US3257318A - Lubricating compositions containing a synergistic mixture of additives - Google Patents

Lubricating compositions containing a synergistic mixture of additives Download PDF

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Publication number
US3257318A
US3257318A US136166A US13616661A US3257318A US 3257318 A US3257318 A US 3257318A US 136166 A US136166 A US 136166A US 13616661 A US13616661 A US 13616661A US 3257318 A US3257318 A US 3257318A
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Prior art keywords
additives
oil
oils
lubricating
compositions containing
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US136166A
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Cohen Max
Tirtiaux Robert
Tourret Roger
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/34—Introducing sulfur atoms or sulfur-containing groups
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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    • C10M2205/20—Natural rubber; Natural resins
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    • C10M2207/02—Hydroxy compounds
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
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Definitions

  • the type (A) additive incorporated in the oil composition of this invention consists :of a phosphosulphurized hydrocarbon further reacted with a C -C alkylene oxide.
  • the hydrocarbons from which the aforesaid type (A) additives may be derived are paraffins, olefins or polymer-s thereof, diolefines, 'acetylenic hydrocarbons, alkyl-aromatic or cycloaliphatic hydrocarbons, and petroleum fractions such as mineral lubricating oils, bright stocks and waxes.
  • the hydrocarbon may be reacted with phosphorus sulphide, for example, P S or a mixture of elemental phosphorus and sulphur, at a temperature between about 190 and 600 F., preferably between 300 and 550 F.
  • the time of reaction may vary between about 1 hour to hours, according to the degree 'of reaction desired.
  • the reaction is preferably carried out in a non-oxidizing atmosphere, for instance nitrogen.
  • alkoxylation may be carried out at elevated temperature, e.g. 230300 F., in the presence of a suitable catalyst, such as a boron 'trifluoride-ether complex or caustic soda, for an extended period of time, e.g., 1 to 5 hours, until the degree of alkoxylation required has been achieved.
  • a suitable catalyst such as a boron 'trifluoride-ether complex or caustic soda
  • 1 to 10 mols of alkylene oxide may be reacted with one mol of phosphosulphurized hydrocarbon.
  • the stability of the final product may be increased by steam-stripping the phosphosulphurized product prior to reaction with the alkylene oxide.
  • the type (B) additives incorporated in the oil composition of this invention are essentially the so-called ashless dipersants hitherto employed in lubricating oils,
  • the aforesaid oxygenor nitrogen-containing polar group may be an ester of a saturated mono-carboxylic acid with vinyl alcohol.
  • it is a derivative of an nap-unsaturated dicar-boxylic acid, particu uarly maleic acid, for instance m-aleic anhydride or a maleic acid ester, including a partial ester in which the remaining acid group may remain free or reacted with a further compound, for instance an alkylene oxide.
  • polar compounds include amines, amino-acids,
  • N-vinyl butyrolactams for example, N-vinyl pyrollidone, pyridines and substituted pyridines.
  • the copolymers may consist of two or more polar monomers hereinbefore enumerated by example, for instance, a copolymer derived from N-vinyl pyrollidone and a pyridine.
  • a copolymer derived from N-vinyl pyrollidone and a pyridine Preferably however at least one of the monomers consists of an alkyl ester of an a-B-unsaturated carboxylic acid.
  • a mono-carboxylic acid such as acrylic, alkyl acrylic, itaconic, or a dicarboxylic acid such as maleic or fumaric acid
  • an aloh-ol e.g., a C C alcohol or alcohol mixture obtained for instance from natural sources, such as coconut oil, or derived by synthesis, as for example by the oxonation of olefines and the subsequent hydrogenation of the aldehyde thus produced.
  • copolymeric additives which constitute the type B additives hereinbefore described are not confined to two-component copolymers, but may be derived from three or more monomers. They may be derived from an alkyl ester of an u-fi-unsatur-ated carboxylic acid and two or more polar monomers. Particularly useful copolymers are those derived from one or more C -C alkyl esters of maleic or fumaric acid, together with an ester of vinyl alcohol and a C -C mon ocarboxylic acid, and one or more further polar monomers, particularly maleic anhydride, partial esters of maleic acid as hereinbefore described, an unsaturated nitrile or N- vinyl pyrollidone.
