GB711211A - Improved lubricant blend - Google Patents

Improved lubricant blend

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Publication number
GB711211A
GB711211A GB20959/50A GB2095950A GB711211A GB 711211 A GB711211 A GB 711211A GB 20959/50 A GB20959/50 A GB 20959/50A GB 2095950 A GB2095950 A GB 2095950A GB 711211 A GB711211 A GB 711211A
Authority
GB
United Kingdom
Prior art keywords
esters
acidity
carbon atoms
ester
dialkyl ester
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
Application number
GB20959/50A
Inventor
Ronald William Morton
Alan James Porter
John Greenwood
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Standard Oil Development Co
Original Assignee
Standard Oil Development Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to BE505439D priority Critical patent/BE505439A/xx
Application filed by Standard Oil Development Co filed Critical Standard Oil Development Co
Priority to GB20959/50A priority patent/GB711211A/en
Priority to FR1046800D priority patent/FR1046800A/en
Priority to DEST3767A priority patent/DE951105C/en
Publication of GB711211A publication Critical patent/GB711211A/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • 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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • C—CHEMISTRY; METALLURGY
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • 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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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • 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
    • 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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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • 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
    • 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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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • C10M2209/111—Complex polyesters having dicarboxylic acid centres
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • C10M2209/112—Complex polyesters having dihydric acid centres
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
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    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043—Polyoxyalkylene ethers with a thioether group
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
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    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators
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    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/17—Electric or magnetic purposes for electric contacts
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

