US3609080A - Lubricant, grease and hydraulic fluid - Google Patents

Lubricant, grease and hydraulic fluid Download PDF

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Publication number
US3609080A
US3609080A US827880A US3609080DA US3609080A US 3609080 A US3609080 A US 3609080A US 827880 A US827880 A US 827880A US 3609080D A US3609080D A US 3609080DA US 3609080 A US3609080 A US 3609080A
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percent
composition
lubricant
ones
compounds
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US827880A
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Inventor
Joachim Dazzi
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Novartis Corp
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Geigy Chemical Corp
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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
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
    • C10M105/70—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen as ring hetero atom
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04—Elements
    • C10M2201/041—Carbon; Graphite; Carbon black
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04—Elements
    • C10M2201/041—Carbon; Graphite; Carbon black
    • C10M2201/042—Carbon; Graphite; Carbon black halogenated, i.e. graphite fluoride
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/10—Compounds containing silicon
    • C10M2201/102—Silicates
    • C10M2201/103—Clays; Mica; Zeolites
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/14—Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—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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    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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    • C10M2207/08—Aldehydes; Ketones
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/24—Epoxidised acids; Ester derivatives thereof
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    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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    • 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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    • C10M2215/065—Phenyl-Naphthyl amines
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Definitions

  • a preferred lubricant contains 69 percent to 77 percent of N,N'-didodecylimidazolidin-2-one and 31 percent to 23 percent of N,N'-di-octyl-S-methylimidazolidin-Z-one.
  • R and R amounts to at least 12 and at most 30, but preferably not more than 24.
  • the compounds of the formula I can also be a constituent of compositions of matter, e.g. used together with mineral or synthetic lubricating oils or other hydraulic fluids, which also contain the usual additions such as antioxidizing agents, thickeners, pour-point depressants, high-pressure additives and/or anticorrosion agents.
  • the lubricants and hydraulic fluids must be compatible with rubber, metals and plastics, as well as resistant to oxidation and hydrolysis; moreover they must have a high flashpoint.
  • organic esters such as diesters of dicarboxylic acids, e.g. adipic acid or sebacic acid, with alcohols having a medium to long carbon chain, also triesters of trimethylol propane and higher fatty acids or esters of pentaerythrite and monocarboxylic acids of average chain length;
  • inorganic esters e.g. orthophosphoric acid esters of organic hydroxyl compounds, especially alkyldiaryl phosphates or trialkyl phosphates; 7
  • aromatic ethers especially polyphenyl ethers having 3 to 6 phenyl rings
  • silicon compounds such as silicone oils or silicates, e.g.
  • heterocyclic compounds of the formula I are suitable as lubricants, as lubricating greases and hydraulic fluids. This is all the more surprising since it is know from the literature (Ullmanns Encylclopaedie der ischen Chemie, 3. Edition, Vol. 15, p. 307, (I964 Publishers Orban and Schwarzenberg), that the lubricating properties of the urea derivatives so far investigated, are unsatisfactory.
  • compositions of the present invention are particularly valuable in a mixture as follows:
  • an additive such as antioxidants, pour-point depressants, antifoaming agents, anticorrosion agents and high-pressure additives or mixtures thereof,
  • N,N-dialkylimidazolidin-Z-ones and N,N'-dialkylhexahydropyrimidin-2-ones of the formula I are in some cases known and can be produced according to processes known per se. They can be produced, for example, according to W. R. Boon, J. Chem. Soc., pp. 307, (1947 by treatment of the diamines with phosgene. Preferably however, the compounds of the formula I are obtained according to A. E. Martell and A, E. Frost, J. Amer. Chem. Soc. 72, 1032-1033, (1950) by heating N,N-dialkylalkylene diamines with a small excess of urea without solvent with the evolution of ammonia.
  • N,N-dialkylalkylene diamines e.g. produced according to J. Org. Chemistry 14, 948, (1949 are as pure as possible.
  • commercial primary amines are used which, for example, in the case of the decyl or octyl amine, are used as a mixture of primary alkylamines with the alkyl radical having an average number of carbon atoms of 10 or 8.
