DE1644870A1 - Basic nitrogen-containing compounds and lubricants containing these compounds - Google Patents

Description

Basic nitrogen-containing compounds and lubricants containing these compounds

The present invention relates to novel, basic nitrogen-containing compounds which act as ashless detergents and dispersants are used, as well as lubricants containing these new compounds.

A very important development in the field of lubricating oil additives is the development of ashless detergents, ie metal-free compounds which are able to reduce paint and sludge deposits in internal combustion engines. An important advantage of the ashless detergents is that the formation of ash in the decomposition of the detergent is avoided in the engine _E. Thus, the deposits on the valves and in the combustion chamber and the resulting requirement to be reduced to the Aktanzahl by avoiding the presence of metal salts will.

009818/1673 ieue documents (Ar ·, ι% - ,. ^ S. ?. No. ι & u 3 des Ämftrunwr ». Ν. Α. 0.1-

164487C

Numerous ashless detergents are found in the patent literature called low molecular weight. Examples include US Pat. Nos. 3,018,251 in which acylated polyamines ", No. 2,764,551, in Polyesters containing amino groups, No. 2,887,452, in which urethanes are described and No. 2,371,333, in which eaters of pentaerythritol are described.

It has now been found that excellent detergents and dispersants for lubricating oils can be obtained if one (at least 2 amino groups and) at least 2 carbon atoms containing alkylenepolyamine with a 1,2-dithiol-3-thione (trithion) of at least 30 carbon atoms (a molecular weight greater than about 400) elevated temperatures so negated that at least partially a composition is formed, the molecules with has a heterocyclic functionality. The composition obtained includes both sulfur and nitrogen present in the i-molecule. The response will be with either or carried out without the addition of an inert solvent.

The molecular weights of the compositions obtained are generally greater than 450 and generally not greater than 10,000, usually in the range between about 750 and 5,000. The molecules contain about 2 to 10 nitrogen atoms, more commonly 2 to 6 nitrogen atoms and at least one sulfur atom · The molecule contains at least one carbon chain having at least about 25 carbon atoms and generally with no more than 300 carbon atoms, usually with no more than 200 carbon atoms. The carbon chain can be formed by polymerizing olefins with about 2 to 6 Carbon atoms are obtained.

The structural formula of the main product is not certain, the spectral properties of the "" "product, as well as other indications however, suggest that the molecule (in

0098 18/1673

164487C

Application of an M ratio of the reaction components from 1: 1) from a [- Tbiono - substituted Piasa heterocycle with 5 "to 6 carbon atoms. This molecule has the following pornel:

^R Y '

in which R an aliphatic carbon group: hydrogen group with at least 25 carbon atoms, Y is hydrogen, Denotes alkyl, aminoalkyl or polyalkyleneaminoalkyl and | η denotes a number from 2 to 3, R generally has an Ilolecular Weight from about 350 to about 5000. R means either hydrogen or aliphatic hydrocarbon with 1 to 1? Carbon atoms. Y can have up to 8 nitrogen atoms contain, and usually does not contain E: or rather than about 4 nitrogen atoms.

If a 2: 1 ratio of thione to alkylene polyamine (at least 4 nitrogen atoms) is used, Y is an alkylene anine with a terminal group representing the radilral bonded to Y ".

i! ii. ;; i ::: i ^ lich 'V'r .U: ak * ionteilr.eii.'. 'ier is to i-'ericrken that (d.'is L'rithi-T. lie follow the formula

has, in * iv> r R "'uiiΛ R aliphati. ci.e Hydrocarbon residueP with iiKV-joa.".! üf ..- ι J ', ⁷ to 300 Kohlonstcf fate: r »en, usually etv. ^! a ^k . ru- 2- ^ C Koiilenstof: '; itüinen mean, where one of the group :. R ^ um R »'asserstcf:' be *. l: ai-ji. Sevichr.lich loading

009818 / 167.1

BATH

164487C

■ - 6 - '

product formed an imidazoline ring; if you see three coals If there are substance atoms between the nitrogen atoms, the product likely to have formed has a ^ etr & hydropyrijüidinring on.

