US3239463A - Lubricating oil composition - Google Patents

Lubricating oil composition Download PDF

Info

Publication number
US3239463A
US3239463A US442472A US44247265A US3239463A US 3239463 A US3239463 A US 3239463A US 442472 A US442472 A US 442472A US 44247265 A US44247265 A US 44247265A US 3239463 A US3239463 A US 3239463A
Authority
US
United States
Prior art keywords
boro
amine
acid
lubricating oil
carbon atoms
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
Application number
US442472A
Inventor
Edwin C Knowles
Edward L Kay
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.)
Texaco Inc
Original Assignee
Texaco Inc
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
Application filed by Texaco Inc filed Critical Texaco Inc
Priority to US442472A priority Critical patent/US3239463A/en
Application granted granted Critical
Publication of US3239463A publication Critical patent/US3239463A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M139/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/282Esters of (cyclo)aliphatic oolycarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/30Complex 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/30Complex 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
    • C10M2207/302Complex 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/30Complex 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
    • C10M2207/304Complex 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/34Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular 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
    • C10M2209/084Acrylate; Methacrylate
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064Di- and triaryl amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064Di- and triaryl amines
    • C10M2215/065Phenyl-Naphthyl amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/066Arylene diamines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061Esters derived from boron
    • C10M2227/062Cyclic esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02Unspecified siloxanes; Silicones
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04Siloxanes with specific structure
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04Siloxanes with specific structure
    • C10M2229/041Siloxanes with specific structure containing aliphatic substituents
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04Siloxanes with specific structure
    • C10M2229/043Siloxanes with specific structure containing carbon-to-carbon double bonds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04Siloxanes with specific structure
    • C10M2229/044Siloxanes with specific structure containing silicon-to-hydrogen bonds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04Siloxanes with specific structure
    • C10M2229/05Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08Resistance to extreme temperature
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/12Gas-turbines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/12Gas-turbines
    • C10N2040/13Aircraft turbines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
    • C10N2040/251Alcohol fueled engines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
    • C10N2040/255Gasoline engines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
    • C10N2040/255Gasoline engines
    • C10N2040/28Rotary engines

