DE1962983A1 - Detergent for lubricating oil mixtures, and oils containing this detergent - Google Patents

Description

RECHTSANWÄLTE 15. D © 2.1969

DR. JUR. DIPL-GHEM. WALTER AT *

ALFRED HOEPPENER '

HE. JUR, Dlf'L-CHEM. H.-J. WOLFP
DR. JUR. HANS CHR. AX

«23 FRANKFURT AM MAIN-HOCHSf

ADELON CHEESE 5 bottles

Our no. 15 991

Chevron Research. Company San Francisco, CaI., Y.St.A.

Detergent for lubricating oil mixtures, and this detergent

containing oils

significant advance in the field of lubricating oils was achieved with the ashless detergents. These ashless detergents originally consisted primarily of Acyl derivatives of amines with relatively long hydrocarbon chains on the acyl group. Numerous patents have been issued for such ashless lubricating oil detergents, see e.g., U.S. Patents Mr. 3,219,666, 3,296,128, 3,200,075, 3,373 112 and 3,275 554.

While the above additives, good dispersion of the sludge is achieved, in many cases, their protective effect against Fimisablagerung not so good. It was therefore further developed

00Ö828 / 191Ö

is looking for additives that not only result in good sludge dispersion, but also minimize the deposition of varnishes keep.

It is an object of the present invention to provide new Compositions made by halogenating an oil-soluble alkenyl succinic acid or equivalent Succinic acid derivative, e.g. of anhydride, of a monoester, Diesters or the like, and then treating the resulting halogenated product with an amine under Formation of an acyl and / or alkylamine product in which the Amine compound in a molar ratio greater than 1: 1 of Amine compound to acid compound is present. The so obtained Materials are useful as detergents for lubricating oils that protect against sludge and varnish formation.

Hereinafter, preferred embodiments of the invention are explained t

The products used as lubricating oil detergents generally have average molecular weights from about 700 to 10,000, and usually from about 1,000 to 6,000. There are at least 30 aliphatic carbon atoms in the molecule and preferably at least 50 aliphatic carbon atoms and usually no more than a total of 650 carbon atoms, in particular, a total of 400 carbon atoms. Bs is at least an aliphatic hydrocarbon group with 14 carbon atoms, preferably having at least 30 carbon atoms and usually no more than 300 carbon atoms.

The compounds generally contain 1-2 succinyl groups, per molecule, usually an average of at least 1 and between 1 and 2 succinyl groups. Succinyl groups are also understood to mean lactone derivatives such as paraconic acid.

The amines control a nitrogen content of at least 1.5

1962383

at, and generally not more than 12% by weight, usually the nitrogen content is between about 2 and 8 wt.

An alkeny-succinic acid is used to prepare the compositions or a succinic acid derivative first halogenated to at least one halogen atom per molecule of alkeny / succinic acid to introduce. The alkeny-succinic acid compound generally has the following formula:

l-CH-CM

in which R is an oil-solubilizing alkenyl group with at least about 14 and up to about 300 carbon atoms, usually about 30 to 250 carbon atoms and preferably about 50 to 200 carbon atoms and with an aliphatic double bond in the C- or ß-position, while the two radicals X are hydroxyl groups or hydrocarbyloxy groups having 1 to carbon atoms, usually 1 to 3 carbon atoms, or together represent the hydrogen atom of an anhydride. Preferably the compound consists of a monoester or the anhydride.

The alkenyl group R is free of heteroatoms typically, although up to about 5 percent, 5> of the residue R may be in the form of heteroatoms _s, form functional groups which do not interfere with the leading to the formation of the products according to the invention reaction.

R is an olefinic double bond in φ - or ß-position to the Siiocinsaurerest; otherwise this remainder is essentially free of further multiple bonds. The remainder R can be straight

008828 / 191Ö

BATH ORIGINAL

- 4 - "■■ -. ■

be chained or branched. Usually R becomes branched aliphatic ^ group with an average of about one side chain with 1 to 4 carbon atoms per 4 carbon atoms will be the longest chain, and in particular will be the side chain consist of 1 to 2 carbon atoms and preferably a methyl group. Preferably R is polypropylene or Polyisobutylene radical, although also other oil-solubilizing agents Alkyl groups can be used.

