US3326801A - Lubricating oil compositions - Google Patents

Lubricating oil compositions Download PDF

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Publication number
US3326801A
US3326801A US472701A US47270165A US3326801A US 3326801 A US3326801 A US 3326801A US 472701 A US472701 A US 472701A US 47270165 A US47270165 A US 47270165A US 3326801 A US3326801 A US 3326801A
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US
United States
Prior art keywords
oil
lubricating oil
moles
reaction product
mole
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
US472701A
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English (en)
Inventor
Roland T Schlobohm
Herbert D Millay
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 USA Inc
Original Assignee
Shell Oil Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US472701A priority Critical patent/US3326801A/en
Priority to FR69315A priority patent/FR1486677A/fr
Priority to NL6609888A priority patent/NL6609888A/xx
Priority to GB31692/66A priority patent/GB1112845A/en
Priority to BE684144D priority patent/BE684144A/xx
Priority to DE1594615A priority patent/DE1594615C3/de
Priority to CH1024366A priority patent/CH487239A/de
Priority to NO163924A priority patent/NO121006B/no
Application granted granted Critical
Publication of US3326801A publication Critical patent/US3326801A/en
Priority to US00868585A priority patent/US3772359A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • 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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/16—Reaction products obtained by Mannich reactions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
    • C—CHEMISTRY; METALLURGY
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
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    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/40—Fatty vegetable or animal oils
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    • C10M2207/402—Castor oils
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    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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    • C10M2209/086—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
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • This invention relates to novel lubricating oil compositions. More particularly, the invention is concerned with new, novel and superior lubricating oil compositions for use in internal combustion engines.
  • ashless polymeric compounds as detergents in lubricating oil compositions
  • Polymers of this type are generally high molecular weight nitrogen-containing polymers such as copolymers of vinyl pyridine or vinyl pyrrolidone and long-chain alkyl methacrylates, or mono(polyolefin)succinimides derived from mono (polyolefin)succinic anhydride and polyalkylene polyamines.
  • polymers and copolymers of this type are excellent detergent-dispersant oil additives they lack corrosion and wear inhibiting properties and therefore require the presence of fortifying agents capable of inhibiting corrosion and wear.
  • an excellent multifunction lubricating oil composition can be made useful in various types of engines such as 4-stroke and 2-stroke engines and particularly for use in the latter type engines by incorporationg in a lubricating oil base a small amount of from 0.1% to about 20%, preferably from 2-8% of an oil-soluble reaction product of (1) a polyamide of a polyalkylene polyamine and an iso-fatty acid or mixture of an iso-fatty acid and a straightchain fatty acid having from 8 to 22 carbon atoms and having at least one and preferably a plurality of from 1-100 (2-50) free basic amino nitrogen atoms in the molecule or derivatives thereof with (2) mixture of condensation product of an alkyl hydroxyaromatic compound and low molecular weight aldehyde.
  • the polyamides (1) of polyalkylene polyamine and isofatty acids or mixtures of straight-chain fatty acids and iso-fatty acids each having from 8 to 22 carbon atoms are prepared by reacting about the mole of a polyalkylene polyamine with 1-4 moles of an iso-fatty acid or mixtures thereof as noted above at between 100 and 250 C., preferably at 150-200" C. for about -24 hours in an enclosed vessel and under atmospheric conditions until the polyamide, preferably a diamide is formed and the product cooled and recovered,
  • the polyamide thus formed can be condensed with from 1-20 moles each of an aldehyde and an alkylated hydroxyaromatic compound, e.g.,
  • alkyl phenol in a Mannich synthesis.
  • each of the aldehyde and an alkyl phenol is used for every mole of polyamide compound (1) and the reaction can be carried out at 35250 C., in the presence or absence of a solvent.
  • a preferred method is to interact the polyamide containing free basic amino nitrogen in the molecule with from 1-4 moles each of an aliphatic aldehyde and a C alkyl phenol at 25-200 C.