Description

United States Patent 3,239,463 LUBRICATING OIL COMPOSITION Edwin C. Knowles, Poughkeepsie, N.Y., and Edward L. Kay, Akron, Ohio, assignors'to Texaco Inc, New York, N.Y., a corporation of Delaware No Drawing. Filed Mar. 24, 1965, Ser. No. 442,472 6 Claims. (Cl. 252-331?) This application is a continuation-in-part of now abandoned application S.N. 83,182.
This invention relates to a lubricating oil composition characterized by having outstanding load-carrying properties. More specifically, the invention relates to a lubricating oil containing a tertiary alkyl primary amine salt of a tetra-covalent boron acid.
Lubricating oil compositions containing certain 'organoboron compounds have been formulated heretofore. Amine salts of acid compounds of boric acid and of borodiol complexes have been employed in lubricating oils to improve resistance to sludge-formation and to improve anti-corrosion properties, see US. Patent Nos. 2,497,521 and 2,568,472. Bora'te esters have also been employed in lubricating oils but their use has been seriously hindered by their hydrolytic instability.
The present invention is concerned with lubricating oil compositions containing tertriary alkyl primary amine salts of tetra-covalent boron acids known as chelate type salts which are represented by the following general formulae:
wherein R is a monovalent tertiary aliphatic hydrocarbyl radical having from to -24 carbon atoms, R is a divalent aryl or alkaryl radical having 6 to 24 carbon atoms and R is a divalent aryl or alkaryl radical having 6 to 24 carbon atoms or an aliphatic hydrocarbyl radical having 2 to 4 carbon atoms. The acid-amine salt is present in the lubricating oil in a concentration range from above 0.5 to 5.0 weight percent an amount effective to impart load-carrying properties.
The amine salts for the present invention are prepared by the reaction of boric acid with a polyhydroxy compound or hydroxy carboxylic acid to form the tetra-covalent boron compound which is thereafter reacted with a tertiary aliphatic primary amine. The reaction mixture is diluted with a solvent such as toluene and heated to reflux temperature at normal atmospheric pressure. The solvents are then removed preferably by azeotropic distillation and the amine'salt recovered.
The amines employed in the formation of the salts of the chelated tetra-covalent boron acid" are represented by the formula:
RNH
wherein R is a monovalent tertiary aliphatic hydrocarbyl radical having 5 to 24 carbon atoms. Preferably R represents a tertiary aliphatic hydrocarbyl radical having from 11 to 22 carbon atoms. Examples of effective tertiary aliphatic primary amines include t-octylamine, tdodecylamine, and mixtures of primary aliphatic amines such as commercially available mixtures of t-alkyl primary amines. A commercial mixture of monovalent tertiary aliphatic hydrocarbyl amines having 11 to 14 carbon "ice pounds and as such do not exist in the isolated state.
They do, however, form stable salts. The acids are formed by reacting 'boric acid with a polyhydroxy compound or hydroxy carboxylic acid which may be illustrated by the following general equation:
wherein R is 'a divalent aryl or alkaryl radical having from 6 to 24 carbon atoms.
The chelated tetra-covalent boron acids employed in the formation of the amine salts of the present invention can be represented by the following formulae:
wherein R is a divalent aryl or alkaryl radical having 6 to 24 carbon atoms, preferably 6 to 12 carbon atoms, and R is a divalent aryl or alkaryl radical having 6 to 24 carbon atoms or an aliphatic hydrocarbyl radical having 2 to 24 carbon atoms, preferably 4 to 18 carbon atoms. Examples of effective acids are boro catecholate acid, alkyl derivatives of boro resorcinate acid, boro salicylate acid, boro alpha hydroxy decanoate acid, boro beta hydroxy decanoate acid, boro glycolate acid, boro propylene glycolate acid, boro tetramethyl ethylene glycolate acid and boro oxalate acid.
Upon the formation of the transistory acids, described above the amine is reacted therewith to obtain the desired amine salt, the reaction for which may be illustrated by the following general equation:
wherein R is a monovalent tertiary alphatic hydrocarbyl radical having 5 to 24 carbon atoms and R is a divalent aryl or alkaryl radical having 6 to 24 carbon atoms.
