US3010906A - Lubricating oil additives - Google Patents

Lubricating oil additives Download PDF

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US3010906A
US3010906A US561676A US56167656A US3010906A US 3010906 A US3010906 A US 3010906A US 561676 A US561676 A US 561676A US 56167656 A US56167656 A US 56167656A US 3010906 A US3010906 A US 3010906A
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ester
additive
oil
lubricating oil
weight percent
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Signouret Jean-Baptiste
Tirtiaux Robert
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Esso SA
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Esso Standard SA
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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
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—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
    • C10M145/16—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 polycarboxylic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C08F22/12—Esters of phenols or saturated alcohols
    • C08F22/20—Esters containing oxygen in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/12—Esters of phenols or saturated alcohols
    • C08F222/20—Esters containing oxygen in addition to the carboxy oxygen
    • C08F222/205—Esters containing oxygen in addition to the carboxy oxygen the ester chains containing seven or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L35/02—Homopolymers or copolymers of esters
    • 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
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • 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
    • 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
    • C10M2207/30—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
    • 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
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • 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
    • C10M2207/40—Fatty vegetable or animal oils
    • 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
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • 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
    • 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
    • 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
    • C10M2209/086—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 polycarboxylic, e.g. maleic acid
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/026—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrile group
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/043—Mannich bases
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
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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
    • C—CHEMISTRY; METALLURGY
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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

