JPH07278142A - Imidazoline derivative, its production and dispersing agent and oil composition obtained by adding these compositions - Google Patents

Abstract

PURPOSE:To obtain a new derivative having the ability to neutralize an acid, excellent in solubilizing ability, exhibiting high cleaning and dispersing performance and capable of providing an ash-free type dispersing agent. CONSTITUTION:This derivative is expressed by the formula [R1 is an olefinic (co)polymer chain having >=600 average molecular weight; R3 is a higher alkyl which may be branched; (m) and (n) each is 1-10] and has >=50mg KOH base value. The derivative is obtained by reacting (A) an adjacent dicarboxylic acid anhydride having >=600 (especially preferably 1000-4000) average-molecular weight and an olefinic (co)polymer chain with (B) a higher fatty acid and (C) a polyalkylene polyamine compound of the formula, H2N[(CH2)aNH]bCH2CH2 NH2 [(a) is 1-10; (b) is 2-10].

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel imidazoline derivative having a specific imidazoline ring structure and a method for producing the same, and further a dispersant containing these compounds as a main component and an oil composition containing the dispersant. Regarding things.

[0002]

2. Description of the Related Art Generally, in a gasoline engine or a diesel engine, fuel or lubricating oil is deteriorated by oxygen or heat, and becomes oil-insoluble acid or sludge to contaminate a metal surface. Therefore, in order to prevent such fouling in the engine, a detergent-dispersant for removing generated acid and dispersing and solubilizing sludge is added. As the detergent-dispersant, a metal type has been conventionally used, but in recent years, particulate emission in the engine combustion chamber has become a problem, and an ashless type has been replaced. As the ashless-type detergent dispersant, polyalkenyl succinimide compounds have been widely used, but the cleaning action of the acid produced is weak and poses a problem.

Generally, as a cleaning action, it is necessary to have both the function of neutralizing the produced acid and the function of solubilizing the neutralized substance in oil. However, in the conventional studies, for example, (1) the base number of a compound has been increased by lowering the molecular weight of the compound or introducing a large number of basic groups in order to enhance the ability to neutralize with an acid. The cleaning action cannot be improved, and (2) on the contrary, if the base number of the compound is lowered and the compatibility with the oil is increased, the acid produced cannot be neutralized, and the base number is high and the compatibility with the oil is high. No excellent compound has been obtained.

On the other hand, an oil composition of a compound having an imidazoline ring has been disclosed. However, many of these have polar groups such as amides or esters, and they have poor compatibility with lubricating oils and cannot be used as detergent dispersants. For example,
JP-A-2-196889 and JP-A-2-2691
Japanese Patent Publication 94 discloses a corrosion inhibitor for fuel oil having a high base number, which comprises a product of an alkenylsuccinic acid and a polyamine and a reaction product of an alkenylsuccinic acid and an imidazoline compound. Excellent acid neutralization ability, but poor oil solubilization ability. Further, JP-A-64-36
Japanese Patent No. 692 discloses a low molecular weight imidazoline-based alkyl ester or amide compound having the ability to improve the lubricity of lubricating oil, but it has almost no clean dispersion performance.

[0005]

DISCLOSURE OF INVENTION Problems to be Solved by the Invention The inventors of the present invention have conducted extensive studies for the purpose of producing an ashless type dispersant having an excellent cleaning action. As a result, a compound having an average molecular weight of 600 or more having a specific imidazoline structure introduced therein. However, they have found that they have a high acid neutralization ability and a high solubilization ability and a high cleaning and dispersing performance, and have completed the present invention.

[0006]

Thus, according to the present invention, (1) the general formula (A)

[Chemical 2] (In the formula, R ₁ represents an olefin (co) polymer chain having an average molecular weight of 600 or more, R ₂ represents a higher alkyl group which may be branched, and m and n each independently represent an integer of 1 to 10.) An imidazoline derivative represented by: (2) an adjacent dicarboxylic acid anhydride having an olefin (co) polymer chain having an average molecular weight of 600 or more, a higher fatty acid, and a general formula H ₂ N
_{((CH 2) a NH)} b CH 2 CH 2 NH 2 ( wherein, a is 1
The integer of 10 and b show the integer of 2-10. ) A polyalkylene polyamine compound represented by the following, and a method for producing an imidazoline derivative of the present invention,
(3) An oil-soluble dispersant containing the imidazoline derivative of the present invention as a main component and (4) an oil composition obtained by adding the dispersant of the present invention are provided.