The effective amine salts are illustrated by the following: t-C C alkyl primary amine boro catecholate, -t-C -C alkyl primary amine boro alkylcatecholate, LC -C alkyl primary amine boro resorcinolate, t-C C alkyl primary amine boro alkylresorcinolate, t-C C alkyl primary amino boro salicylate, t-C C alkyl primary amine boro alkylsalicylate, ec -c alkyl primary amine boro alpha hydroxy decanoate, t-C C alkyl primary amine boro alpha hydroxy alkyldecanoate, ec -c alkyl primary amine boro glycolate, t-'C C alkyl primary amine boro propylene glycolate, t-C -C alkyl primary amine boro tetramethyl ethylene glycolate, ec -c alkyl primary amine boro oxalate, PC -C alkyl primary amine boro catecholate, FO -C alkyl primary amine boro alkylcatecholate, t-C -C alkyl primary amine boro resorcinolate, t-C C alkyl primary amine boro alkylresorcinolate, t-C -C alkyl primary a amine boro salicylate, t-C C alkyl primary amine boro alkylsalicylate,t-C C alkyl primary amine boro alpha hydroxy decauoate, t-C C alkyl primary amine boro alpha hydroxy alkyldeconoate, t-Cm-C alkylprimary amine boro glycolate, PC alkyl primary amineboro propylene glycolate, vo -cs alkyl primary amine boro tetramethyl ethylene glycolate, tC C alkyl primary amine boro oxalate, t-octyl amine boro catecholate, t-octyl amine boro alkylcatecholate, t-octyl amine boro resorcinolate, t-octyl amine boro alkylresorcinolate, t-octyl amine amine boro alpha hydroxy decanoate, t-octyl amine boro alpha hydroxy alkyl decanoate, t-octylamineboro gly'-.. colate, t-octyl amine boro propylene glycolate, t-octyl;
amine boro tetramethyl ethylene glycolate, and t-octyl amine boro oxalate.
The concentration of the tertiary alkyl primary amine salt of a tetra-covalent boron acid of the invention in a lubricating oil composition is. critical. Generally,.a concentration ranging from above 0.5 percent by weight to i from hydrocarbonsynthetic ilubricating oilbases. The.
- hydrocarbon oils found, to be useful for this invention include oils. having a viscosity in the .rangerequired for lubricating fluids and in particular hydrocarbon mineral oils which include parafiinzbase, naphthene base, mixed 1 paraflinnaphthenebase and mineraloilsiof the residual or distillate type The hydrocarbon lubricating base gener- '10 boro salicylate, t-octyl amine boro alkylsalicylate, t-octyl 5.0 percent by weight is essential to impart load carrying EXAMPLE I.-PREPARATION OF CHELATE AMINE BORO SALT OF SALICYLIC ACID 123.6 grams, 2.0 mols of boric acid, 552 grams 4.0
mols, sali cylic acid and 500 mls. of benzene were refluxed and the Water of the reaction removed by azeotropic distillation. Thereafter 400 grams, 2.0 mols of a mixture oft-alkyl primary'amine wherein the t-alkyl radical contains 11 to 14 carbon atoms .was added to the reaction mixture. The pot temperature rose from 75 C. to 85 C.
Q has been found eifective and are generally incorporated After-stripping solvents to a pot temperature of 150 .C., 944 grams of clear viscous t-C -C primary amine boro salicylate liquid were isolated and at ambient tempera-- ture the reaction product solidified.
EXAMPLE II.PREPARATION OF 'CHELATE AMINE BORO SALT OF 'ALPHA-HYDROXY DECANOIC ACID 61.8 grams, 1.0 mol of boric acid, 200 mls..of toluene and 376 grams, 2.0 mols, of alpha hydroxy decanoic acid were refluxed and 46 mls. of water were removed by azeotropic distillation. The toluene was stripped 'at "a pot temperature of 195 C. Uponthe addition of..195 grams, 1.0 mols of amixture of t-alkyl primary amines 'wherein the t-alkyl groups contained 11 'to 14 carbon atoms mixture, the pot temperature rose from 50 C. to 92 C. 350 mls. of pentane were added to the reaction mixture and the solution was filtered. Pentane was re-' moved by heating the product and 558 grams of-clear amber t-C -C primary amine boro alpha hydroxw decanoate liquid were isolated.
EXAMPLE III.-PREPARATION OF CHELATE: AMINE BORO SALT OF CATECHOL" 61.8 grams, 1.0 mol of boric acid, 220 grams, 2.0 mols of catechol and 200 mls. of toluene were refluxed and 51 mols of water were isolated by azeotropic distillation. Solvents were strippedto a pot temperature of 170 0.
Upon cooling to room temperature a solid separated.-
195 grams, 0.1 mol of a mixtureof t-alkyl primary amine wherein the t-alkyl groups contained 11 to, 14 carbon atoms mixture were added and the pot temperature roseally has-been subjected to solvent refiningto improve its oxidation and thermal stability and viscosity-temperature properties asswell as solv'ent dewaxingto remove vwaxy components and .to improve the-pour. properties: of :the
oil. Broadly speaking,ihydrocarbon lubricating oils having an SUSviscosity at;l00 Fiof between-5010 :2500 are vus'edini'thei formulation'of the improved lubricants:
of this invention; V
The minerallubricating oils to designed to impart-desirableg: properties thereto. For example, viscosity, index improvers, such as the 'polymeth-f acrylates having .a molecular weight ranging from 500 to 25,000 are usually included .therein'.: The improver having the following normally used is a polymethacrylate recurring structural unit: I
