GB797452A - Improved lubricating oil compositions - Google Patents

Improved lubricating oil compositions

Info

Publication number
GB797452A
GB797452A GB1756/56A GB175656A GB797452A GB 797452 A GB797452 A GB 797452A GB 1756/56 A GB1756/56 A GB 1756/56A GB 175656 A GB175656 A GB 175656A GB 797452 A GB797452 A GB 797452A
Authority
GB
United Kingdom
Prior art keywords
acids
acid
sulphonic
salicylic
alkylated
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
GB1756/56A
Inventor
John Hughes
Philip James Garner
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.)
Shell Research Ltd
Original Assignee
Shell Research 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 to NL108234D priority Critical patent/NL108234C/xx
Application filed by Shell Research Ltd filed Critical Shell Research Ltd
Priority to GB1756/56A priority patent/GB797452A/en
Priority to US633518A priority patent/US2862883A/en
Priority to FR1170861D priority patent/FR1170861A/en
Priority to DES51954A priority patent/DE1042808B/en
Publication of GB797452A publication Critical patent/GB797452A/en
Expired legal-status Critical Current

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    • 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
    • C10M3/00Liquid 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
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B60VEHICLES IN GENERAL
    • B60TVEHICLE BRAKE CONTROL SYSTEMS OR PARTS THEREOF; BRAKE CONTROL SYSTEMS OR PARTS THEREOF, IN GENERAL; ARRANGEMENT OF BRAKING ELEMENTS ON VEHICLES IN GENERAL; PORTABLE DEVICES FOR PREVENTING UNWANTED MOVEMENT OF VEHICLES; VEHICLE MODIFICATIONS TO FACILITATE COOLING OF BRAKES
    • B60T13/00Transmitting braking action from initiating means to ultimate brake actuator with power assistance or drive; Brake systems incorporating such transmitting means, e.g. air-pressure brake systems
    • B60T13/10Transmitting braking action from initiating means to ultimate brake actuator with power assistance or drive; Brake systems incorporating such transmitting means, e.g. air-pressure brake systems with fluid assistance, drive, or release
    • B60T13/58Combined or convertible systems
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16Amides; Imides
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    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08Inorganic acids or salts thereof
    • C10M2201/082Inorganic acids or salts thereof containing nitrogen
    • C10M2201/083Inorganic acids or salts thereof containing nitrogen nitrites
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026Butene
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/04Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/22Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/14Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/144Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/14Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/146Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent of thirty or more carbon atoms
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    • C10M2207/40Fatty vegetable or animal oils
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    • C10M2207/402Castor oils
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    • 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
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/044Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
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    • C10M2215/082Amides containing hydroxyl groups; Alkoxylated derivatives
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    • C10M2215/26Amines
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • C10M2229/02Unspecified siloxanes; Silicones
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • C10N2040/22Metal working with essential removal of material, e.g. cutting, grinding or drilling

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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)
  • Engineering & Computer Science (AREA)
  • Transportation (AREA)
  • Mechanical Engineering (AREA)
  • Lubricants (AREA)

