US3282847A - Hydraulic fluids - Google Patents

Hydraulic fluids Download PDF

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Publication number
US3282847A
US3282847A US475571A US47557165A US3282847A US 3282847 A US3282847 A US 3282847A US 475571 A US475571 A US 475571A US 47557165 A US47557165 A US 47557165A US 3282847 A US3282847 A US 3282847A
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Prior art keywords
phosphoric acid
ester
group
parts
monochloride
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US475571A
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Schneider Karl
Kauczor Hans-Werner
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Bayer AG
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Bayer AG
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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
    • C10M3/00—Liquid 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
    • 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
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/043—Ammonium or amine salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • the present invention relates to hydraulic fluids; more particularly it concerns hydraulic fluids based on arylor alkylaryl esters of phosphoric acid, which possess an active amount of the amides produced from aliphatic or araliphatic amines and halides of partially esterified phosphoric acid.
  • Suitable amides are for example obtainable by reacting, preferably in a molecular proportion of 1:24, phosphoric acid diphenyl ester monochloride, phosphoric acid octyl phenyl ester monochloride, phosphoric acid dicresyl ester monochloride, and phosphoric acid dicresyl ester monobromide with aliphatic or araliphatic amines, such as e.g.
  • the content of the amides in the hydraulic fluids amounts in general to 0.1 to 15 percent by Weight, preferably 0.5 to 5 percent by weight.
  • chlorinated hydrocarbons such as chlorinated paraflin, chlorinated diphenyl, and chlorinated terphenyl
  • polyethers such as those from tetrahydrofuran and 1,2-oxide compounds
  • the hydraulic fluids can also contain further additives, usual for hydraulic fluids, e.g. stabilizers, thickeners, antifoaming agents, anticorrosives and de-emulsifiers.
  • the hydraulic fluids of the present invention possess outstanding lubricant properties. On account of the content of the amides herein before defined only very small frictional forces are set up even in the range of boundary lubrication.
  • the parts given in the following table are by weight.
  • Tricresyl phosphate 260 Mixture of 98 parts of tricresyl phosphate and 2 parts of the amide produced from phosphoric acid diphenyl ester monochloride and dodecylamine 150
  • (II) Mixture of 50 parts of tricresyl phosphate and 50 parts of tetrachlorodiphenyl 240 Mixture of 49 parts of tricresyl phosphate, 49 parts of tetrachlorodiphenyl, and 2 parts of the amide produced from phosphoric acid diphenyl ester monochloride and dodecylamine 170 Measured at 1000 kg. applied pressure on the Almen-Wieland machine. Cf. Zerbe, Mineraltile 'und verwaudte Kunststoff Patented Nov. 1, 1966 The amide applied was produced from phosphoric acid diphenyl ester monochloride and dodecylamine in the following manner:
  • a fluid composition consisting essentially of (A) a hydraulic fluid consisting of a member selected from the group consisting of aryl ester and an alkylaryl ester of phosphoric acid and (B) about .1-15 by weight of an amide additive obtained by reacting (a) a component selected from the group consisting of Z-ethyl hexylamine, n octylamine, di n butyl amine, dodecylamine, oleyl amine, stearyl amine, benzylamine, and w-phenyldodecylamine with (b) a component selected from the group consisting of phosphoric acid diphenyl ester mono-chloride, phosphoric acid octyl phenyl ester monochloride, phosphoric acid dicresyl ester monochloride, and phosphoric acid dicresyl ester m-onobromide, the molar proportion of (b) to (a
  • composition of claim 1 containing at least one additional additive in a flame-retarding amount, the additive being a member selected from the group consisting of tetrachlorodiphenyl, and a copolymerization product of tetrahydrofuran, ethylene oxide and 1,2-propylene oxide, said copolymerization product possessing an average molecular weight of 6000.
  • propylene oxide and 2 parts of the amide produced by reacting phosphoric acid diphenyl ester monochloride with dodecylarnine.

