US2958660A - Detergent and wear inhibiting mineral lubricating oil compositions - Google Patents

Detergent and wear inhibiting mineral lubricating oil compositions Download PDF

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Publication number
US2958660A
US2958660A US536747A US53674755A US2958660A US 2958660 A US2958660 A US 2958660A US 536747 A US536747 A US 536747A US 53674755 A US53674755 A US 53674755A US 2958660 A US2958660 A US 2958660A
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United States
Prior art keywords
oil
lubricating oil
detergent
compositions
mineral lubricating
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US536747A
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English (en)
Inventor
John A Edgar
Bergstrom Roland Frederick
Robert C Jones
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Shell USA Inc
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Shell Oil Co
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Publication date
Priority to NL102109D priority Critical patent/NL102109C/xx
Priority to BE551242D priority patent/BE551242A/xx
Priority to NL102108D priority patent/NL102108C/xx
Priority to NL102110D priority patent/NL102110C/xx
Priority to US536746A priority patent/US2958662A/en
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US536747A priority patent/US2958660A/en
Priority to FR1158245D priority patent/FR1158245A/fr
Priority to DEN12755A priority patent/DE1058187B/de
Priority to GB29137/56A priority patent/GB799036A/en
Priority to DEN12754A priority patent/DE1053699B/de
Priority to GB29139/56A priority patent/GB799037A/en
Priority to DEN12756A priority patent/DE1053700B/de
Priority to GB29138/56A priority patent/GB810685A/en
Application granted granted Critical
Publication of US2958660A publication Critical patent/US2958660A/en
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M165/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a compound of unknown or incompletely defined constitution, each of these compounds being essential
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
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    • C10M2207/02—Hydroxy compounds
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Definitions

  • This invention relates to lubricating oil compositions and more particularly to highly detergent or dispersant lubricating oil compositions which also possess good extreme pressure properties and prevent wear.
  • lubricating oil detergents generally employed were polyvalent metal salts or soaps of organic carboxylic acids, organic naphthenic acids, or organic sulfonic acids.
  • Detergents of this type although effective in engines operating at relatively high temperatures, are generally ineffective at low temperatures such as are encountered in engines operating under severe, stopand-go, conditions.
  • the Xs can be the same or different polar groups such as is hydrogen or a short alkyl radical of not more than 4 carbon atoms and preferably an alkyl radical of from 1 to 3 carbon atoms;
  • R can be the same as R or a long alkyl radical of 8 or more carbon atoms, and preferably from 14 to .18 carbon atoms or a basic group, e.g., (CH ),,N wherein n is an integer of 1 to 20, preferably of from 4 to 12;
  • m can be Zero or one;
  • X can be the same as XR or a long alkyl radical of atleast 8 carbon atoms. At least one of the Rs should be a long alkyl radical of at least 8 carbon atoms.
  • a principal object of this invention is to produce a lubricating composition having desirable detergent or dispersant and anti-wear properties.
  • Another object of this invention is to produce a lubricating composition suitable for use under stop-and-go driving conditions.
  • oil-soluble polymeric detergents as represented by the general formula (I) can be characterized as polymers containing a non-polar oil-solubilizing group such as long chain alkyl radicals and polar active detergent groups of which preferred are the:
  • R is hydrogen or a long chain alkyl radical such as an alkyl radical of from 12 to 18 carbon atoms, and R, is a short alkyl radical of from 1 to 4 carbon atoms. It is preferred that the non-polar oilsolubilizing groups and the polar detergent groups be attached either directly or indirectly to different carbon atoms of a long hydrocarbon backbone chain as indicated in Formula I.
  • alpha-olefinic hydrocarbons such as alphaalkenes containing from 10 to about 40 carbon atoms and preferably 12 to 30 carbon atoms
  • hydrolyzable vinyl compounds such as vinyl halides ⁇ vinyl chloride) and vinyl esters (vinyl acetate)
  • copolymers of such alpha-olefins with other low molecular weight polymerizable polar-substituted alpha-alkenes such as the acrylo compounds, as illustrated by acrylic acid, acrylonitrile, acrylarnide, methacrylic acid, methacrylonitrile, methacrylamide, as Well as mixtures and derivatives thereof.