  • esters of fumaric or maleic acid and one or more C C alcohols 160% by weight
  • esters of fumaric or maleic acid and one or more C C monohydric alcohols 160% by weight
  • Partial ester of maleic acid and one or more C C mon ohydric alcohols 0.1 to 20% by weight
  • compositions of this invention are particularly suitable for use as fuels or lubricants in internal combustion engines.
  • the A and B type additives are each present in proportions of from 0.05 to 10% by weight.
  • the total of the two components is preferably about 01-15%, more preferably 0.5-5 by weight, based on the total lubricating or fuel compositions.
  • the compositions according to this invention also include concentrates containing substantially greater proportions of the addtive components, which may then be diluted with further oil to obtain compositions suitable for use in internal combustion engines, including fourstroke or two-stroke spark ignition or compression ignition engines.
  • lubricating compositions of this invention are not confined to those using an automotive lubricating oil, but may be based on cutting oils, including emulsion-type lubricating oils, hydraulic fluids, kerosine-b-ased lubricating or fuel oils and spindle oils.
  • the base oils may be mineral lubricating or fuel oils, or may be synthetic oils, including oxidized mineral oils, monoor di-esters for example dioctyl adipate or sebacate, complex esters, including complex esters derived from a mixture of monoor di-oarboxylic acids, monoor di-hydroxy alcohols, and a polyalkylene glycol or glycol ether, or mixtures of such synthetic oils, or the base oils may be of animal or vegetable origin, for instance castor oil or fish oils.
  • oil composition of this invention may contain other additive constituents which are commonly added to fuel or lubricating oils.
  • oil-soluble anti-oxidant compounds may be incorporated, for instance aor 3- naphthylamine, including alkyl substituted derivatives thereof, alkyl phenols, for instance 2,4-dimethyl-6-tert. octyl phenol, substituted diphenylamines, including dioctyl dip'henylamine, and bisphenols.
  • Extreme-pressure additives such as alkylor aryl-substituted phosphates and phosphites, 'sulphurized hydrocarbons, sulphurized sperm oil or metal dialkyl dithiophosphates may be included in the compositions, as may also be polyisoolefines or degraded rubbery copolymers and other compounds which act as viscosity index improvers.
  • Blend Component A Alkoxylated phosphosulphurized polybutene (designated Component A) obtained by reacting polyisobutylene of molecular weight 1,200 with 15% by weight of P S for 8 hours at 430 F., diluting the resultant product in 100 parts of mineral oil, steam stripping for 4 hours at 250 F., and further reacting the resulting product with 8 parts of ethylene oxide at 340 F. for 3 hours with the aid of a BF ether complex.
  • Component A Alkoxylated phosphosulphurized polybutene obtained by reacting polyisobutylene of molecular weight 1,200 with 15% by weight of P S for 8 hours at 430 F., diluting the resultant product in 100 parts of mineral oil, steam stripping for 4 hours at 250 F., and further reacting the resulting product with 8 parts of ethylene oxide at 340 F. for 3 hours with the aid of a BF ether complex.
  • B1 Copolymer (designated copolymer B1) obtained by copolymerizing a mixture of -0 alcohol fumarates, butyl half ester of maleic acid and vinyl acetate, using azodi-isobutyronitrile catalyst, the polymerization being carried out in a mineral oil diluent at 175 F.
  • B2 Copolymer (designated copolymer B2) obtained by reacting a mixture of C -C alcohol fumarate, vinyl acetate and maleic anhydride, the polymerization being carried out in a mineral oil diluent using a benzoyl peroxide catalyst.
  • a lubricating oil composition suitable for use in an internal combustion engine comprising a major proportion of a mineral lubricating oil and a synergistic mixture with regard to engine cleanliness of (a) in the range of 0.05 to 4.0 wt. percent of a phosphosulphurized hydrocarbon alkylene oxide lubricating oil additive prepared by reacting mole of phosphosulp-hurized hydrocarbon with from 1 to 10 moles of a C -C alkylene oxide at 230 to 340 F. for about 1 to 5 hours and (b) in the range of 0.05 to 10 wt. percent of oil-soluble ashless dispersant lubricating oil additive prepared by cop-olymerizing:

