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Lubricating oil compositions containing bis-alkenyl succinimides of xylylene diamines

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US3505227A
US3505227A US3505227DA US3505227A US 3505227 A US3505227 A US 3505227A US 3505227D A US3505227D A US 3505227DA US 3505227 A US3505227 A US 3505227A
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Chevron Research and Technology Co
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    • C07D207/34Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with heteroatoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10N2210/00Nature of the metal present as such or in compounds, i.e. in salts
    • C10N2210/02Group II, e.g. Mg, Ca, Ba, Zn, Cd, Hg
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    • C10N2240/00Specified uses or applications of lubricating compositions
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    • C10N2240/00Specified uses or applications of lubricating compositions
    • C10N2240/10Internal-combustion engines
    • C10N2240/102Diesel engines
    • C10N2240/103Small diesel engines

Description

United States Patent LUBRICATING OIL COMPOSITIONS CONTAINING BIS-ALKENYL SUCCINIMIDES OF XYLYLENE DIAMINES Warren Lowe, El Cerrito, Califl, assignor to Chevron Research Company, San Francisco, 'Calif., a corporation of Delaware No Drawing. Filed Dec. 18, 1967, Ser. No. 691,225

Int. Cl. C10m 1/30, N32

US. Cl. 252-515 4 Claims ABSTRACT OF THE DISCLOSURE Bis-alkenyl succinimidyl alkyl benzenes having from to 4 halogens on the benzene ring find use as lubricating oil detergents. The alkenyl group has from 40 to 125 carbon atoms.

BACKGROUND OF THE INVENTION Field of the invention Description of the prior art Ashless detergents comprising the reaction product of a carboxylic acid of relatively high molecular weight with a variety of amines have been reported in US. Patent Nos. 3,024,237, 3,275,554, 3,219,666 and 3,172,892. The preferred compositions have been the alkenyl succinic anhydrides of alkylene propylamines, although other amines and amine derivatives have also been disclosed.

SUMMARY OF THE INVENTION Pursuant to this invention, compositions having excellent detersive and detergent capability and being capable of retaining this capability for long periods of time, while being compatible with a wide variety of other lubricating oil additives, are provided, which are bis-alkenyl succinimidyl alkyl benzenes, wherein the alkenyl group is of from about 40 to 125 carbon atoms. The benzene ring may have from 0 to 4 halogen atoms, particularly of atomic No. 17 to 35.

DESCRIPTION OF THE PREFERRED EMBODIMENTS For the most part, the compositions of this invention will have the following formula:

wherein X is halogen of atomic No. 17 to 35 (chlorine or bromine) preferably chlorine, n is an integer of from 0 to 4, preferably 0 to 2 to 4 and A is of the formula:

RCH-CO /NU OH2CO wherein R is a branched chain oil solubilizing aliphatic group or from 40 to 125 carbon atoms, more usually of from 50 to 100 carbon atoms, and U is alkylene of from 1 to 2 carbon atoms, i.e., methylene and ethylene. The bracket indicates the two positions to which A may be bonded on the benzene ring.

As indicated from the above formula, the alkenyl succinimidyl alkyl groups may be situated meta or para or there may be a mixture of the two. The halogens may be situated at any of the remaining places. The aliphatic hydrocarbyl succinimidyl alkyl groups in being situated meta or para, are separated by at least 3 annular carbon atoms.

The aliphatic hydrocarbon radical may be aliphatically saturated or unsaturated, usually having not more than 2 sites of unsaturation, more usually not more than 1 site of unsaturation. There should be at least 1 branch per 4 carbon atoms along a chain and preferably at least 1 branch per 2 carbon atoms along a chain. The branch will ordinarily be a methyl group (1 carbon atom). Illustrative aliphatic hydrocarbyl groups are polyisobutenyl, polypropenyl, the copolymer of ethylene and isobutylene, etc. These groups may be readily obtained by polymerizing aliphatic olefins of from 2 to 6 carbon atoms, more usually of from 3 to 4 carbon atoms.

Particularly preferred compositions of this invention have the following formula:

mono 0 o 0 CHR omoo CHEN o 0 on,

(06rd wherein R is a polyolefin of olefins of from 3 to 4 carbon atoms, e.g., polypropylene or polyisobutylene, having from 40 to 125 carbon atoms, preferably 50 to carbon atoms, and n is an integer of from 0 to 4, preferably 0 or 2 to 4. A preferred orientation for the succinimidyl radical is para. Also preferred is a mixture of meta and para having at least 50% meta, usually 50 to 80 mole percent meta.