In the above general formula, R ₁ is not particularly limited to a polymerization method and the like as long as it is a chain formed by polymerizing or copolymerizing an olefinic monomer and having an average molecular weight of 600 or more. The olefinic monomer has usually 20 or less carbon atoms, preferably in the range of 2 to 10, and more preferably 2 to 6
And α-olefins are particularly preferable. Specific examples include ethylene, propylene, n-butene, isobutene, n-pentene, isopentene, n-hexene, n-octene, n-decene, n-dodecene, etc., preferably ethylene, propylene, isobutene and the like. Is. These may be used alone or as a mixture. Moreover, you may add nonconjugated diolefins as needed.

The average molecular weight of R is at least 600 or more, preferably in the range of 800 to 5000, more preferably 1000 to 4000. If the molecular weight is too small, the compatibility with the lubricating oil is poor and the cleaning action is poor. If the molecular weight is too large, the solubility is poor depending on the type of oil.

R ₂ in the formula is a higher alkyl group which may be branched, and usually has 6 or more carbon atoms, preferably 8 to 30, more preferably 10 to 20. Specific examples thereof include, but are not limited to, an octyl group, a lauryl group, a stearyl group, an isostearyl group and a behenyl group.

M in the formula is an integer of 1 to 10, preferably 2 to 6. Further, n in the formula is an integer of 1 to 10 and is selected according to the use and compatibility with the oil to be added.

The base number of the imidazoline derivative of the present invention is
Although not particularly limited, it is preferably 50 mgKOH / g or more, preferably 60 to 100 mgKOH / g. The base number is determined in accordance with JIS K2501 and m of potassium hydroxide or perchloric acid equivalent to hydrochloric acid or perchloric acid required to neutralize all basic components contained in 1 g of a sample.
It is expressed in g.

The method for producing the imidazoline derivative of the present invention is not particularly limited, and examples thereof include a method of reacting an adjacent dicarboxylic acid anhydride having an average olefinic (co) polymer chain with a polyalkylene polyamine compound and a higher fatty acid. Can be mentioned. In this method, the three members can be mixed at the same time to carry out the reaction, but from the viewpoint of efficiency, (1) the polyalkylene polyamine compound is reacted with the higher fatty acid, and (2) the dicarboxylic acid anhydride is reacted. Is preferred.

The polyalkylene polyamine compound used in the reaction has the general formula H ₂ N ((CH ₂ ) _a NH) _b CH ₂ CH ₂
Examples thereof include those represented by NH ₂ (wherein a is an integer of 1 to 10 and b is an integer of 2 to 10). Specific examples thereof include, but are not limited to, triethylenetetramine, tetraethylenepentamine, pentoethylenehexamine, and hexaethyleneheptamine.

The higher fatty acid used may be branched and usually has 6 or more carbon atoms, preferably in the range of 8 to 30, more preferably in the range of 10 to 20. Specifically, octanoic acid, decanoic acid, lauric acid, myristic acid,
Palmitic acid, stearic acid, arachidic acid, behenic acid, montaic acid, palmitooleic acid, oleic acid, erucic acid, linoleic acid, linolenic acid, isooctylic acid, isodecanic acid, isolauric acid, isomyristic acid, isopalmitic acid, isostearic acid Acids, fatty acids such as isoarachidic acid; and natural fatty acids such as lanolin fatty acids, fish oil fatty acids, soybean fatty acids, coconut oil fatty acids, beef fatty acids, and hydrogenated fatty acids thereof, but are not limited thereto.

The adjacent dicarboxylic acid anhydride used has an adjacent dicarboxylic acid structure and an average molecular weight of 60.
There is no particular limitation as long as it is 0 or more. For example, U.S. Pat. No. 3,018,250 and No. 3024.
No. 195, a polyalkenyl succinic acid such as polybutenyl succinic acid or an olefin (co) polymer such as an ethylene-propylene copolymer and a maleic anhydride are reacted with each other, or a halogenated olefin ( Examples thereof include those obtained by reacting a (co) polymer with maleic anhydride, but the present invention is not limited thereto.
The monomer and molecular weight of the olefin (co) polymer are
The same applies to the description of the olefin (co) polymer described above.