  • the compounds of the formula I are characterized by a particularly good thermostability. They have not decomposed even after a period of 2 hours at 380 C., whereas the hitherto most thermostable organic esters, e.g. the triesters of fatty acids with trimethylol propane, are unusable after 2 hours at temperatures from 360 C.
  • a further advantage of the compounds of the formula I, compared with lubricants based on organic or inorganic esters, is that, in contrast to the esters, they form practically no acid decomposition products in the case of thermal decomposition.
  • the low tendency of the N,N-dialkylimidazolidin-2-ones or N,N-dialkylhexahydropyrimidin-2 ones to form acid decomposition products, which are responsible for the corrosion action, is shown by the fact that the volatile compounds and also the residue formed, e.g. by the exposure for 6 hours of N,N-didodecylimidazolidin-Z-one or N,Ndidecylimidazolidin-2-one to a temperature of 380 C. under a nitrogen atmosphere, are neutral whereas the substances which are formed from the triester of trimethylol propane and pelargonic acidat 360 C. in a nitrogen atmosphere, have a combined acid number for volatile fractions and residue of around 78 mg. KOH/g.
  • a further advantage of the compounds of the formula 1, to be used according to the invention is that, for example, a mixture of 73 percent of N,N'-didodecylimidazolidin-Z-one and 27 percent of N,N'-dioctyl-5methylimidazolidin-Z-one at 210 F. (98.8 C.) has a viscosity of 5.0 centistoke (c St) and thus satisfies the specification of the Pratt and Witney-Tests Type 11. The solidification point too is lowered with application of this mixture.
  • the compounds of the formula I, to be used according to the invention are characterized by a better lubricating effect and, compared to polyphenyl ethers, also by a lower pour point, a more favorable temperature viscosity relationship, as well as a lower density.
  • the compounds of the formula 1, usable according to the invention are suitable for lubricating the most varied types of surfaces. Thus they appreciably reduce the friction of metal on metal, but they also reduce the friction of metal on silicate, such as glass.
  • a further advantage of compounds of the formula 1, usable according to the invention is their surprisingly good miscibility with other common hydraulic fluids and lubricants, e.g. with those based on organic esters, polyaryl ethers, polyalkyl melamines, high-boiling phosphoric acid esters, high-boiling mineral oils, N-alkylcyclohexane-1,2-dicarboxy1ic acid imides, certain silicone oils or orthosilicates.
  • This favorable miscibility renders possible the production of special lubricants in that the properties required, but not attainable by means of the separate components, for a specific application, can be obtained by producing suitable mixtures.
  • additives for improving or modifying the properties such as antifoaming agents, agents which lower the pour point and thickeners.
  • the usual additives such as phosphites, phosphates, sulphurized sperm oil, are suitable as high-pressure additives in lubricants or hydraulic fluids, usable according to the invention.
  • the N,N' -dialky1imidazolidin-2-ones and -hexahydropyrimidin-Z-ones, usable according to the invention can also contain antifoaming agents, e.g. such as are based on silicone oil.
  • compositions of matter fluid at room temperature which, according to the invention, can be used as lubricant or hydraulic fluid having a thermal stability of at least 360 C., contain at least 25 percent by weight, relative to the total weight ofthe composition of matter, of compounds of the formula 1, and up to 75 percent by weight of at least one hydraulic fluid or one lubricant based on esters, aromatic ethers, silicon compounds, N-alkylcyclohexane-1,2-dicarboxylic acid imides, melamines and high-boiling mineral oil fractions.
  • the specific mixture ratio used depends on the purpose of application.
  • the invention also embraces greases consist ing of compounds of the formula 1 and thickeners.
  • suitable thickening agents are metal soaps, bentonites, phthalocyanines, violanthrones, graphite.
  • ASTM Viscosity Temperature Chart for Liquid Petroleum Products
  • column 5 is contained the viscosity index which is likewise calculated from the viscosity values determined at 100 F. or 210 F.
  • the method for calculating the viscosity index can be found, for example, in Standard Methods for Testing Petroleum and its Products," The Institute of Petroleum, 61 New Cavendish Street, London, W.1, Eighteenth Edition, 1959, pages 734-739.
  • the ASTM-Slope and the viscosity index are empirical values, which describe the temperature dependence of the viscosity of a lubricant. The corresponding values of some commercial lubricants have been given for the purpose of comparison.
  • N,N'didodecylimidazolidin-l-one is suitable for the lub'rication of metal surfaces.