  • Polymeric compounds of this class can be represented by the general formula
  • R is a long alkyl radical which can contain from 10 to 18 carbon atoms and Y can be:
  • the catalysts suitable for use in making the polymers and copolymers include various oxygen-yielding catalysts, for example, various organic peroxides, such as aliphatic, aromatic, heterocyclic, and alicyclic peroxides, such as diethyl peroxide, tertiary butyl hydroperoxide, dibenzoyl peroxide, dimethylthienyl peroxide, dicyclohexyl peroxide, dilauroyl peroxide and urea peroxide.
  • various organic peroxides such as aliphatic, aromatic, heterocyclic, and alicyclic peroxides, such as diethyl peroxide, tertiary butyl hydroperoxide, dibenzoyl peroxide, dimethylthienyl peroxide, dicyclohexyl peroxide, dilauroyl peroxide and urea peroxide.
  • organic peroxides suitable for use in the preparation of additives for use in compositions of this invention.
  • Other catalysts include sodium bisulfite, diethyl sulfoxide, ammonium persulfate, alkali metal perborates, azo compounds such as alpha, alpha-azodiisobutyronitrile, etc.
  • Copolymers of this invention can be prepared by any suitable means, such as described in US. Patents 2,421,971 and 2,467,774. They may also be produced by themethod described in US. Patent 2,551,643, followed by hydrolyzing the copolymer by the method described in the first two patents. Suitable copolymers also can be prepared by the method described in US. Patents 2,421,971, and 2,467,774, except that for vinyl esters, acrylonitriles, acrylamides, or acrylic acids are used or these copolymer-s can be prepared by the general method described in US. Patents 2,436,926, and
  • This product was alcoholized in about 1,800 ml. of methanol to which about 1 gram of metallic sodium was added. The mixture was distilled to remove the methyl acetate and the excess methanol and the product was then dispersed in heptane and topped. The resulting residue product was an alkanepolyol (polyhydric alkanol) having a molecular weight of about 8,000 as determined bylight scattering means. From the molecular weight and the aforesaid number of gram equivalents of ester groups per 100 grams of the ester, it can be calculated that for the alkane polyol there is a ratio of alcoholic hydroxyl groups to hydrocarbyl (hexadecyl) radicals of about 2.2.
  • the average alkanepolyol molecule contains about 50 hydroxyethylene radicals and about 23 octadecylene-1,2 radicals; there is a total of about 73 hydrocarbyl and hydroxyl radicals per molecule.
  • the molecule is a chain of 146 C-atoms having 50 hydroxyl and 23 hexadecyl radicals attached to 73 different C-atoms of the chain throughout the chain length. Those 73 C-atoms have attached thereto 73 H-atoms (one each) and the remainder of the C-atoms are saturated with 2 H-atoms each.
  • the molecule can be represented by the formula:
  • polymeric detergents can be prepared by polymerizing unsaturated polymerizable heterocyclic nitrogen base compounds and derivatives thereof with another polymerizable unsaturated material free of heterocyclicnitrogen radicals, such as acrylic compounds, vinyl and vinylidine compounds, allyl compounds, or unsaturated polycarboxylic acids and the like.
  • Polymers of this class can be represented by the general formula having units of:
  • Z is a basic heterocyclic nitrogen group such as 4 a C-pyridyl radical
  • Z is an oil-solubilizer polar group, e.g.,
  • the copolymers of this type can be prepared by any suitable means, the reaction preferably being carried out in the presence of a polymerization catalyst.
