JPS61257968A - Reformed succine imide, lubricating oil and fuel compositioncontaining same - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to additives useful as dispersants and/or detergents in lubricating oils and fuels. In particular, the present invention provides that one or more of the nitrogens in the polyamino moiety is R40R4OR30(C) [wherein R4 is hydrocarbyl of 7-1 to 30 carbon atoms; R5 is a hydrocarbyl of 2 to 30 carbon atoms] selected from the group consisting of hydrocarbyl and -R6-(OR6)-p, where R6 is alkylene of 2 to 5 carbon atoms and p is an integer from 1 to 100; and m is 0 to 1
is an integer of ].

The modified polyaminoalkenyl or alkylsuccinimide of the present invention has excellent dispersibility and (
or] was found to have detergency. These modified succinimides are also useful as detergents and/or dispersants in fuels.

Alkenyl or alkyl succinimides were previously modified with alkylene oxides to their poly(oxyalkylene) hydroxy derivatives.

These alkylene oxide treated succinimides are
It is taught as an additive for lubricating oils (U.S. Pat.
．． No. 373.111 and No. 373.111 discloses a vaporizer cleaner for gasoline obtained by reacting a diamine with ethylene carbonate to form a two-component detergent additive consisting of a carbamate and a urea compound. U.S. Pat. No. 3,652,240 discloses a carburetor wash additive for hydrocarbon fuels that is a carbamate formed by the reaction of an amino-amide with ethylene carbonate. Karol et al.
No. 30.381 discloses that the reaction products of oxalic acid and heptano or bis-succinimide are useful as fuel stabilizers and as carburetor cleaners. U.S. Pat.
A succinimide modified by treatment with a hydroxyalkylene carboxylic acid selected from -bis-hydroxymethylpropionic acid is disclosed. These modified succinimides of US Pat. No. 4,482,464 are disclosed as lubricating oil additives. No. 4,490,154 discloses fuels containing alkenylsuccinyl polyglyfur carbonate esters as antifouling additives. US Pat. No. 3,216,936 discloses products made from aliphatic amines, polymeric substituted succinic acids, and aliphatic monocarboxylic acids. In particular, US Patent Specification No. 4
．． No. 191.537 discloses hydrocarpyl side chain poly(oxyalkylene) polyaminocarbamates useful as fuel and lubricating oil dispersants and detergents. However, in these patents or apparently in other documents, there is no description of complete modification of these polyaminoalkenyl or alkylsuccinimides as in the present invention.

SUMMARY OF THE INVENTION A polyaminoalkenyl or alkylsuccinimide is modified so that one or more nitrogens of the polyamino moiety are R,OR5OR30(C) [wherein R4 is hydrocarbyl of 1 to 30 carbon atoms] R5 is selected from the group consisting of hydrocarbyl of 2 to 30 carbon atoms or -R6+0RI5+p, where R6 is alkylene of 2 to 5 carbon atoms and p is an integer from 1 to 100; and , m is 0 to 1] can produce alkylsuccinimides.

These modified succinimides are dispersants and/or detergents for fuels or oils. Accordingly, the present invention also provides for lubricating oil compositions comprising a major amount of an oil of lubricating viscosity and an amount of a modified polyaminoalkenyl or alkylsuccinimide sufficient to impart dispersibility and detergency. related.

Other composition embodiments of the invention include a predominant amount of a hydrocarbon having a boiling point t-V in the gasoline or diesel range and a modified polyaminoalkenyl or alkylsuccinimide in an amount sufficient to impart dispersibility and/or detergency. is a fuel composition containing.

Preferably R4 is a hydrocarbyl group of 2 to 20 carbon atoms, while R5 is a straight or branched alkylene group of 2 to about 30 carbon atoms or an aryl group of 6 to 10 carbon atoms, or a carbon atom. Straight or branched alkylene groups of 2 to about 30 carbon atoms substituted with 7 to 12 alkaryl are preferred. Most preferably, R5 is a straight or branched alkylene group of 2 to about 30 carbon atoms.

p is preferably an integer of 1 to 50, more preferably p is an integer of 2 to 30, and most preferably p is an integer of 2 to 20, while R6 is an 02 to C4 alkylene group. preferable.

The alkenyl or alkyl group of succinimide generally has 10 to 300 carbon atoms. The modified succinimides of this invention have excellent detergency with alkenyl or alkyl groups of less than 20 carbon atoms, although dispersibility is facilitated with alkenyl or alkyl groups of at least 20 carbon atoms. Thus, in preferred embodiments, the alkenyl or alkyl group of the succinimide is at least 20 carbon atoms (i.e., 20 to 3 carbon atoms).
00 alkenyl or alkyl groups).

The hydrocarbyl used to describe R4 and R5 is
Refers to an organic group consisting of carbon and hydrogen which may be aliphatic, aromatic or a combination thereof such as aralkyl, alkaryl. Suitable hydrocarbyl groups include alkyl groups such as ethyl, propyl; alkenyl groups such as propenyl, isobutenyl; aralkyl groups such as benzyl; alkaryl groups such as dodecylphenyl (C12Hga-CCl2H); and phenyl, na7 It is an aryl group such as a tail.

Straight or branched chain nalkylene groups of 2 to about 30 carbon atoms include 1,2-ethylene; 1,3-propylene, 1,5
-pentylene, 1.20-eicosylene, 1.30-)
Straight chain alkylene groups such as recontylene,
,2-propylene;1,6-butylene;1,2-(2-
Refers to branched alkylene groups such as methyl)pentylene; 1,2-(2-ethyl)hexylene; 1,10-eicosylene, and the like.

Aryl of 6 to 10 carbon atoms or 7 to 12 carbon atoms
2 to about 30 carbon atoms substituted with alkaryl
A straight-chain or branched alkylene group refers to a straight-chain or branched alkylene group as described above which is substituted with an aryl or alkaryl group. Suitable aryl groups include phenyl, naphthyl, and the like. Suitable alkaryl groups include benzyl and the like.

The modified polyaminoalkenyl or alkylsuccinimide of the present invention is produced from the polyaminoalkenyl or alkylsuccinimide. Alkenyl or alkyl succinimides are prepared by reaction of alkenyl or alkyl succinic anhydrides with the appropriate amines as shown below: ■ where R is an alkenyl or alkyl group of 10 to 300 carbon atoms: R1 is the remainder of the polyamino moiety).

These alkenyl or alkyl succinimides that can be used in the present invention have been described in numerous publications and are well known in the art. The basic types of succinimide and related substances encompassed by the technical term "succinimide" are disclosed in U.S. Patent Nos. 2.992,708; 3.018,291;
3,100,673; 3,219,666; 3.172.892 and 3.272.7
No. 46, all of which are disclosed herein.
It's great for reference.

The term "succinimide" is understood in the art to also include a number of amide, imide and amidine compounds that are similarly formed by zero reactions. However, the major product is succinimide, so the term is generally interpreted as the product of the reaction of an alkenyl-substituted succinic acid or anhydride with a polyamine as shown in reaction (1) above. ing. As used herein, this term includes alkyl mono-,
Also included are bis-succinimide and other higher analogs.