If the succinic acid compound consists of a mono- or diester, so the ester group can be derived from any number of hydroxyl groups Hydrocarbons are formed because the Hydroc.arbyloxyrest X is normally lost for the most part during the manufacture of the product of the invention. Usually X becomes a lower alkoxy group with 1 to 3 carbon atoms, in particular be a methoxy group. The monoester can be preformed or formed in situ. V

The halogen used is either chlorine or bromine (halogen with an atomic number of 17 or 35) and is preferably used Chlorine. Suitable halogenating agents are those under form a positive halogen ion under the reaction conditions, e.g. tert-butyl hypochlorite.

'' ■ "■■ ^:

^r The halogenation of a solvent in the presence or absence. It is carried out as an ion reaction. The halogen is usually added to the double bond. In the case of alkenylsuccinic acid derivatives, it is assumed that only one halogen is added to the double bond and that a lactone or other derivative is formed.

Various solvents that are not involved in the halogenation of the Alkenyl succinic acid can be used. As , Solvents are aromatic hydrocarbons, aliphatic compounds containing hydroxyl groups or other polar ones

ÖÖ9828 / 191Ö

or non-polar solvents and mixtures thereof. One the preferred method is to halogenate the anhydride in the presence of a hydroxyl-containing solvent.

Hydroxyl group-containing solvents are for example. Water and alkanols with 1 to 6 carbon atoms, preferably with 1 to 2 carbon atoms i.e. methanol and ethanol. In addition to the hydroxyl-containing solvent, an inert hydrocarbon or halogenated hydrocarbon can be used as the solvent be used. Preferred inert solvents are aromatic hydrocarbons such as benzene © or tert-butylbenzene, or inert halogenated hydrocarbons such as chlorine. benzene.

The reaction temperatures are generally between about -TO and about 100 ⁰ C, more usually between about 0 and about 50 ⁰ O. The halogenation should be such that side reactions of the halogen to be kept to a minimum.

The amounts of inert solvent and hydroxyl group-containing Solvents can be varied within wide limits, based on the alkenylsuccinic acid compound, the amount of inert solvent between about 0.1 and about 2 parts of solvent per part of succinic acid compound. A Hydroxyl containing solvent is usually present in an amount of from about 0.01 to about 1 part per part of the succinic acid compound.

The halogenation is continued until at least about 1 halogen atom per molecule of the succinic acid compound and no more than about 2 halogen atoms, preferably about 1 to 1.5 halogen atoms. Of course, less halogen can also be introduced, but this will result the amount of ultimately desired product is reduced. However, if one strives to produce mixtures of materials

009828/1910

according to the prior art and products according to the invention, when the amount of halogen is reduced below the amount of 1 halogen atom per molecule of succinic acid compound one such Mixture provided directly.

As soon as the reaction is over, the volatile ones become Materials removed and the residue can be used in the following process step.

Suitable amines are other than tertiary amines, i. primary and secondary amines, which mono- or polyamines or P can be hydroxyalkyl or poly, alkyl enoxyamines. Tertiary Amines can coexist with primary or secondary amines. 'Ammonia or amines are also suitable as amines 1 to 30 carbon atoms, usually 1 to 20 carbon atoms and 1 to 10 amine nitrogen atoms and if to 10 hydroxylic ones or ether oxygen atoms. The amines are free from heteroatoms other than those mentioned above. Usually lie no more than 3 of the oxygen atoms in the form of hydroxyl groups before, and generally not more than 2 oxygen atoms.