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
US136166A 1960-09-15 1961-09-06 Lubricating compositions containing a synergistic mixture of additives Expired - Lifetime US3257318A (en)

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FR838696A FR1275406A (fr) 1960-09-15 1960-09-15 Amélioration des compositions lubrifiantes

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US3257318A true US3257318A (en) 1966-06-21

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BE (1) BE608231A (da)
DE (1) DE1245526B (da)
FR (1) FR1275406A (da)
GB (1) GB959327A (da)
NL (1) NL268950A (da)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3904535A (en) * 1971-07-26 1975-09-09 Chevron Res Phosphosulfurized lubricating oil additives
US6123742A (en) * 1999-08-09 2000-09-26 Smith; Eugene P. Fuel additive

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3389086A (en) * 1966-06-01 1968-06-18 Texaco Inc Product of reaction of an epoxy resin with an hydrolyzed polyolefin-p2s5 amine reaction product and lubricating oil containing same

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2694685A (en) * 1947-02-14 1954-11-16 Standard Oil Dev Co Maleinoid-vinyl copolymer and its use in lubricants
GB758203A (en) * 1952-12-26 1956-10-03 California Research Corp Lubricant composition
GB792553A (en) * 1955-09-08 1958-03-26 Exxon Standard Sa Improved additives suitable for lubricating oil compositions
GB797266A (en) * 1955-11-23 1958-06-25 Exxon Standard Sa Improvements to lubricant compositions
GB807737A (en) * 1956-07-27 1959-01-21 Exxon Research Engineering Co Mineral oil compositions
GB808665A (en) * 1956-03-23 1959-02-11 Exxon Research Engineering Co Oils containing copolymers

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1076398A (fr) * 1952-04-07 1954-10-26 Du Pont Perfectionnements aux fuel-oils stabilisés
GB757915A (en) * 1952-09-30 1956-09-26 California Research Corp Lubricant composition
GB767033A (en) * 1954-04-22 1957-01-30 Exxon Research Engineering Co Polymerisation process
GB760994A (en) * 1954-06-11 1956-11-07 Exxon Research Engineering Co Improvements in or relating to lubricating oil additives
GB822620A (en) * 1955-08-31 1959-10-28 Chemon Corp Lubricating oil additives

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2694685A (en) * 1947-02-14 1954-11-16 Standard Oil Dev Co Maleinoid-vinyl copolymer and its use in lubricants
GB758203A (en) * 1952-12-26 1956-10-03 California Research Corp Lubricant composition
GB792553A (en) * 1955-09-08 1958-03-26 Exxon Standard Sa Improved additives suitable for lubricating oil compositions
GB838928A (en) * 1955-09-08 1960-06-22 Exxon Standard Sa Oxyalkylated phosphosulphurised hydrocarbons and lubricating compositions therefrom
GB797266A (en) * 1955-11-23 1958-06-25 Exxon Standard Sa Improvements to lubricant compositions
GB808665A (en) * 1956-03-23 1959-02-11 Exxon Research Engineering Co Oils containing copolymers
GB807737A (en) * 1956-07-27 1959-01-21 Exxon Research Engineering Co Mineral oil compositions

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3904535A (en) * 1971-07-26 1975-09-09 Chevron Res Phosphosulfurized lubricating oil additives
US6123742A (en) * 1999-08-09 2000-09-26 Smith; Eugene P. Fuel additive

Also Published As

Publication number Publication date
FR1275406A (fr) 1961-11-10
BE608231A (da)
DE1245526B (de) 1967-07-27
GB959327A (en) 1964-05-27
NL268950A (da)

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