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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)

Description

United States Patent 3,282,847 HYDRAULIC FLUIDS Karl Schneider, Leverkusen, and Hans-Werner Kauczor, Cologne, Germany, assignors to Farbeufabriken Bayer Aktiengesellschaft, Leverkusen, Germany, a corporation of Germany No Drawing. Filed July 28, 1965, Ser. No. 475,571 Claims. (Cl. 252-78) The present invention relates to hydraulic fluids; more particularly it concerns hydraulic fluids based on arylor alkylaryl esters of phosphoric acid, which possess an active amount of the amides produced from aliphatic or araliphatic amines and halides of partially esterified phosphoric acid.
This application is a continuation-in-part application of our co-pending application Serial No. 182,977, filed March 21, 1962, and now abandoned.
Suitable amides are for example obtainable by reacting, preferably in a molecular proportion of 1:24, phosphoric acid diphenyl ester monochloride, phosphoric acid octyl phenyl ester monochloride, phosphoric acid dicresyl ester monochloride, and phosphoric acid dicresyl ester monobromide with aliphatic or araliphatic amines, such as e.g. Z-ethylhexylamine, n-octylamine, di-n-butyl amine, dodecylamine, oleylamine, stearylamine, benzylamine, and w-phenyldodecylamine, with heating if required, in an inert organic solvent, in which the simultaneously formed hydrochlorides of the amines are insoluble, for instance in ligroin, removing the salts and'evaporating the solvent.
The content of the amides in the hydraulic fluids amounts in general to 0.1 to 15 percent by Weight, preferably 0.5 to 5 percent by weight.
If desired, chlorinated hydrocarbons, such as chlorinated paraflin, chlorinated diphenyl, and chlorinated terphenyl, or polyethers, such as those from tetrahydrofuran and 1,2-oxide compounds, can be added to the hydraulic fluids in order to improve the non-inflammability or the viscosity temperature characteristics. The hydraulic fluids can also contain further additives, usual for hydraulic fluids, e.g. stabilizers, thickeners, antifoaming agents, anticorrosives and de-emulsifiers.
The hydraulic fluids of the present invention possess outstanding lubricant properties. On account of the content of the amides herein before defined only very small frictional forces are set up even in the range of boundary lubrication. The parts given in the following table are by weight.
TABLE Friction in kg,
(I) Tricresyl phosphate 260 Mixture of 98 parts of tricresyl phosphate and 2 parts of the amide produced from phosphoric acid diphenyl ester monochloride and dodecylamine 150 (II) Mixture of 50 parts of tricresyl phosphate and 50 parts of tetrachlorodiphenyl 240 Mixture of 49 parts of tricresyl phosphate, 49 parts of tetrachlorodiphenyl, and 2 parts of the amide produced from phosphoric acid diphenyl ester monochloride and dodecylamine 170 Measured at 1000 kg. applied pressure on the Almen-Wieland machine. Cf. Zerbe, Mineraltile 'und verwaudte Produkte Patented Nov. 1, 1966 The amide applied was produced from phosphoric acid diphenyl ester monochloride and dodecylamine in the following manner:
Within one hour 670 g. (3.6 mol) of dodecylamine were added dropwise to a solution of 472 g. (1.75 mol) of phosphoric acid diphenyl ester monochloride in 500 com. of ligroin while the reaction temperature was kept at 3540 C. by cooling. Thereupon the reaction mixture was stirred at room temperature for a further three hours, then shaken three times with 2 normal sodium hydroxide solution and finally distilled in vacuo. After the solvent and the excess of dodecylamine were distilled off the amide produced distilled at 210-270" C./0.5 mm. Hg. The yield amounted to 823 g.
Similar favourable results are obtained if instead of the amide produced from phosphoric acid diphenyl ester monochloride and dodecylamine the other amides are applied which are obtainable in the same manner as herein before described from the amines and partially esterified phosphoric acid halides mentioned above.
We claim:
1. A fluid composition consisting essentially of (A) a hydraulic fluid consisting of a member selected from the group consisting of aryl ester and an alkylaryl ester of phosphoric acid and (B) about .1-15 by weight of an amide additive obtained by reacting (a) a component selected from the group consisting of Z-ethyl hexylamine, n octylamine, di n butyl amine, dodecylamine, oleyl amine, stearyl amine, benzylamine, and w-phenyldodecylamine with (b) a component selected from the group consisting of phosphoric acid diphenyl ester mono-chloride, phosphoric acid octyl phenyl ester monochloride, phosphoric acid dicresyl ester monochloride, and phosphoric acid dicresyl ester m-onobromide, the molar proportion of (b) to (a) being about 1:24.
2. The composition of claim 1 containing at least one additional additive in a flame-retarding amount, the additive being a member selected from the group consisting of tetrachlorodiphenyl, and a copolymerization product of tetrahydrofuran, ethylene oxide and 1,2-propylene oxide, said copolymerization product possessing an average molecular weight of 6000.
3. A fluid composition containing 98 parts of tricresyl phosphate and 2 parts of the amide produced by reacting phosphoric acid diphenyl ester monochloride with dodecylamine.
4. A fluid composition containing 49 parts of tricresyl phosphate, 49 parts tetrachlorodiphenyl, and 2 parts of the amide produced by reacting phosphoric acid diphenyl ester monochloride with dodecylamine.
3 5. A fluid composition containing 95 parts of diphenyl Xylenyl phosphate; 3 parts of a polyether having an average molecular weight of 6000 produced by copolymerization of (a) tetrahydrofuran (b) ethylene oxide and 1,2-'
propylene oxide; and 2 parts of the amide produced by reacting phosphoric acid diphenyl ester monochloride with dodecylarnine.
References Cited by the Examiner UNITED STATES PATENTS 2,933,449 4/1960 Moreton 25278 X 5 LEON D. ROSDOL, Primary Examiner.
JULIUS GREENWALD, ALBERT T. MEYERS,
10 R. D. LOVERING, Assistant Examiner.
Examiners.