PREPARATION OF THE COMPOSITIONS The compositions of this invention are readily prepared by combining the desired aliphatic hydrocarbon substituted succinic anhydride of the formula:

wherein R is as defined previously with an amine of the formula:

Wherein U, X and n are all as defined previously, either neat or in the presence of a hydrocarbon solvent. Usually, about stoichiometric amounts of materials will be used, a small excess of the succinic anhydride being preferred. The temperature for the reaction will generally be in the range of about C. to 250 C., more usually in the range of about C. to 200 C. The time for the reaction will range from about 30 minutes to 6 hours, the course of the reaction being followed by the evolution of Water.

EXAMPLES The following examples are offered by way of illustration and not by way of limitation.

Example I (A) Into a reaction flask was introduced 55 g. of xylylene diamine (70% meta; 30% para) 1,745 g. of a.

40 weight percent solution in neutral oil of polyisobuteuyl succinic anhydride (polyisobutenyl group of about 1,000 molecular weight) and 150 cc. of benzene. The mixture was heated at reflux, collecting water in a Dean Stark Trap, and the temperature slowly raised to a final temperature of about 170 C. while taking the benzene overhead. A mild vacuum was then applied to the mixture for about one-half hour while maintaining the temperature. The residue was filtered hot and the product isolated.

Analysis (percent) .--N=0.60.

Example II Into a reaction flask was introduced 68.5 g. of 2,3,5,6- tetrachloro-paraxylylene diamine, 1,090 g. of a 40 weight percent solution in neutral oil of polyisobutenyl succinic anhydride (polyisobutenyl of about 1,000 molecular weight) and 300 cc. of benzene. The mixture was heated and stirred at reflux and the water removed as formed. The temperature was slowly raised to 160 C. while taking water and solvent overhead. The temperature was then held for 15 minutes while a mild vacuum was applied to the system. The product weighed 1,151 g. Analysis (percent) .N=0.62.

The compositions of this invention may be used under a wide variety of conditions in internal combustion engines. These compositions, however, find particular use under the hot conditions of diesel engines working under severe conditions of operntion.

The compositions of this invention may be formulated with various lubricating fluids (hereinafter referred to as oils) which are either derived from natural or synthetic sources. Oils generally have viscosities of from about 35 to 50,000 Saybolt Universal Seconds (SUS) at 100 F. Among natural hydrocarbonaceous oils are paraifin base, naphthenic base, asphaltic base and mixed base oils. Illustrative of synthetic oils are: hydrocarbon oils such as polymers of various olefins, generally of from 2 to 8 carbon atoms, and alkylated aromatic hydrocarbons; and nonhydrocarbon oils, such as polyalkylene oxides, aromatic ethers, carboxylate esters, phosphate esters, and silicon esters. The preferred media are the hydrocarbonaceous media, both natural and synthetic.

The above oils may be used individually or together whenver miscible or made so by the use of mutual solvents.

When the detergents of this invention are compounded with lubricating oils for use in an engine, the detergents will be present in at least about 0.1 weight percent and usually not more than 20 weight percent, more usually in the range of about 2 to 15 weight percent. The compounds can be prepared as concentrates due to their excellent compatibility with oils. As concentrates, the compounds of this invention will generally range from about 10 to 70 weight percent, more usually from about 20 to 50 weight percent of the total composition.

A preferred aspect in using the compounds of this invention in lubricating oils is to include in the oil from about 1 to 50 mm./kg. of a dihydrocarbyl phosphorodithioate, wherein the hydrocarbyl groups are from about 4 to 36 carbon atoms. Uusually, the hydrocarbyl groups will be alkyl or alkaryl groups. The remaining valence of the phosphorodithioate will usually be satisfied by zinc, but polyalkyleneoxy or a third hydrocarbyl group may also be used. (Hydrocarbyl is an organic radical composed solely of carbon and hydrogen which may be aliphatic, alicyclic, aromatic or a combination thereof.)

Other additives may also be included in the oil such as pour point depressants, oiliness agents, antioxidants, rust inhibitors, etc. Usually, the total amount of these additives will range from about 0.1 to 10 weight percent, more usually from about 0.5 to 5 weight percent. The individual additives may vary from about 0.01 to 5 weight percent of the composition.

In order to demonstrate the excellent effectiveness of the compounds of this invention as detergents and dispersants in lubricating oils, the compound of Example II was tested in a lG Caterpillar test (MIL-L45 199 conditions) for 60 hours. The oil used was a Mid-Continent SAE 30 oil, 12.3 weight percent of this additive was used, and 12 mm./kg. of zinc di(alkylphenyl)phosphorodithioate (the alkyl groups were polypropylene of about 12 to 15 carbon atoms) was included. The following table indicates the results. Also included for comparison are the results for the base oil containing only the phosphorodithioate. The rating of groove deposits is based on a range of 0 to 100, being completely filled grooves. The rating for land deposits is based on a range of 0 to 800, 800 being completely black. The rating for underhead deposits is based on a range of 0 to 10, 10 being completely clean.