Particularly preferred polyamines are ethylene diamine and polyethylene polyamines of the following formula:

in which m represents an integer from 1 to 6.

Examples of alkylenepolyamines are ethylenediamine, propylenediamine, Isobutylenediamine, diethylenetriamine, triethylene- tetramine, bipropylenetriamine, hexamethylenediamine, tetraethylene pentamine, Pentaethylene hexamine, Nonaäthylendecamin, ΪΤ, Ι-Γ— Dimethyl diethylenetriamine etc.

Most of the N-alkylalkylenediamines have the following formula . - ~

Y ³ MHB ² IlH ₂

in which Y ^{y is} an alkyl having about 10 to 20 carbon atoms

ρ
and B is an alkylene of about 2 to 3 carbon atoms. The alkyl groups can be straight or branched, preferably they are straight. They can be saturated or contain aliphatically unsaturated bonds. The aliphatic hydrocarbon substituents can be derived from both naturally occurring and synthetic hydrocarbons.

Allphatic N-alkylalkyleneamines are e.g. N-Bodecyi-ethylenediamine, N-tetradecyl-ethylenediamine, N-hexadecyl-ethylenediamine, N-octadecyl-ethylenediamine, IT-eicosyl-äthyJjendiaain, N-tetradecenylethylenediamine, N-octadecenylethylenediamine, N-tetradecylpropylenediamine, 1-hexadecylpropylenediamine N-eicosyl-propylenediamine, li-hexadecenyl-propy3. "Ndiamiii, etc.

009818/1673

164487G

Both the trithione and the tolyamine "do not need any being single links, in fact, they usually consist of !!! loops of links with an intersection composition. In the Tritbion, the molecules have for the most part molecular weights which correspond to the average molecular weight nearcomnräen. Forms in the case of polyamines the composition generally refers to the main, if not the predominant part of the mixture. ".

The reaction between the sithione and the amine also takes place at ambient temperatures (20 °), generally be | However, the elevated temperatures applied, z.3. over 80, usually in the range between about 90 and about 175 "Die time required for response depends on the as well as other factors affecting speed away. Usually the reaction time is about 1 to 1-2 hours, preferably no more than 8 hours:

The reaction can be carried out at ambient pressures. In general, an inert atmosphere, e.g. Nitrogen, 'during the course of the reaction over the reaction - ■ .mixture is kept frozen. The order of addition of the Materials is not critical and the reaction can be discontinuous or be carried out continuously.

In -'- ίύτ the reaction uurciiführung be etv: a! "0.1 to 2.1 moles per tfrithion vervienuet K-ol ^Polyarain: -." Ei.:tens is the f 1 ^c 1-fro-iu-kt erwün. - Right, and in this case approximately equimolar i-lei _4f : en amine and sithione are used; however, an excess of amine is preferably present, large excesses of anine can be used, the molar ratio of anine to trithione .. However, if it usually does not exceed 10 to 1, Dr.'s usual molar ratio of amine to trithione is usually in the range between about -1: 1 and 10: 1, more often in the range between about 2: 1 and 6: 1.

009818/1673

BATH ORIGINAL

164487C

E stands from a long-chain aliphatic hydrocarbon radical, while .R is hydrogen or alkyl of 1 to carbon atoms, more often lower alkyl, i. an alkyl having about 1 to 6 carbon atoms,

Examples of these compounds include 4-tert-butyl _{0-5-polyisobutenyl-1,2-dithiol-3-thione,} 5-Polyäthylenyl-1, 2-dithiol-3-thione, 4-methyl-5-polypropenyl-1, 2-dithiol-3-thione etc.

In part, the "compounds are easily prepared from aliphatic olefins and sulfur by combining the two reactants at elevated temperatures" The article by Phillip S. Landis, Cheffi.Rev _o Volume 65, pages 237-245 (1965) referenced, in which the production of trithions from polyisobutylene and Schv.'efel is discussed and described.

Numerous aliphatic olefins with the specified number of carbon atoms or the specified i-molecular weight can be used be used,. Most often they will go through the polymerization of low molar olefins, i.e. with 2 to 6 carbon atoms, especially of isobutylene, produced. Other olefins are, for example, ethylene, propylene, Butene-1, etc. The method of polymerization is not critical to the present invention and is any suitable Procedure can be applied.