Claims (1)

1. A FLUID COMPOSITION CONSISTING ESSENTIALLY OF (A) A HYDRAULIC FLUID CONSISTING OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF ARYL ESTER AND AN ALKYLARYL ESTER OF PHOSPHORIC ACID AND (B) ABOUT .1-15% BY WEIGHT OF AN AMIDE ADDITIVE OBTAINED BY REACTING (A) A COMPONENT SELECTED FROM THE GROUP CONSISTING OF 2-ETHYL HEXYLAMINE, N-OCTYLAMINE, DI-N-BUTYL AMINE, DODECYLAMINE, OLEYLAMINE, STEARYL AMINE, BENZYLAMINE, AND W-PHENYLDODECYLAMINE WITH (B) A COMPONENT SELECTED FROM THE GROUP CONSISTING OF PHOSPHORIC ACID DIPHENYL ESTER MONO-CHLORIDE, PHOSPHORIC ACID OCTYL PHENYL ESTER MONOCHLORIDE, PHOSPHORIC ACID DICRESYL ESTER MONOCHLORIDE, AND PHOSPHORIC ACID DICRESYL ESTER MONOBROMIDE, THE MOLAR PROPORTION OF (B) TO (A) BEING ABOUT 1:2-4.
US475571A 1965-07-28 1965-07-28 Hydraulic fluids Expired - Lifetime US3282847A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3468802A (en) * 1965-11-24 1969-09-23 Mc Donnell Douglas Corp Corrosion inhibited hydraulic fluids
US3873464A (en) * 1970-12-28 1975-03-25 Mobil Oil Corp Flame resistant hydraulic fluid

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2933449A (en) * 1956-09-21 1960-04-19 Douglas Aircraft Co Inc Functional fluid and lubricant
US2994638A (en) * 1958-02-20 1961-08-01 Bayer Ag Agent for combating rodents
US2995596A (en) * 1956-09-01 1961-08-08 Benckiser Gmbh Joh A Production of phosphoric aciddialkylester-amines
US3056745A (en) * 1957-04-30 1962-10-02 Bayer Ag Hydraulic oil compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2995596A (en) * 1956-09-01 1961-08-08 Benckiser Gmbh Joh A Production of phosphoric aciddialkylester-amines
US2933449A (en) * 1956-09-21 1960-04-19 Douglas Aircraft Co Inc Functional fluid and lubricant
US3056745A (en) * 1957-04-30 1962-10-02 Bayer Ag Hydraulic oil compositions
US2994638A (en) * 1958-02-20 1961-08-01 Bayer Ag Agent for combating rodents

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3468802A (en) * 1965-11-24 1969-09-23 Mc Donnell Douglas Corp Corrosion inhibited hydraulic fluids
US3873464A (en) * 1970-12-28 1975-03-25 Mobil Oil Corp Flame resistant hydraulic fluid

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