A(1) The production of alkenyl-substituted succinic anhydrides by the reaction of succinic anhydride polyolefins with maleic anhydride is described, for example, in U.S. Pat.
．． No. 018.250 and No. 3.024,195. Such methods include the thermal reaction of polyolefins with maleic anhydride and the reaction of halogenated polyolefins, such as chlorinated polyolefins, with maleic anhydride. Reduction of the alkenyl-converted succinic anhydride yields the corresponding alkyl derivative. Alternatively, alkenyl-substituted succinic anhydrides are prepared as described in U.S. Pat. No. 4,388,471 and U.S. Pat. can.

The ninth polyolefin polymer for reaction with maleic anhydride is a polymer consisting primarily of 02-C5 monoolefins such as ethylene, progylene, butylene, imbutylene and pentene. This polymer is
Homopolymers such as polyisobutylene as well as copolymers of two or more olefins such as copolymers of ethylene with propylene, butylene and imbutylene may be used. Other copolymers include e.g.
20 molti 04~CB conjugated diolefin 1
copolymers containing one copolymer monomer, copolymers of imbutylene and butadiene, or copolymers of ethylene, propylene, and 1,4-hexadiene.

Polyolefin polymers, designated R in FIG. 1, usually contain about 10 to 300 carbon atoms, but preferably 20 to 300 carbon atoms. In another preferred embodiment, the gold contains 12 to 100 carbon atoms, more preferably 20 to 100 carbon atoms.

A particularly preferred class of olefin polymers includes polybutenes made by the combination of one or more of 1-butene, 2-butene, and isobutene. Particularly desirable are polybutenes containing M in a substantial proportion of unit gold derived from isobutyne. The polybutene may contain small amounts of butadiene, which may or may not be incorporated into the polymer.

Most importantly, the imbutene unit is the 8th unit in the polymer.
0, preferably at least 90. These polybutenes are readily available commercial materials well known to those skilled in the art. These disclosures are disclosed in, for example, U.S. Pat.
, 215.707; 3.231,587; 3.515,669: and 3.579,450
No. 3,912,764.

The disclosures of suitable polybutenes in these patents are incorporated herein by reference.

In addition to the reaction of polyolefins with maleic anhydride, a number of other alkylating hydrocarbons are also used with maleic anhydride to produce alkenylsuccinic anhydrides. Other suitable alkylating hydrocarbons include molecular weights within the range of 100 to 4,500 and higher, within which
Included are cyclic, thin, branched and internal or alpha-olefins with preferred molecular weights within the range of 2.000.

For example, α-
It is an olefin. Generally, these olefins have 5 to
The length ranges from 20 carbon atoms. Another source of α-olefins is the ethylene growth process, which produces even-carbon olefins.
It is. Another source of olefins is the conversion of alpha-olefins over suitable catalysts, such as the well-known Ziegler catalysts. Internal olefins are readily obtained by isomerization of alpha-olefins over suitable catalysts such as silica.

A(2) Polyamine Polyamino Alkenyl Polyamine fc is an alkyl succinimide The polyamine used for the preparation is preferably a polyamine having from 2 to about 12 amine nitrogens and from 2 to FJ40 carbon atoms. The polyamine is reacted with alkenyl or alkyl hydrosuccinic acid to form the polyaminoalkenyl 17' (alkyl succinimide) used in the present invention.
It is chosen to provide at least one basic amine per ttjJ. Polyamine has a carbon:nitrogen ratio of approximately 1
=1 to about 10:1i is preferred.

Since conversion of basic amines is believed to be efficient to primary or secondary amines, at least one basic amine in the polyamine moiety should be either a primary or secondary amine. It is.

A polyaminoalkenyl compound is a polyamino moiety of an alkylsuccinimide, (B) 1 to about 10 carbon atoms.
hydrocarbyl i, (C1 substituted with an acyl group of 2 to FIIO carbon atoms and a substituent selected from monoketo, monohydroxy, mononitro, monocyano, lower alkyl and lower alkoxy derivatives of (Dl and (C)) Lower alkylma fc is used as in lower alkoxy, and "lower" means 1 carbon atom.
~Means the fundamental tone of about 6 pieces.

Hydrocarbyl, as used to describe the polyamine component of the present invention, refers to carbon and aqueous compounds which may be aliphatic, aromatic or combinations thereof, such as aralkyl. Hydrocarbyl groups are aliphatic unsaturated, i.e.
Preference is given to those relatively free from ethylenic and acetylenic unsaturation, especially acetylenic unsaturation. The substituted polyamines of the present invention are generally, but not necessarily, N-substituted polyamines. Examples of hydrocarbyl groups and substituted hydrocarbyl groups include methyl, ethyl, progyl,
Alkyl such as butyl, isobutyl, pentyl, hexyl, octyl etc.; Alkenyl such as propenyl, imbutenyl, hexenyl, octenyl etc.; Ketoalkyl such as 2-ketozolo2yl, 6-kedooctyl etc.: Ethoxyethyl, ethoxyprogyl , soloboxyethyl, 2-(2-ethoxyethoxy)ethyl, 2-[2-
(2-ethoxyethoxy)ethoxyethyl, 3.6,9
．． Included are alkoxy and lower alkenoxyalkyl such as 12-tetraoxatetradecyl, 2-(2-ethoxyethoxy)hexyl, nato. The acyl group of the C1 substituent is proonyl, acetyl, etc. More preferred substituents are hydrogen, C1-C6 alkyl and 01-C6 hydroxyalkyl).

In substituted boryanyl groups, any atom that can accept the substituents is found.

Substituted atoms, such as substituted substituent atoms, are generally geometrically non-uniform, and therefore substituted amines that can be used in the present invention include monomers in which the substituents are located on equivalent and/or non-equivalent atoms. - and polyf[L polyamine. 'More preferred polyamines useful in the present invention are polyalkylene polyamines containing substituted polyamines such as alkywanediamines, such as alkyl-opposed polyalkylene poly'amines.

Preferably, the alkylene group contains 2 to 6 carbon atoms and preferably has 2 to 6 carbon atoms between nitrogen atoms.

Examples of such groups are ethylene, 1°2-7'robylene,
2,2-dimethyl 7'o fillet, trimethylene, etc. Examples of such polyamines include ethylenediamine, diethylenetriamine, di(trimethylene)triamine, dipropylenetriamine, triethylenetetramine, tripropylenetetramine, tetraethylenepentamine, and pentaethylenehexamine. Such amines also include the sub-substituted polyamines described above, including isomers such as branched chain polyamines and hydrocarpyls polyamines. Among the polyalkylene polyamines, those having 2 to 12 amine nitrogen atoms and 2 to 24 carbon atoms are particularly preferred, especially lower polyalkylene polyamines such as ethylene diamine, dipropylene triamine, etc. C5 alkylene polyamines are most preferred.

