GB757241A - Improvements in or relating to lubricating compositions - Google Patents

Improvements in or relating to lubricating compositions

Info

Publication number
GB757241A
GB757241A GB2411/54A GB241154A GB757241A GB 757241 A GB757241 A GB 757241A GB 2411/54 A GB2411/54 A GB 2411/54A GB 241154 A GB241154 A GB 241154A GB 757241 A GB757241 A GB 757241A
Authority
GB
United Kingdom
Prior art keywords
thioether
hydroxyphenyl
methyl
tri
esters
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
GB2411/54A
Inventor
John Scotchford Elliott
Eric Descamp Edwards
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.)
CC Wakefield and Co Ltd
Original Assignee
CC Wakefield and Co Ltd
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 claimed from GB25753/53A external-priority patent/GB757219A/en
Application filed by CC Wakefield and Co Ltd filed Critical CC Wakefield and Co Ltd
Priority to GB2411/54A priority Critical patent/GB757241A/en
Priority to US456063A priority patent/US2836565A/en
Priority to US483824A priority patent/US2820766A/en
Publication of GB757241A publication Critical patent/GB757241A/en
Expired legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G04—HOROLOGY
    • G04B—MECHANICALLY-DRIVEN CLOCKS OR WATCHES; MECHANICAL PARTS OF CLOCKS OR WATCHES IN GENERAL; TIME PIECES USING THE POSITION OF THE SUN, MOON OR STARS
    • G04B31/00—Bearings; Point suspensions or counter-point suspensions; Pivot bearings; Single parts therefor
    • G04B31/08—Lubrication
    • 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
    • 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
    • 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
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • 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
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • 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
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
    • 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
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
    • 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
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • 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
    • 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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    • 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
    • C10M2207/30—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
    • 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
    • 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
    • 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
    • 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
    • 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
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • 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
    • C10M2209/02—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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • C—CHEMISTRY; METALLURGY
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    • 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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    • 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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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26—Amines
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    • C10M2215/30—Heterocyclic compounds
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    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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    • C10M2219/088—Neutral salts
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    • C10M2219/089—Overbased salts
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    • C10M2223/04—Phosphate esters
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    • C10M2223/041—Triaryl phosphates
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    • C10M2223/042—Metal salts thereof
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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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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • 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
    • C10N2040/13—Aircraft turbines

Abstract

The invention comprises a lubricating composition as claimed in the parent Specification which lubricating composition has incorporated therein a minor proportion of a neutral organic phosphate or phosphite ester. The composition of the parent Specification compries a neutral ester or mixture of esters derived from aliphatic or cycloaliphatic dicarboxylic acids having from four to ten carbon atoms in the molecule, and branched-chain aliphatic or alkyl substituted cycloaliphatic alcohols having at least four carbon atoms in the molecule or from mixtures of such alcohols with glycols, and a minor proportion of a di (hydroxyaryl) thioether. The dicarboxylic acid ester may have the general formula <FORM:0757241/III/1> where R is a aliphatic or cycloaliphatic hydrocarbon radical having 2 to 8 carbon atoms, and R1 and R2 are branched-chain alkyl or alkyl-substituted cycloalkyl radicals having at least 4 carbon atoms; R may be -CH=CH-, (CH2)n where n is 2 to 8, or <FORM:0757241/III/2> The ester may be obtained by esterifying the dicarboxylic acid with a mixture of an alcohol and a glycol, and have the formula R2OOC.R.COOR3OOC.R.COOR1 where R, R1 and R2 are as above and <FORM:0757241/III/3> is a glycol or polyglycol havng not more than 12 carbon atoms. The ester may also be obtained by esterifying a dicarboxylic acid with a glycol and a monocarboxylic acid or with a glycol, a monocarboxylic acid and a monohydric alcohol. Lists of acids and glycols are given. Examples of esters are di(1-methyl-4-ethyl octyl) glutarate, di(2-ethyl hexyl) adipate, di(3-methyl butyl) azelate, di(2-ethyl hexyl) azelate, di(2-ethyl hexyl) sebacate, di(3 : 5 : 5-trimethylhexyl) sebacate, di(3 : 5 : 5-trimethyl hexyl) adipate di(2-ethyl hexyl) maleate, di(methyl cyclohexyl) adipate, 2-ethyl-hexyl 1-methyl heptyl sebacate, di(2-ethyl hexyl) pinate. The organic phosphate esters have the formulae <FORM:0757241/III/4> or where R1, R2 and R3 are alkyl, aryl, alkaryl or cycloalkyl radicals, and R4 is an alkylene or arylene radical. Examples of phosphate esters are trimethyl, triethyl, tri(n-butyl), tri(2-ethyl hexyl), triphenyl, tri-o-tolyl, tri-m-tolyl, tri(p-tertiary amyl phenyl), tri(methyl cyclohexyl) tri(butoxyethyl) phosphates and tetraethyl p-phenylene diphosphate. The phosphate esters are present in amounts of 0.5 to 10 per cent by weight of the composition. The organic phosphite esters have the formula <FORM:0757241/III/5> where R1, R2 and R3 are alkyl, aryl, alkaryl or cycloalkyl radicals, or they may be phosphite esters of hydroxy-substituted aromatic thioethers and have the formula <FORM:0757241/III/6> or (RO)m-P-(O-Ar-S-Ar-OH)n where the R's are hydrocarbon radicals which may have ether or ester substituents, the Ar's are aromatic radicals which may have alkyl, ether or ester substituents, m is zero, 1 or 2, and n is 1 to 3, the sum of m and n being 3. Examples of phosphite esters are tri(n-butyl), triphenyl, tritolyl, tricyclohexyl, tri(methyl cyclohexyl) phosphites and p-octyl phenyl thioether phosphite, and di(3-carbomethoxy-4-hydroxyphenyl) thioether ditolyl phosphite. The phosphite esters are present in amounts of 0.1 to 5 per cent by weight of the composition. The di(hydroxyaryl) thioethers have the formula <FORM:0757241/III/7> where Ar's are aromatic nuclei, x, y and z are 1 to 3 and n is zero or 1 to 6. Examples are p p1-dihydroxy diphenyl thioether, di(3-methyl-4-hydroxyphenyl) thioether, di(5-methyl-2-hydroxyphenyl) thioether, di(2 - methyl - 4 - hydroxyphenyl) thioether,di(4-methyl-6-hydroxyphenyl)thiether, di(6-methyl-2-hydroxyphenyl) thioether di(3 : 5-dimethyl-4-hydroxyphenyl) thioether,di(4-methyl-3-tertiary butyl-2-hydroxyphenyl) thioether, polymerized di(5-octyl-2-hydroxyphenyl) thioether, mixed isomeric bis (dihydroxy tertiary butyl phenyl) thioethers prepared from tertiary butyl catechol, di(3-methoxy-4-hydroxyphenyl) thioether, and mixed isomeric di(o-phenyl hydroxyphenyl) thioethers prepared from o-phenyl phenol. The thioethers are present in concentrations from 0.2 to 5.0 per cent by weight of the composition. The compositions may also include amines boiling above 140 DEG C., in amounts of 0.01 to 1.0 per cent by weight, polymers of esters of acrylic or alkyl-substituted acrylic acids in amounts of 1 to 15 per cent by weight, metal petroleum sulphonates and up to 20 per cent mineral oil. Examples of compositions are given. Specifications 574,445 and 696,064 also are referred to.
GB2411/54A 1953-09-17 1954-01-26 Improvements in or relating to lubricating compositions Expired GB757241A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB2411/54A GB757241A (en) 1953-09-17 1954-01-26 Improvements in or relating to lubricating compositions
US456063A US2836565A (en) 1953-09-17 1954-09-14 Lubricating compositions
US483824A US2820766A (en) 1953-09-17 1955-01-24 Lubricating compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB25753/53A GB757219A (en) 1953-09-17 1953-09-17 Improvements in or relating to lubricating compositions
GB2411/54A GB757241A (en) 1953-09-17 1954-01-26 Improvements in or relating to lubricating compositions