Suitable alkylene polyamines have 2 to 24 carbon atoms and 2 to 10 amine nitrogen atoms, preferably 2 to 6 amine Nitrogen atoms and alkylene groups with 2 to 6 and preferably 2 to 3 carbon atoms, with at least 2 carbon atoms between the nitrogen atoms. In the category The alkylene polyamines also include piperazine derivatives and aminoalkylene-piperazines. The piperazine compounds are common in addition to the alkylene polyamines, according to the method of preparation of the alkylene polyamines. ,

Commercially available alkylene polyamines are seldom defined individual compounds. Usually one compound predominates and the product has an average composition accordingly this dominant connection. If a special alkylene polyamine is mentioned below, in

000 * 28/1910

In these cases, such mixtures are included which are considered to be essentially considered equivalent to the corresponding alkylene polyamine " can be.

The alkylene polyamines generally have the following formula:

in the U an alkylene radical with 2 "to 6 and usually 2-3 Represents carbon atoms, with at least 2 carbon atoms between nitrogen atoms, and η an integer means from 2 to 10, usually 2 to 6, as an average. . . ,

Examples of alkylenepolyamines are ethylenediamine, propylenediamine, Diethylenetriamine, dipropylenetriamine, dihexamethylenetriamine, Trläthylenetetramine, Tetraäthylenpentamin, Pentaäthylenhexamln, Nonethylene decamine and the like.

Monoamines and diamines in which at least one hydrocarbon group is bound to only 1 nitrogen atom, have the following form.

H (NH- U ¹ ) _Q NRR ¹

C *

in IT represents an alkylene radical with 2-3 carbon atoms ι where'at least 2 carbon atoms between the nitrogen atoms R is a hydrocarbon radical without aromatic Double bonds with 0-2 ethylenic double bonds and with 1 - 20 carbon atoms, R is hydrogen or a hydrocarbon radical free of aromatic double bonds with 0-2 ethylenic double bonds and 1-20 carbon atoms, which is identical to or thereof with the radical R can be different, and a is the number 0 or 1.

009828/1910

BATH ORIGINAL

The entire molecule has 1 - 24 carbon atoms and usually 4 - 20 carbon atoms. '

Examples of such compounds are dimethylamine, propylamine, cyclohexylamine, N-hexyl-propylenediamine, N-dodecylpropylenediamine, N-hexadecyl-propylenediamine, U-octadecenylethylenediamine, N-Octadeceny! -Propylenediamine, N, N-dimethylpropylenediamine, and the same.

The alkanolamines and polyalkyleneoxyamines usually have the following Formula on:

in which m is an integer from 0 - 2, % is an integer from ο - 2, the sum auei and m = 2, ρ is an integer from 0-5, q and q is the number of units AO in a nitrogen-attached unit Represent a chain and each amount to between 0 and 10, the sum of q. + q / is in the range between 1 and 10, r is an integer from 0-1, the sum of m and r = 1 or greater than 1, s is an integer from 0-1 and A is an alkylene radical with 2 - represents 3 carbon atoms, with at least 2 carbon atoms between the heteroatoms.

The total number of units AO is in the range 1 - 10, usually between 1 and 6.

Examples of suitable alkanolamines are Xthanolamine, di- · ethanolamine, ίί-hydroxylalkylethylenediamine, H-hydroxyethylpropylenediamine, Tetraethyleneoxyethylene diamine, the reaction product from tetraethylene pentamine and ethylene oxide in a molar ratio of 1 to 5, Pentaäthylenoxyamiia and Diethylenoxyamin ,,

The reaction between amine and halosuccinic acid product - Can in the absence or presence of an inert hydrocarbon solvent take place; also can be done in two stages, work first in solution and then without solvents. Inert solvents are usually the hydrocarbons substances or acyl halides, generally with boiling points or boiling ranges between 100 and 175 ° C. Examples of suitable Solvents are xylene, cumene, tert-butylbenzene, Chlorobenzene and the like.

The molar ratio of amine to halosuccinic acid product is at least 1: 1, and usually about 1.5-10: 1, especially about 2 to 7: 1. -. ".. '

The concentration of the reactants is generally in the range between about 0.5 and 20 parts of total reactants per part of solvent, and usually between 1 and 10 parts per part solvent.