What about the polyamine component? The Jl ring can contain all heterocyclic polyamines, heterocyclic substituted amines, and substituted heterocyclic compounds consisting of one or more 5- to 6-membered rings containing oxygen and/or nitrogen. The force double ring may be saturated or unsaturated, and the above-mentioned (Al, (B) (C
It may be substituted with a group selected from 1 and (DJ.
2-bis-(N-piperazinyl)ethane and N,ze-
bis < t N-(6-
Aminozolovir) morpholine, etc. Among the polycyclic compounds, piperazine is preferred.

Typical polyamines that can be used to form the compounds of this invention include: ethylenediamine,
1,2-propylene diamine, 1.3-7'' robylene diamine, diethylene triamine, triethylene tetramine, hexamethylene diamine, tetraethylene pentamine, methylaminopropylene diamine, N-(β-aminoethyl) piperazine, N, N'-di(β-aminoethyl)imidazolitone-2, N-(β-cyanoethyl)ethane-1,2-diamine, 1,3,6.9-tetraaminooctadecane, 1,3.6-triamino-9 −
These are oxadecane, N-methyl-1,2-propanediamine, and 2-(2-aminoethylamino)ethanol.

Another group of suitable polyamines is propanediamine, (bisaminopropyl-ethylenediamine). Propylene amine is acrylonitrile and ethylene amine, for example 2H2N (CH2CH2NH), in the HC formula, 2 is 1
n,7' (prepared by hydrogenation of the intermediate).

For example, the product made from ethylenediamine and acrylonitrile is )I2N (CH2) 3NH(C
H2) 2NH(CH2) 3NH2.

In many instances, the polyamines used as intermediates in the preparation of the succinimides of the present invention are not single compounds, but mixtures of one or several compounds in which the average compositions shown predominate.

For example, tetraethylenepentamine, produced by the polymerization of aziridine and the reaction of dichloroethylene with ammonia, can be used to synthesize lower and higher amine compounds such as triethylenetetramine, substituted piperazine, and pentaethylenehexamine. However, the composition is predominantly tetraethylenepentamine, and the gauze formula of the total amine composition will closely approximate tetraethylenepentamine. After all, in the production of succinimide for use in the present invention, if the various nitrogen atoms of the polyamine are not geometrically equivalent, #: one-wing substituted isomers are possible and the final product contained within. The production of polyamines and their reactions were described in Octasford, Claren F.P. 1/1966.
Sydziewicz (81) published by ndOn Press
dgewick) “De Organic Chemistry”
Op Nitrodiene J (TheOrganic C
hemistry of nitrogen)
``Chemistry of Ol' Nick Compound'' by N0IIθr, published by Sanders (5uncLers), Philadelphia, 2nd edition.
Qrganic compoundL); and
Kirk-male? - (Kirk -Qthmer) "Encyclopedia of Chemical Technology" (T!tncyclopedia of Ch.
Chemical Technology) Chapter
2nd edition, especially Volume 2, pages 99-116.

The reaction of polyamines with alkenyl or alkyl succinic anhydrides to produce polyaminoalkenyl or alkyl succinimides is well known in the art and is described in U.S. Pat. Nos. 2,992,708; 3,018,29.
No. 1: No. 3.024.237; No. 3.100.6
No. 73; No. 3.219.666; No. 3,172,
No. 892 and No. 3,272.746. The entire disclosures of these patents relating to the preparation of alkenyl or alkyl succinimides are incorporated herein by reference.

As noted above, the term "polyaminoalkenyl or alkylsuccinimide" refers to polyaminoalkenyl tf
ch Refers to both alkyl mono- and bissuccinimides and higher analogs of polyaminoalkenylmathanialkylborisuccinimides. Preparation of bis- and higher analogs can be accomplished by adjusting the molar ratio of the drugs. For example, a product consisting primarily of mono-bis-succinimide can be prepared by determining the molar ratio of polyamine to succinic anhydride. For example, reacting one mole of polyamine with one mole of alkenyl or alkyl substituted succinic anhydride produces a primarily monosuccinimide product. 2 moles of alkenyl tfc
Reacting u-alkyl-substituted succinic anhydride with 1 mole of polyamine produces bissuccinimide.

A particularly preferred class of polyaminoalkenyl tfcU alkylsuccinimides for use in the present invention has the formula...
c is alkyl and di; R2 is alkylene of 2 to 10 carbon atoms; 5: R3 [hydrogen, lower alkyl or fC is lower hydroxyalkyl; -NH2, or formula ■: (wherein Rh is alkenyl or alkyl having 10 to 300 carbon atoms) provided that when W is a group of formula 1u above, a is not 0, and R3 It can be expressed by the conditional property that at least one of the hydrogen atoms is hydrogen.

As mentioned above and below, the polyamines used in the preparation of succinimide are often mixtures of different compounds that assume an average composition shown as the formula...

Therefore, each 110 of R2 and R3 in the formula... is the same as or different from the value of other R2 and R3.

R2 is preferably alkenyl or alkyl having 20 to 300 carbon atoms. In another preferred embodiment, R preferably has 12 to 100 carbon atoms, more preferably 20 to 100 carbon atoms.

R2 is preferably alkylene having 2 to 6 carbon atoms, more preferably ethylene or 7'C is propylene.

R3 is preferably hydrogen or lower alkyl.

a is preferably an integer of 1 to 6.

In formula H, it is convenient to view the polyaminoalkenyl or alkylsuccinimide as consisting of 6 moieties, i.e. the alkenyl or fc represents the alkyl moiety R.
a succinimide moiety, represented by the formula 1; and a polyamino moiety, represented by the group + R2-N +&R2-W.

The alkylene polyamine used in this reaction is
It is generally represented by the formula: H2N+R2NH)&-R2NH2, where R2 is an alkylene moiety of 2 to 10 carbon atoms and a is an integer from FIO to 10. However, the production of these alkylene polyamines does not produce a single compound, and some cyclic heterocyclic compounds such as piperazine are included in the alkylene diamines.

A polyaminoalkenyl or alkylsuccinimide substituted with one or more of the nitrogens of the polyamino moiety (same definition as one or more of the nitrogens of the polyamino moiety) can undergo the following reaction (11 R8F17NH+ C'IC(C)mOR50F),
→ R2H, FNC(C)mOR, OR.

IV V VI
Polyaminoalkenyl or alkylsuccinimide (l■ It is produced by the reaction between chloroformate and chloroformate.

Reaction (11 is chloroformate■) and polyaminoalkenyl! This is carried out by contacting fcH alkylsuccinimide ■. Do not dilute this reaction.
'! 7' (can be carried out in a suitable inert solvent,
Suitable diluents include ethyl acetate, toluene, xylene,
Contains oil etc. A basic base such as pyridine, triethylamine, etc. can also be added during the reaction to scavenge any generated acid.