  • the iso-fatty acids used to form the polyamides with polyalkylene polyamines included saturated and unsaturated fatty acids having from 8 to 22 carbonatoms such as iso-oleic acid, dimerized or trimerized unsaturated fatty acids having from 16 to 20 carbon atoms such as dimerized oleic and linoleic acids, or mixtures of said unsaturated acids and/or hydrogenated derivatives thereof such as iso-stearic acid or mixtures of iso-fatty acids and straight-chain C1240 saturated fatty acids such as lauric, myristic, palmitic and/0r stearic acids.
  • the straightchain fatty acids comprise 5-30 mole percent and the balance (70-95 mole percent) being the iso-fatty acids or branch-chain fatty acids.
  • the polyamines used to form the diamides include diethylene triamine, triethylene tetr-amine, tetraethylene pentamine, tripropylene tetramine, tetrapropylene pentamine and the like Other suitable polyamines are the result of polymerizing ethylene imine to a molecular weight of from 500 to 40,000.
  • Specific conditions for making the diamides are by reacting approximately one mole of a polyamine, e.g., tetraethylene pentamine, and one or more moles of saturated and/or unsaturated fatty acids, e.g., iso-oleic acid or dimerized oleic acid or iso-stearic acid or mixtures of stearic and is-stearic acids at between C. and 250 C. for a period of 1-10 or more hours, preferably under atmospheric pressure.
  • 1 mole of alkyl substituted diethylene triamine H NCH CH N(C H )CH CH NH and two moles of iso-oleic acid were mixed and heated at -200 C. for about 1-10 hours in an enclosed vessel under atmospheric conditions until the diamide was formed, after which the reaction was cooled and the end product has the following formula:
  • diamides include (Id) dioleylamide of diethylene triamine, (Ic) dimerized oleylamide of diethylene triamine, (Id) dimerized linoleylamide of diethylene triamine, (12) mixed diand trimerized oleylamide of diethylene triamine, (If) diisooleyamide of diethylene triamine, (Ig) diisooleylamide of N-2-aminoethyl piperazine, (Ih) diamide of tetraethylene pentamine and iso-stearic acid, (Ii) diamide (if tetraethylene pentamine and a mixture of 10 mole percent stearic acid and 90 mole percent iso-stearic acid, and mixtures thereof.
  • aldehydes useful in forming reaction products of this invention include aliphatic aldehydes, e.g., formaldehyde (paraformaldehyde) acetaldehyde, butyraldehyde or aromatic aldehydes, e.g., benzaldehyde or salicylaldehyde or heterocyclic aldehydes, e.g., furfural and mixtures thereof.
  • aliphatic aldehydes e.g., formaldehyde (paraformaldehyde) acetaldehyde, butyraldehyde or aromatic aldehydes, e.g., benzaldehyde or salicylaldehyde or heterocyclic aldehydes, e.g., furfural and mixtures thereof.
  • the alkylated hydroaromatic compounds include C alkyl monoand polyhydroxy aromatics such as C alkyl phenol, naphthol, anthranol and preferably C alkyl phenol such as nonyl phenol, dodecyl phenol, dinonyl phenol, benzyl phenol and mixtures thereof.
  • Example I One mole of diamide identified above as (Ij) was reacted with 2 moles each of formaldehyde and dodecyl phenyl at around 50160 C. for about 5 hours. The final product was oil-soluble and possessed excellent detergent and sludge inhibiting properties.
  • Example II Diisostearamide of tetraethylene pentamine was reacted with 2.5 moles each of formaldehyde and dodecylphenol under reaction conditions of Example I and the final reaction product was oil-soluble and exhibited excellent detergent and corrosion inhibiting properties.
  • Example IV -Reaction product of 1 mole of diamide (Ic)-1 mole formaldehyde-1 mole dodecylphenol.
  • Example V Reaction product of 1 mole of diarnide (ID-3 mole-s formaldehyde-3 moles dodecylphenol.
  • Example VH -Reaction product of 1 mole of (Ilt)-2 moles of formaldehyde-2 moles dodecylphenol.