In the reaction (1), the polyalkylene polyamine compound and the higher fatty acid are mixed in a molar ratio of 1: 1.0 to 1.0.
It is charged so as to be 1.4 and reacted under reduced pressure. The reaction conditions are usually a reaction temperature of 100 to 250 ° C., preferably 150 to 230 ° C., and a degree of reduced pressure of 1 to 5 in the mercury column.
It is in the range of 0 mmHg, preferably 10 to 30 mmHg. The reaction time is appropriately used depending on the applied temperature and the degree of reduced pressure and the type of fatty acid component used, but is usually 1 to
It is 24 hours, generally about 3 to 8 hours. Furthermore, if necessary, an appropriate amount of toluene or xylene may be added as an azeotropic dehydration solvent. As the catalyst, a metal of Group II or IV of the Periodic Table, and oxides, hydroxides, chlorides, carbonates and organic carboxylates thereof of 0.0001 per mol of the higher fatty acid component used are used. Is in the range of 0.1 mol.

Next, in the imidization reaction of (2), at 80 to 160 under normal pressure in the presence of an azeotropic dehydration solvent such as toluene or xylene, or under reduced pressure in the absence of solvent.
It may be carried out while dehydrating at a temperature of 100 ° C., preferably 100 to 140 ° C., and these are appropriately selected depending on the type of raw material and solvent used. For example, at a temperature of 120 ° C. or higher, imidization is often completed within 2 hours.

The resulting product is then isolated by vacuum distillation or the like, if necessary, to remove the solvent used and unreacted polyalkylene polyamine. Also 100 and 150 used to dilute the compounds of the invention.
The reactions (A) and (B) may be carried out in light oil such as neutral.

The imidazoline derivative of the present invention can be reacted with one or more post-treatment reactants usually selected from the group consisting of boric acid (boronic acid), boron oxide, boron halide and boron ester. Although the thermal stability of the present compound can be remarkably improved by this treatment, the reaction of such post-treatment is described in, for example, US Pat.
According to the No. 1, about 1 to 3% by weight boron compound, preferably boron, is added and the reaction mixture is adjusted to about 135 to
It can be carried out by heating and stirring at 165 ° C. for 1 to 5 hours, and then performing, if desired, stripping and filtration.

The imidazoline compound of the present invention thus obtained can be used as an excellent dispersant. Since the imidazoline compound has high fat solubility, it has excellent compatibility with various organic media, has a large dispersing effect with a small amount of addition, and can disperse various inorganic or organic substances.

Specific examples of the inorganic substance to be dispersed include, for example, metal as an inorganic reinforcing agent, clay, carbon black, calcium carbonate, barium sulfate, silica, mica,
Glass and asbestos; Metal compounds such as zinc, magnesium, lead and aluminum as reactive inorganic materials; Titanium dioxide, iron oxide, zinc chromate etc. as inorganic pigments; Zinc oxide, magnesium oxide as inorganic filler, Antimony oxide, barium ferrite, strontium ferrite, beryllium oxide, pumice, aluminum hydroxide, magnesium hydroxide, basic magnesium carbonate, dolomite, tosonite, calcium sulfate, ammonium sulfate, calcium sulfite, talc, mica, glass balloons, glass beads, glass Fiber, calcium silicate, montmorillonite, bentonite, graphite, carbon fiber, molybdenum sulfide, boron fiber, silicon carbide fiber, zinc borate, barium metaborate, zirconium titanate, etc .; It is but, not limited to this.

As the organic substance, thioindigo,
Examples thereof include, but are not limited to, dioxazine, anhalaquinone, phthalocyanine, quinacridone, perylene, and β-naphthol organic pigment.

As the organic medium, benzene, toluene,
Various solvents such as hexane, cyclohexane, methyl ethyl ketone, acetone, methyl acetate, alcohols; mineral oil base oils for various lubricating oils, α-olefin base oils, etc .;
Aromatic and naphthenic process oils; Dioctyl phthalate, dibutyl phthalate and other plasticizers; Waxes,
Kerosene, etc .; Polymers such as rubber and plastics; Alkyd resin, melanin resin, acrylic resin, urethane resin,
Examples thereof include a vehicle such as a polyether resin; paints, printing inks, etc., but are not limited to these examples.

Since the dispersant of the present invention has an excellent detergency against acidic substances, it is particularly useful as a detergent dispersant for oil.