wherein R is an aliphaticradical ranging from'butyl to stearyl andxn is an integer of morethan -l.
The use of various metal? baseforganic type additives in the lubricating oils of this invention, particularly those:
oils used in high speed, spark ignition and diesel engines to reduce ring. sticking, minimize carbon deposits.
lacquer. formation and- The hydrocarbon lubricating oils of this invention may:
also contain other additives such as metal ,sulfonatesto afiord additional detergent-dispersant properties, metal,
dialkyl dithiophosphates to afford additional. corrosion and oxidation resistance, and anti-foam agents such as silicone polymers in the amount of'about 5 to. 200 parts per million, etc.
from 60 C. to 'C. A water bath was then used-to cool the mixture. Some solids were still presentin the reaction mixture and thereafter 500 mls. of pentane were added. The mixture was filtered and stripped of pentane. 391 grams of dark amber t-alkyl C C amine boro catecholate liquid were isolated.
The lubricating oils of this invention are prepared,
The esters which constituted the synthetic lubricant composition of this invention are broadly described as;
They are. high esters "of hydrocarbyl carboxylic acids. molecular weight'materials of lubricating oil characteristics derived from alcohols which are ;usually aliphatic; alcohols containing 1 or more, hydroxyl radicals and monocarboxylic acids which are usually aliphatic-canboxylic 'acids containing 1 or; more carboxylic acid radicals.
Widely used synthetic ester lubricants arealiphatic diesters of aliphatic dicarboxylic acids containing 6 to 12 L carbonatoms. From the standpoint of cost and availability, the preferred dibasic acidsrare adipic acid, sebacic acid and azelaic acid. The aliphatic-alcohols used to form the diesters usually contain at :least 4 carbon atoms and up to 20m more carbon atoms. C to C alcohols are most commonly used. Ether alcohols such as Cellosolve and Carbitol may also beused inthe formation of the aliphatic diesters of organic dicarboxylic acids used as the lubricating base in-the compositions ofthis invention. Alcohols containing 2 for more hydroxyl radicals and no hydrogen substituted: on ;the beta carbon atom such as trimethylol. propane. and .pentaerythritolhave .proven particularly elfective in formulating stable high temperature .ester lubricants.
Examples of alkyl esters-of aliphatic carboxylic. acids are the following; difisooctyl .azelate, di-2-ethylhexyl.v sebacate, di-2-ethylhexy1 azelate, di-Z-ethylhexyl adipate,
dilauryl azelate, di-sec-amyl sebacate, di-2-ethylhexyl alkenyl-succinate, di-Z-ethoxyethyl sebacate, di-2-(2,--
methoxy-ethoxy) ethyl Tsabacate, di-2- (2-ethylb;utoxy) ethyl sebacate, di-Z-butoxyethyl azelate, di-2-(2'-ibutoxywhich the amine salts of this invention are added usually contain other additives 7 ethoxy) ethyl alkenyl-succinate, pentaerythritol tetracaproate and trimethylol propane tri-isooctanoate.
In addition to such esters, polyester lubricants formed by a reaction of an aliphatic dicarboxylic acid, a dihydroxy compound and a monofunctional compound, which is either an aliphatic monohydroxy alcohol or an aliphatic monocarboxylic acid, in specified mol ratios are also employed as the synthetic lubricating base in the compositions of this invention; polyesters of this type are described in U.S. 2,628,974 on Polyester Synthetic Lubricants, which issued to R. T. Sanderson on February 17, 1953. Polyesters formed by reaction of a mixture containing specified amounts of 2-ethyl-1,3-hexanediol, sebacic acid, and 2-ethylhexanol and by reaction of a mixture containing adipic acid, diethylene glycol and 2- ethylhexanoic acid illustrate this class of synthetic polyester lubricating bases.
The sulfur analogs of the above-described esters are also used in the formulation of the lubricating compositions of this invention. Dithioesters are exemplified by di-Z-ethylhexyl thiosebacate, di-n-octyl thioadipate and the dilaurate of 1,5-pentanedithiol; sulfur analogs of polyesters are exemplified by the reaction product of adipic acid, thio glycol and 2-ethylhexyl mercaptan.
Alkyl-substituted phenols are usually incorporated in the lubricants of the invention as anti-oxidants. The preferred and most commonly used alkyl phenol antioxidants is 2,6-di-tertiary octylphenol; 2,6-di-tertiary amyl-4-methylphenol; and 2,6-di-isopropyl-4-methylphenol. Hindered phenols of this type are employed in concentrations between 0.1 and 1.0 weight percent.