The reaction temperature is generally between 100 and 225 ^° C. and usually between 110 and 200 ^° C.

The reaction time depends on the temperature used, the respective reactants, the size of the batch and other variables.

As soon as the reaction has ended, the reaction mixture is left cool, with a phase separation generally occurring. The organic layer is made up of the amine salt layer separated and worked up in a conventional manner. Usually the organic layer is made up of unreacted amine freed and purified by extraction, chromatography or the like.

00982871010

Example 1 . -

11 34 g of polyisobutenyl succinic anhydride were placed in a reaction vessel (Average molecular weight of the polyisobutenyl about 1000), 500 ml of benzene and 60 ml of water introduced, chlorine was then bubbled into the reaction mixture for 3 hours (dosing meter 1044B-Sapphire Ball, reading 5), after which nitrogen was blown through the mixture for 1 hour directed. Benzene and .Wasser are then removed in vacuo. The complete removal of the water is achieved by adding made of 300 ml of benzene and azeotropic evaporation of the benzene fc while passing nitrogen through. A rehearsal was made further stripped in vacuum and used for analysis; Chlorine content = $ 4.29.

The above product was added to 500 g of diethylenetriamine and 250 ml of xylene. Residual benzene was stripped off and the solution was heated ^{to 145 ° C.} The xylene and water were stripped overhead over about 1 hour. Then, the temperature was at 170 - 175 ⁰ C increased, wherein all volatile materials escaped, and this temperature was then maintained for 6 hours. When the reaction mixture stood while cooling, two layers formed. After decanting off the liquid upper layer, the lower solid layer was washed with an aliphatic thinner and the 2 organic layers were combined.

The combined organic solutions were poured into 3.8 l of methanol. The mixture was stirred, allowed to settle and the above layer was decanted off. The precipitate was extracted with methanol, then dissolved with acetone and then in a hexane mixture and reprecipitated with acetone. This precipitate was dissolved in benzene to give a product which was easy to handle for the preparation of oil solutions.
Analytical nitrogen content = £ 2.54. 2.57 ° M chlorine content = $ 0.20

0-09829 / 1910

i ^ -BAD ORIGINAL

Molecular Weight (ThermoNAM) 3113.

Example 2

In a reaction vessel, 600 g of polyisobutenylsuccinic anhydride (average molecular weight of polyisobutenyl about 1,000), 400 ml of benzene and 50 ml of methanol were charged. Chlorine was then passed through the reaction mixture for 11/2 hours (dosage 1G44B-Sapphire Ball, reading 5), after which nitrogen was passed in for 1/2 hour. volatile components were removed in vacuo, keeping the temperature was increased to a maximum bath temperature of 95 ⁰ C. Analysis: chlorine content = 5 »11 5 *>.

To the residue 120 ml of xylene and 250 g of diethylene triamine were added "The solution was then for 6 hours at 145 - 160 ⁰ C heated while water and xylene were removed overhead. All volatile materials were then removed in vacuo at a final temperature of 150 ° C. After the mixture was cooled, 300 ml of an aliphatic diluent was added, followed by 700 ml of a 50:50 (by volume) mixture of methanol and water. The mixture emulsified upon stirring. 3.8 liters of methanol and 400 ml of water were then added to the emulsion and allowed to settle. The liquid layer was decanted and the solid layer was extracted with aqueous methanol and then with acetone. The liquid layer and the joint extract were combined, a portion was removed from the resulting mixture and the solvent was removed in vacuo.

Analysis: 3.33 ^ nitrogen; $ 1.07>chlorine; Molecular Weight (ihermoNAM) 3578.