A lubricating composition (see Group III) comprises a dialkyl ester of a saturated dicarboxylic acid together with a polymer soluble in the dialkyl ester, the viscosity of the composition being greater than that of the dialkyl ester and the acidity of the dialkyl ester being less than 0.3 mg. KOH/gm. In the examples, lubricating compositions are described consisting of (a) dinonyl sebacate (acidity 0.07 mg. KOH/gm.), mineral oil solution of polymethyl methacrylate and phosphosulphurized alpha-pinene and (b) dinonyl sebacate (acidity 0.05 mg. KOH/gm.), polybutyl methacrylate and phenthiazine.ALSO:A lubricating composition (see Group III) comprises a dialkyl ester of a saturated dicarboxylic acid together with a polymer or a complex ester soluble in the dialkyl ester, the viscosity of the composition being greater than that of the dialkyl ester and the acidity of the dialkyl ester being less than 0.3 mg. KOH/gm. Complex esters mentioned are as follows: (1) esters of the formula R1OOC.R2.COOR3.OOCR4.COOR5 (some of which are described in Specifications 666,697, 687,346 and 687,347) where R1 and R5 are aliphatic alcohol or ether alcohol residues, R2 and R4 are the hydrocarbon radicles of aliphatic dicarboxylic acids and R3 is the hydrocarbon or oxygenated hydrocarbon radicle of a glycol or a polyglycol, all the radicles R1-R5 being saturated; (2) esters (including those described in Specification 668,663) formed by fully esterifying a dicarboxylic acid R(COOH)2 (where R is a hydrocarbon radicle containing 0-26 carbon atoms or an organic radicle consisting of a series of saturated aliphatic hydrocarbon radicles linked by at least one non-carbon atom chosen from the elements oxygen and sulphur, the total number of carbon atoms and said non-carbon atoms in the radicle being 3-80, there being at least 2 carbon atoms between each pair of said non-carbon atoms and a total of not more than 2 sulphur atoms) with a hydroxy ester of the formula <FORM:0711211/IV (b)/1> where R1 is either an aliphatic hydrocarbon radicle containing 1-22 carbon atoms or a radicle containing 2-22 carbon atoms and consisting of two aliphatic hydrocarbon groups interlinked by one atom of oxygen or sulphur, R11 is either an aliphatic hydrocarbon radicle containing 1-20 carbon atoms or a radicle consisting of a series of saturated aliphatic hydrocarbon radicles (each having at least 2 carbon atoms) linked through 1-5 non-carbon atoms chosen from the elements oxygen and sulphur so that the total number of carbon atoms and said non-carbon atoms is 4-20 and the total number of sulphur atoms is not more than 2, R1, R2, R3 and R4 are each chosen from hydrogen, methyl and ethyl, m is an integer from 1 to 20 and n is 1 or 2; (3) esters (including those described in Specification 664,992) of formula <FORM:0711211/IV (b)/2> where R1 is an aliphatic hydrocarbon group which may contain one or more hydroxyl groups, R is an aliphatic hydrocarbon group, R11 is hydrogen or an alkyl or alkylene group containing not more than 6 carbon atoms, R111 is hydrogen or a methyl group, m is an integer from 1 to 3, n is an integer and x is an integer from 1 to 30; (4) esters (including those described in Specification 662,650) of formula R11OOCRCOOR1OOCR111 and prepared by reacting 1 mol. of a dibasic acid with one mol. of a glycol in such a manner that a half ester is formed and esterifying the terminal OH and COOH groups with a monobasic acid and a monohydric alcohol respectively; and (5) esters (including those described in Specification 659,103) of formula R2COOR1OOCR3COOR11OOCR12 and prepared by reacting, under esterification conditions, 2 mols. of a monobasic aliphatic acid with 2 mols. of a glycol and 1 mol. of a dibasic aliphatic or aromatic acid. The blend of a complex ester with a dialkyl ester of a saturated dicarboxylic acid may be made mechanically, or it may be made chemically as described in Provisional Specification 683,803 and in Specification 687,347. The complex ester may also be of the prescribed low-acidity and the esters may be treated separately to lower their acidity to the prescribed value or the blend may be so treated. Methods described and exemplified for reducing acidity are (a) treatment of the esters with alumina, fuller's earth, attapulgus clay, charcoal or other solid adsorbents; (b) treatment of the esters with aqueous or dry alkali such as sodium carbonate, aqueous sodium carbonate preferably being used in presence of isopropyl alcohol, and optionally being followed by treatment (a); (c) prolongation of the esterification reaction in the preparation of the esters; (d) treatment of the esters with anion exchange resins such as m-phenylene diamine-formaldehyde resins; and (e) treatment with a mixture of solid adsorbent and dry alkali such as sodium carbonate. Specification 600,325 also is referred to.ALSO:A lubricating composition, of sufficiently low corrosivity to permit its use in the lubrication of prop-jet engines, comprises a dialkyl ester of a saturated dicarboxylic acid together with a polymer or a complex ester soluble in the dialkyl ester, the viscosity of the composition being greater than that of the dialkyl ester and the acidity of the dialkyl ester being less than 0.3 mg. KOH/gm. The complex esters referred to are defined as esters containing in the molecule more than 3 monocarboxylic acid, monohydric alcohol, polycarboxylic acid or polyhydric alcohol residues, and in which there is at least one polyhydric alcohol and one polycarboxylic acid residue, each of which has at least two of its functional groups. They are formed by the esterification, in one or more stages, of mixtures of polycarboxylic acids and polyhydric alcohols with or without monocarboxylic acids, monocarboxylic acids and monohydric alcohols, or monohydric alcohols. The various types of suitable complex esters are discussed (see Group IV (b)) and they include the complex esters of Specifications 659,103, 662,650, 664,992, 666,697, 668,663, 687,346, and 687,347. Polymers mentioned are polyolefins, polymerized unsaturated esters, copolymers of olefins and aromatic hydrocarbons with unsaturated side chains, copolymers of two or more unsaturated esters, and mixtures of such polymers. The lubricating composition may contain additional ingredients such as dyes, antioxidants, detergents, mineral and synthetic hydrocarbon oils, and other synthetic lubricating oils such as those of the polyglycol ether type. Methods of reducing the acidity of the dialkyl ester of a saturated dicarboxylic acid to the prescribed value are described (see Group IV (b)) and it is stated that the acidity of the complex ester may similarly be reduced. If desired, the acidity may be reduced only after the formation of the lubricating composition. Although primarily intended for aviation turbine lubricants, the lubricating compositions may also be employed as motor lubricants, as recoil oils and hydraulic fluids, for example in gun control mechanisms, as lubricants and working fluids for precision tools and as electrical oils. In the examples, lubricating compositions are described consisting of (a) dinonyl sebacate of acidity 0.07mg. KOH/gm., mineral oil solution of polymethyl methacrylate and phosphosulphurized alpha-pinene, (b) dinonyl sebacate of acidity 0.05mg. KOH/gm., polybutyl methacrylate and phenthiazine and (c) dinonyl sebacate of acidity 0.07mg. KOH/gm., complex ester of acidity 0.05mg. KOH/gm. and phenthiazine. The complex ester of example (c) is one prepared by esterifying 1 mol. of crude polyethylene glycols, having a mean molecular weight approximating to that of tetraethylene glycol, with 2 mols. of sebacic acid and then esterifying the half ester thus formed with 2 mols. of 2-ethyl-hexanol. Specifications 600,325 and 683,803 also are referred to.
GB20959/50A 1950-08-24 1950-08-24 Improved lubricant blend Expired GB711211A (en)