Abstract

Aromatic acid salts of partially acylated aliphatic di- or polyamines for addition to lubricating oils (see Group III) are prepared by direct neutralization of the amidoamines with the acids in a solvent, e.g. petroleum or by double decomposition of the hydrochlorides or sulphates of the amidoamines with alkali metal salts of the acids in a solvent. Salt-forming aromatic acids mentioned are carboxylic acids, e.g. butyl and octyl benzoic acids, naphthoic acids, and octadecyl, di-isopropyl and mixed C8-18 alkylated salicylic acids; sulphonic acids, e.g. benzene and alkyl (e.g. nonyl and dodecyl) benzene sulphonic acids, di-isopropyl naphthalene sulphonic acid, butyl phenol sulphonic acids and sulphonic acids derived from aromatic fractions from petroleum and their alkylated products; and phenols, e.g. octyl and dodecyl phenols, butyl and amyl naphthols, and the condensation products of formaldehyde or acetaldehyde with alkylated phenols such as p-octyl phenol. Typical di- and polyamines include 1,2-diaminoethane, 1,2- and 1,3-diaminopropane, 1,2-, 1,3- and 1,4-diaminobutane, 2,3-diaminohexane, 1,8-diamino-octane, diethylene triamine, triethylene tetramine, tetraethylene pentamine, dipropylene triamine, tripropylene tetramine, N-butyl ethylene diamine and di-(2-aminoethyl) sulphide. These may be partially acylated with any carboxylic acid, e.g. benzoic, salicylic, octyl salicylic, naphthoic, resin, tall oil, caproic, lauric, stearic or palmitic acid or the naphthenic acids from petroleum. The partial amides may be prepared by mixing equimolecular parts of the amine and the acid, or a halide, nitrile or ester thereof, and heating in an autoclave at 170-200 DEG C. for 5 to 8 hours. In examples preparative details are given for: (i) the salt obtained by double decomposition between sodium C14-18 alkyl salicylate and the hydrochloride of N-(2-aminoethyl) naphthenamide obtained by partially acylating ethylene diamine with naphthenic acids; (ii) the salt obtained by double decomposition between sodium "Kerex" sulphonate and the hydrochloride of (i) ("Kerex" is a Registered Trade Mark for an aromatic extract derived from kerosine); and (iii) the salt obtained by neutralization with C14-18 alkyl salicylic acids of ethylene diamine partially acylated with tall oil acid. Other salts which may be prepared by similar means are the di-isopropyl salicylate, benzene sulphonate and dodecyl benzene sulphonate of ethylene diamine partially acylated with naphthenic acid and the "Kerex" sulphonates of 1,2- or 1,3-diaminopropane, 1,8-diamino-octane or diethylene triamine partially acylated with naphthenic acid. Specification 783,882 is referred to.ALSO:A lubricating oil composition comprises a major proportion of a lubricating oil and a minor proportion of an oil-soluble salt of an aromatic acid and a partially acylated di- or polyamine. The lubricating oil may be natural or synthetic, e.g. paraffinic, naphthenic or asphaltic mineral oils or synthetic oils such as polymerized olefines, esters, e.g. di(2-ethylhexyl) sebacate, dioctyl phthalate and trioctyl phosphate and silicone polymers or any blend of such oils with one another or with fatty oils such as castor oil or lard oil. Salt-forming aromatic acids mentioned are carboxylic acids, e.g. butyl and octyl benzoic acids, naphthoic acids, octadecyl and di-isopropyl salicylic acids and mixtures of C8-C18 alkylated salicylic acids; sulphonic acids, e.g. benzene and alkyl (e.g. nonyl and dodecyl) benzene sulphonic acids, di-isopropyl naphthalene sulphonic acid, butyl phenol sulphonic acids and sulphonic acids from aromatic fractions from petroleums and their alkylated products; and phenols, e.g. octyl and dodecyl phenols, butyl and amyl naphthols and the condensation products of formaldehyde or acetaldehyde with alkylated phenols such as p-octyl phenol. Typical di- and poly-amines include 1,2-diaminoethane, 1,2- and 1,3-diamino propane, 1,2-, 1,3- and 1,4-diamino butane, 2,3-diaminohexane, 1,8-diamino-octane, diethylene triamine, triethylene tetramine, tetraethylene pentamine, dipropylene triamine, tripropylene tetramine, N-butyl ethylene diamino and di-(2-aminoethyl) sulphide. These may be partially acylated with any carboxylic acid, e.g. benzoic, salicylic, octyl salicylic, naphthoic, rosin, tall oil, caproic, lauric, stearic, or palmitic acids especially naphthenic acids from petroleum refining. The preparation of such compounds is described and exemplified (see Group IV (b)). Optional ingredients mentioned include detergents, e.g. alkaline earth metal salts of C14-18 alkylated salicylic acids and of organic sulphonic acids such as petroleum sulphonic acids; V.I. improvers, e.g. "Acryloids," polymerized isobutylene and alkyl styrenes; pour point depressants, e.g. wax-naphthalene condensation products; corrosion inhibitors, e.g. nitrites, such as sodium, lithium, di-isopropyl ammonium, and dicyclohexyl ammonium nitrites; E.P. agents, e.g. S-and P-containing compounds such as P2S5-terpene reaction products, calcium or zinc dicyclohexyl or methylcyclohexyl thiophosphates; and anti-foam agents, e.g. organic silicone polymers such as dimethyl silicone. In the examples there are mentioned the salts of N-(2-aminoethyl) naphthenamide with a mixture of C14-18 alkylated salicylic acids and with "Kerex" (Registered Trade Mark) sulphonic acid; the salt of ethylene diamine partially acylated with tall oil acid and a mixture of C14-18 alkylated salicylic acids; the di-isopropyl salicylic acid, benzene sulphonic acid, and dodecyl benzene sulphonic acid salts of ethylene diamine partially acylated with naphthenic acid; and the "Kerex" sulphonic acid salts of the mono-amides of 1,2-diamino propane, 1,3 - diaminopropane, 1,8 - diamino octane and diethylene triamine and naphthenic acid. These salts are tested in admixture with mineral lubricity oils. Specification 783,882, [Group IV (b)], is referred to.
GB1756/56A 1956-01-18 1956-01-18 Improved lubricating oil compositions Expired GB797452A (en)

