US2438446A - Lubricant and hydraulic fluid composition - Google Patents

Lubricant and hydraulic fluid composition Download PDF

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Publication number
US2438446A
US2438446A US595883A US59588345A US2438446A US 2438446 A US2438446 A US 2438446A US 595883 A US595883 A US 595883A US 59588345 A US59588345 A US 59588345A US 2438446 A US2438446 A US 2438446A
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chlorinated
lubricant
oil
viscosity
hydraulic fluid
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US595883A
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Hollis L Leland
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Standard Oil Development Co
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Standard Oil Development Co
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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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty 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
    • C10M2207/10—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
    • 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
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • 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 an improved oil useful as a lubricant, power transmission medium, hydraulic oil, and for other purposes.
  • the specification deals with the oil and its properties as well as method of the manufacture.
  • lubricating oils and hydraulic oils and the like require an unusual combination of properties which, while they may be obtained singly without great difliculty, are extremely difficult to obtain in certain combinations.
  • Hydrocarbon lubricating oils can be obtained with pour points quite loW, for example, 40 F., and in some instances even lower, but such oils are, of course, highly inflammable and at the same time have extremely steep temperature viscosity curves, that is to say, their temperature-viscosity coefficients are very large.
  • it has been very desirable to produce a hydraulic oil, lubricating oil or power transmitting fluid which'has an extremely low pour point so that it can be used in very cold climates, and at the same time to be possessed of a very flat temperature-viscosity curve.
  • chlorinated aromatic oils may be used as the base or vehicle for such products and they may be thickened and given a flatter viscosity curve by the addition of hydrocarbon polymer thickeners.
  • hydrocarbon polymer thickeners no product which might be said to be highly satisfactory has been produced along these lines.
  • the pour points obtainable are not low enough to be entirely satisfactory andthe viscosity curves are still steeper than desired, at least for the most exacting services.
  • the materials that have been employed as vehicles were the halogenated double ring compounds such as chlorinated diphenyl, chlorinated naphthalene, chlorinated anthracene and the like.
  • single 4 ring aromatic compounds is considerably superior to the previously used double ring compounds for vehicles in this particular service.
  • Such single ring aromatic compounds can be halogenated, for example, chlorinated, and they should contain from 1 to 5 atoms of halogen per mol of the aromatic compound and should average from about 2.5 to 4.0 atoms per mol. It will be understood that these materials will be mixtures resulting from the direct chlorination of the aromatic hydrocarbon.
  • the compounds which are preferred are not merely the simple ring compounds as represented by benzol but are the alkylated single ring compounds containing at least one side chain of about 2 to 4 carbon atoms such as ethyl, propyl and butyl benzenes. Among all the compounds that have been tried oumene has proved to be the most satisfactory.
  • a small amount of a linear polymeric thickener is then added to obtain increase in viscosity and improvement in the shape of the viscosity curve.
  • Materials of this type are represented by polyisobutylene and the polymerized esters of acrylic or methacrylic acids, specifically the esters made from aliphatic alcohols of 2 to 15 carbon atoms. These compounds are known to commerce and preferably those having molecular weights within the range of 1,000 to 15,000 are the grades required for the present material. They are added in a proportion from say 2 to 20%, depending on the degree of thickening required, the oil initially used and the molecular weight of the polymer employed.
  • chlorinated cumene While the chlorinated cumene is not completely incombustible, it burns only very slowly and will not support its own combustion. Increasing the amount of the halogen tends to increase the resistance to combustion and also to raise the boiling temperature of the vehicle. In some instances, it has been iounddesirable to add a relatively small amount of very highly chlorinated products such as cai'bon tetrachloride and perchlorethylene, which tend to improve the low temperature characteristics, and at the same time to increase resistance to burning.
  • compositions may be added to the present composition for special purposes such as oiliness agents, corrosion inhibitors and the like, and dyes and perfumes may be added if there is particular need in the application contemplated.
  • Example 1 Cumene is chlorinated by direct action of chlorine which is bubbled through the liquid at a low temperature, approximately F. in the absence of light with a ferric chloride catalyst in order to introduce the chlorine into the rin instead of the side chain. This is continued so as to obtain a product containing 3.22 atoms of chlorine per mol of cumene. This material is then purified of traces of acidic materials and the first 2 to 5% distillate rejected.
  • This material proved to be an excellent low temperature lubricant and power transmission oil. It had a pour point of '80 F. and a suitable-viscosity. The slope of the viscosity-temperature curve was found to be very fiat as seen from the following data:
  • Example 2 showed the following:
  • composition of matter consisting essen- -tially of nuclearly chlorinated cumenes contain,-
  • V alinear organic polymer thickener selectedfrom the group which consists of polymerized isobutylene, acrylic. acid esters, and methacrylic acid esters, said. polymer thickener having a molecular weight within the range of 1,000 to 1 53.000;
  • composition according to claim 1 which contains from 2 to 20% polyisobutylene having a molecular weight between 1,000 and 15,000.
  • Composition according to claim. 1. which contains from: 2 to 20% of a polymerized ester of acrylic acid,
  • Composition according to claim 1 containing from 2 to. 20% of a polymerized ester of methacrylic. acid. 7 i
  • An oil composition consisting essentially of nuclearly chlorinated cumene and 2 to 20% by weight of an organic'linear polymer thickener selected from the group which consists of poly-- merized isobutylene, acrylicv acid esters, and methacrylic acid. esters, said polymer thickener having a molecular weight. within'the range of' 1,000 to 15,000. 2
  • a composition of matter consisting esseni tially of a nuclearly chlorinated single ring aromatic hydrocarbon containing an alkyl side chain of from 2 to 4 carbon atoms, and-2 to 20% by weight of a linear organic polymer thickener selected from the. group which consists of polymerized isobutylene, acrylic acid esters and methacrylic acid esters, said polymer thickener having a molecular weight within the range'of 1,000 to 15,000. r s