  • Example IX Reaction product of 1 mole of (Ih)-2 moles of acetaldehyde-Z moles C1448 alkylphenol.
  • Example X Reaction product of 1 mole of diamide (Ic)-1 mole of formaldehyde-1 mole C alkyl naphthanol.
  • Reaction products of the present invention can be added in small amounts of from 0.1% to about preferably from 1% to 15% in various lubricants of the natural and/or synthetic type such as mineral lubricating oils in the viscosity range of from SAE 5W to SAE 140, preferably in the SAE viscosity range of 2090.
  • the mineral lubricating oils can be of the same base stock or blends of different base stocks or blends of mineral lubricating oil and synthetic lubricants such as polymerized olefins, organic esters of organic and inorganic acids, e.g., di-2-ethylhexyl sebacate, pentaerythritol esters of mixed C fatty acids; polyalkyl silicone polymers, e.g., dimethyl silicone polymer, and the like. If desired, the synthetic lubricants may be used as the sole base lubricant.
  • synthetic lubricants may be used as the sole base lubricant.
  • Mineral lubricating oils which are particularly desirable for use in compositions of this invention were obtained from West Texas Ellenburger crudes, East Texas crudes, Oklahoma crudes, California crudes.
  • a useful refined oil therefrom has the following properties:
  • SAE 30 mineral oil having the following properties:
  • reaction products of the present invention are useful additives in motor oils, diesel oils, various industrial oils such as hydraulic fluids, gear oils, cutting fluids and the like, they are particularly useful in lubricants for 2-stroke engines.
  • Two-stroke engine lubricants containing the reaction product of the present invention can be used in 2-stroke engines operating on neat or leaded gasolines.
  • leaded gasolines When leaded gasolines are used the presence of a halogen scavenger is normally desirable although not necessary.
  • the lead compounds can be tetramethyl, tetraethyl, ethylmethyl, diethyl dimethyl, triethyl methyl lead and mixtures thereof.
  • the scavengers include saturated and unsaturated halogenated (Cl, Br, I) olefins such as ethylene dibromide, ethylene dichloride or mixtures thereof. Still other scavengers include organic halide wherein the halogen atom is attached directly to an unsaturated carbon atom there are mentioned haloethylenes, e.g., iodoethylene, 1,1-dichloroethylene, 1,2-dichloroethylene, 1,2- dibromoethylene, trichloroethylene, tetrachloroethylene;
  • halogen derivatives of butadiene e.g., 1-chloro-l,3-butadiene, 2 chloro 1,3 butadiene, 1,1,2,3,4,4-hexachlorobutadiene, aryl halides, e.g., chlorobenzene, bromobenzene, dichloro'benzene, dibromobenzene, diiodobenzene, trichlorohenzene, tribromobenzene, tetrachlorobenzene, tetrailuorobenzene, hexafluorobenzene, halogen derivatives of unsaturated heterocyclic compounds, e.g., 2-chloropyridine, 3-chloropyridine, 4-chloropyridine, 3-bromopyridine, 3-chloropyrrole, 2-chlorothiophene and certain substituted haloacetylenes, e.g., l-chlorohexyne-
  • Preferred halides are those which contain the greatest amount of halogen per unit weight of halide consistent with adequate oil solubility.
  • the fuel can also contain organic phosphites, phosphates, e.g., tricresyl phosphate, diphenyl cresyl phosphate, or boron esters and the like.
  • An excellent lubricant base for use in Z-stroke engines containing the reaction product of the present invention is an oil blend consisting of a mixture of from 10% to 50% bright stock and from to 50% of a high viscosity index (80-140 VI) mineral lubricating oil having a viscosity at F. SUS of from 100 to 600. A portion of the high viscosity oil can be replaced with a medium viscosity oil.
  • An oil base mixture for 2-stroke engines consists of (a) a bright stock fraction rich in aromatics (570%) and Which has a viscosity index of at least 80, preferably between 90 and and is obtained during the refining of mineral oils from the short residue after the distillate fractions have been removed.