However, even if no base is added to the generated acid, the reaction solution after the reaction is completed can be washed with alkaline water (pH 8-9 or higher) or washed with alkaline salt water (pH 8-9 or higher). It can also be removed by higher pi(). This reaction is generally carried out between 0° and 50°C and is generally 0.5
Complete within ~24 hours. The product can then be further isolated by conventional methods such as chromatography, chromatography, etc. When the succinimide contains hydroxyalkyl, it can be heated at relatively low temperatures (-78° to 0°
Using C) can prevent the formation of carbonates. The carbonate can be removed by reaction of the succinimide amine with an alcohol (eg, ethanol) under transesterification conditions.

At least 20% amine'i-C(C)mOR50R
, more preferably at least 50% of the amine should be converted; most preferably all of the reactable amine should be converted.

? The maximum conversion of the reactive amine of the lyaminoalkenyl case or alkylsuccinimide is generally determined at a molar loading ratio of chloroformate:alkenylma fc of the theoretical basic nitrogen of the alkylsuccinimide of 0.7:1 to about 1:1t.
- Obtained by using. In some cases, a slight excess of chloroformate may be used to promote scheelite rate.

Alternatively, the products of the invention can be used in reaction 1 (&
) : N Vl (la
) (wherein R4, R5, R,, R8 and m are the same as defined above, and aryl is p
phenyl or substituted phenyl such as -nitrophenyl, p-/lorophenyl natono is preferred), which can also be produced by reacting polyaminoalkenyl'f, fcfl alkylsuccinimide (IV') with an aryl carzanate. can.

Reaction 1 (alfl) can be carried out by contacting an aryl carbonate with a polyaminoalkenyl or an alkyl succinimide with 0.5 g of an aryl carbonate. This reaction can be carried out undiluted or in a suitable inert diluent. Suitable diluents include toluene,
Contains xylene, sinoh, oil, etc. This reaction is
It is generally carried out at 50°C and is generally completed within 1 to 4 hours. The product can then be isolated by conventional methods such as stringing, chromatography, filtration, and the like.

Aryl carbonates are prepared by conventional methods using aryl alcohols and chloroformates under conditions known per se.

Chloro and formate in formula V can be obtained by the following reaction (2) W
■ ■ (wherein R5 and R4 are the same as defined above).

This method is a conventional method well known in the art and can be carried out by using phosdan (m-0)t or oxalyl chloride (m-1)k, generally in excess. The reaction is carried out by adding a suitable diluent such as toluene, benzene, methylene chloride, etc. to the alcohol surface.

Phosdan ffC adds oxalyl chloride to the system over a period of time. Alternatively, the phosdenane matanioxalyl chloride may be added to the diluent prior to the addition of the alcohol. Generally, about 1.1 to 2.5 equivalents of phosdan or oxalyl chloride are added per equivalent of alcohol (VID). The reaction is carried out at -78° to 50°C, preferably -10° to 10°C, and generally /2
Complete within ~12 hours.

Chloroformate (which can be isolated by conventional methods such as distillation, but it is preferable to remove some or all of the inert diluent by IJ tubing, and the hydrogen chloride and Excess drug is also removed. The product C%/) found in the remaining diluent is then used as in reaction (1) above.

As used herein, the term "chloroformate" includes both chloroformates (m=0 in formula V) and chlorodicarbonyloxy analogs (m=1 in formula V).

As used herein, the term "chloroformate: polyaminoalkenyl!7jH alkylnuccinimide molar charge of basic nitrogen" refers to the molar charge of chloroformate used in the reaction in the succinimide. It means based on the theoretical number of basic nitrogens contained. For example, triethylenetetramine (TKTA) '
k Reacts with 1 equivalent of succinic anhydride +! If near′c,
The resulting monosuccinimide should theoretically contain 6 basic nitrogens. Therefore, at a molar charge of 1,
The addition of 1 mole of chloroformate is required for each basic nitrogen, i.e. in this case 96 moles of chloroformate for each 17 moles of monosuccinimide prepared from 'I'lTA. .

Alcohol■ can be easily produced commercially by hand.
can be easily produced by known methods.

Examples include hydrocarbyl-blocked poly(oxyalkylene) monools (i.e., Rs''-R6(ORa)
m) is described in US Pat. No. 4,191,537.

These hydrocarbyl-terminated poly(
Oxyalkylene) polymers are often monohydroxy polyethers, monohydroxy compounds called ``blocked friends'' poly(oxyalkylene) glycols, ie , alcohol, and non-hydrocarpyl-terminated, i.e., unblocked poly(oxyalkylene) glycol (
Diols) are also distinguished from polyols. A hydroxy compound R,OH ( where R6 is a hydrocarbyl group blocking the poly(oxyalkylene) chain)
The preparation and properties of these polymers are described in U.S. Pat. No. 2,841,4.
No. 79, No. 2,782,240, and the aforementioned "Encyclopedia Opchemical Technology" by Kirk-Othmer, Vol. 19, p. 507. In a one-coat reaction, a single type of alkylene oxide, such as butylene oxide, can be used, in which case the product is a homopolymer, such as poly(oxyzolopyrene)propanol. However, copolymers are equally satisfactory, and random copolymers are readily prepared by contacting a hydroxy-containing compound with a mixture of alkylene oxides, such as a mixture of propylene oxide and butylene oxide. Block copolymers of oxyalkylene units are also suitable poly(oxyalkylene)s for use in the practice of this invention.
Provide polymers. If the oxide reactivities are equal, random polymers are more easily produced. In some cases, when ethylene oxide is copolymerized with Kamiike oxide, the relatively high reaction rate of ethylene oxide makes it difficult to produce random copolymers. Block copolymers can be produced in either case. The block copolymer consists of a hydroxyl-containing M compound and the first one.
The species alkylene oxide is then contacted with each of the other oxides in any order under polymerization conditions. Certain block copolymers are prepared by polymerizing progylene oxide onto a suitable monohydroxy compound to form a total poly(oxypropylene) alcohol, and then polymerizing butylene oxide onto the poly(oxypropylene) alcohol. typified by the polymers produced.

Poly(oxyalkylene) polymers are generally mixtures of compounds with different polymer chain lengths. However, their properties closely approximate those of polymers as expressed by average composition and molecular weight.

It consists of oxyalkylene units. Hydrocarbyl groups contain 1 to about 30 carbon atoms, preferably 2 to 20 carbon atoms. Oxyalkylene unit or 3 carbon atoms
~4 t-terminals, and the molecular weight of the hydrocarbyl poly(oxyalkylene) moiety is approximately 44 to F110,00.
0, more preferably from about 100 to about 5,000. Each poly(oxyalkylene) polymer is 1
~100 (161 oxyalkylene units, preferably 2 to about 50 oxyalkylene units, more preferably about 2 to 30 oxyalkylene units, and most preferably about 2S
oxyalkylene units. Generally, the oxyalkylene unit may be branched or unbranched. C3
~C5 oxyalkylene unit can be of any isomeric structure well known to organic chemists, e.g. n-progylene, -CH
2CH2CH2-; isopropylene, -C(CH3)C
H2-; n-butylene, -CH2CH2CH2CH2
-;aea-butylene, -CH(C)12CH3)CH
2-; t-butylene, -C(CH3)2""2- aeQ-detylene, -CH(CH3)CH(CH3
)-; inbutylene, -CH2CH(CH3)CH2-
etc. Preferred poly(oxyalkylene compounds) consist of 1 to fJ50 oxyalkylene units, more preferably fJ2 to 30 oxyalkylene units, and most preferably 2 to #20 such units.