  • the diameter of the wearing calotte in a precision 4-ball apparatus was measured. These measurements were carried out in accordance with the US Federal Specifications Lubricants and Related Products VV-L 79 1e. Method 6503 Load Carrying Capacity (means Hertz Load)." This apparatus ran for 30 minutes at a speed of 1480 rotations per minute with a loading of 40 kg. and using /2-inch steel balls SKF A-quality and with an initial temperature of ca. 40. in the case of the compound 1 in table 11, on the other hand, the N,N -didodecylimidazolidin-Z-one was measured at 70.
  • EXAMPLE 4 In order to be able to adjust the properties of lubricants and hydraulic fluids to be suitable for any desired application, it is important that they be miscible with other lubricants or hydraulic fluids. in order to test the behavior, in this respect, of the compounds of the formula 1, be used according to the invention, their miscibility at 25 with various commercial lubricants and hydraulic fluids was examined. The viscosity in centistokes of the mixture concerned was determined at 100 F. (378) and at 210 F. (98.8”) and the figures obtained are given in column 3 of table 111. The ASTM-slope is given in column 4.
  • column 1 In column 1 is shown the second component of the mixture and in column 2 is given the mixture ratio with N,N- didecylimidazolidin-Z-one.
  • the corresponding data for the pure unmixed N,N-didecylimidazolidin-Z-one is given at the end of table 111.
  • the N,N'-didecylimidazolidon-Z-one is miscible at 0 as well as at 25, in any proportion, also with a bis-(phenox yphenyl)-ether (e.g. Dow ET-378 of the Dow Chemical Co. Midland Mich. U.S.A.), as well as with tetra2-ethylhexyl silicate and methylphenyl silicone oil (e.g. Silicone DC 550 Fluid of The Dow Corning Co. Midland Mich. U.S.A. or Silicone MS 550 of the Midland Silicons Ltd.), and also with 2,4- bis-(dibutylamino)-6-diethylamino-s-triazine.
  • a bis-(phenox yphenyl)-ether e.g. Dow ET-378 of the Dow Chemical Co. Midland Mich. U.S.A.
  • tetra2-ethylhexyl silicate and methylphenyl silicone oil e.g. Silicone
  • EXAMPLE 5 To produce a lubricant or hydraulic fluid containing an antioxidant, 98 g. of N,N-didecylimidazolidin-2-one are mixed by stirring with 2 g. of di-tert.octyldiphenylamine as an antioxydant, until the latter has completely dissolved. The obtained mixture, compared with that containing no antioxydant, exhibits an increased resistance to oxidation.
  • EXAMPLE 6 97 g. of N,N'-didecylimidazolidin-2-one are homogeneously mixed, by stirring, with 3 g. of polymeric methacrylic acid ester, e. g. poly-Zethylhexyl-methacrylate (HF 825 of Fa. Rohm and Haas Co., Philadelphia, U.S.A.). This mixture has a lower pour point than the compound not containing this active substance. W
  • EXAMPLE 7 it 97.8 g. of N,N-didecylimidazolidin-2-one are mixed with 2 g. of di-tert.octyl-diphenylamine as antioxidant, and with 0.2 g. of henztrinzole as an anticorrosion agent, a lubricant is obtained which exhibits lower sensitivity to oxidation and lower corrosivity than :1 corresponding lubricant not contnining the stated nctive substances.
  • EXAMPLE 9 To produce a lubricant containing antioxidant, anticorrosion agent and high-pressure additive, 94.8 g. of N,N'- didecylimidazolidin-Z-one are mixed with 2 g. of di-tert.octyldiphenylamine as an antioxidant, 0.2 g. of benztriazole as an anticorrosion agent and 3 g. of trikresyl phosphate as a highpressure additive. A lubricant is obtained which exhibits a lower oxidation sensitivity and lower corrosivity and which withstands higher compressive loads than the corresponding lubricant not containing the stated active substances.
  • EXAMPLE 10 99 g. of N,N'-didodecylimidazolidin-2-one and l g. of iminodibenzyl are mixed together until the latter has completely dissolved. The obtained mixture exhibits, compared to the pure N,N-didodecylimidazolidin-Z-one, an improved oxidation stability.
  • EXAMPLE 11 99.8 g. of N,N-dioctylimidazolidin-2one and 0.2 g. of benztriazole are mixed. The obtained mixture possesses, compared to the pure compound of the formula I, a lower corrosion action, particularly in the case of copper and its alloys.
  • EXAMPLE l2 97.5 g. of N',N-didodecylimidnzolidin-Z-one. l.5 g. ol'dibutyl phosphite and l g. of phenyl-a-nuphthylamine are mixed by stirring. The obtained mixture exhibits, compared to the pure N,N'-didodecylimidazolidin-2-one, an improved oxidation stability and a better lubricating-film load capacity.
  • composition comprising:
  • a compound of formula I Il -N WhCTCIH X is Um
  • R is alkyl offrom l to 18 carbon atoms;
  • R is alkyl of from 6 to 18 carbon atoms,
  • a lubricating oil thickener in the range from 0 to about 2.
  • the lubricant is selected from organic acid esters, polyarylether, polyalkyl melamines, N-alkyl-cyclohexane-l, 2-dicarboxylic acid imides, high-boiling phosphonic acid esters, high-boiling mineral oils, silicone oils and orthosilicates.
  • component (a) is a mixture of:
  • N,N'-didodecylimidazolidin-Z-one and N,N'-dioctyl-5-methylimidazolidin-2one the former being present in an amount of from about 69 percent to 77 percent and the latter in an amount of about 31 percent to 23 percent, these percentages being by weight calculated on the total weight of the composition.
  • composition as defined in claim 1, wherein said thickener is copper phthalocyanine.