Examples of the oil added as the detergent-dispersant include fuel oil and lubricating oil, with lubricating oil being preferred. Examples of the lubricating oil include natural oils such as liquid petroleum, paraffin-based, naphthene-based or paraffin-naphthene-mixed solvent-treated or acid-treated mineral oils, oils having a lubricating oil viscosity derived from coal or Teiwa; Polyisobutylene,
Polymerization or copolymerization olefin such as ethylene-propylene copolymer, α-olefin; hydrocarbon oil such as alkylbenzene, polyphenyl, alkylated diphenyl ether and alkylated diphenyl sulfide and its derivatives, analogs and homologs, and halo-substituted carbon Hydrogen oil; alkylene oxide polymers such as polyethylene oxide; synthetic lubricating oils such as esters of dicarboxylic acids and various alcohols. Also, automatic transmission fluids, conduction shaft lubricants, gear lubricants, metalworking lubricants, pressure fluids and other lubricating oils and grease compositions and the like will benefit from the addition of the compounds of the present invention.

The amount of the (cleaning) dispersant used in the present invention varies depending on the substance to be dispersed, the medium thereof, the molecular weight of the dispersant, etc., but it is usually at least 0.005 with respect to the medium.
%, Preferably 0.05 to 50% by weight, more preferably 0.5 to 20% by weight.

The dispersant of the present invention can be used in combination with various additives usually used depending on the intended use. Examples of such additives include metallic detergents, corrosion and antioxidants, pour point effect agents, viscosity index improvers, colorants, defoamers, abrasion resistance additives, abrasion modifiers and the like.

The oil composition containing the dispersant of the present invention can be used for various purposes. For example, crankcase lubricants for spark-added and compression-added internal combustion engines such as automobile and truck engines, two-cycle engines, aircraft piston engines, marine and railway diesel engines, and the like can be mentioned. It can also be used as a lubricant for gas engines, stationary power engines, turbines and the like.

[0029]

EFFECTS OF THE INVENTION By carrying out the present invention, the cleaning action, which has been a drawback of ashless detergent dispersants, can be greatly improved, and it is excellent not obtained by conventional polyalkenyl succinimide compounds. A dispersant having the above properties and an oil composition containing the dispersant are obtained. This dispersant is added to lubricating oils (as detergent dispersants), polymers, paints, inks, etc., to bond magnets and magnetic recording (toners, disks,
Tape), magnetic materials such as magnetic fluids; paints and molded products compatible with EMI; conductive materials such as conductive / electrostatic composite materials; flame-retardant materials such as electric wires and building materials; pigments, catalysts, reaction inhibitors, laminated heat dissipation plates It is suitable as a dispersant for antifriction materials, dyes, FRTP, and the like, and an oil composition containing this dispersant can be used for fuel oils, lubricants, and the like.

[0030]

The present invention will be described in detail below with reference to examples, but the scope of the present invention is not limited thereto.

Example 1 A 1-liter four-necked flask equipped with a stirrer, a thermometer, a sample extraction tube, a condenser and a pressure gauge was charged with 312 g of isostearic acid and 146 g of triethylenetetramine (hereinafter referred to as TETA). . At this time, the number of moles of isostearic acid relative to TETA was 1.1.

Next, this is sealed and the pressure is 400 mmH.
g at 150 ° C. for 3 hours, then the reaction system is heated to 8 mm at a pressure of 30 mmHg and a temperature of 200 ° C.
The reaction was carried out over time. At this point, the acid value was 1.5, and it was confirmed that almost no acid component of the raw material remained. After cooling, unreacted TETA was removed by vacuum distillation, and the infrared spectrum of the reaction product was measured. Primary amino group (3300
cm ^-1 N-H stretching vibration) and imidazoline ring (166
The presence of a 0 cm ⁻¹ imine band) was confirmed, and the specific absorption of unreacted components could hardly be confirmed. Therefore, this dehydration cyclization reaction proceeded almost completely, and 1- (N-
It was determined that (2-aminoethyl) -2-aminoethyl) -2-isoheptadecylimidazoline was obtained. In addition, the composition of the reaction product was analyzed by liquid chromatography (GPC; reverse phase partition mode).
It was 3%.