  • the short residue is dewaxed and deasphalted and if desired, solvent and claytreated.
  • the rafdnate which remains after this treatment is called bright stock.
  • Table I and II illustrate examples of useful bright stocks.
  • the other portion of the oil blend is a high viscosity index lubricating oil distillate fraction and specifically is a refined distillate fraction having a viscosity index of at least 80, preferably 90410, an SUS viscosity at 100 F.
  • Base blends which are particularly preferred are:
  • oil bases may also contain fortifying agents such as viscosity index improvers (e.g., polymeric acrylic esters), pour point depressants (e.g., methacrylate polymers), oxidation inhibitors, e.g., bis(2,6-di-t-butyl-4-hydroxy phenyl)methane, metal deactivators, e.g., di-salicylal ethylene diimine, rust inhibitors, e.g., the condensation product of maleic anhydride and long-chain alkenes, anti-foaming agents e.g., silicone polymers, EP additives, provided that such EP additives do not contain halogens, e.g., triphenyl phosphate, and anti-seizure agents, e.g., acidless tallow or a non-drying fatty oil, e.g., castor oil.
  • viscosity index improvers e.g., polymeric acrylic esters
  • gasoline as used in 2-stroke engines is intended to mean a hydrocarbon oil, or a mixture of a hydrocarbon oil with an alcohol, distilling substantially continuously at atmospheric pressure throughout the temperature range 10 C. to 250 C. and containing a lead tetra-alkyl, for example, tetraethyl lead, tetramethyl lead, ethyl triethyl lead, diethyl dirnethyl lead, triethyl methyl lead or mixtures thereof.
  • the hydrocarbon oil Will normally be derived from petroleum but may be derived from other sources, e.g., from coal or from synthetic processes.
  • the gasoline may contain other anti-knock agents, for example, methyl cyclopentadienyl manganese tricarbonyl, and any of the additives of fortifying agents known to the art, e.g., vapor pressure modifiers such as butanes, co-anti-knock agents, e.g., tertiary butyl acetate, scavengers, e.g., alkyl halides, deposit modifiers, e.g., tritolyl phosphate, anti-icing additives, e.g., isopr-opyl alcohol, anti-foaming agents, e.g., silicones, anti-oxidants, e.g., 2,4-methyl-6tertiary butyl phenol or di sec. butyl para phenylene diamine and dyestuffs or coloring agents.
  • vapor pressure modifiers such as butanes
  • co-anti-knock agents e.g., tertiary buty
  • the reaction product of the present invention can be used in amounts of from 0.1% to 10% in conventional motor lubricants such as used in 4-stroke engines, or in gear lubricants and the like. When this reaction product is used as a lubricant for 2-stroke engines the additive is used in higher concentrations of from 1% to 25%, preferably from 3% to 10%.
  • the compounded lubricant is blended with a suitable fuel, e.g., gasoline, diesel fuel, etc., in amounts of from about 0.2 to about 10 pints, preferably 1-5 pin-ts of lubricant per gallon of fuel, e.g., neat or leaded gasoline or the lubricant of the present invention can be used in the ratio of 1 part of oil compositions to -100 parts of fuel. Generally, 1 part of the oil composition to to 50 parts of fuel is preferred.
  • Example VI reaction product percent wt 5 1,1 bis(3,5 ditert butyl 4 hydroxyphenyl)methane percent 0.5
  • Example VI reaction product -percent wt 10 Base blend (A) Balance The lubricating oil compositions were tested as 2- stroke engine lubricants in Homelight motor-generators, and in Mercury 650 and Johnson 40 HP Outboard 2- stroke engines under conditions shown below.
  • Test fuel Shell gasoline leaded to 3 ml./gal. motor mix TEL and containing 0.2 theory phosphorus as diphenyl cresyl phosphate Fuel/oil ratio: 15/1
  • Base oil Blend A Mercury 650 outboard engine test conditions Test conditions and duration: hours alternate periods of 5 minutes idle and 55 minutes full-throttle at 5000 r.p.m.