The terminal hydrocarbyl moiety (R-) of the oxyalkylene chain contains 1 to about 30 hydrogen atoms, preferably 2 to +120 carbon atoms, and is the first site of alkylene oxide addition in the polymerization reaction. Generally derived from certain monohydroxy compounds (ROE()), such monohydroxy compounds are preferably aromatic alcohols, preferably aromatic alcohols, more preferably alkanols or alkylphenols, of from 1 to about 30 carbon atoms;
and, most preferably, alkyl is from 1 to about 2 carbon atoms.
It is an alkylphenol with four straight or branched chains. One such preferred alkyl group is obtained by the l:combination of an average of 4 units of zorolylene and has the common name of propylene tetramer. Preferred materials can be referred to as alkylphenyl poly(oxyalkylene alcohols or polyalkoxylated alkylphenols).

Similarly, hydrocarbyloxyhydrocarbyl alcohol (i.e., R5 = hirrocarbyl in formula Can be prepared from the corresponding glycol: HORsOH+ C'H3COH4HO'R50CCH
3+ H, O (311X
3(4)■ I R, CI+■→RA 0% 0CCH3(5J■
V constant + base → R40R50H (6) ■ (where Ra >, t and R5 are the same as defined above, and the base is an inorganic base such as potassium bicarbonate, sodium carbonate, sodium hydroxide, etc. ).

Each of reactions 31-(6) are well-known and art-recognized methods.

Reaction (31) is a conventional esterification reaction in which p1 diol ([) and acid (x) are combined to produce a monoester button. Acetic acid is used in reaction (3), but trichloroacetic acid Any suitable carboxylic acid can be used to form the monoester (XI), such as , zolopionic acid, benzoic acid, etc. In some instances, monoester (XI) such as sulfuric acid, hydrochloric acid, etc. can be used to accelerate the reaction rate. Acid catalysts can also be used. An excess of diol (■) is used to prevent the formation of diesters. Generally, v1.1 to 4 equivalents of diol (■) per equivalent of acid (X), preferably 2 equivalents of diol ([) are used in reaction (3).

This reaction can be carried out undiluted or in a suitable diluent such as toluene, benzene, and the like. The water generated during the reaction is produced by Dean-Stark (Dsan-8
tark)) Can be easily removed with plastic wrap. The product ester (XI) may be isolated by conventional methods such as chromatography, filtration, etc., or used in reaction (4) without purification.

Reaction (4) is a conventional reaction in which an alcohol is reacted with sodium or potassium metal to form a sodium or potassium salt. Alternatively, potassium t-butoxide can be used instead of potassium in the t1 metal sodium solution.

The reaction is generally carried out by adding an equimolar amount of sodium or potassium metal to the alcohol contained in an anhydrous inert diluent such as tetrahydrocane, dioxane, toluene, and the like. The reaction is generally conducted at 0° to 30°C and is generally complete within 1 to 24 hours. The resulting salt (XI) is generally isolated and (
or) used in reaction (5) without purification.

Reaction (5) is a metathesis reaction that forms ether (XIV). This reaction is generally carried out by adding an equimolar amount of hydrocarbylchloride IF (XI) to the sodium (or potassium) salt O1). This reaction is carried out in an inert diluent such as toluene, dioxane, etc. The reaction is generally conducted at 0° to 110°C and is generally complete within 1 to 24 hours. The resulting ether ester (XIV) can be isolated by conventional methods such as chromatography, filtration, or
It can be used in reaction (6) without being prepared.

Reaction (6) is a conventional hydrolysis reaction to form alcohol-ether (■). This reaction is carried out by adding ether-ester N (XIV) to an aqueous alcoholic solvent such as water/methanol, water/ethanol, etc. An inorganic base such as sodium carbonate, sodium hydroxide, potassium bicarbonate, etc. is added to the reaction.

The reaction is generally conducted at room temperature to about 80°C and is generally complete within 1 to 24 hours. The alcohol-ether (■) obtained can be isolated by conventional methods such as chromatography, filtration, distillation, etc.

Locarbyl chloride (XI) can be prepared from the corresponding alcohol by a chlorinating agent such as thionyl chloride. This reaction is well known and was described by Wley & Sons, New York (1977).
5urvey of Organic Synthesis J by Bushier and Person.
c8ynthssis) Volume 1, pages 630-632.

Therefore, chloroformate (V) and the above reaction (1
) is used to form a compound of the following formula: alkylene; a is an integer from 0 to 10') s R6
is hydrogen, lower alkyl of 1 to 6 carbon atoms, 1 carbon atom
~6 lower hydroxyalkyl, R7L is hydrocarbyl of 1 to 30 carbon atoms, and R5 is a straight or μ branched alkylene group of 2 to about 30 carbon atoms, 6 to 10 carbon atoms or -R6 (0Ra
)p- (wherein R6 is alkylene of 2 to 5 carbon atoms and p is an integer from 1 to 100); T is or -NHR8 (wherein at least one of R8 is (same as the above definition)].

Preferably R is alkenyl or alkyl of about 20 to 100 carbon atoms. Preferably R2 is alkylene of 2 to 6 carbon atoms and 0:a is an integer from 1 to 6. Preferred R8 is hydrocargyl. Preferably R5 is -Ra(ORs)p-, where p is an integer from 2 to 30.

The modified succinimides of this invention can be reacted with boric acid or similar boron compounds at temperatures sufficient to effect the reaction to form borated dispersants useful within the scope of this invention. In addition to boric acid (boronic acid), suitable boron compounds include boron oxide, /% boron lodenide and esters of boric acid.

Generally about 0.1 to 10 equivalents of boron compound to the modified succinimide can be used.

The modified polyaminoalkenyl or alkylsuccinimides of this invention are useful as detergent and dispersant additives when used in lubricating oils. When used in such methods, the modified polyaminoalkenyl or alkylsuccinimide additive composition is present in an amount of 0.2 to 10%, preferably about 0.5 to 5% by weight of the total composition. The lubricating oil used with the additive composition of the present invention is a mineral or synthetic oil of lubricating viscosity and is preferably suitable for use in the crankcase of an internal combustion engine. Crankcase lubricating oil is normally about 13,000at to 21O at 0''F.
It has a viscosity of 22.7 cst at ff (99°C).

Lubricating oils may be synthetic or derived from natural sources. Mineral oils for use as base oils of the present invention include paraffinic, naphthenic and other oils commonly used in lubricating oil compositions.