Example 3

650 g of polyisobutenyl succinic anhydride were placed in a reaction vessel (average molecular weight of the poly

.009828- / 1910

BATH ORIGINAL

isobutenyl - about 1000), 400 ml of benzene and 50 ml of methanol were introduced. Chlorine was then passed in at room temperature for 1 3/4 hours (dosage 1044B -%> phire ball, reading 5), then nitrogen was passed through the mixture. Highly volatile components were removed by slowly reducing the pressure and increasing the temperature up to a final pressure of 10 mm Hg and a bottom temperature of 100 ^° C.

To the residue were added 200 ml of xylene and 200 ml Ä'thylendiamin and the mixture was boiled for 64 hours at about 110 ⁰ C to reflux. After cooling, 550 ml of a ψ aliphatic thinner were added and the solution was filtered through Celite. 800 ml of water, 550 ml of hexane mixture and 3.8 l of methanol were added to the mitrat. The solution was allowed to settle, the layers were separated, and the aqueous layer was washed with aqueous methanol. The organic layer was then filtered through Celite and the product was isolated * analysis; 2.76 # nitrogen, 1.06 # chlorine, molecular weight (ThermoNAM) 2558.

Example 4

650 g of polyisobutenylsuccinic anhydride (average molecular weight of polyisobutenyl "about 1000), 400 ml of benzene and 50 ml of methanol were introduced into a reaction flask. Chlorine was then passed through the reaction mixture for 4 hours (dosage 1044B Sapphire Ball, reading at 3 * 5)" after that 1 / 2stÜndiges introducing was of nitrogen the solvent was abdestiiliert in a vacuum by lowering the pressure to 15 mm Hg and increase the temperature to 115 ⁰ C 714 g of residue analysis was obtained:. # 5-5,5 chlorine, molecular weight ( ThermoHAM) 1100.

A portion of the above product (0.59 moles) would be 250 g (2.42 mol) diethylenetriamine combined and for 7 hours in

00 & S2S / 191Ö

Heated to 160 ⁰ O nitrogen atmosphere. The mixture was then ^{cooled to 100 °} C., 850 ml of an aliphatic diluent were added, then the mixture was stirred, poured into a separating funnel and the resulting phases were separated. The upper layer was filtered through Gelite, then the solvent and other volatile components were stripped by heating at 155 ⁰ C at 5 mm Hg The residue weighed 680 g, Analysis:. ^ 4.05 nitrogen, molecular weight (ThermoNAM) 4245th

Example 5

650 g of polyisobutenylsuccinic anhydride (average molecular weight of the polyisobutenyl radical about 1000), 400 ml of benzene and 50 ml of methanol were introduced into a reaction vessel. Chlorine gas was bubbled through the mixture for 1 3/4 hours (metered with 1Q44B Sapphire Ball reading 5-5.2). After chlorination, nitrogen was bubbled through the mixture for 1 hour, then the solvent was evaporated in vacuo and the temperature raised to about 95 ⁰ C increased. The residue weighed 707 g, analysis: 4.74 $ chlorine.

The above procedure was repeated to give an end product having a chlorine content of 4.91 ° F.

Each of the two batches was diluted with 120 ml of xylene and then 250 g of diethylenetriamine were added. The two batches were treated in parallel as follows: the solution was azeotroped for 6 hours at 160 ° C., cooled to room temperature, then the resulting salt layer was decanted off. The salt layer was washed with hexane mixture, the hexanes were evaporated and the residue was added to the decanted solution. Then the mixture further 250 g of diethylenetriamine were added and it was stirred for 2 hours-η 105 ⁰ C for examples. After cooling to room temperature, about 2 liters of an aliphatic thinner were added and the resulting mixture was filtered through gelite, the solution

009628/1010 '

PUBLIC BATHROOM

medium was evaporated from the filtrate. The residue from the first batch weighed 666 g, the residue from the second batch 63O g. Analysis? 1st batch 4.30 % nitrogen, $ 1.39 chlorine, molecular weight (ThermoNAM) 2934; 2nd batch 4.20 # nitrogen, 0.71 # chlorine, molecular weight (ThermoiTAM) 2442.