Priority Applications (4)

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BE505439D BE505439A (en) 1950-08-24
GB20959/50A GB711211A (en) 1950-08-24 1950-08-24 Improved lubricant blend
FR1046800D FR1046800A (en) 1950-08-24 1951-08-17 Lubricant mixture
DEST3767A DE951105C (en) 1950-08-24 1951-08-21 lubricant

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GB20959/50A GB711211A (en) 1950-08-24 1950-08-24 Improved lubricant blend

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GB711211A true GB711211A (en) 1954-06-30

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GB20959/50A Expired GB711211A (en) 1950-08-24 1950-08-24 Improved lubricant blend

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BE (1) BE505439A (en)
DE (1) DE951105C (en)
FR (1) FR1046800A (en)
GB (1) GB711211A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2929786A (en) * 1956-05-18 1960-03-22 Sinclair Refining Co Synthetic lubricating oil composition
US2971912A (en) * 1956-05-14 1961-02-14 Castrol Ltd Lubricating oil compositions
US3047504A (en) * 1959-12-31 1962-07-31 Exxon Research Engineering Co Process for treating complex esters to improve viscosity stability
US3049493A (en) * 1957-09-06 1962-08-14 Sinclair Research Inc Lubricating compositions
US3360546A (en) * 1963-09-16 1967-12-26 Monsanto Co Purification of hydroxyalkyl fumarate esters

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL100929C (en) * 1955-03-04
US3022259A (en) * 1955-05-06 1962-02-20 John W Pearce Process for purifying acid-containing compositions
DE1225628B (en) * 1955-07-11 1966-09-29 Exxon Research Engineering Co Process for the production of mixed esters serving as lubricating oils
NL108351C (en) * 1958-01-02

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2104408A (en) * 1933-09-20 1938-01-04 Standard Oil Dev Co Lubricant
GB592214A (en) * 1942-08-22 1947-09-11 Standard Oil Dev Co An improved manufacture of hydraulic fluids
US2417281A (en) * 1944-11-10 1947-03-11 Standard Oil Dev Co Instrument lubricant
BE461872A (en) * 1944-12-30
US2467147A (en) * 1945-03-22 1949-04-12 Standard Oil Dev Co Low-temperature lubricant

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2971912A (en) * 1956-05-14 1961-02-14 Castrol Ltd Lubricating oil compositions
US2929786A (en) * 1956-05-18 1960-03-22 Sinclair Refining Co Synthetic lubricating oil composition
US3049493A (en) * 1957-09-06 1962-08-14 Sinclair Research Inc Lubricating compositions
US3047504A (en) * 1959-12-31 1962-07-31 Exxon Research Engineering Co Process for treating complex esters to improve viscosity stability
US3360546A (en) * 1963-09-16 1967-12-26 Monsanto Co Purification of hydroxyalkyl fumarate esters

Also Published As

Publication number Publication date
FR1046800A (en) 1953-12-09
DE951105C (en) 1956-10-25
BE505439A (en)

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