Although hindered phenol type anti-oxidants are the most widely used anti-oxidants in the lubricant compositions of the invention, aryl-substituted amine anti-oxidants such as phenylnaphthylamine, phenylene diamine, and diphenylamine are also used in lubricants in conjunction with the extreme pressure additive of the invention. The amine anti-oxidants are employed in the same concentrations as the hindered phenol anti-oxidant.
Organic silicones are normally incorporated in the lubricants of the invention to impart thereto anti-foam properties. The silicones are usually of the d-ialkyl or mixed alkyl-aryl silicone type. Dimethyl silicone is normally employed as the anti-foam agent. The silicone is incorporated in the lubricant by means of a kerosene concentrate containing 5 to 15 weight percent silicone. A very satisfactory anti-foam agent is a kerosene concentrate weight percent dimethyl silicone. The kerosene concentrate is employed in an amount sufiicient to provide a silicone polymer concentration of from 50 to 250 parts per million based on the total lubricant composition.
To demonstrate the excellent improvement in the loadcarrying ability of lubricating oil containing the amine salts of the present invention, high speed gear scuff test was used. This test is called the LAB. Gear Test and is intended for the evaluation of the load-carrying ability of the scuff limited load-carrying ability of those lubricants used in reduction and accessory drives of turbo-jet and turbo-prop engines. The I.A.E. Gear Test is one of the requirements of the British specification D.E.R.D. 2,487 Lubricating Oil, Aircraft Turbine Engine, Synthetic Type. The I.A.E. Gear Test is also designed to evaluate the scuti limited, load-carrying ability of aircraft gear hydrocarbon lubricants.
The results of the I.A.E. Gear Test on lubricating oil compositions of the present invention are set forth in the following tables:
Table 1.l.A.E. gear test Oil:
Base oil B consisted of a paraffin base crude which has been furfural refined, lightly acid treated, clay contacted and solvent dewaxed and has an SUS viscosity at F. of 150.
The criticality in the concentration of the additive as well as the load-carrying properties of a synthetic lubricating oil composition are demonstrated by the results given in Table II. Base oil C, which was employed in these tests, was di-Z-ethyl hexylsebacate, a synthetic oil of lubricating viscosity.
Table II.I.A.E. gear test Tooth loadpounds Blend: 2000 sl'bglg. test Base oil C 50,60 Base oil C plus 0.1% PO -C primary amine 'borosalicylate 50 Base oil C plus 0.25% ec -c primary borosalicylate 60 Base oil C plus 0.5% EC -C primary amine borosalicylate 80 Base oil C plus 2.0% tC C primary amine borosalicylate The foregoing results show that significant load-carrying properties begin when the concentration of the additive is above 0.5 percent by weight, lesser amounts of the additive producing no improvement in load-carrying properties over those of the base oil itself.
In addition to the load-carrying properties, the amine salts of the chelated tetra-covalent boron acids of the invention also impart a high degree of oxidation and corrosion resistance to lubricating oil compositions. Many organo borate compounds do not perform as satisfactory additives for lubricants because of their hydrolytic instability. In this respect, the salts of the present invention have another improtant advantage, namely that the amine salts of the chelated tetra-covalent boron acids are hydrolytical'ly stable in both water and lubricating oils.
We claim:
1. A lubricating oil containing above 0.5 to 5 percent by weight of an amine salt of a tetra-covalent boron acid, said amine salt having the formula:
wherein R isa monovalent tertiary aliphatic hydrocarbyl radical having from 5 to 24 carbon atoms and R" is selected from the group consisting of divalent aryl and alkaryl radicals having from 6 to 24 carbon atoms.
2. A lubricating oil as described in claim 1 wherein R is a mixture of monovalent tertiary aliphatic hydrocarbyl radicals having from 11 to 14 carbon atoms.
3. A lubricating oil as described in claim 1 wherein R is a mixture of monovalent tertiary aliphatic hydrocarbyl radicals having from 18 to 22 carbon atoms.
4. A lubricating oil composition according to claim 1 in which said amine salt is present in a concentration of from 0.6 to 2.0 weight percent.
5. A lubricating oil as described in claim 1 containing above 0.5 to 5.0 weight percent of an amine salt having the formula:
HRNH:
wherein R is a mixture of tertiary alkyl groups having from 11 to 14 carbon atoms.
vwherein R is a mixture of tertiary alkyl groupsbhaving 6.: A lubricating oil as described in claim 1 containing: I References (literd by the rExaminer."v
above 0.5 to 5.0 weight percent of an amine'sa'lt having I "UNITED -1. P
from 11 to 14 carbon atoms.