The products according to the invention can be formulated with various lubricating fluids (referred to as oils in the following description), which can be either of natural origin or of synthetic origin. The oils generally have viscosities of about 35 to 50,000 Saybolt Universal ψ 'seconds (SUS) at 38 ° C. To. Natural hydrocarbon-containing oils include paraffin-based, naphthene-based, asphalt-based and mixed oils.

Examples of synthetic oils are hydrocarbon oils such as Polymers from various olefins, generally with 2-8 Carbon atoms and alkylated aromatic hydrocarbons; Non-hydrocarbon oils such as polyalkylene oxides, aromatic Ether, carboxylate ester, phosphate ester and silicone ester. The preferred media are the hydrocarbonaceous media of both natural and synthetic origin "

fe The above oils can be used individually or in a mixture, if they are mixable or by using each other Solvents have been made miscible.

Be detergents according to the invention with lubricating oils formulated for the purpose of use in an engine, so they do not lie in amounts of at least about 0.1 percent, "^ and usually more than 20 wt fo before, in amounts of about 1 in general -. 10 wt. ^. The compounds can be made as concentrates because of their excellent compatibility with oils. The compounds according to the invention are generally present in concentrates in amounts of about 10-70% by weight and usually about 20-50% by weight. .

009028/1910

ORJOfNAL

According to a preferred embodiment of the invention, the lubricating oils contain about 1-50 Hillimol p. kg of a dihydrocarbyl phosphorodithioate, in which the hydrocarbyl groups have about 4-36 carbon atoms. Usually the hydrocarbyl groups consist of alkyl or alkaryl groups. The remaining valences of the phosphorodithioate are usually satisfied by zinc, but a polyalkyleneoxy group can also be used or a third hydrocarbyl group may be present (hydrocarbyl is understood to mean an organic radical which consists only of carbon and hydrogen and can be aliphatic, alicyclic, aromatic or mixed).

Other additives to the oil are agents to lower the pour point, Oil formers, antioxidants, rust inhibitors and the like. Usually the total amount of these additives is at about 0.1-10 wt. #, in particular between about 0.5 and 5 wt. The individual additives can be used in amounts of about 0.01-5% by weight are present in the composition.

In order to show the effect of the compositions according to the invention in pistons on varnish formation, the composition according to Example 2 was tested in a Ford 6-cylinder Varnish Engine Test. It .If an oil having the following formulation is used: _f 1 9 wt $ of the compound of Example 2, 50 mM / kg of calcium in the form of Galciumcarbonat with calcium mahogany sulfonate overbased, and 15 millimoles per kg Zlnk-OjO-dialkyl. -phosphorodithioate (alkyl radicals with 4-6 carbon atoms). The oil used consisted of a mixture of Sunray DX 250 neutral oil and Sunray DX 150 light oil in a weight ratio of 6.16: 1.

The test was carried out with a Ford 6 cylinder engine with 3930 ecm displacement. The operating conditions were like in the ASTM Sequence VB test. They were aggravated by Use of a "dirty" fuel made up of 30 volume

00 9828/1810

BATH ORIGINAL

-16 - ■ '■ "" ■

Percent FCC cut with a boiling range of 122 - 218 ⁰ C and 70 io of a commercial gasoline of regular quality. The fuel contained 2 ml per 3.8 liters of lead and about 0.1% by weight of sulfur. The crankcase waste was kept at one inch of water. The engine test was carried out for 60 hours »

If the above oil is used without any further addition, the rating of the piston varnish is 5 _f 3 (based on a scale 0-10, OK as clean). After adding the additive according to the invention, the rating is 7 »3», ie there is a substantial improvement % .