Definitions

  • the present invention relates to a new class of lubricating oil additives which impart improved properties to lubricating oils containing them, and particularly relates to such additives which comprise the polymers or copolymers of alkoxy esters, and to lubricating oils containing them.
  • additive compounds it is often desirable to improve the physical properties of lubricating oils, and one of the most useful ways of doing so is to incorporate additive compounds into the lubricating oils.
  • additives 'to improvefthedetergency of lubricating oils is well-known.
  • Such detergent oils when used in internal combustion engines inhibit corrosion, piston ring sticking, cylinder Wear, and the formation of varnish on metal engine parts, as well as preventing the formation of sludge deposits within the engine;
  • Well known types of detergents for lubricating oils are alkaline or alkaline earth metal-containing compounds.
  • the additive compounds of the present invention are polymeric or copolymeric materials derived from partly esterified and alkoxylated unsaturated dibasic acids. While generally any unsaturated dibasic acid, may be used, it is preferred to usesu'bstituted or unsubstituted monoethylonic acids, such as fumaric or maleic acids which are alpha beta unsaturated or butenedioic acids or their alkyl derivatives.
  • the unsaturated dibasic acid is partly esterified with any aliphatic alcohol, although such alcohols having from 3 to 20 carbon atoms per molecule are preferred, and those having from 9 to 18 carbon atoms per molecule particularly preferred,
  • the alcohols may be of straightchain or branched configuration, and those alcohols produced by the x0 process are preferred. It is within the scope of the invention to use a mixture of such alcohols.
  • partly esterified it is meant that less than two gram molecules of alcohol is reacted with a gram molecule of organic dibasic acid during the esterification process.
  • Particularly useful proportions of reactants include 1 gram molecule of dibasic acid with about 1.6 gram molecules of alcohol.
  • the partly-esterified dibasic acid is reacted with any alkylene oxide to produce
  • the alkylene oxido used is preferably one which contains from' 2 to 6 carbon atoms per molecule, and is particularly ethylene oxide or propylene oxide; It is within the scope the alkoxy-ester compounds.
  • the additive compounds of the present invention are obtained by polymerising the alkoxy-ester compounds described above, or by copolymerizing such compounds with an unsaturated organic compound.
  • the preferred unsaturated organic compounds include unsaturated hydrocarbons, such as styrene, unsaturated esters derived from either unsaturated alcohols such as vinyl alcohols, or unsaturated acids such as fumaric or maleic acids, or methacrylic acid.
  • unsaturated organic compounds include nitriles, e.g., acrylonitrile, or the anhydrides of unsaturated dibasic acids, such as maleic anhydride. While the above'iinsafurated'organic' compounds are the preferred compounds thealkoxy-esters may be copolymerized with, any other :copolymerizable organic compound etc.
  • the present invention therefore comprises an oil-soluble lubricating oil additive comprising a polymer or coploymer of an alkoxy-ester, said alkoxy ester being derived from a partly esterified unsaturated dibasic acid further reacted with an alkylene oxide.
  • the polymerization or copolymerization process be carried out with the aid of a peroxide type of catalyst, preferably benzoyl peroxide, at temperatures ranging from 50 to 150 C., for periods of time ranging from 2 to 100 hours. It may be convenient to carry out the polymerization or copolymerization process in .the presence of an inert solvent, such as gasoline, light lubricating oils, or chloroform. By the use of such solvents it is possible to control the reaction velocity and the molec-.
  • a peroxide type of catalyst preferably benzoyl peroxide
  • the additive compounds of the present invention are intended to be used in any lubricating oil, whether derived from animal, vegetable or mineral sources, and including synthetic lubricating oils especially those comprising complex esters, diesters, formals, methacrylates, or blends thereof.
  • the additive compounds of the present invention may be incorporated in lubricating oils in proportions from 0.01% to 20% by weight.v
  • additive compounds of the present invention are restricted to those compounds which are soluble in the lubricating oil in which they are incorporated. Such solubility may be determined by a simple test.
  • the lubricating oils containing the additive compound of the present invention may also contain other additive compounds, such as oxidation inhibitors, extreme-pressure additives and anti-frothing agents.
  • This ester was condensed at 140 C. with ethylene oxide in the presence of traces of a BF phenol complex. After 16 hours reaction the acid number of the ester was 6, the weight of ethylene oxide combined with the ester being equal to 8% by weight of the said ester.
  • the ethoxylated ester thus obtained wasfcopolytnerized' 10 with. 25% by weight of vinyl acetate at 70 C. for'an hour in the presence of 2 grammes benzoyl. peroxide.
  • copolymer A when added to a parafiinic oil having a viscosity index of 113, yielded the following results givenin Table L e Table I Percentage of copolymer A Viscosity in centistokes Viscosity Index us 32; 1 i 12s as. 4 136.6 41- New vamp
  • EXAMPLE II 7 One gram molecule of maleic acid was partly esterified. with 1.5 gram molecules of a C Ono alcohol in the presence of paratoluene sulphonic acid as catalyst, and 100-220% of gasoline. After washing in water and distilling the gasoline off, an. ester was obtained having an acid number of 30. a V
  • This ester was condensed with gaseous ethylene oxide at 140 C. in. the presence of traces of the BF;;/ ether complex. After 18. hours reaction, the acid number was 1.1: the weight of ethylene oxide combined with the ester being equal to 7% of. the weightof the said ester.
  • The-test was carried out according tothe standard CRC 7 FL-Z adapted for a Peugeot 203 engine (4 cylinder, bore mm., stroke 73 mm, total stroke capacity 1290 cc., volumetric compression 6.8, speed 2500 r.p.m., length of test 50 hours, output 20 H.P.
  • This test is of the type known as cold test.
  • Additive 1 to b invention Poratfinic oil of viscosity 35 ceutistokes at i 37.8 C. viscosity index 112, percent 99.1 95. Oopoly'rner 13, per 3. 25
  • Anti-oxidising agent polymer oi di-isobutylene phenol with formaldehyde and ammonia, percent 0. 4 0. 4
  • Anti-corrosion additive alpha plnene phosphosulphide, percent 0; 5 0. 6 Chief characteristics of these oils-Viscosity nd x 7 112 131 Four point, 0;- .w g --9' 7 -27 The results of the engine test are as follows:
  • ester thereby formed with ethylene oxide in sufiicient amount to incorporate about 7 to 8 weight percent of ethylene oxide into the partial ester, and thereafter copolymerizing the resulting ethoxylated ester within the range of 25 to 50 weight percent of vinyl acetate in the presence of a peroxide type catalyst.
  • oil-soluble lubricating oil additive having detergency and viscosity index improving properties prepared by partially esterifying one mole of abutenedioic acid with from about 1.5 to about 1.6 moles of an aliphatic alcohol having in the range of 3 to 20 carbon atoms per molecule, condensing the partial ester: thereby formed with an alkylene oxide having. in the range of 2 to 6 carbon atoms per molecule in sufficient amount to n corporate about 1 to 8 weight percent of alkylene oxide into the partial ester, and thereafter copolyrnerizing the resulting alkoxylated ester within the range of from 25 V to 50 weight percent of viuylacetate.
  • a lubricating composition consisting essentially. of a major proportion of a' lubricating oil and from 0.01 to .20 weight percent of the additive defined by claim 2.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
US561676A 1955-03-09 1956-01-26 Lubricating oil additives Expired - Lifetime US3010906A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR1123354T 1955-03-09
FR72338T 1958-03-03
FR759580A FR73165E (fr) 1955-03-09 1958-03-03 Produits d'addition pour huiles lubrifiantes et leur procédé de fabrication