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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)
  • Lubricants (AREA)
US827880A 1968-05-29 1969-05-26 Lubricant, grease and hydraulic fluid Expired - Lifetime US3609080A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH797268A CH496082A (de) 1968-05-29 1968-05-29 Verwendung von heterocyclischen Verbindungen als Schmiermittel und hydraulische Flüssigkeiten

Publications (1)

Publication Number Publication Date
US3609080A true US3609080A (en) 1971-09-28

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ID=4333188

Family Applications (1)

Application Number Title Priority Date Filing Date
US827880A Expired - Lifetime US3609080A (en) 1968-05-29 1969-05-26 Lubricant, grease and hydraulic fluid

Country Status (5)

Country Link
US (1) US3609080A (de)
CH (1) CH496082A (de)
DE (1) DE1927094A1 (de)
FR (1) FR2009607A1 (de)
GB (1) GB1215785A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5730906A (en) * 1996-07-12 1998-03-24 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils (Law406)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3218258A (en) * 1962-11-14 1965-11-16 Rohm & Haas Dispersant compositions
US3301784A (en) * 1964-11-16 1967-01-31 Chevron Res Substituted pyrrolidinones as lubricating oil additives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3218258A (en) * 1962-11-14 1965-11-16 Rohm & Haas Dispersant compositions
US3301784A (en) * 1964-11-16 1967-01-31 Chevron Res Substituted pyrrolidinones as lubricating oil additives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5730906A (en) * 1996-07-12 1998-03-24 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils (Law406)

Also Published As

Publication number Publication date
FR2009607A1 (fr) 1970-02-06
GB1215785A (en) 1970-12-16
CH496082A (de) 1970-09-15
DE1927094A1 (de) 1969-12-04

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