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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

Patented Mar. 23., 1948 LUBRICANT AND HYDRAULIC FLUID COMPOSITION Hollis L. Leland, Cranford, N. .L, assignor to Standard Oil Development Company, a corporation of Delaware No Drawing. Application May 25, 1945, Serial No. 595,883
6 Claims. (01. 252-78) The present invention relates to an improved oil useful as a lubricant, power transmission medium, hydraulic oil, and for other purposes. The specification deals with the oil and its properties as well as method of the manufacture.
For certain uses lubricating oils and hydraulic oils and the like require an unusual combination of properties which, while they may be obtained singly without great difliculty, are extremely difficult to obtain in certain combinations. Hydrocarbon lubricating oils can be obtained with pour points quite loW, for example, 40 F., and in some instances even lower, but such oils are, of course, highly inflammable and at the same time have extremely steep temperature viscosity curves, that is to say, their temperature-viscosity coefficients are very large. For certain purposes it has been very desirable to produce a hydraulic oil, lubricating oil or power transmitting fluid which'has an extremely low pour point so that it can be used in very cold climates, and at the same time to be possessed of a very flat temperature-viscosity curve. Furthermore it would be highly desirable in such an oil to provide a high degree of non-inflammability or at least decrease the flammability so as to reduce the danger of operation. As indicated above, these single properties can be obtained without great difiiculty but it has been found extremely difiicult to obtain fluids possessing all of these properties in combination. Such fluids are particularly valuable for lubricating purposes, hydraulic oils in airplanes, recoil mechanisms and power transmitting devices employing fluid drives, but they are also useful for many other purposes, as will be fully understood.
It has already been suggested that chlorinated aromatic oils may be used as the base or vehicle for such products and they may be thickened and given a flatter viscosity curve by the addition of hydrocarbon polymer thickeners. Heretofore no product which might be said to be highly satisfactory has been produced along these lines. The pour points obtainable are not low enough to be entirely satisfactory andthe viscosity curves are still steeper than desired, at least for the most exacting services. The materials that have been employed as vehicles were the halogenated double ring compounds such as chlorinated diphenyl, chlorinated naphthalene, chlorinated anthracene and the like.
It has now been found that the class of single 4 ring aromatic compounds is considerably superior to the previously used double ring compounds for vehicles in this particular service. Such single ring aromatic compounds can be halogenated, for example, chlorinated, and they should contain from 1 to 5 atoms of halogen per mol of the aromatic compound and should average from about 2.5 to 4.0 atoms per mol. It will be understood that these materials will be mixtures resulting from the direct chlorination of the aromatic hydrocarbon. The compounds which are preferred are not merely the simple ring compounds as represented by benzol but are the alkylated single ring compounds containing at least one side chain of about 2 to 4 carbon atoms such as ethyl, propyl and butyl benzenes. Among all the compounds that have been tried oumene has proved to be the most satisfactory.
To the halogenated product of the type described above, a small amount of a linear polymeric thickener is then added to obtain increase in viscosity and improvement in the shape of the viscosity curve. Materials of this type are represented by polyisobutylene and the polymerized esters of acrylic or methacrylic acids, specifically the esters made from aliphatic alcohols of 2 to 15 carbon atoms. These compounds are known to commerce and preferably those having molecular weights within the range of 1,000 to 15,000 are the grades required for the present material. They are added in a proportion from say 2 to 20%, depending on the degree of thickening required, the oil initially used and the molecular weight of the polymer employed.
While the chlorinated cumene is not completely incombustible, it burns only very slowly and will not support its own combustion. Increasing the amount of the halogen tends to increase the resistance to combustion and also to raise the boiling temperature of the vehicle. In some instances, it has been iounddesirable to add a relatively small amount of very highly chlorinated products such as cai'bon tetrachloride and perchlorethylene, which tend to improve the low temperature characteristics, and at the same time to increase resistance to burning.