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US3010906A true US3010906A (en) 1961-11-28

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US (1) US3010906A (de)
DE (2) DE1037630B (de)
FR (3) FR1123354A (de)
GB (3) GB788129A (de)

Cited By (8)

* Cited by examiner, † Cited by third party
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US3223636A (en) * 1961-05-23 1965-12-14 Exxon Research Engineering Co Lead corrosion inhibitor
US3244631A (en) * 1961-12-29 1966-04-05 Shell Oil Co Lubricating composition containing non-ash forming additives
US3254058A (en) * 1963-03-06 1966-05-31 Exxon Research Engineering Co Gel and sediment prevention in polymeric additives for hydrocarbon oils
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US3459733A (en) * 1964-10-15 1969-08-05 Mobil Oil Corp Monomeric polyesters of polyhydroxy compounds and process for preparing same
US3933761A (en) * 1971-03-17 1976-01-20 The Lubrizol Corporation Nitrogen-containing ester and lubricant containing the same
US4931197A (en) * 1981-09-17 1990-06-05 Akzo Nv Copolymers for α-β-unsaturated dicarboxylic acid esters wherein said esters are comprised of ethoxylated esters, methods for their production as well as their use as lubricant for the working-up of plastics

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Cited By (8)

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Publication number Priority date Publication date Assignee Title
US3223636A (en) * 1961-05-23 1965-12-14 Exxon Research Engineering Co Lead corrosion inhibitor
US3244631A (en) * 1961-12-29 1966-04-05 Shell Oil Co Lubricating composition containing non-ash forming additives
US3215632A (en) * 1962-06-22 1965-11-02 Shell Oil Co Lubricating compositions
US3285887A (en) * 1962-07-30 1966-11-15 Chevron Res Microgel polymers
US3254058A (en) * 1963-03-06 1966-05-31 Exxon Research Engineering Co Gel and sediment prevention in polymeric additives for hydrocarbon oils
US3459733A (en) * 1964-10-15 1969-08-05 Mobil Oil Corp Monomeric polyesters of polyhydroxy compounds and process for preparing same
US3933761A (en) * 1971-03-17 1976-01-20 The Lubrizol Corporation Nitrogen-containing ester and lubricant containing the same
US4931197A (en) * 1981-09-17 1990-06-05 Akzo Nv Copolymers for α-β-unsaturated dicarboxylic acid esters wherein said esters are comprised of ethoxylated esters, methods for their production as well as their use as lubricant for the working-up of plastics

Also Published As

Publication number Publication date
DE1037630B (de) 1958-08-28
FR73165E (fr) 1960-09-23
DE1071869B (de) 1959-12-24
GB788129A (en) 1957-12-23
FR1123354A (fr) 1956-09-20
FR72338E (fr) 1960-04-06
GB833977A (en) 1960-05-04
GB832057A (en) 1960-04-06

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