In order to demonstrate the effectiveness of the compositions of this invention under extremely severe engine conditions, the compositions of Examples I and II were compounded in a Mid-Continent SAE 30 neutral oil at 6.1 and 6.25 weight percent respectively. Also included was 12 rum/kg. of a common oxidation inhibitor; namely, zinc 0,0-dialkylphenyl phosphorodithioate (the alkyl groups are from 12 to 14 carbon atoms).

The test used is a particularly severe test which is referred to as the 240 BMEP (brake mean effective pressure) Caterpillar Test. The conditions are for a supercharged caterpillar test wherein the pressure of the supercharged air is 76.5" mercury absolute, the water temperature of the cooling jacket is 200 F., the air temperature is F., the oil temperature of the bearing is F., the sulfur content of the fuel is 0.4 weight percent, the speed of the engine is 1200 r.p.m., and the rate of fuel input is at a rate which provides 6900 B.t.u.s per minute. The test was carried out for 60 hours and the following table indicates the results. The results are reported as described previously.

TABLE II Deposits Example Groove Land Underhead iijiij:::::::::::::::::::::::: iijlj lii 8o, w?'13 5:?

and II is of the formula:

wherein X is halogen of atomic No. 17 to 35, n is an integer of from 2 to 4, and A is of the formula:

wherein R is a branched chain oil sol-ubilizing aliphatic group of from 40 to 125 carbon atoms and U is alkylene of from 1 to 2 carbon atoms.

2. A lubricating oil composition according to claim 1 wherein n is from 2 to 4, X is chlorine, and R is of from 50 to 100 carbon atoms.

3. A lubricating oil composition according to claim 2 wherein R is polyisobutylene and U is methylene.

4. A lubricating oil composition having an oil of lubricating viscosity and from to 80 weight percent of a material consisting essentially of I or II, or mixtures thereof, wherein I is of the formula:

and II is of the formula:

wherein X is halogen of atomic No. 17 to 35, n is an integer of from 2 to 4, and A is of the formula:

ROE-Cg /NU CHzOO wherein R is a branched chain oil solubilizing aliphatic group of from to carbon atoms and U is alkylene of from 1 to 2 carbon atoms.

References Cited

US3505227A 1967-12-18 1967-12-18 Lubricating oil compositions containing bis-alkenyl succinimides of xylylene diamines Expired - Lifetime US3505227A (en)

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3622514A (en) * 1969-09-12 1971-11-23 Mobil Oil Corp Imido polyphenyl oxides and lubricants containing same
US4471091A (en) * 1982-08-09 1984-09-11 The Lubrizol Corporation Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4486573A (en) * 1982-08-09 1984-12-04 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4489194A (en) * 1982-08-09 1984-12-18 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4564460A (en) * 1982-08-09 1986-01-14 The Lubrizol Corporation Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4575526A (en) * 1982-08-09 1986-03-11 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same
US4596663A (en) * 1982-08-09 1986-06-24 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4613342A (en) * 1982-08-09 1986-09-23 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4623684A (en) 1982-08-09 1986-11-18 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US5041622A (en) * 1988-04-22 1991-08-20 The Lubrizol Corporation Three-step process for making substituted carboxylic acids and derivatives thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3131150A (en) * 1961-04-12 1964-04-28 California Research Corp Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines
US3219666A (en) * 1959-03-30 1965-11-23 Derivatives of succinic acids and nitrogen compounds
US3306907A (en) * 1963-04-29 1967-02-28 Standard Oil Co Process for preparing n n-di

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3219666A (en) * 1959-03-30 1965-11-23 Derivatives of succinic acids and nitrogen compounds
US3131150A (en) * 1961-04-12 1964-04-28 California Research Corp Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines
US3306907A (en) * 1963-04-29 1967-02-28 Standard Oil Co Process for preparing n n-di

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3622514A (en) * 1969-09-12 1971-11-23 Mobil Oil Corp Imido polyphenyl oxides and lubricants containing same
US4471091A (en) * 1982-08-09 1984-09-11 The Lubrizol Corporation Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4486573A (en) * 1982-08-09 1984-12-04 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4489194A (en) * 1982-08-09 1984-12-18 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4564460A (en) * 1982-08-09 1986-01-14 The Lubrizol Corporation Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4575526A (en) * 1982-08-09 1986-03-11 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same
US4596663A (en) * 1982-08-09 1986-06-24 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4613342A (en) * 1982-08-09 1986-09-23 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4623684A (en) 1982-08-09 1986-11-18 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US5041622A (en) * 1988-04-22 1991-08-20 The Lubrizol Corporation Three-step process for making substituted carboxylic acids and derivatives thereof

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