"The alkylene polyamine or polyalkylene polyamine generally contains about 2 to 24 carbon atoms, usually 2 to 20 carbon atoms.» The polyamines for the most part have the following formula

in which A is an alkylene group with 2 to 6 carbon atoms, / 009818/1673

BATH ORIGINAL

164487C

and generally means 2 "to 3 carbon atoms, where 2 to 3 carbon atoms are between the nitrogen atoms; B is an alkylene group with 2 to 6 carbon atoms, generally represents 2 to 3 carbon atoms, el is an integer from 0 to 9, usually from 0 to 5 and

ι ρ
Y and Y are hydrogen or aliphatic hydrocarbyl with 1 to

1 2 20 carbon atoms means · Y and Y can be the same or

to be different. When m is 0, Y must be hydrogen. The polyamines used in the present invention must therefore have a primary and a secondary amine group, which are separated by 2 to 3 carbon atoms.

For the most part, the polyamines belong to two preferred categories: alky-helene polyamines and N-alkyl-alkylene-diamines.

1 2

In the case of the alkylene polyamines, Y and Y usually mean Hydrogen, but they can also mean lower alkyl. In the case of the N-alkylalkylenepolyamines, Y is hydrogen and Y is an alkyl group, usually about 12 to 20 carbon atoms contains .; The alkylene polyamines generally contain from about 2 to 20 carbon atoms, more usually 2 to 12 carbon atoms. Contain the N-alkylalkylenediamines generally 14 to 22 carbon atoms, more often 16 to 20 carbon atoms. '

As already indicated, alkylenepolyamines and (

ϊί-Alkylalkylenediamines preferred «, The alkylenepolyamines are discussed first. The alkylene polyamines have the greatest partly the following formula:

H (NHB ¹ ) _m1 NH

in which B is alkylene having 2 to 3 carbon atoms and

1
m is an integer from 1 to 6

When the alkylene group has two carbon atoms, between the Contains nitrogen atoms, it probably has

0098 18/1673

164487C

The reactants can be brought together without a solvent or an inert solvent can be used. Various inert solvents are, for example, ₀ hydrocarbons, both aromatic and aliphatic. The solvent preferably has a boiling point which is at least as high as the reaction temperature. Examples of solvents include benzene, toluene, xylene, mesitylene, hexane, heptane, octane, etc.

When a solvent is used, the concentration of the reactants is not critical. In general, φ make up about 5 to 80% by weight of the reaction solution, .. "" ■ ".. ': _'-_

The. the following examples serve to illustrate the invention ",

Example A.

To a reaction flask containing a nitrogen atmosphere were charged 160 g (5 gram atoms) of Schv: efel and 260 g of 4-neopentyl-5-tert-butyl-1,2-dithiol-3-thione; the mixture was heated to 200 ° and 900 g (about 1 mole) of polyisobutylene were added over about an hour. The temperature was maintained for 12 hours - "ach Ab> -. JK running this ^ e-it, the temperature was raised to 210 °, the pressure to 4 to 5 mrn Hg reduced and distilled off the volatile material above The residue weighed 1028 g . · an infrared spectrum dea - ^L roduktes agreed with that of Trithion match.

Example 1 _ ₌ . ""'-.; ■

450 g (0.5 Hol) polyiso- ^; butylenetrithione and 378 g (2.0 mol) of a Ki .-. Polyäthylenpolyarainen with a through-hole composition of - ^ etraäthylenpentamin introduced and the mixture ■ ■ heated at 150 ° for about 16 hours after it had been cooled

009818/1673 ß ί "■"^;

164487C

had allowed to cool, one liter of hexane was added. An attempt to wash the mixture with water for ₂ u failed and the water was removed by adding benzene and azeotropically distilling off the benzene-water mixture.