  • Test fuel Shell gasoline leaded to 3 ml./gal. motor mix TEL and containing 0.2 theory phosphorus as diphenyl cresyl phosphate Fuel/ oil ratio: 20/ 1 Base oil: Blend C Johnson 40 HP outboard engine test conditions Test conditions and duration: 98-hour test alternate 5 minutes idle, 55 minutes full throttle, 4800 r.p.m. with one hour shutdown after each 7 running hours Test fuel: Shell gasoline leaded to 3 ml./ gal.
  • compositions X and Y containing 5% each of additive (Ih) and (Ij) when tested in the Homelite engine under similar test conditions described above resulted in reduction of engine cleanliness rating of from 3% to 15% when compared to results obtained with Compositions V, VI and VII as noted above.
  • Examples V, VI and VII reaction products and intermediate compounds (Ih) and (1 were subjected to differential thermal analysis and it was found that the reaction products of Examples V, VI and VII begin thermal decomposition in the presence of air, about 100 F. higher than the compounds (Ih) and (Ij) indicating that the decomposition rate of (Ih) and (Ij) is much greater than that of Examples V, VI and VII reaction products of the present invention. This is clear evidence that the reaction products of the present invention are much more stable than the intermediate compounds (Ih) and (Ij).
  • compositions of the present invention can be used also as gear lubricants, as truck, railroad and automotive lubricants, as hydraulic fluids, greases, fuels and the like.
  • a lubrication oil composition comprising a major amount of lubricating oil and containing a minor amount, sufficient to impart detergency, of an oil-soluble reaction product prepared by reacting at 25-250 C. a polyamide of an iso-fatty acid and a polyalkylene polyamine with from 1-4 moles each per mole of the polyamide of an aldehyde selected from the group consisting of formaldehyde, paratormaldehyde, acetaldehyde, butyraldehyde, benzaldehyde, salicylaldehyde, furfural and mixtures thereof and a C alkyl phenol.
  • a lubricating oil composition comprising a major amount of lubricating oil and from 0.1% to 20% of an oil-soluble reaction product prepared by reacting at 25- 250 C. a polyamide of an iso-fatty acid having from 8 to 22 carbon atoms and a polyalkylene polyamine with from 1-4 moles each per mole of the polyamide of an aldehyde selected from the group consisting of formaldehyde, paraformaldehyde, acetaldehyde, butyraldehyde, benzaldehyde, salicylaldehyde, furfural and mixtures thereof and a C alkyl phenol.
  • a lubricating oil composition comprising a major amount of mineral lubricating oil and from 0.1% to 20% of an oil-soluble reaction product prepared by reacting at 25-250 C. the diamide of iso-stearic acid and tetraethylene pentamine with from 1-4 moles each per mole of the diamide of formaldehyde and C alkyl phenol.
  • a lubricating oil composition comprising a major amount of mineral lubricating oil and from 0.1% to 20% of an oil-soluble reaction product prepared by reacting at 25-250 C. the diamide of tetraethylene pentamine and a mixture of iso-stearic and stearic acid with from 1-4 moles each per mole of the diamide of formaldehyde and dodecyl phenol.
  • a lubricant for 2-stroke engines employing a lubricant-fuel mixture, said lubricant consisting of a blend of -50% bright stock and 90-50% mineral lubricating oil having a viscosity index of 80-140 and a SUS at 100 F. of
  • an oil-soluble reaction product prepared by reacting at 25-250 C. a polyamide of an iso-fatty acid and a polyalkylene polyamine with from l-4 moles each per mole of the polyamide of an aldehyde selected from the group consisting of formaldehyde, paraformaldehyde, acetaldehyde, butyraldehyde, benzaldehyde, salicylaldehyde, furfural and mixtures thereof and a C alkyl phenol.