Claims (1)

1. A LUBRICATING OIL CONTAINING ABOVE 0.5 TO 5 JPERCENT BY WEIGHT OF AN AMINE SALT OF A TETRA-COVALENT BORON ACID, SAID AMINE SALT HAVING THE FORMULA:
US442472A 1965-03-24 1965-03-24 Lubricating oil composition Expired - Lifetime US3239463A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US442472A US3239463A (en) 1965-03-24 1965-03-24 Lubricating oil composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US442472A US3239463A (en) 1965-03-24 1965-03-24 Lubricating oil composition

Publications (1)

Publication Number Publication Date
US3239463A true US3239463A (en) 1966-03-08

Family

ID=23756916

Family Applications (1)

Application Number Title Priority Date Filing Date
US442472A Expired - Lifetime US3239463A (en) 1965-03-24 1965-03-24 Lubricating oil composition

Country Status (1)

Country Link
US (1) US3239463A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050172543A1 (en) * 2004-01-29 2005-08-11 Muir Ronald J. Detergent / anti-oxidant additives for fuels and lubricants
US20060019838A1 (en) * 2004-07-21 2006-01-26 Muir Ronald J Fuel and lubricant additive containing alkyl hydroxy carboxylic acid boron esters
US20070155631A1 (en) * 2006-01-04 2007-07-05 Muir Ronald J Lubricating oil and fuel compositions
WO2012128714A1 (en) 2011-03-22 2012-09-27 Antzutkin Oleg N Ionic-liquid-based lubricants and lubrication additives comprising ions
WO2015160525A1 (en) 2014-04-17 2015-10-22 Chemtura Corporation Low ash lubricant and fuel additive comprising polyamine
EP3072951A1 (en) 2015-03-23 2016-09-28 Chemtura Corporation Low ash lubricant and fuel additive comprising reaction product of alkoxylated amine

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2497521A (en) * 1947-12-03 1950-02-14 Gulf Research Development Co Oil compositions containing amine salts of boro-diol complexes
US2568472A (en) * 1950-01-12 1951-09-18 Gulf Research Development Co Oil compositions containing amine salts of acid compounds of boric acid and hydroxy carboxylic acids

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2497521A (en) * 1947-12-03 1950-02-14 Gulf Research Development Co Oil compositions containing amine salts of boro-diol complexes
US2568472A (en) * 1950-01-12 1951-09-18 Gulf Research Development Co Oil compositions containing amine salts of acid compounds of boric acid and hydroxy carboxylic acids

