazoline intermediate with the hydrocarbyl carbonyl compound.   50. Process according to claim 49, characterized in that the reaction conditions for the formation of the polyamine-imidazoline intermediate comprise heating at reaction temperatures in the range from 150 ° C to 250 ° C.   51. Process for forming an additive compound, characterized in that it comprises the reaction of a dicarbonyl compound and a monohydrocarbylpolyamine.   52. A process according to claim 51, characterized in that the dicarbonyl compound is a compound of the formula I: wherein n is 0 to 20; and R2, R 'and R "are independently selected from hydrogen and alkyl.   53. Process according to claim 51, characterized in that the monohydrocarbyl polyamine is a fatty amine.   54. Process according to claim 51, characterized in that the monohydrocarbyl polyamine is formed by reacting a hydrocarbyl carbonyl compound with a polyamine.   55. Process according to claim 54, characterized in that the polyamine is a compound of formula II: NH2 ((CH2) qCHNH), wherein R6 represents a hydrogen atom or a low molecular weight alkyl group having 1 at 6 carbon atoms, q represents an integer of 1 to 3, and m represents an integer of 2 to 10.   56. A process according to claim 54, characterized in that the hydrocarbyl carbonyl compound is a compound of the following Formula IV wherein R14 is a hydrocarbyl group.   57. Process according to claim 51, characterized in that the additive compound comprises a central polyamine chain of one or more polyamine groups bonded together with one or more groups selected from diamide groups, imidazolineamide groups and bis-amino groups. imidazoline, a hydrocarbyl carbonyl group being attached to at least one end of the polyamine chain.