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NL108234D NL108234C (en) 1956-01-18
GB1756/56A GB797452A (en) 1956-01-18 1956-01-18 Improved lubricating oil compositions
US633518A US2862883A (en) 1956-01-18 1957-01-11 Lubricating oil compositions containing acylated polyamine salts
FR1170861D FR1170861A (en) 1956-01-18 1957-01-14 Lubricating oil composition
DES51954A DE1042808B (en) 1956-01-18 1957-01-16 Lubricating oil

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CN109852797A (en) * 2017-12-16 2019-06-07 虔东稀土集团股份有限公司 A method of extractant and its extraction and separation elemental lithium for extraction and separation elemental lithium

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US4200545A (en) * 1976-01-28 1980-04-29 The Lubrizol Corporation Amino phenol-detergent/dispersant combinations and fuels and lubricants containing same
US4162223A (en) * 1978-03-21 1979-07-24 Phillips Petroleum Company Residue of hydrogenation product of branched aliphatic dinitriles as lubricant additive
US4249912A (en) * 1978-04-27 1981-02-10 Phillips Petroleum Company Aminoamide fuel detergents
US4861504A (en) * 1988-01-25 1989-08-29 Atlantic Richfield Company Oil additive having reduced lacquer forming tendencies
JP2006515384A (en) * 2003-01-21 2006-05-25 ザ ルブリゾル コーポレイション Sulfur-free and lubricant compositions and methods thereof
US7851418B2 (en) * 2005-06-03 2010-12-14 Exxonmobil Research And Engineering Company Ashless detergents and formulated lubricating oil containing same
US7820600B2 (en) * 2005-06-03 2010-10-26 Exxonmobil Research And Engineering Company Lubricant and method for improving air release using ashless detergents

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US2336070A (en) * 1942-09-18 1943-12-07 Du Pont Lubricating oil
US2481585A (en) * 1945-09-17 1949-09-13 Michael W Freeman Lubricating oil composition
US2493483A (en) * 1948-04-26 1950-01-03 Shell Dev Marine engine lubricant
US2604451A (en) * 1948-09-16 1952-07-22 Gulf Research Development Co Mineral oil compositions
US2580881A (en) * 1949-05-21 1952-01-01 Du Pont Stabilized petroleum products and stabilizing compositions
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
US2668100A (en) * 1951-11-15 1954-02-02 Nat Aluminate Corp Corrosion inhibitor for liquid hydrocarbons
US2693448A (en) * 1952-12-30 1954-11-02 Socony Vacuum Oil Co Inc Demulsified antirust turbine oil

Cited By (2)

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Publication number Priority date Publication date Assignee Title
US3267034A (en) * 1965-05-27 1966-08-16 Shell Oil Co Lubricating oil composition containing polyalkylene imine salicylate salts
CN109852797A (en) * 2017-12-16 2019-06-07 虔东稀土集团股份有限公司 A method of extractant and its extraction and separation elemental lithium for extraction and separation elemental lithium

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US2862883A (en) 1958-12-02
FR1170861A (en) 1959-01-20
DE1042808B (en) 1958-11-06

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