After the remaining product had been heated to 120 in order to drive off as much solvent as possible, the mixture was diluted with an equal volume of hexane, heated. and then a volume of ethanol equal to the volume of hexane was added. While keeping the entire mixture warm, 700 to 800 cc of water were added with stirring. The stirring was stopped and the Λ

Mixture could separate. The aqueous portion was discarded and the volatile solvents were removed in vacuo; removed at 80 to 90 ° and 5 mm Hg. The residue weighed 400 g. The infrared spectrum was compatible with 'one in it existing imidazoline,.

Example 2. .-, - .. ■

601 g (10 mol) of ethylenediamine and 500 ecm of toluene were introduced into a reaction flask. The mixture was heated to 120 °. 1500 g (1 mole) of polyisobutylenetrithione in one liter of toluene were slowly added over the course of one hour. The mixture was refluxed for 9 hours, drained *

cools and with a water-ethanol solution with a. relationship washed from 50! 50. The aqueous phase was discarded and the organic phase was dried, filtered and the volatiles removed in vacuo. Of the The residue weighed 1300 g. The infrared spectrum agreed with that present imidazoline match.

A number of other examples were made according to the procedures Example 1 or 2 carried out, the latter being differ mainly in the presence of a hydrocarbon solvent. The following table shows the - Reactants, the amounts used and the conditions under which the reaction ^ would be carried out

00 9 818/1 ^ 7 3 "U

Table I.

at Polyisobutylene MoI 2
Amine MoI Tegipera- Time, solvent ecm analysis fo S • I.
O
I. game 0.25 .0.2 .tur, ⁰ C hours fo N 2.68. 3 A. 0.25 A. 1 1 50 12th _ / 4.56 3 * 50 4th A. 0.11 B. Oj 5 110 4th - 600 1.75 VJl C. 1.0 A. 2 120 1 600 0.76 4.0 6th A. 0.75 B. 3 150 - τ . · 1.1 3.96 7th A. 1.0 ^: B. 5 110
120 4th
4th 800 2.34 8th . B. C. 125 '4: " 1.14

^m B - "" w 1500

c *>σ> » " "3000

A - polyalicylenepolyarain with an average - '

Composition of tetraethylene pentamine

B *. Ethylenediamine ,,. , ■. ■ '■■' ■.,

G, Polyalkylenpolyarain with an ^average: ■

. composition of, 'i'etraäthylenetetramine,,,

■ ^ T - toluene,. ς ^

■. ■ \ ■ ■ ■ ■ ■, ':. ■ ■. ■ ■ ■ '■: ·''. ■ ■ ■ ■. ■■ ■■: J ^ ■■■ '.. ■■''■■' ■. '' ■■ - '. '' ■ oo

■. ■. ■ '■■ ■■ (■;. "■. ■' .... ■ '■■ <-»

^; 164487C

In a reaction vessel 150 g 1 "(1 mole) Polyisobutylentrithion were introduced in 500 cc of toluene and heated to 50 ⁰ C. The warm solution was added slowly 51.2 g (0.35 mol) of a mixture of alkylene polyamines _added. As the The main component contained triethylenetetrrin, dissolved in 50% of toluene. The addition took 8 hours. The mixture was then heated to 115 ° and refluxed for one hour.

ι -

treated cooler. The product was then with a Ethanol-Wassex ^ solution 50:50 fite-Vie-gchen and then dried. The infrared spectrum was consistent with imidazoline formation.

As has already been stated, find the inventive Verbxr5'iui * f '«n as dispersants and detergents in oils with cu> r viscosity of lubricating oils .. use. They are both under ien hot temperature conditions of the diesel engine as well as among the different and in general colder conditions of the gasoline car engine in city traffic v'irknam. If the connections according to the invention a Blended with Schnüeröl for use in an engine they are in an amount of at least about 0.1 % By weight, and usually not more than 20% by weight, more common in the. -er-eich "between 2 and 10 wt. fi available.