Other materials may be added to the present composition for special purposes such as oiliness agents, corrosion inhibitors and the like, and dyes and perfumes may be added if there is particular need in the application contemplated.
In order to more fully understand the present invention, the following examples are given for illustration:
Example 1 Cumene is chlorinated by direct action of chlorine which is bubbled through the liquid at a low temperature, approximately F. in the absence of light with a ferric chloride catalyst in order to introduce the chlorine into the rin instead of the side chain. This is continued so as to obtain a product containing 3.22 atoms of chlorine per mol of cumene. This material is then purified of traces of acidic materials and the first 2 to 5% distillate rejected.
To a sample of this chlorinated product polybutene having a molecular weight of 12,000 was added and gave the following composition:
To this mixture was then added small-quantities of an organic amine inhibitor and an oil:-
soluble metal soap to remove any traces of hydrochloric acid that might be released by hydrolysis.
This material proved to be an excellent low temperature lubricant and power transmission oil. It had a pour point of '80 F. and a suitable-viscosity. The slope of the viscosity-temperature curve was found to be very fiat as seen from the following data:
Centistokes Vis. at 100 F. 36.0 Vis. at 210 F. 11.4
When these data were plotted on the standard A. S. T. M. viscosity chart and the straight line connecting them was drawn, it was observed that the slope was approximately .38, which is unusually flat.
The viscosity data on the chlorinated cumene were as follows: a
' Centistokes Vis. at 100 F. 2.23 Vis. at 210515. .87
The slope of the plot on the A. S. T. M. chart was 1.02.
Example 2 showed the following:
Vis. at 100 F. centistokes 38.6 .Vis. at 210 F ..do 128 Slope of A. S. T. M. curve .38 Pour point F -85 Example 3 For comparison with the above data, there are given the data on a hydrocarbon oil which was made up for similar service and the superiority of the above products canbe readily seen from the following data:
Vis. at 100 F centistokes' 46.8 Vis. at 210 F. do 8.2 A. S. T. M. slope .63
Pour point F --40 I claim:
1. A composition of matter consisting essen- -tially of nuclearly chlorinated cumenes contain,-
ing an average of 2.5 1204.0 atoms of-chlorine per mol of cumene, and 2 to 20% by weight of V alinear organic polymer thickener selectedfrom the group which consists of polymerized isobutylene, acrylic. acid esters, and methacrylic acid esters, said. polymer thickener having a molecular weight within the range of 1,000 to 1 53.000;
' 2. Composition according to claim 1 which contains from 2 to 20% polyisobutylene having a molecular weight between 1,000 and 15,000.
3. Composition according to claim. 1. which contains from: 2 to 20% of a polymerized ester of acrylic acid,
4. Composition according to claim 1 containing from 2 to. 20% of a polymerized ester of methacrylic. acid. 7 i
5. An oil composition consisting essentially of nuclearly chlorinated cumene and 2 to 20% by weight of an organic'linear polymer thickener selected from the group which consists of poly-- merized isobutylene, acrylicv acid esters, and methacrylic acid. esters, said polymer thickener having a molecular weight. within'the range of' 1,000 to 15,000. 2
6. A composition of matter consisting esseni tially of a nuclearly chlorinated single ring aromatic hydrocarbon containing an alkyl side chain of from 2 to 4 carbon atoms, and-2 to 20% by weight of a linear organic polymer thickener selected from the. group which consists of polymerized isobutylene, acrylic acid esters and methacrylic acid esters, said polymer thickener having a molecular weight within the range'of 1,000 to 15,000. r s
V HOLLIS L. LELAND.
REFERENCES CITED The following references are of record: in the file of: this patent: 7
UNITED STATES PATENTS Number V Name I Date; 2,058,899 Matheson Oct. 27, 1936 2,091,627 Bruson- Aug. 31, 1937 2,157,99'1- Brous- May 9 1939. 2,340,946 Ellis Feb. 8, 1944 2,391,092 Horbark Dec. 18, 1945. 2,397,744 Kertesz Apr. 2, 1946 2,413,170 Clark Dec. 24,1946
FOREIGN. PATENTS Number Country Date. 552,056 Great Britain. Mar. 22, 1943 Chem., v01. 32, No. 3,, March 1940, pages 299-304.
US595883A 1945-05-25 1945-05-25 Lubricant and hydraulic fluid composition Expired - Lifetime US2438446A (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2509620A (en) * 1947-05-13 1950-05-30 Shell Dev Nonflammable hydraulic fluid
US2549270A (en) * 1948-07-19 1951-04-17 Shell Dev Lubricant and hydraulic fluid composition
US2583588A (en) * 1949-06-08 1952-01-29 Mosteller James Calvin Less inflammable hydraulic fluid
US2662055A (en) * 1949-08-25 1953-12-08 Texas Co Oil compositions
US3129186A (en) * 1961-03-24 1964-04-14 Westinghouse Electric Corp Damping and flotation fluid
US3136726A (en) * 1957-06-28 1964-06-09 Douglas Aircraft Co Inc Fire-resistant hydraulic fluid and lubricant