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090088350A1 (en) * 2004-01-29 2009-04-02 Muir Ronald J Detergent / anti-oxidant additives for lubricants
US7629300B2 (en) 2004-01-29 2009-12-08 Chemtura Corporation Detergent / anti-oxidant additives for lubricants
US7621971B2 (en) 2004-01-29 2009-11-24 Chemtura Corporation Detergent/anti-oxidant additives for fuels
US7618467B2 (en) 2004-01-29 2009-11-17 Chemtura Corporation Detergent / anti-oxidant additives for fuels and lubricants
US20090084027A1 (en) * 2004-01-29 2009-04-02 Muir Ronald J Detergent / anti-oxidant additives for fuels
US20050172543A1 (en) * 2004-01-29 2005-08-11 Muir Ronald J. Detergent / anti-oxidant additives for fuels and lubricants
WO2006022934A2 (en) 2004-07-21 2006-03-02 Chemtura Corporation Fuel and lubricant additive containing alkyl hydroxy carboxylic acid boron esters
US7857870B2 (en) 2004-07-21 2010-12-28 Chemtura Corporation Fuel and lubricant additive containing alkyl hydroxy carboxylic acid boron esters
US20100162616A1 (en) * 2004-07-21 2010-07-01 Chemtura Corporation Fuel and lubricant additive containing alkyl hydroxy carboxylic acid boron esters
US7691793B2 (en) 2004-07-21 2010-04-06 Chemtura Corporation Lubricant additive containing alkyl hydroxy carboxylic acid boron esters
WO2006022934A3 (en) * 2004-07-21 2006-05-04 Chemtura Corp Fuel and lubricant additive containing alkyl hydroxy carboxylic acid boron esters
US20060019838A1 (en) * 2004-07-21 2006-01-26 Muir Ronald J Fuel and lubricant additive containing alkyl hydroxy carboxylic acid boron esters
CN101031575B (en) * 2004-07-21 2011-08-10 科聚亚公司 Fuel and lubricant additive containing alkyl hydroxy carboxylic acid boron esters
EP2316838A1 (en) * 2004-07-21 2011-05-04 Chemtura Corporation Fuel and lubricant additive containing alkyl hydroxy carboxylic acid boron esters
US7622431B2 (en) 2006-01-04 2009-11-24 Chemtura Corporation Lubricating oil compositions
US7691794B2 (en) 2006-01-04 2010-04-06 Chemtura Corporation Lubricating oil and fuel compositions
US7618466B2 (en) 2006-01-04 2009-11-17 Chemtura Corporation Fuel compositions
US20090094885A1 (en) * 2006-01-04 2009-04-16 Muir Ronald J Fuel compositions
US20090099049A1 (en) * 2006-01-04 2009-04-16 Muir Ronald J Lubricating oil compositions
US20070155631A1 (en) * 2006-01-04 2007-07-05 Muir Ronald J Lubricating oil and fuel compositions
WO2012128714A1 (en) 2011-03-22 2012-09-27 Antzutkin Oleg N Ionic-liquid-based lubricants and lubrication additives comprising ions
US9518243B2 (en) 2011-03-22 2016-12-13 Oleg N. Antzutkin Ionic-liquid-based lubricants and lubrication additives comprising ions
WO2015160525A1 (en) 2014-04-17 2015-10-22 Chemtura Corporation Low ash lubricant and fuel additive comprising polyamine
US9546341B2 (en) 2014-04-17 2017-01-17 Chemtura Corporation Low ash lubricant and fuel additive comprising polyamine
EP3072951A1 (en) 2015-03-23 2016-09-28 Chemtura Corporation Low ash lubricant and fuel additive comprising reaction product of alkoxylated amine

Similar Documents

Publication Publication Date Title
US3224971A (en) Borate esters and lubricant compositions containing said esters
US3185644A (en) Lubricating compositions containing amine salts of boron-containing compounds
CA1065298A (en) Triaryl phosphate ester functional fluids
US3250708A (en) Synthetic lubricating agents and hydraulic liquids
US3321506A (en) Borate amine salt
US2930758A (en) Ester-base lubricant containing anti-oxidant mixtures
US2599761A (en) Extreme pressure lubricant
US3134737A (en) Novel titanium compound and lubricating composition containing said compound
US3239463A (en) Lubricating oil composition
US4162224A (en) Solubilized borates of bis-oxazoline and lubricant compositions containing the same
US3053768A (en) Synthetic lubricant compositions
US4927553A (en) Haze-free boronated antioxidant
US2796404A (en) Extreme pressure lubricant compositions
US3011976A (en) Stabilization of lubricants
US2971912A (en) Lubricating oil compositions
US3804762A (en) Antioxidants
EP0191967A2 (en) Reaction products of alkenylsuccinic compounds with aromatic amines and lubricant compositions thereof
US3422017A (en) Lubricant compositions containing amine salts
US3216939A (en) Stabilization of lubricants
EP0089844B1 (en) Boron-containing esters, their preparation and use as antioxidants
US3779919A (en) Synthetic aircraft turbine oil
US3761405A (en) Anti oxidants
US4599183A (en) Multifunctional additives
US3507918A (en) Amine salts of mono- and difluorophosphoric acids
US2676149A (en) Stabilized grease composition containing a sterol and a selenium compound