As a result of the excellent compatibility of the invention Raässen liusarunensetzünden with ocher oils can be used by the amrrrrrrr as lubricating oil concentrates. as

tr-ite- form the compounds according to the invention in what I mean by about 20 to 70 weights. gov.'öhnlich about 25 to 65 wt -.% ■ the total SusäumenSetzung. -

A foremost aspect of the use: that according to the invention Connections ir. Intersection be * always thin, that in the oil about 1 to 50 riillimol / kg of a Ο, Ό-dihydrocarbyl phcsphorodithioate » in particular of zinc salsa, incorporated, its

009818/1673

■ BATHROOM

164487C

Hydrocarbon groups contain about 4 Ms 36 carbon atoms, Usually these are called the hydrocarbyl groups to alkyl or alkaryl. Other phosphorodithioates such as ζOB Trialkyl or polyethylene oxydihydrocarbyl phosphorodithioate can also be used to advantage. on the other hand can be a polyisobutylenetrithione having a molecular weight of about 260 to 1500 in an amount of about 0.05 to 5 wt .- ^, based on the composition, alone or can be used in combination with a phosphorodithioate.

The lubricants, which together with the fiction φ used in accordance with connections (and hereinafter: as ■ Oils can be called natural or synthetic Sources come from. Oils generally have viscosities from about 35 to 50,000 Saybolt Universal Seconds (SUS) at 37.8 °, among the natural hydrocarbons Oils include paraffin-based oils, naphthene-based, Asphalt base and mixed base. Examples of synthetic oils are hydrocarbon oils such as polymers of various olefins with generally 2 to 8 carbon atoms and alkylated aromatic hydrocarbons; and non-hydrocarbon oils such as polyalkylene oxides, aromatic ethers, carboxylate esters, phosphate esters, and silicone esters. The preferred media are both natural and ■ Ρ also synthetic media containing hydrocarbons. "".

The above oils can be used individually or together, if they are miscible or through the use of common - seed solvents are made miscible. . .

Other additives can the oil be added, such as pour point depressants, S _C hmierfähigkeitsmittel, antioxidants, Rosthemrrmngsmittel, bearing corrosion inhibitors, etc. other detergents - "ei oils to be used liotor in one, the Ge amt amount is these additives is between about 0.1 and 10 wt .-; £, usually

00 98 18/167 3

V 164487C

between about. 0.5 and 5 wt .- ^ ₀ The individual additives may in e, iner amount between about 0,0.1, and 5 wt .- $, based on the total composition, may be present. In concentrates, the amount of these additives is usually between about 0.3. and .30 wt.

In order to demonstrate the excellent effectiveness of the compounds according to the invention, a number of the compositions prepared were ^{tested according to the '1} IG Caterpillar test ¹ (conditions according to MIIr-L-45199). The oil used was a SAE 30 oil from Central America and. there were different ones. Qxydatipnshemmen.de means used. -. j (

The protruding deposits were rated on a scale from 0 to 800: Q means completely clean and 800 is completely black. Base oil containing 12 millinio.1 / kg of zinc-di- (alkylphenyl) -phQsphor4ithip.at (the alkyl groups were polypropylene with about 12 to 15 foal atoms) is rated 500-800-330. The grooves deposits et bewert ^to search for a scale of 0 bi.s 100: Q, is completely clean and 100ist fast.völlig gefüllt.Jpasisöl containing the indicated amount of -the Phosphordithloat is rated 93-15-5-3 " The. Deposits on the ünt er.se it θ are rated on a scale from Q to 10ί 0. is completely black, while 10 is completely clean, ·. . · "

The following table explains the composition used, the anti-oxidant used in un ^ clif quantities, the duration of the experiment and the results · "-... '

ÖQ981S / 1673

T a b e 1 1 e II

CD CO

OO

example

Ψ :

pxydat ionshemiaende

middle

.Deposits

ν

.in the protruding Under hours : Grooves " Abalagerun page 60 32-2-0-0 :: 85-10-0 7.5 60 28-8-0-0 35-15-15 9.0 1.20 46-9-0-0, ' 255-20-25 8.0 60 13-4-0-0 130-15-20 6.9

A - Polyisobutylenetrithione has a molecular weight of around 1100

B - Zn-iDipolypropylene- ^ dithiophosphate (polypropylene with 12 to 15 carbon atoms)