Synthetic oils include both hydrocarbon synthetic oils as well as synthetic esters. Useful synthetic hydrocarbon oils include polymers of alpha-olefins having suitable viscosities. Particularly useful are hydrogenated liquid oligomers of C6-C]2α-olefins, such as 1-done trimers. Similarly, alkylbenzenes of suitable viscosity, such as didodecylbenzene, can also be used. Useful synthetic esters include esters of both monocarzanoic and polycarzanoic acids, as well as esters of monohydroxy"alkanols and polyols. Typical examples are di"decyl adipate, pentaerythritol tetracazolate, , G2-
These include ethylhexyl adipate and dilauryl sebacate. Complex esters made from mixtures of mono- and dicarboxylic acids and mixtures of mono- and dihydroxy alkanols can also be used.

Mixtures of hydrocarbon and synthetic oils are also useful.

For example, 10-25% by weight of hydrogenated 1-decene trimer and 75-90% by weight of 150 SUS (100″1?)
Mixtures with mineral oils make excellent lubricating base oils.

Additive concentrates are also included within the scope of this invention. Concentrates of the invention typically contain about 90-10% by weight of oil of lubricating viscosity and about 10-90% by weight of the composite additive of the invention. Concentrates typically contain sufficient diluent to facilitate handling during transportation and storage. Preferable power diluents for concentrates include any diluent, but oils of lubricating viscosity are preferred as diluents so that the concentrate can be easily mixed into the lubricating oil to produce a lubricating oil composition. .

Suitable lubricating oils that can be used as diluents typically include:
having a viscosity in the range of about 65 to about 500 Saybolt universal seconds (5 US) at 100'F (38°C);
Oil of lubricating viscosity can be used.

Other additives that may be present in the formulation include anti-rust intrusion foam inhibitors, corrosion inhibitors, metal deactivators, pour point depressants, antioxidants and various other well known additives. .

It is also anticipated that the modified succinimides of the present invention may be used as dispersants and detergents in hydraulic fluids, marine engine crankcase lubricants, and the like. When used, it is added in an amount of about 11-10% by weight based on the modified succinimide substitute.

0.5 to 5% by weight is preferred.

When used in fuels, the proper concentration of additive needed to achieve the desired cleaning will vary depending on the type of fuel used, the presence of other detergents or dispersants or other additives, etc. depends on factors.

However, in general, and in preferred embodiments, the concentration range of the additive in the base fuel ranges from 910 to 1
0.000 pp”% by weight preferably 30-2.000
weight ppm 1 and most preferably 30-700 weight ppm
It is a modified succinimr of pm.

If other detergents are present, relatively small amounts of modified succinimide are used.

The modified succinimide additives of the present invention are about 150° to 4°
Inert, stable, lipophilic organic solvents with boiling points within the range of 00'F' can be used to formulate fuel concentrates.

When using an aliphatic or aromatic hydrocarbon solvent such as benzene, toluene, or xylene, it is preferable to use a relatively high-boiling aromatic compound or an aromatic thinner. Combinations of aliphatic alcohols of about 6 to 8 carbon atoms and hydrocarbon solvents, such as infropanol, inbutylcarbinol, n-butanol, etc., are also suitable for use with the above fuel additives. In fuel concentrates, the amount of said additive is usually at least 10% by weight, generally not more than 70% by weight, and preferably from 10 to 25% by weight.

The following examples are presented to provide a detailed explanation of the invention. These examples and illustrations should not be construed as limiting the scope of the invention in any way.

Examples Example 1 Methylene chloride containing 18.9 g of oxalyl chloride was placed in an fclA three-necked flask equipped with a mechanical stirrer and a nitrogen inlet. Add this mixture at room temperature to
165. ! i' (0.10 mol) of tetrafluorylene phenyl polyoxydetylene alcohol (Cx2Hss-
Methylene chloride containing CsHt-0(CaHgO)~18H) was added dropwise over 30 minutes.

Once the addition is complete, the solution is stripped to remove methylene chloride and excess oxalyl chloride, and the chlorodicarzanyloxy derivative O (C1sH*5-C5-C6H4-0(C4H~l9
CCCj) was obtained t0 This chlorodicarzanyloxy derivative was redissolved in 300-methylene chloride.

A methylene chloride solution containing a chlorodicarbonyloxy derivative was added to 200 WL of methylene chloride solution. ,
5014 Triethylamine and 406J Succinimide Dispersant Composition [1 mole of polyisobutenyl cohelic anhydride in which the polyisobutenyl groups have a number average molecular weight of about 950 was reacted with 0.87 mole of tetraethylenepentamine, then in diluent oil. prepared by diluting to about 65% activity]. The system was extruded for 2 hours at room temperature, the system was partially stripped, diluted with IA hexane, extracted twice with brine (F88-9), dried (MgSOa), filtered, and
The strizoamide was a monosuccinimide amide.

Example 2 A three-neck flask equipped with a mechanical stirrer and a nitrogen inlet was charged with 3QQmj of dry toluene.

The system was cooled to 0° C. and phosdene gas was bubbled through until 19.9 g was contained in the toluene.

At this point, 165 g (0.10 mol) of tetrazolopenylphenyl polyoxydetylene alcohol in toluene
was added over 30 minutes, and the system was warmed to room temperature.
Stir for hours. At this point, the reaction system was vigorously flushed with nitrogen for 2 hours to remove excess phosgene, and the toluene solution containing the tetrazolopenylphenyl polyoxybutylene chloroformate was poured into the solution.

The methylene chloride solution containing the chloroformate derivative was then added to 2001 ml of methylene chloride, 3
01R1 triethylamine and 406J succinimide dispersant composition [polyisobutenyl group is about 950
prepared by reacting 1 mole of polyimbutenyl succinic anhydride with a number average molecular weight of added to. This system was punched out for 2 hours at room temperature, a part of the system was stripped, and 1! of hexane, extracted twice with brine (p18-9), dried (Mg80m), filtered, and stripped of monosuccinimide carba/).
(C1zHs+5-C6Hi-0+CtH90)-1
ecN) was obtained.

Example 3 18.9 g of oxalyl chloride was contained in an IJ3 three-necked flask equipped with a mechanical stirrer and a nitrogen inlet.
001E+i! of methylene chloride was added.

Add 11.8 g (0.10 mol) of 2 to this mixture at room temperature.
-butoxyshetanol CH3(CHBCH,C
A methylene chloride solution containing H-OCH2CH,OH) was added dropwise over 30 minutes. Once the addition is complete,
The solution was stripped to remove methylene chloride and excess oxalyl chloride, and the chlorodicarbonyloxy derivative was redissolved in 300 g of methylene chloride.

The methylene chloride solution containing the chlorodicarzanyloxy derivative was then mixed with 200 g of methylene chloride, 30 g of triethylamine, and 406 g of a succinimide dispersant composition [1 mole of polyisobutenyl succinic anhydride in which the polyimbutenyl groups have a number average molecular weight of about 950]. and 0.87 moles of tetraethylenepentamine and then diluted with diluent oil to about 35% activity. After stirring the system for 2 hours at room temperature, the system was partially stripped, diluted with 1 J of hexane, and diluted with brine (p. 88-9) for 2 hours.
Extracted twice, dried (MgSOa), filtered and stripped to monosuccinimate.