  • a polymerization catalyst e.g., acrylate
  • the reactions in the mol ratio of 1:10 to 10:1 and preferably from 1:1 to 1:4 of a C-vinyl pyridine to other polymerizable material, e.g., acrylate can be reacted in the presence of from 0.1 to 5% of a catalyst such as a peroxide or azo compound in the presence or absence of an inert solvent such as a hydrocarbon under a blanket of nitrogen or carbon dioxide and at a temperature varying fromroom temperature or lower to about 180 C. or higher for a period of from about 2 to 48 hours until the average molecular weight of the copolymer exceeds 50,000 and preferably is within the range of from 75,000 to 700,000.
  • a catalyst such as a peroxide or azo compound
  • an inert solvent such as a hydrocarbon under a blanket
  • EXAMPLE II A mixture of about 1 mole of lauryl methacrylate, 1 mole of 2-methyl-5-vinyl pyridine and 0.4% wt. of benzoyl peroxide were placed in a suitable reaction vessel and the mixture reacted for a period of over 2 hours at -85 C. in a nitrogen atmosphere. The unreacted materials were stripped off at 185 C. and 1 mm. pressure and the resulting copolymer was a rubbery product containing around 3% nitrogen, having a molecular weight in excess of 150,000, and was soluble in hydrocarbon oils.
  • EXAMPLE III A copolymer of lauryl methacrylate and Z-methyl-S- vinyl pyridine was prepared by the method of Example II, but in which the mole ratio of the reactants was 4 to 1, respectively.
  • the nitrogen content of the product was about 2%, the molecular weight was in excess of 75,- 000, and it had a sticky rubbery consistency but was oil soluble.
  • Still another class of polymeric detergents can be represented by the formula having repeating units:
  • D is a polar radical such as where R; is a long alkyl radical, e.g. C -C alkyl radical, and E is a basic radical, e.g.,
  • R4 i JO-R4N and R is the same as in Formula III;
  • Polymers of this type can be prepared by the methods described in US. Patents 2,584,968, 2,666,044, and 2,680,717, and include lauryl methacrylate/diethylamino ethyl methacrylate (:10) copolymer lauryl methacrylate/styrene/dibutylaminoethyl methacrylate, lauryl methacrylate/4-dimethylaminocyclohexyl methacrylamide (90/ 10), lauryl methacrylate/tertoctaylaminoethyl methacrylate, and mixture thereof.
  • lauryl methacrylate/diethylamino ethyl methacrylate (:10) copolymer lauryl methacrylate/styrene/dibutylaminoethyl methacrylate, lauryl methacrylate/4-dimethyla
  • the second essential additive used in compositions of this invention which imparts wear inhibiting properties to said compositions is a highly basic metal salt of an organic sulfonic acid.
  • basic salts is meant that the amount of neutralizing agent used is far in excess, namely, in the range of from 30 to 1000, and preferably between asseeso" 5 50 and 800 percent in excess of that normally required to neutralize the acid to produce the normal salt.
  • the basic sulfonates can be derived from any suitable material and prepared by any of the Well-known methods. Preferred materials for making sulfonates include liquid petroleum fractions, alkyl substituted aromatic compounds and alkyl substituted polar-containing aromatic compounds. Although various basic metal sulfonates are contemplated for use in compositions of this invention, the basic sulfonates of the metals of group II of the periodic table having an atomic number of from 12 to 56 inclusive, are preferred, and especially the alkaline earth metals (Ca, Ba, Mg, or Sr) Within that group of metals. Basic sulfonates suitable for use in compositions of this invention are described in US.
  • Specific basic sulfonates which are useful in compositions of this invention include basic calcium, barium, magnesium, strontium, and lead petroleum sulfonates, of oil-soluble petroleum sulfonic acids, tetra-tertiarybutyl-naphthalene sulfonates, di- Waxbenzene sulfonates, stearyl benzene sulfonates, diwaxnaphthalene sulfonates, ditertiary amyl phenol sulfonates, and mixtures thereof.
  • compositions of this invention can be added auxiliary additives such as anti-oxidants or corrosion inhibitors of which organic compounds containing inorganic phosphorus acidic radicals are particularly preferred.
