US2509620A - Nonflammable hydraulic fluid - Google Patents

Nonflammable hydraulic fluid Download PDF

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Publication number
US2509620A
US2509620A US747844A US74784447A US2509620A US 2509620 A US2509620 A US 2509620A US 747844 A US747844 A US 747844A US 74784447 A US74784447 A US 74784447A US 2509620 A US2509620 A US 2509620A
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Prior art keywords
parts
hydraulic
compositions
viscosity index
compounds
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US747844A
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English (en)
Inventor
Forrest J Watson
Rupert C Morris
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Shell Development Co
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Shell Development Co
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Priority to FR966140D priority Critical patent/FR966140A/fr
Priority to US747844A priority patent/US2509620A/en
Application filed by Shell Development Co filed Critical Shell Development Co
Priority to GB11798/48A priority patent/GB656854A/en
Priority to NL140410A priority patent/NL71899C/xx
Publication of US2509620A publication Critical patent/US2509620A/en
Application granted granted Critical
Priority to GB186/54A priority patent/GB759284A/en
Priority to FR1091127D priority patent/FR1091127A/fr
Priority to NL184080A priority patent/NL91728C/xx
Priority to BE525466D priority patent/BE525466A/xx
Priority to DEN8267A priority patent/DE939523C/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
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Definitions