Example 4 A 2J three-necked flask equipped with a mechanical stirrer and a nitrogen inlet was charged with 3QQd of dry toluene. The system was cooled to 0° C. and phosdene gas was bubbled in until 59.7 g was contained in the toluene. At this point, 495 g (0.30 mol) of tetrapropenylphosphoryoxybutylene alcohol in toluene were added over 30 minutes.

The system was allowed to warm to room temperature and stirred at room temperature for 2 hours. At this point, nitrogen was blown into the reaction system for 2 hours to remove excess phosgene, and a toluene a solution of tetrazolopenylphenyl polyoxydetylene chloroformate was obtained.

The sultoluene solution containing the chloroformate conductor was then mixed with 300 d of methylene chloride, 90 d of triethylamine, and 406 g of succinimide dispersant composition [1 mole of polyisobutenyl succinic anhydride having a number average molecular weight of about 950 and 0.0 .87 moles of tetraethylenepentamine, and then
(prepared by diluting with diluent oil to about 65% active ingredient). This system was extruded for 2 hours at room temperature, a part of the system was stripped, and 2! diluted with hexane, extracted twice with brine (p) 18-9), dried (
Mg80i), filtered and stripped monosuccinimized carbamate Example 5 In a three-necked flask equipped with a mechanical stirrer and a nitrogen inlet, 18.9 g of oxalyl chloride was added.
00d of ethylene chloride was added. 10.4 to this mixture at room temperature! Methylene chloride containing i' (0,10 mol) of 6-nitoxy 1-propatur (CI(,CH20CR2CH2CH20H)) was added dropwise over 30 minutes. After the addition was complete, the solution was stripped and the ethylene chloride and Excess oxalyl chloride was removed, and the chlorodicarbonyloxy derivative was redissolved in 300-methylene chloride.

A methylene chloride solution containing the chlorodicarbonyloxy derivative was then added to a 200-methylene chloride, 30-d triethylamine, and 406 g succinimide dispersant composition [1.0 moles of polyisobutenyl anhydride in which the polyisobutenyl groups have a number average molecular weight of about 950]. (prepared by reacting co/phosphoric acid with 0.5 moles of tetraethylenepentamine and then diluting to about 65% active with diluent oil). After stirring the system for 2 hours at room temperature, the system was partially stripped, diluted with 1 J of hexane, and brine (p) 18-9
Example 6 (4) As in Example 2, n-butoxyethoxyethanol-1 (n-C4FgOCH2CH20CH2CH20H
) was added to a Phosde 1J three-hole round bottom flask, 94 g of phenol, 79 g of pyridine and 300 rIll of toluene were added.90 The system was stirred at room temperature and 1 mol (approximately 224 Ii) of the above Chlorormate was gradually added to this system and after the reaction was completed, the product was extracted with hexane and the mixture was extracted with hexane. The organic layer was washed three times with brine and then taken over anhydrous magnesium sulfate.

Carbonate: (n-C2FgOCH2CH20CH2CH20COC
2Hs) I got k.

472 g of a succinimide dispersant composition [the polyisobutenyl groups have a number average molecular weight of about 950] are reacted with 1 mole of polyisobutenyl cohelic anhydride and 0.5 moles of tetraethylenepentamine, and then dissolved in a diluent oil at about 5
It is manufactured by diluting it to 0% activity, and the alkalinity =
29.7] to 22 reaction flasks. Initially the alkalinity of the mixed system = 25.8 to the system was then heated to 165°C and sparged under nitrogen for 2 hours, at which point the alkalinity of the system = 14.5 . The system was cooled to -80°C and an additional 0.0255 mole (about 7.2 g) of carzanate was added. This system was heated to t-165°C and stirred for an additional 40 minutes under nitrogen, alkalinity = 13.6t.
- a product with is obtained and bissus Example 7

Claims (56)