  • auxiliary additives such as anti-oxidants or corrosion inhibitors of which organic compounds containing inorganic phosphorus acidic radicals are particularly preferred.
  • Compounds of this type can be obtained by reacting monoor polyhydroxy or merc-apto organic compounds, aliphatic olefins, e.g., isobutylene, cyclic olefins, e.g., terpenes, and mixtures thereof, with P POClg, P 5 P501 or P Se salts of said products are also included and are obtained by neutralizing the reaction products mentioned with oxides, hydroxides, carbonates, or halides of alkali, monoor polyvalent metals such as the alkali, alkaline earth or heavy metals exemplified by Na, K, Ca, Ba, Sr, Mg, A1, C0,
  • Compounds of this type include salts such as Na, Ca, Ba, Zn, and Al salts of alkyl, alkaryl, aralkyl, cycloalkyl, aryl phosphates, thiophosphates, and specifically illustrated by Na,
  • Lubri- Zol 304 or 1060 (Lubri-Zol Corp); Aerolube 70 (American Cyanamid Co.); Stan-Add 48 (Standard Oil Co. of Indiana); and Santolube 394C (Monsanto Chemical Co.).
  • Other phosphorus compounds which can be used are of the type described by Smalheer et al. in Petroleum Processing, December, 1952.
  • a particularly preferred list of such compounds includes the Zn and Ba salts of alkyl dithiophosphate, Na, K, and Ba salts of P S -polybutene reaction products and/or P S -terpene (pinene) reaction products, said products being commercially available from Lubri-Zol Corporation, Standard Oil Company of Indiana, and Monsanto Chemical Company, respectively, under the trade names of Lubri-Zol 304, and Lubri-Zol 1060; Stan-Add 47, 48, and L-9l03; and Santolube 394-C.
  • Lubricating oils for additives of this invention can be any natural or synthetic material having lubricating properties.
  • the base may be a hydrocarbon oil of wide viscosity range, e.g., 100 SUS at 100 F. to 150 SUS at 210 F.
  • the hydrocarbon oils may be blended with fixed oils such as castor oil, lard oil, and the like, and/ or with synthetic lubricants such as polymerized olefins, copolymers of alkylene glycols and oxides; organic esters of poly-basic organic and inorganic acids, e.g., di-Z-ethylhexyl sebacate, dioctyl phthalate, trioctyl phosphate; polymeric tetrahydrofuran; polyalkyl silicone polymers, e.g., dimethyl silicone polymer, and the like.
  • the synthetic lubricants may be used as the sole base lubricant or admixed with fixed oils and their derivatives.
  • Mineral lubricating oils which are particularly desirable for use in compositions of this invention and which have been used as a base for the compositions of this invention were obtained from West Texas Ellenburger crudes, East Texas crudes, Oklahoma crudes, California crudes. A useful refined oil therefrom, had the following properties:
  • Another such oil is an SAE 30 mineral oil having the following properties:
  • compositions of this invention can be represented by:
  • compositions of this invention are illustrated by the following compositions:
  • COMPOSITION A Copolymer oflauryl methacrylate/diethylamino ethyl methacrylate (90:10) 5% Wt.
  • COMPOSITION B Copolymer of laurylmethacrylate/2-methyl-5- vinyl pyridine (4:1) 2% wt. Basic calcium petroleum sulfonate 2% wt. Mineral lubricating oil Balance.
  • COMPOSITION C Hydrolyzed copolymer of octadecene-l/vinyl acetate 2%.
  • compositions of this invention include mineral lubricating oils of the SAE 10, 20, 30, or 10W-30 type containing from about 1% to 6% by weight of copolymers of lauryl methacrylate/styrene/dibutylaminoethyl methacrylate, lauryl methacrylate/4-dimethylamino-cyolohexyl methacrylamide; lauryl methacrylate/Z-niethyl-S-vinyl pyridine, lauryl methacrylate/ 2-ethyl-5-vinyl pyridine, lauryl methacrylamide/ 2-methy1- 5-vinyl pyridine, hydrolyzed copolymer of hexadecene- 1/vinyl acetate and mixtures thereof; and from about 0.5% to about 5% by weight of oil-soluble basic calcium or barium petroleum sulfonate, diwax benzene sulfonate and mixtures thereof.