The above reading was repeated using 3% by weight of a 50% by weight solution of the combined compositions according to Example 5 in central continent neutral oil 100. The result was a value for the piston varnish of 8.0 «. or based on a 'scale of 0-50, where 50 designates clean) were 40.9, 42.5. ; ; · ■

The compositions of the invention were also tested for their effectiveness in dispersing sludge in oil and preventing deposits in a 120 hour * trial with a 1-G crawler. The oil used was Central Continent Oil SAE 30, - the 2.25 Weight > of the composition according to Example 2 and containing 12 millimoles / kg of zinc di (alkylphenyl) phosphorodithioate (the alkylene groups were polypropylene groups with about 12-15 carbon atoms). The deposits in the recesses were measured on a scale from 0 to 100 (100 completely filled recesses). The deposits on the protruding parts were rated on a scale of 0-800 (800 completely black). If the above oil is used without detergent, the values for the deposition are in the recesses 93-15-5-2, those on the elevations 500-800-330. In an oil with the invention

009828 / 1Ö1Ö

Detergent, the results are as followsί Pur. The grooves '64 -0.8-0.2-0; for surveys 60-0-10.

From the above information it can be seen that the products according to the invention are not only effective for preventing Deposition τοη varnish, but also to prevent Sludge deposits. These products also do not carry through their own decomposition to whiten deposits but they remain stable for long periods of time and are able to disperse sludge and deposit-forming products in oil.

009828 / 111Ö

Claims (1)

PATEH T AFSPR Ü QH E Process for the preparation of a product suitable as a detergent for lubricating oils, characterized in that one (A) an alkenyrsuccinic acid compound of the formula: R-CH C-X CH ₂ - CX in R an oil-solubilizing alkenyl group with at least about 14 and up to about 300 carbon atoms with an ethylenic double bond in the oC or ß position, and the radicals X, which can be identical or different, are hydroxyl or hydrocarbyloxy radicals having 1-12 carbon atoms or together represent the oxygen atom of an anhydride moiety, with (B.) a halogenating agent converts, in which the halogen has an atomic number between 17 and 35, with the introduction of at least about \ 1 halogen atom per succinic acid molecule with formation of the halogenated succinyl compound (C), and with increased Temperature the compound (C) with an amine (D) having 1-30 carbon atoms and 1-10 amine nitrogen atoms ^ if necessary Bringing 1-10 hydroxylic or ether oxygen atoms into contact, the Kol ratio of (D) to (C) is 1.5-10; 1. Method according to claim 1, characterized in that the remainder »X is the oxygen atom of an acid anhydride group 009828 / 191Ö a hydroxyl-containing solvent at a temperature between -10 and about 100 ⁰ C and is reacted represent (A) with (B) in the presence. 3. The method according to claim 2, characterized in that the halogen in the halogenating agent consists of chlorine. 4. The method according to claim 1, characterized in that the amine (D) is an alkylene polyamine having 2-6 amine nitrogen atoms and an alkylene group having 2-3 carbon atoms is, where there are at least 2 carbon atoms between the nitrogen atoms, and R is a polyisobutenyl radical with about 50-200 carbon atoms. 5. The method according to claim 4, characterized in that the molar ratio of amine (D) to halogenated succinyl compound (C) is in the range of 2 - 7: 1. 6. The method according to claim 1, characterized in that E represents a polyisobutenyl radical having 50-200 carbon atoms, the halogen in the halogenating agent is chlorine, the reaction of (A) with (B) in the presence of an alkanol having 1-6 carbon atoms at one temperature between -10 and about 50 ⁰ C is carried out with the introduction of about 1-1.5 chlorine atoms per succinyl compound (A), and the amine is an alkylene polyamine of the following formula: is, in which U is an alkylene radical with 2-3 carbon atoms represents, with at least 2 carbon atoms between the nitrogen atoms and η an integer from 2-6 is. 000828/1910 7. The method according to claim 6, characterized in that
h = 5. 8. Use of the according to the method of any one of claims 1-7 The composition obtained as a detergent for lubricating oils, characterized in that an oil with lubricating viscosity and 0.1-70% by weight of the product of the process. Pur Chevron Research Company San Francisco, CaI., V.St.A. Lawyer 0098 28/1910