Subsequently, 1- (N- (2
-Aminoethyl) -2-aminoethyl) -2-isoheptadecyl imidazoline was transferred into a 2 liter reactor equipped with a stirrer, a Dean-Stark device and a temperature control device, and 200 g of xylene and polyisobutenyl succinic anhydride ( Nippon Petrochemical Co., Ltd. HV-100M; average molecular weight 110
0) 1045 g was added. While increasing the reaction temperature while stirring and removing the reaction water by azeotropic distillation, 3
Reflux for hours. Xylene was removed to obtain the compound. From the infrared spectrum, the imidazoline ring structure (1660c
m ⁻¹ ), a primary amino group (3300 cm ⁻¹ ).
And acid anhydrides (1710 cm ^-1 and 1770 cm ^-1 )
Absorption of almost completely disappeared and a new acid imide (1640
Since the absorption of cm ⁻¹ ) appeared, it was judged that the imidization reaction proceeded completely. This compound is a compound A in which R1 of the general formula (A) having an imidazoline ring is a polyisobutenyl group having an average molecular weight of 1100, R2 is an isoheptadecyl group, m is 2 and n is 1.

Example 2 In a 1-liter four-necked flask equipped with a stirrer, a thermometer, a sample extraction tube, a condenser and a pressure gauge, tallow fatty acid (C14 to C18 mixture, average molecular weight 273)
273 g and tetraethylenepentamine (hereinafter TEPA
Is written. ) 189 g was charged. At this time, the molar number of tallow fatty acid to TEPA was 1.0.

Next, this is sealed and the pressure is 400 mmH.
g at 150 ° C. for 3 hours, then the reaction system is heated to 8 mm at a pressure of 30 mmHg and a temperature of 200 ° C.
The reaction was carried out over time. During this time, the acid value dropped to 1.5,
It was confirmed that almost no acid component remained. continue,
The heating was stopped and the reaction mixture was cooled. The reaction yield confirmed by GPC was 89%. In the same manner as in Example 1,
The progress of the reaction was confirmed from the specific absorptions at 3300 cm ^-1 and 1660 cm ^-1 .

Subsequently, the reaction product was stirred with a dean.
The mixture was transferred into a 2-liter reactor equipped with a Stark apparatus and a temperature controller, and 200 g of xylene and 990 g of polyisobutenylsuccinic anhydride (HV-100M) were added. While stirring, the reaction temperature was raised, and the reaction water was removed by azeotropic distillation, and the mixture was refluxed for 3 hours. Xylene was removed to obtain the compound. The reaction was confirmed in the same manner as in Example 1,
R1 of the general formula (A) having an imidazoline ring was a polyisobutenyl group having an average molecular weight of 1100, R2 was a tallow fatty acid residue, and m was 2 and n was 2.

Example 3 In the second-stage imidization reaction, 1000 g of a maleated ethylene-propylene copolymer (Rucant A-6020 manufactured by Mitsui Petrochemical Co .; average molecular weight 3000) was added instead of polyisobutenylsuccinic anhydride. Otherwise in the same manner as in Example 1, R1 of the general formula (A) having an imidazoline ring is an ethylene-propylene polymer chain having an average molecular weight of 3000, R2 is an isoheptadecyl group, m is 2, and n is 1 To obtain compound C.

Comparative Example 1 In a 2 liter reactor equipped with a stirrer, a Dean-Stark apparatus and a temperature controller, 440 g of polyisobutenyl succinic anhydride (HV-100M) and 408 g of xylene were added.
Put in. Then, at room temperature with stirring, 143 g of xylene
145 g of 1- (2-hydroxyethyl) -2-heptadecenyl imidazoline diluted therein was added dropwise. Then, the reaction water was removed by azeotropic distillation, and the mixture was refluxed for 3 hours. The amount of water recovered was 2.2 ml. The compound obtained by removing xylene was designated as D.

Comparative Example 2 1- (2-Aminoethyl) -2-instead of 1- (2-hydroxyethyl) -2-heptadecenylimidazoline
Compound E was obtained in the same manner as in Comparative Example 1 except that 145 g of heptadecenyl imidazoline was added.

Example 4 Compounds A to E and a commercially available polybutenyl succinimide dispersant (average molecular weight 2100; hereinafter referred to as comparative agent).
1% to 100 neutral oil, 100 g of this oil
While stirring in a 200 ml beaker at 25 ° C, concentrated sulfuric acid was added dropwise from a microburet, and the amount of concentrated sulfuric acid added until the cloudiness started was measured. In Table 1, the sulfuric acid solubilizing ability is shown by an index with the concentrated sulfuric acid titer of the comparative agent being 100.