  • compositions can be added in amounts of from about 0.1% to about 1% other additives, such as metal dithiophosphates (Zn dialkyl dithiopliosphat-e), metal thiocarbamates, such as zinc 'dibutyl dithiocarbamate, amines, such as phenylalpha-naphthyla-mine octadecylamine; viscosity index and pour point depressants, such as the Acryloids, and specifically, Acryloid, 150, 618, 710, and/or 768, made by Rohm and H-ass and described in US.
  • additives such as metal dithiophosphates (Zn dialkyl dithiopliosphat-e), metal thiocarbamates, such as zinc 'dibutyl dithiocarbamate, amines, such as phenylalpha-naphthyla-mine octadecylamine; viscosity index and pour
  • Patent 2,710,842 condensation product of chlorinated parafiin wax and naphthalene; extreme pressure agents, such as oil-soluble polyhaloalkanephosphono components, such as 'trichloromethanephosphonic acid, esters, amides, or amine salts thereof, such as di-Z-ethylhexyl amine salt of trichloromethanejphosphonic acid; organic sulfides, and mixtures thereof.
  • extreme pressure agents such as oil-soluble polyhaloalkanephosphono components, such as 'trichloromethanephosphonic acid, esters, amides, or amine salts thereof, such as di-Z-ethylhexyl amine salt of trichloromethanejphosphonic acid
  • organic sulfides and mixtures thereof.
  • compositions of this invention were demonstrated when Composition A was tested in a Chevrolet engine under EX-3 test procedure and at the end of the test, the engine was clean, no sign of wear or corrosion was noted, no piston rings were stuck, and the engine was in excellent condition.
  • Composition A was tested in a Chevrolet engine under EX-3 test procedure and at the end of the test, the engine was clean, no sign of wear or corrosion was noted, no piston rings were stuck, and the engine was in excellent condition.
  • Compositions X and Y neutral Ca petroleum sulfonate
  • compositions B, C, or D Similar results as with Composition A can be obtained with Compositions B, C, or D, or other compositions of this invention in the EX-3 engine test procedure.
  • Compositions of this invention can be used as engine oils, turbine oils, gear oils, and various other fields of lubrication where detergency and wear inhibiting properties are essential.
  • a lubricating oil composition comprising a major amount of mineral lubricating oil and a minor but detergent amount of an oil-soluble copolymer of an acrylate ester of an acrylic acid and a long chain aliphatic alcohol 8 and a vinyl pyridine in the mol ratio of 1:1 to 10:1 respectively and having a molecular weight of from 50,000 to 700,000 and a minor, but wear inhibiting amount of an oil-soluble basic alkaline earth metal petroleum sulfonate containing from to 800% excess base.
  • a lubricating oil composition comprising a major amount of mineral lubricating oil and a minor but detergent amount of an oil-soluble copolymer of lauryl methacrylate and a vinyl pyridine in the mol ratio of 1:1 to 10:1 respectively and having a molecular weight of from 50,000 to 700,000 and a minor but wear inhibiting amount of an oil-soluble basic alkaline earth metal petroleum sulfonate containing from 50% to 800% excess base.
  • a lubricating oil composition comprising a major amount of mineral lubricating oil and a minor but detergent amount of an oil-soluble copolymer of lauryl methacrylate and 2-methyl-5-vinyl pyridine in the mol ratio of 1:1 to 10:1 respectively and having a molecular weight of from 50,000 to 700,000 and a minor but wear inhibiting amount of an oil-soluble basic calcium petroleum sulfonate containing from 50% to 800% excess base.