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2058899A (en) * 1932-12-01 1936-10-27 Standard Oil Dev Co Viscous liquid for use in shock absorbers
US2091627A (en) * 1934-06-08 1937-08-31 Rohm & Haas Composition of matter and process
US2157997A (en) * 1938-06-16 1939-05-09 Goodrich Co B F Method of treating polyvinyl halides
GB552056A (en) * 1941-09-15 1943-03-22 Du Pont Improvements in or relating to power transmission devices
US2340946A (en) * 1940-07-16 1944-02-08 Jasco Inc Quick-drying printing ink
US2391092A (en) * 1942-06-09 1945-12-18 Celanese Corp Polystyrene sheet material
US2397744A (en) * 1944-07-01 1946-04-02 Du Pont Metallic coating composition and structure produced therefrom
US2413170A (en) * 1943-04-01 1946-12-24 Gen Electric Liquid stable at low temperatures

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2058899A (en) * 1932-12-01 1936-10-27 Standard Oil Dev Co Viscous liquid for use in shock absorbers
US2091627A (en) * 1934-06-08 1937-08-31 Rohm & Haas Composition of matter and process
US2157997A (en) * 1938-06-16 1939-05-09 Goodrich Co B F Method of treating polyvinyl halides
US2340946A (en) * 1940-07-16 1944-02-08 Jasco Inc Quick-drying printing ink
GB552056A (en) * 1941-09-15 1943-03-22 Du Pont Improvements in or relating to power transmission devices
US2391092A (en) * 1942-06-09 1945-12-18 Celanese Corp Polystyrene sheet material
US2413170A (en) * 1943-04-01 1946-12-24 Gen Electric Liquid stable at low temperatures
US2397744A (en) * 1944-07-01 1946-04-02 Du Pont Metallic coating composition and structure produced therefrom

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2509620A (en) * 1947-05-13 1950-05-30 Shell Dev Nonflammable hydraulic fluid
US2549270A (en) * 1948-07-19 1951-04-17 Shell Dev Lubricant and hydraulic fluid composition
US2583588A (en) * 1949-06-08 1952-01-29 Mosteller James Calvin Less inflammable hydraulic fluid
US2662055A (en) * 1949-08-25 1953-12-08 Texas Co Oil compositions
US3136726A (en) * 1957-06-28 1964-06-09 Douglas Aircraft Co Inc Fire-resistant hydraulic fluid and lubricant
US3129186A (en) * 1961-03-24 1964-04-14 Westinghouse Electric Corp Damping and flotation fluid

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