  • an aldehyde selected from the group consisting of formaldehyde, paraformaldehyde, acetaldehyde, butyraldehyde, benzaldehyde, salicylaldehyde, furfural and mixtures thereof and a C alkyl phenol.
  • a lubricant for 2-stroke engines employing a lubricant-fuel mixture, said lubricant consisting of a blend of 10-50% bright stock and 90-50% mineral lubricating oil having a viscosity index of -140 and a SUS at 100 F. of 100-600 and having incorporated therein from 33-10% of an oil-soluble reaction product prepared by reacting at 25-250 C.
  • an aldehyde selected from the group consisting of formaldehyde, paraform aldehyde, acetaldehyde, 'butyraldehyde, benzaldehyde, salicylaldehyde, furfural and mixtures thereof and a C alkyl phenol.
  • a lubricant for 2-stroke engines employing a lubricant-fuel mixture, said lubricant consisting of a blend of 10-50% bright stock and -50% mineral lubricating oil having a viscosity index of 80-140 and a SUS at F. of 100-600 and having incorporated therein from 3-10% of an oil-soluble reaction product prepared by reacting at 25-250 C. the diamide of iso-stearic acid and tetraethylene pentamine with from 1-4 moles each per mole of diamide of formaldehyde and C alkyl phenol.
  • a lubricant for Z-stroke engines employing a lubricant-fuel mixture, said lubricant consisting of a blend of 10-50% bright stock and 90-50% mineral lubricating oil having a viscosity index of 80-140 and a SUS at 100 F. of 100-600 and having incorporated therein from 3-10% of an oil-soluble reaction product prepared by reacting at 25 -250 C. the diamide of tetraethylene pentamine and a mixture of iso-stearic and stearic acid with from 1-4 moles each per mole of the diamide of formaldehyde and dodecyl phenol.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
US472701A 1965-07-16 1965-07-16 Lubricating oil compositions Expired - Lifetime US3326801A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US472701A US3326801A (en) 1965-07-16 1965-07-16 Lubricating oil compositions
FR69315A FR1486677A (fr) 1965-07-16 1966-07-13 Additif utilisable pour une huile lubrifiante
GB31692/66A GB1112845A (en) 1965-07-16 1966-07-14 Additive suitable for a lubricating oil,and lubricants and fuels containing such additives
BE684144D BE684144A (de) 1965-07-16 1966-07-14
NL6609888A NL6609888A (de) 1965-07-16 1966-07-14
DE1594615A DE1594615C3 (de) 1965-07-16 1966-07-14 Schmiermittel
CH1024366A CH487239A (de) 1965-07-16 1966-07-14 Additiv für ein Schmieröl
NO163924A NO121006B (de) 1965-07-16 1966-07-14
US00868585A US3772359A (en) 1965-07-16 1969-10-22 Polyamide-containing mannich reaction products as lubricant additives

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US472701A US3326801A (en) 1965-07-16 1965-07-16 Lubricating oil compositions
US86858569A 1969-10-22 1969-10-22

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US00868585A Expired - Lifetime US3772359A (en) 1965-07-16 1969-10-22 Polyamide-containing mannich reaction products as lubricant additives

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BE (1) BE684144A (de)
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DE (1) DE1594615C3 (de)
GB (1) GB1112845A (de)
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NO (1) NO121006B (de)

Cited By (23)

* Cited by examiner, † Cited by third party
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US3660126A (en) * 1970-01-16 1972-05-02 Chevron Res Ashphalt compositions containing polyamide