  • a lubricating oil composition comprising a major amount of mineral lubricating oil and a minor but detergent amount of an oil-soluble copolymer of octadecyl Inethacrylate and 2-methyl-5-vinyl pyridine in the mol ratio of 1:1 to 10:1 respectively and having a molecular Weightof from 50,000 to 700,000 and a minor but Wear inhibiting amount of an oil-soluble basic calcium petroleum sulfonate containing from 50% to 800% excess base.

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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US536747A 1955-09-26 1955-09-26 Detergent and wear inhibiting mineral lubricating oil compositions Expired - Lifetime US2958660A (en)

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US536747A US2958660A (en) 1955-09-26 1955-09-26 Detergent and wear inhibiting mineral lubricating oil compositions
US536746A US2958662A (en) 1955-09-26 1955-09-26 Detergent and wear inhibiting mineral oil compositions
FR1158245D FR1158245A (fr) 1955-09-26 1956-09-24 Compositions d'huiles lubrifiantes
DEN12755A DE1058187B (de) 1955-09-26 1956-09-24 Schmiermittel
GB29137/56A GB799036A (en) 1955-09-26 1956-09-24 Lubricating oil compositions
DEN12754A DE1053699B (de) 1955-09-26 1956-09-24 Schmieroel
GB29139/56A GB799037A (en) 1955-09-26 1956-09-24 Lubricating oil compositions
DEN12756A DE1053700B (de) 1955-09-26 1956-09-24 Schmieroel
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US3192158A (en) * 1962-04-18 1965-06-29 Shell Oil Co Lubricating compositions containing a detergent copolymer and an alkaline earth petroleum sulfonate-trialkyl amine complex
US3211652A (en) * 1962-12-03 1965-10-12 Ethyl Corp Phenolic compositions
US4867890A (en) * 1979-08-13 1989-09-19 Terence Colclough Lubricating oil compositions containing ashless dispersant, zinc dihydrocarbyldithiophosphate, metal detergent and a copper compound

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GB922878A (en) * 1958-06-26 1963-04-03 Monsanto Chemicals Oil-soluble copolymeric materials and compositions containing the same
US3205170A (en) * 1958-08-08 1965-09-07 Universal Oil Prod Co Stabilization of organic compounds
NL243555A (fr) * 1958-09-22
US3397145A (en) * 1958-12-29 1968-08-13 Universal Oil Prod Co Hydrocarbon oils containing alkylthiophosphoric acid salts of polymeric condensation products
US3159578A (en) * 1960-02-26 1964-12-01 Shell Oil Co Organic functional fluids and polymeric amine salt additives therefor
DE1160967B (de) * 1960-06-15 1964-01-09 Shell Int Research Schmiermittel
US3198739A (en) * 1960-11-25 1965-08-03 Shell Oil Co Lubricants and polymeric additives therefor
US3336237A (en) * 1963-05-16 1967-08-15 Shell Oil Co Lubricating oil composition
NL6404814A (fr) * 1964-04-29 1965-11-01
DE2926474C2 (de) * 1979-06-30 1984-08-30 Chemische Fabriek Servo B.V., Delden Acrylester-Mischpolymerisate und ihre Verwendung als Kristallisationsinhibitoren für paraffinhaltige Rohöle

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US3192158A (en) * 1962-04-18 1965-06-29 Shell Oil Co Lubricating compositions containing a detergent copolymer and an alkaline earth petroleum sulfonate-trialkyl amine complex
US3211652A (en) * 1962-12-03 1965-10-12 Ethyl Corp Phenolic compositions
US4867890A (en) * 1979-08-13 1989-09-19 Terence Colclough Lubricating oil compositions containing ashless dispersant, zinc dihydrocarbyldithiophosphate, metal detergent and a copper compound

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DE1053700B (de) 1959-03-26
GB810685A (en) 1959-03-18
GB799037A (en) 1958-07-30
NL102108C (fr)
NL102109C (fr)
BE551242A (fr)

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