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GB757241A true GB757241A (en) 1956-09-19

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US2999740A (en) * 1956-11-27 1961-09-12 Tidewater Oil Company Surface ignition suppression
BE566072A (en) * 1957-04-05
US2983678A (en) * 1958-12-31 1961-05-09 Gulf Research Development Co Synthetic oil containing a rare earth metal diester phosphate
DE1217382B (en) * 1960-04-11 1966-05-26 Ethyl Corporation, New York, N. Y. (V. St. A.) Stabilization of motor fuels, lubricating oils or greases based on hydrocarbons or polymeric hydrocarbons
US3245979A (en) * 1961-01-30 1966-04-12 Sinclair Refining Co Phosphorus phenol condensation compounds
US3239464A (en) * 1961-09-05 1966-03-08 Sinclair Research Inc Extreme pressure lubricant
GB959545A (en) * 1963-02-21 1964-06-03 Shell Res Ltd Improvements in or relating to lubricating oil compositions
US4044033A (en) * 1975-04-14 1977-08-23 Milliken Research Corporation High temperature lubricant
US4115287A (en) * 1976-04-22 1978-09-19 Exxon Research And Engineering Company Lubricating compositions
US4517105A (en) * 1983-03-07 1985-05-14 Aluminum Company Of America Metalworking lubricant composition containing a novel substituted malonic acid diester

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US2085045A (en) * 1933-12-27 1937-06-29 Standard Oil Dev Co Inhibitors for lubricating oils
BE415008A (en) * 1935-04-15
US2209463A (en) * 1937-12-04 1940-07-30 Standard Oil Dev Co Wax composition
US2229858A (en) * 1938-10-22 1941-01-28 Standard Oil Co Lubricant manufacture
US2234096A (en) * 1939-01-28 1941-03-04 Sinclair Refining Co Lubricating oil
GB574445A (en) * 1941-03-25 1946-01-07 Elliott Alfred Evans Improvements in or relating to lubricating compositions
US2375007A (en) * 1943-04-15 1945-05-01 Shell Dev Antifoaming composition
US2481372A (en) * 1946-09-27 1949-09-06 Shell Dev Rust protective lubricants
US2575195A (en) * 1948-10-01 1951-11-13 Standard Oil Dev Co Dibasic acid esters and method for producing them
US2559521A (en) * 1948-11-27 1951-07-03 Standard Oil Dev Co Synthetic lubricant
US2499984A (en) * 1948-12-16 1950-03-07 Rohm & Haas Oily complex esters
US2639266A (en) * 1951-04-07 1953-05-19 Texas Co Lubricating grease comprising a complex ester base and sodium myristate
US2760934A (en) * 1953-05-28 1956-08-28 Exxon Research Engineering Co Synthetic lubricant

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US2820766A (en) 1958-01-21
US2836565A (en) 1958-05-27

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