US3877887A (en) * 1969-03-06 1975-04-15 Texaco Inc Motor fuel composition
US5264005A (en) * 1991-08-09 1993-11-23 The Lubrizol Corporation Two-cycle lubricants and methods of using the same
US5399274A (en) * 1992-01-10 1995-03-21 Marcus; R. Steven Metal working lubricant
US5814111A (en) * 1995-03-14 1998-09-29 Shell Oil Company Gasoline compositions
US6242394B1 (en) 1991-05-30 2001-06-05 The Lubrizol Corporation Two-stroke cycle lubricant and method of using same
WO2010005947A2 (en) 2008-07-11 2010-01-14 Innospec Fuel Specialties, LLC Fuel composition with enhanced low temperature properties
US20100258070A1 (en) * 2007-09-27 2010-10-14 Innospec Limited Fuel compositions
US20100293844A1 (en) * 2007-09-27 2010-11-25 Macmillan John Alexander Additives for Diesel Engines
WO2010136822A2 (en) 2009-05-29 2010-12-02 Innospec Limited Method and use
US20100299992A1 (en) * 2007-09-27 2010-12-02 Jacqueline Reid Fuel compositions
WO2010139994A1 (en) 2009-06-01 2010-12-09 Innospec Limited Improvements in efficiency
EP2302020A1 (de) 2007-07-28 2011-03-30 Innospec Limited Verwendung von Additiven zur Verbesserung von Treibstoffzusammensetzungen
WO2011110860A1 (en) 2010-03-10 2011-09-15 Innospec Limited Fuel composition comprising detergent and quaternary ammonium salt additive
WO2011141731A1 (en) 2010-05-10 2011-11-17 Innospec Limited Composition, method and use
WO2012076896A1 (en) 2010-12-09 2012-06-14 Innospec Limited Improvements in or relating to additives for fuels and lubricants
EP2644684A1 (de) 2009-02-25 2013-10-02 Innospec Limited Verfahren und verwendungen betreffend kraftstoffzusammensetzungen.
US20140165942A1 (en) * 2012-12-18 2014-06-19 Ford Global Technologies, Llc Engine-lubricant octane boost to quiet sporadic pre-ignition
US9243199B2 (en) 2007-09-27 2016-01-26 Innospec Limited Fuel compositions
US9315752B2 (en) 2007-09-27 2016-04-19 Innospec Limited Fuel compositions
US11015137B2 (en) 2017-03-30 2021-05-25 Innospec Limited Composition, method and use
US11174442B2 (en) 2017-03-30 2021-11-16 Innospec Limited Fuel compositions, methods and uses relating to quaternary ammonium salt additives for fuel used in spark ignition engines
US11186791B2 (en) 2017-03-30 2021-11-30 Innospec Limited Composition, method and use

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US4454059A (en) * 1976-11-12 1984-06-12 The Lubrizol Corporation Nitrogenous dispersants, lubricants and concentrates containing said nitrogenous dispersants
US4162143A (en) * 1978-03-13 1979-07-24 Ici Americas Inc. Emulsifier blend and aqueous fuel oil emulsions
US4396517A (en) * 1981-08-10 1983-08-02 Mobil Oil Corporation Phenolic-containing mannich bases and lubricants containing same
JP2005523374A (ja) * 2002-04-19 2005-08-04 ザ　ルブリゾル　コーポレイション パワーバルブを含む２ストロークエンジン用の方法および潤滑剤および燃料組成物
US7795192B2 (en) * 2002-04-19 2010-09-14 The Lubrizol Corporation Lubricant composition suitable for direct fuel injected, crankcase-scavenged two-stroke engines

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US3169980A (en) * 1961-03-31 1965-02-16 California Research Corp Fatty acid polyamide
US3235494A (en) * 1963-04-25 1966-02-15 Gulf Research Development Co Two-cycle engine lubricating composition

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Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3877887A (en) * 1969-03-06 1975-04-15 Texaco Inc Motor fuel composition
US3660126A (en) * 1970-01-16 1972-05-02 Chevron Res Ashphalt compositions containing polyamide