■? ■■ r *

164487C

As a further test for the usefulness of the compounds according to the invention in lubricating oils, a modified PL-2 test method was used, as described in the report of the ¹¹ Coordinating Research Council "dated June 21, 1948. In this test, the behavior in a car engine is used A standard procedure requires maintaining a cooling jacket temperature of 35.0 ° and

ο '/ an oil temperature door in the crankcase of ^ 68.3 at 2500 rpm.

and 45 braking horsepower for the duration of 40 hours (here the conditions of the relatively "cold" engine are well simulated, as they normally occur when driving around town). At the end of each experiment, the hotter will be remedied and the amount of total sludge (rating 0 to 50, no sludge = 50)., total varnish deposit (Rating from 0 to 50, no paint deposit> 50) and the Soiling of the rings and the oil strainer (evaluation of 0 to 100, no contamination = 0) are determined. Of the . The above test was modified by the fact that the duration would be extended and the oil pan temperature periodically from 73.7 ° to 96.1 ° and the cooling water jacket temperature from 35.0 ° was increased to 76.7 °. /

Without any detergent addition in the Cl, the engine is about 12

Hours _t no longer operational · "I

The compositions were made using an SAE 30 base oil made from central arerica. Besides the detergent 10 millimoles / kg of zinc O, O-di- (alkyl) -dithiophosphate were added to the oil (Alkyl of 4 to 6 carbon atoms) and 2 ilillimol / kg Zinc-ü, O-di- (al / .ylphenyl) -dithiophosphate (alkyl is polypropylene with 12 to 15 carbon atoms) added. the the following table shows the results obtained.

009818/1673

ORIGINAL INSPECTED

164487C

Table III

at
game Weight 2 Time
Hours. entire paint
storage overall
mud Pollution
tongue of the
Oil filter, ° / o Ringver
dirt
tongue, ^ 1 1 2 80 29 29 2 60 3 1, O 60 25th 30th 7th 90 - 4th 1, 40 17th 34 7 - 84 3, 80 23 42 5 28

The above applies to both diesel engines and gasoline car engines The results obtained show the excellent effectiveness of the compositions according to the invention as Detergents urici dispersant - within a wide range Range of 'lotor conditions. The compositions according to the invention not only have an excellent one Detergent action under the very hot conditions that occur in a diesel engine, but also under the changing conditions of a gasoline engine. Furthermore carry the detergents according to the invention only insignificantly to undesirable loving effects such as corrosion, Rust formation etc. furthermore, the compositions of the present the invention compatible with a large Ansalil other lubricating oil additives, especially with the oxidizing agents used.

The erfir; lun _: -: r; _Fo 'en:; Auxiliary additives can be used in fuels and other hydrocarbon fluids that require detergent or dispersion properties. The Detergenseigenscho.fi also includes. Emulsification properties, and therefore the compositions according to the invention can also be used as emulsifiers.

0098 18/167 3

BAD ORlGiNAL

Claims (1)