[Claims] (1) One or more nitrogen atoms in the polyamino moiety are ▲Mathematical formula, chemical formula, table, etc.▼ [In the formula, R_4 is a hydrocarbyl having 1 to 30 carbon atoms; R_5 is a hydrocarbyl having 2 to 30 carbon atoms. hydrocarbyl, and -R_6-(OR_6)-_p (wherein R_6
is an alkylene of 2 to 5 carbon atoms, and p is an integer of 1 to 100; and m is an integer of 0 to 1. Characterized polyaminoalkenyl or alkylsuccinimide. (2) The polyaminoalkenyl or alkylsuccinimide according to claim 1, wherein R_4 is hydrocarbyl having 2 to 20 carbon atoms. (3) the alkenyl or alkyl moiety is about 20
3. The polyaminoalkenyl or alkylsuccinimide of claim 2 which has ˜300 carbon atoms. (4) R_5 is substituted with a straight or branched alkylene group of 2 to about 30 carbon atoms, or an aryl of 6 to 10 carbon atoms or an alkaryl of 7 to 12 carbon atoms; 4. The polyaminoalkenyl or alkylsuccinimide of claim 3 which is about 30 straight or branched alkylene groups. (5) The polyaminoalkenyl or alkylsuccinimide of claim 4, wherein R_5 is a straight or branched alkylene group of 2 to about 30 carbon atoms. (6) The polyaminoalkenyl or alkylsuccinimide according to claim 5, wherein m is 0. (7) The polyaminoalkenyl or alkylsuccinimide according to claim 5, wherein m is 1. (8) R_5 is -R_6-(OR_6)-_p (in the formula,
4. The polyaminoalkenyl or alkylsuccinimide of claim 3, wherein R_6 is alkylene of 2 to 5 carbon atoms, and p is an integer of 1 to 100. (9) The polyaminoalkenyl or alkylsuccinimide according to claim 8, wherein R_6 is alkylene having 3 to 4 carbon atoms. (10) Claim 9, where p is an integer from 1 to 50
The polyaminoalkenyl or alkylsuccinimide described in Section. Claim 10, wherein (11) is an integer from 2 to 20.
The polyaminoalkenyl or alkylsuccinimide described in Section. (12) The polyaminoalkenyl or alkylsuccinimide according to claim 11, wherein m is 0. (13) The polyaminoalkenyl or alkylsuccinimide according to claim 11, wherein m is 1. (14) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc.▼ The polyaminoalkenyl or alkylsuccinimide according to claim 1. Formula (15), ▲ Numerical formulas, chemical formulas, tables, etc.▼ [In the formula, R is alkenyl or alkyl with 10 to 300 carbon atoms; R_2 is alkylene with 2 to 10 carbon atoms; a is 0 ~10; R_8 is hydrogen, lower alkyl having 1 to 6 carbon atoms; ~30 hydrocarbyl; R_5 is a straight or branched alkylene group of 2 to about 30 carbon atoms, or 6 to 1 carbon atoms;
a straight or branched alkylene group of 2 to about 30 carbon atoms substituted with 0 aryl or alkaryl of 7 to 12 carbon atoms, or -R_6-(OR_6
)-_p (wherein R_6 is alkylene with 2 to 5 carbon atoms, and p is an integer of 1 to 100); T is ▲ mathematical formula, chemical formula, table, etc. ▼ or -NHR_8 (wherein R and R_8 are as defined above), provided that at least one of R_8 is ▲a numerical formula, a chemical formula, a table, etc.▼]. (16) The compound according to claim 15, wherein R is alkenyl or alkyl having 20 to 300 carbon atoms. (17) The compound according to claim 16, wherein R is alkenyl or alkyl having 20 to 100 carbon atoms. (18) Claim 17, where a is an integer from 1 to 6
Compounds described in Section. (19) The compound according to claim 18, wherein R_2 is alkylene having 2 to 6 carbon atoms. (20) The compound according to claim 19, wherein R_4 is hydrocarbyl having 2 to 20 carbon atoms. (21) The compound according to claim 20, wherein R_5 is a straight or branched alkylene group having 2 to about 30 carbon atoms. (22) R_5 is -R_6-(OR_6)-_p (wherein R_6 is alkylene having 2 to 5 carbon atoms, and p is an integer from 1 to 100) Claim 20 Compounds described in Section. (23) The compound according to claim 22, wherein R_6 is alkylene having 3 to 4 carbon atoms, and p is an integer of 2 to 20. (24) ▲There are mathematical formulas, chemical formulas, tables, etc.▼, but ▲There are mathematical formulas, chemical formulas, tables, etc.▼ A compound according to item 19 of the desired scope. (25) ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ A compound according to item 19 of the desired scope. (26) A lubricating oil composition comprising an oil of lubricating viscosity and an effective amount of a polyamino alkenyl or alkyl succinimide as a dispersant, wherein one or more of the nitrogens in the polyamino moiety is etc. ▼ [wherein R_4 is a hydrocarbyl of 1 to 30 carbon atoms; R_5 is a hydrocarbyl of 2 to 30 carbon atoms and -R_6-(OR_6)-_p (wherein R_6 is a hydrocarbyl of 2 to 5 alkylenes, p is 1 to 100
), and m is an integer of 0
an integer from 1 to 1. (27) The lubricating oil composition according to claim 26, wherein R_4 is hydrocarbyl having 2 to 20 carbon atoms. (28) The lubricating oil composition of claim 27, wherein said alkenyl or alkyl moiety has about 20 to 300 carbon atoms. (29) 2 carbon atoms in which R_5 is substituted by a straight or branched alkylene group of 2 to about 30 carbon atoms or an aryl of 6 to 10 carbon atoms or an alkaryl of 7 to 12 carbon atoms; 29. The lubricating oil composition of claim 28, wherein the lubricating oil composition is from about 30 straight or branched chain alkylene groups. (30) The lubricating oil composition of claim 29, wherein R_5 is a straight or branched alkylene group of 2 to about 30 carbon atoms. (31) The lubricating oil composition according to claim 30, wherein m is 0. (32) The lubricating oil composition according to claim 30, wherein m is 1. (33) R_5 is R_6-(OR_6)-_p (in the formula,
R_6 is alkylene with 2 to 5 carbon atoms, p is 1
29. The lubricating oil composition of claim 28, wherein: (34) The lubricating oil composition according to claim 33, wherein R_6 is alkylene having 3 to 4 carbon atoms. (35) Claim 3 in which p is an integer from 1 to 50
The lubricating oil composition according to item 4. (36) Claim 3 in which p is an integer of 2 to 20
The lubricating oil composition according to item 5. (37) The lubricating oil composition according to claim 36, wherein m is 0. (38) The lubricating oil composition according to claim 36, wherein m is 1. (39) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc.▼Patent claims The lubricating oil composition according to item 26. (40) Formula for effective amount as oil of lubricating viscosity and dispersant ▲
There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R is alkenyl or alkyl with 10 to 300 carbon atoms; R_2 is alkylene with 2 to 10 carbon atoms; a is an integer of 0 to 10; ; R_8 is hydrogen, lower alkyl of 1 to 6 carbon atoms, and ▲ has a numerical formula, chemical formula, table, etc. ▼ {where m is an integer of 0 to 1; R_4 is hydrocarbyl of 1 to 30 carbon atoms; Yes; R_5 is a straight or branched alkylene group of 2 to about 30 carbon atoms, or 2 to about 30 carbon atoms substituted with an aryl of 6 to 10 carbon atoms or an alkaryl of 7 to 12 carbon atoms; 30 straight or branched alkylene groups, or -R_6-(OR_6)-
T
is ▲There is a mathematical formula, chemical formula, table, etc.▼ or -NHR_8 (in the formula, R and R_8 are as defined above), but at least one of R_8 is ▲There is a mathematical formula, chemical formula, table, etc.▼ A lubricating oil composition characterized by containing a compound. (41) The lubricating oil composition according to claim 40, wherein R is alkenyl or alkyl having 20 to 300 carbon atoms. (42) The lubricating oil composition according to claim 41, wherein R is alkenyl or alkyl having 20 to 100 carbon atoms. (43) Claim 42, where a is an integer from 1 to 6
The lubricating oil composition described in Section. (44) The lubricating oil composition according to claim 43, wherein R_2 is alkylene having 2 to 6 carbon atoms. (45) The lubricating oil composition according to claim 44, wherein R_4 is hydrocarbyl having 2 to 20 carbon atoms. (46) The lubricating oil composition according to claim 45, wherein R_5 is a straight or branched alkylene group having 2 to about 30 carbon atoms. (47) Claim 45, wherein R_5 is -R_6-(OR_6)-_p (wherein R_6 is alkylene having 2 to 5 carbon atoms, and p is an integer from 1 to 100)
The lubricating oil composition described in Section. (48) The lubricating oil composition according to claim 47, wherein R_6 is alkylene having 3 to 4 carbon atoms, and p is an integer of 2 to 20. (49) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc.▼Patent claims The lubricating oil composition according to item 44. (50) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc.▼ The lubricating oil composition according to item 44. (51) Oil of lubricating viscosity of about 10 to 90% by weight and about 9
A lubricating oil concentrate comprising from 0 to about 10% by weight of a compound according to claim 1. (52) A lubricating oil concentrate comprising from about 10 to about 90% by weight of an oil of lubricating viscosity and from about 90 to about 10% by weight of a compound of the formula of claim 15. thing. (53) A fuel composition comprising a hydrocarbon with a boiling point in the gasoline or diesel range and 10 to 10,000 ppm of the compound according to claim 1. (54) A fuel composition comprising a hydrocarbon with a boiling point in the gasoline or diesel range and 10 to 10,000 ppm of the compound according to claim 15. (55) A fuel concentrate comprising from about 30 to 90% by weight of an inert lipophilic organic solvent and from about 10 to about 70% by weight of a compound according to claim 1. (56) A fuel comprising from about 30 to about 90% by weight of an inert lipophilic organic solvent and from about 10 to about 70% by weight of a compound of the formula of claim 15. Concentrates.