[0041]

[Table 1]

Example 5 The degree of sludge formation was compared by an ISO method oil deterioration test. Compounds A to E and the comparative agent were added to 200 ml of 150 neutral oil at 1% and vigorously stirred at 160 ° C. for 48 hours in the presence of copper. Next, this oil was dropped on about 1 ml of filter paper, and the degree of sludge formation was observed. The results are shown in Table 2.

Example 6 Compounds A to E and a comparative agent were added to hydrorefined paraffinic mineral oil in an amount of 1% to obtain a clean dispersion performance according to JIS K25.
According to No. 14, the lacquer adhesion to the varnish stick was evaluated. The results are shown in Table 2.

[0044]

[Table 2]

From Tables 1 and 2, the compounds of the present invention have a sufficiently high concentrated sulfuric acid solubilizing ability, almost no sludge formation is observed, and very little lacquer adhesion, as compared with the comparative agent. It can be seen that it shows excellent clean dispersibility. On the other hand, the compounds D and E as comparative examples have the same molecular weight as the compound of the present invention and an imidazoline structure, but have poor ester or amide bond compatibility with oil, and It has a low base number and poor ability to neutralize sulfuric acid, etc., resulting in poor cleaning performance.

The embodiments of the present invention will be described below. (1) General formula (A)

[Chemical 3] (In the formula, R ₁ represents an olefin (co) polymer chain having an average molecular weight of 600 or more, R ₂ represents a higher alkyl group which may be branched, and m and n each independently represent an integer of 1 to 10.) An imidazoline derivative represented by. (2) Base number of imidazoline derivative is 50 mgKOH /
The imidazoline derivative according to (1), which is g or more. (3) The imidazoline derivative according to (1) or (2), wherein the olefin-based (co) polymer is a lower olefin (co) polymer. (4) The imidazoline derivative according to (3), wherein the lower olefin is at least one selected from ethylene, propylene and isobutene. (5) The imidazoline derivative according to any one of (1) to (4), which has an average molecular weight of 800 to 5000. (6) A method for producing an imidazoline derivative, which comprises reacting an adjacent dicarboxylic acid anhydride having an olefin (co) polymer chain having an average molecular weight of 600 or more, a higher fatty acid and a polyalkylene polyamine compound. (7) The total base number of the imidazoline derivative produced is 50
The manufacturing method of (6) which is more than mgKOH / g. (8) The production method according to (6) or (7), wherein the higher fatty acid is reacted with the polyalkylene polyamine and then the adjacent dicarboxylic acid anhydride is reacted. (9) The polyalkylene polyamine has the general formula H ₂ N ((C
H ₂ ) _m NH) _n CH ₂ CH ₂ NH ₂ (wherein, m and n each independently represent an integer of 1 to 10), and any of (6) to (8) The production method described in Crab. (10) The production method according to any one of (6) to (9), wherein the olefin is a lower olefin. (11) The lower olefin is at least one selected from ethylene, propylene and isobutene (10)
The manufacturing method described. (12) The production method according to any one of (6) to (11), which has an average molecular weight of 800 to 5,000. (13) An oil-soluble dispersant containing the imidazoline derivative according to any one of (1) to (5) as a main component. (14) The dispersant according to (13), wherein the dispersant is a detergent dispersant. (15) An oil composition to which the dispersant according to (13) or (14) is added. (16) The oil composition as described in (15), which comprises at least 0.005% by weight of a dispersant. (17) The oil composition according to (15) or (16), wherein the oil is a lubricating oil.

Claims (5)

[Claims] 1. A compound represented by the general formula (A): (In the formula, R ₁ represents an olefin (co) polymer chain having an average molecular weight of 600 or more, R ₂ represents a higher alkyl group which may be branched, and m and n each independently represent an integer of 1 to 10.) An imidazoline derivative represented by. 2. The base number of the imidazoline derivative is 50 mg.
The imidazoline derivative according to claim 1, which has a KOH / g or more. 3. An adjacent dicarboxylic acid anhydride having an olefin (co) polymer chain having an average molecular weight of 600 or more, a higher fatty acid and a general formula H ₂ N ((CH ₂ ) _a NH) _b CH ₂ C.
_3. A polyalkylene polyamine compound represented by H ₂ NH ₂ (wherein a is an integer of 1 to 10 and b is an integer of 2 to 10) is reacted with the polyalkylene polyamine compound. A method for producing the imidazoline derivative of. 4. An oil-soluble dispersant containing the imidazoline derivative according to claim 1 as a main component. 5. An oil composition obtained by adding the dispersant according to claim 4.