1 β compound obtained by reacting a - 1-, 2-dithiol-3-thione, which has at least 30 carbon atoms and at least the equimolar amount of an alkylenepolyamine which is at least zv / ei amino groups, one primary and one of the primary Aiuinog group by 2 "to 3 C-atoms, separated secondary amino group on v / eist, at elevated temperatures en v / ird. 2. A compound according to claim 1, characterized in that by reacting a compound of the general formula Rt> in which R and R aliphatic ^ hydrocarbyl groups with a total of 25 to 300 carbon atoms, where one of the G groups R and R can be hydrogen, with - ([ an alkylene polyamine of the formula H (FlIA) (HHA) WT ¹ Y ² - ... in which A is an alkylene group with 2 to 6 carbon · atoms means in which there are 2 to 3 carbon atoms between the nitrogen atoms, 13-an alkylene group with 2 12th up to 6 carbon atoms, Y and Y are hydrogen or aliphatic hydrocarbyl groups with 1 to 20 Represent carbon atoms and m an integer ι des Xnderuntaoes. ». 4.9, 19f : 164487C from Q to 9, where Y is hydrogen, vienii ru = O and where d; is I ^v : oil ratio of l'rithione to alkylenepolyamine is in the range "between 0.1: 1 and 2: 1, at least 80 ⁰ O, preferably at about 90-175 C and before ^ ur; sv; ei-3e in a ine .M -or ·. I.ösiui; st! Ii.t ⁺ el, erha.l ^f , -ri "' will. 3 "Verbiif-.f'iug m> ch Claims: 1, thereby galenite ie- ret _f that d 'π.-Iclve KMual tr: is from j clyalkylenpol./ar-iin" U ; 2r: L- thion from 2 : 1 to 8: 1. 4o connection n ^c _e li statement 1, thereby marked :, .das; they by reaction etv; a of a lol of a 1,2-dithiol-3-fchicns of the allo'-enBiric-rt I'Ornel in which R ⁵ and R ins ^ esa-t contain about 50 to 200 carbon atoms, R is an aliphatic hydrocarbyl group and R is an alk, yl group with 1 -frie - ^ - carbon atoms, with about 1 to 8 moles of an alitylene polyamine the iOrmel H (IiI-ICH ₂ Gn ₂ ) _ra 1 HH ₂ . ' in the m a ^. ^v -nze, Jahl means from 1 to 6, is obtained at 90 to 175 ° C. 5. Connection rr-iCh claim 1, characterized gekfcnnrieictmet ,. that one of the two G groups R ^, and R. polyisobutylene means" 0 0 9 8 18/1673 BAD ORiGINAL 164487C 6. Sciriermi t " ( ¹ I,." Okenniieichnet by a content of the product of the reaction at elevated temperatures of a 1,2-l) it-hi-ol-3-thione with at least 30 carbon atoms with an alkylene polyanine with at least two amino groups, one primary amino group and one secondary amino group separated from the primary amino group by 2 to 3 carbon atoms, the "alkyl enpolyarain" being in at least equinolent amounts, 7. Schuifirniittel η <ch claim 6, characterized by a ■ content of the * ve mr.t der Ums et sun. * at a temperature of at least 80 ° C, preferably at a temperature of 90-175 ° G and preferably in an inert solvent, a normal compound of the formula in the R and R 'aliphatic hydrocarbyl groups with a total of 25 to. 3 ^ "- mean carbon atoms, one dor ^ rupj-en R ^ and R can mean hydrogen, miL an alkylenepolyamine of the formula. H (NHA) (NHB) JiY ¹ Y ² in which A denotes an alkylene group with 2 to 6 carbon atoms, in which 2 to 3 carbon atoms are "alternating stick." ⁺ , of ^ atoms, -B is an alkylene group with 2 to 6 1 2 Carbon atoms means, 'Y and Y' hydrogen or aliphatiache Represent hydrocarbyl groups with 1 to .20 carbon atoms and α eiti «ganae 3 number from 0 to 9, with the condition that Y means fuel when m = 0, where the ratio of trithione to alkylenepolyamine in the range 00 98 18/1: 673, " _1M .. BAD ORSG ^ AL 164487C is between 0.1: 1 and 2: 1. · 8. Lubricant according to claim 6, characterized by a Content of reaction product, which is the molar ratio of poly- . alkylenepolyamine to trithione of 2: 1 to 8: 1. 9. A lubricant according to claim 6, characterized by a content of the ^r roduct the reaction at a temperature of 9O ⁰ C to 175 ° C of about 1 mol of a 1,2-dithiol-3-thione of the formula S O * = S ^v s /. -. ■ - .. ■ in which R and R a total of about 50 to 200 carbon atoms contain, R is an aliphatic hydrocarbyl group and R is an alkyl group having 1 to 12 carbon atoms, with about 1 to 8 moles of an alkylene polyamine of the formula H (IHiCH ₂ CH ₂ ) 1MH ₂ - in which ήι is an integer from 1 to 6. 10. Lubricant according to claim 9 »characterized by a Content of a reaction product in which one of the groups R- and R are polyisobutylene. 11. Lubricant according to claim 6, characterized by a content of about 0.05 to 5 wt .- ^ of a polyisobutylene trithione with a molecular weight of about 260 to 15Cü. Pur Chevron Research Company Lawyer 009818/1673 ■ "" ■ '■ ■ ORIGINAL INSPECTED