US6242394B1 (en) 1991-05-30 2001-06-05 The Lubrizol Corporation Two-stroke cycle lubricant and method of using same
US5264005A (en) * 1991-08-09 1993-11-23 The Lubrizol Corporation Two-cycle lubricants and methods of using the same
US5399274A (en) * 1992-01-10 1995-03-21 Marcus; R. Steven Metal working lubricant
US5814111A (en) * 1995-03-14 1998-09-29 Shell Oil Company Gasoline compositions
EP2302020A1 (de) 2007-07-28 2011-03-30 Innospec Limited Verwendung von Additiven zur Verbesserung von Treibstoffzusammensetzungen
US9243199B2 (en) 2007-09-27 2016-01-26 Innospec Limited Fuel compositions
US9034060B2 (en) 2007-09-27 2015-05-19 Innospec Fuel Specialties Llc Additives for diesel engines
US20100293844A1 (en) * 2007-09-27 2010-11-25 Macmillan John Alexander Additives for Diesel Engines
US20100299992A1 (en) * 2007-09-27 2010-12-02 Jacqueline Reid Fuel compositions
US9315752B2 (en) 2007-09-27 2016-04-19 Innospec Limited Fuel compositions
US20100258070A1 (en) * 2007-09-27 2010-10-14 Innospec Limited Fuel compositions
US9163190B2 (en) 2007-09-27 2015-10-20 Innospec Limited Fuel compositions
US9157041B2 (en) 2007-09-27 2015-10-13 Innospec Limited Fuel compositions
WO2010005947A2 (en) 2008-07-11 2010-01-14 Innospec Fuel Specialties, LLC Fuel composition with enhanced low temperature properties
US9394499B2 (en) 2009-02-25 2016-07-19 Innospec Limited Methods relating to fuel compositions
EP2644684A1 (de) 2009-02-25 2013-10-02 Innospec Limited Verfahren und verwendungen betreffend kraftstoffzusammensetzungen.
US9085740B2 (en) 2009-02-25 2015-07-21 Innospec Limited Methods relating to fuel compositions
WO2010136822A2 (en) 2009-05-29 2010-12-02 Innospec Limited Method and use
WO2010139994A1 (en) 2009-06-01 2010-12-09 Innospec Limited Improvements in efficiency
US20120260876A1 (en) * 2009-06-01 2012-10-18 Innospec Limited Method of increasing fuel efficiency
EP3447111A1 (de) 2010-03-10 2019-02-27 Innospec Limited Kraftstoffzusammensetzungen enthaltend detergens und quaternisiertes ammoniumsalz additiv
EP2966151A1 (de) 2010-03-10 2016-01-13 Innospec Limited Kraftstoffzusammensetzungen enthaltend quaternisiertes ammoniumsalz additiv
WO2011110860A1 (en) 2010-03-10 2011-09-15 Innospec Limited Fuel composition comprising detergent and quaternary ammonium salt additive
WO2011141731A1 (en) 2010-05-10 2011-11-17 Innospec Limited Composition, method and use
US9493720B2 (en) 2010-05-10 2016-11-15 Innospec Limited Gasoline composition, method and use
US9932536B2 (en) 2010-05-10 2018-04-03 Innospec Limited Gasoline composition, method and use
WO2012076896A1 (en) 2010-12-09 2012-06-14 Innospec Limited Improvements in or relating to additives for fuels and lubricants
US20140165942A1 (en) * 2012-12-18 2014-06-19 Ford Global Technologies, Llc Engine-lubricant octane boost to quiet sporadic pre-ignition
US11015137B2 (en) 2017-03-30 2021-05-25 Innospec Limited Composition, method and use
US11174442B2 (en) 2017-03-30 2021-11-16 Innospec Limited Fuel compositions, methods and uses relating to quaternary ammonium salt additives for fuel used in spark ignition engines
US11186791B2 (en) 2017-03-30 2021-11-30 Innospec Limited Composition, method and use

Also Published As

Publication number Publication date
BE684144A (de) 1967-01-16
GB1112845A (en) 1968-05-08
NO121006B (de) 1971-01-04
NL6609888A (de) 1967-01-17
DE1594615B2 (de) 1974-08-01
CH487239A (de) 1970-03-15
DE1594615A1 (de) 1970-05-06
US3772359A (en) 1973-11-13
DE1594615C3 (de) 1975-06-05

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