  • This invention relates to oleaginous compositions, and particularly to compositions suitable for use as hydraulic fluids and/or insulating oils. More specifically, the invention is concerned with nonflammable synthetic oils having excellent viscosity indices.
  • Mineral oils have for many years been universally used as bases for lubricants and for hydraulic fluids. This has been due in large part to the abundant supplies of petroleum and to the fact that with improved means of refinement, and through treatment with chemical .addition agents, it has been possible to modify or overcome some of the inherent properties of these oils which are undesirable for a number of purposes involving lubrication, electrical insulation, etc.
  • the structural complexity of petroleum oils, and their relations of the chemical and physical properties are conducive to many problems in performance. have relatively poor viscosity indices. This property may at times be improved to a limited degree by the addition of certain materials which raise the viscosity index.
  • the essential bases which comprise hydraulic fluids of the present composition are substantially completely halogenated organic compounds which are liquid at normal temperatures.
  • normal temperatures is meant temperatures varying from about 20- C. to about 200 C.
  • These include chlorinated, brominated, iodinated and fiuorinated organic compounds, especially the fully halogenated lower hydrocarbons (whether saturated or unsaturated) wherein substantially all of the hydrogen atoms have been replaced by the same or different halogen atoms.
  • the compound most suitable for use in the subject hydraulic fluid is hexachlorobutadiene.
  • Other suitable bases for the present composition include hexachloropropylene, hexabrornopropylene, as well as their fully halogenated homologs and analogs.
  • Viscosity index improving agents It was appreciated that mineral oils could be modified by a variety of substances in order to improve the viscosity indices thereof. However, it was found that the action of many of these modifying substances was specific to mineral oil alone and that for the most part such modifiers had substantially no effect upon the viscosity in dices of fully halogenated carbon compounds. However, it was discovered that two classes of substances form highly effective agents for the improvement of the viscosity indices of fully halogenated organic compounds, namely, highly polymerized olefins and polymerized unsaturated esters.
  • Suitable polymerized olenns include polyisobutylene, polystyrene, polyindene, polymerized 1,3-butadiene and polyisoprene.
  • the more satisfactory polymers for the present use are those obtained by polymerizing esters of run saturated acids, especially esteriiied methacrylic and more particularly, those in which the alcohol portion of the ester contains from about a to about 16 carbon atoms.
  • Corrosion inhibitors One of the essential features of oleaginous compositions, especially when used for such purposes as hydraulic fluids or insulating oils is that they be of low, preferably negligible corrosivity. Especially when such compositions are employed as hydraulic fluids, it is an essential feature thereof that the corrosion characteristics be so low that the relatively moving parts of the hydraulic apparatus are not corroded during extended period of use. Any appreciable amount of corrosion whatsoever in a hydraulic apparatus such as landinggear might be fatal in its consequences to the safety of an aircraft and its passengers.
  • halogenated epoxides such as epichlorohydrin.
  • Another highly satisfactory class of unsaturated corrosion inhibitors for halogenated compounds are the epoxides containing at least one unsaturated hydrocarbon group such as butadiene monoxide, and styrene oxide.
  • a third type of satisfactory corrosion inhibitor includes the glycidyl cycloaliphatic ethcrs such as glycidylcyclohexyl ether and substituted derivatives thereof such as the alkylated glycidylcyclohexyl ethers.
  • a fourth type of corrosion inhibitor for use in the present composition is the glycidyl aromatic ether such as glycidylphenyl ether and its alkylated derivatives, alkyl groups being substituted either in the glycidyl or on the aromatic radical.
  • Two other types of corrosion inhibitors which substantially reduce the corrosion characteristics of fully halogenated carbon compounds are the condensates of aldehydes with phenols such as the condensates of formaldehyde such as para-octylphenol, and the metallic salts of alkylated aromatic acids such as zinc or magnesium disopropylsalicylate.
  • a further accomplishment of this addition is the adjustment of the viscosity of these compositions to a desired degree for a specific purpose.
  • mineral oils may be added having a suitable viscosity from about that of gas oil to about that of heavy lubricating 011, depending upon the viscosity of the composition which is required.
  • the flammability of the resulting composition is substantially that of the unmodified fully halogenated carbon compounds. As greater amounts than those specified above are employed the composition becomes more and more inflammable.
  • the mineral oils added to modify the wear characteristics, density and/or viscosity of the hydraulic fluids may contain any of the well known additives employed with mineral oil such as oxidationinhibitors, corrosion inhibitors, viscosity index improvers, pour point depressants,
  • the hy-- draulic fluid contains more than about parts of mineral oil per 100 parts of the fully halogenated carbon compound it is desirable to modify the oil with a viscosity index improving agent.
  • a viscosity index improving agent may includes the two types specified above but any of the other well known types of viscosity index improvers may be used for this purpose.
  • Partially halogenated organic compounds It is known according to past experience that other partially halogenated organic compounds contain a certain amount of non-flammability, but for maximum safety, such compounds can not be used as hydraulic fluids when substantially complete non-flammability is highly desirable. This is especially true of hydraulic fluids used in aircraft equipment.
  • partially halogenated organic compounds and particularly partially halogenated hydrocarbons may be included in the composition if desired up to about 50 parts per 100 parts of the fully halogenated organic compound without appreciably impairing the flammability of the resulting composition.
  • halogenated hydrocarbons include the partially chlorinated aromatic hydrocarbons such as-partially chlorinated benzene, diphenyl, naphthalene or their derivatives such as alkylated, arylated. or alkyarylated aromatic hydrocarbons. Suitable examples of this variety include especially trichlorocumene, 2,2-dichlorophenol. 3,5-dichloronaphthalene, and 1,3-dichlorobenzene. If amounts of the partially halogenated hydrocarbons are increased by the limit set above the resulting composition becomes increasingly flammable and less suitable for uses where maximum safety is a major requirement.
  • Oxidation inhibitors While the compositions of the present invention ordinarily have satisfactory oxidation stabilization it has been found that the addition of substituted phenols, amino phenols, and aromatic amines, appreciably improve the stability of the composition especially when the latter are subject to attack by oxygen. Under normal conditions, such as in full enclosed hydraulic systems, hydraulic fluid is not subject to oxygen attack, but, for storage purposes and under more Tl stringent use the inclusion of 0.5-5 parts of the above types of inhibitors per 100 parts of fully halogenated organic compounds is desirable.
  • compositions according to the present invention include the polymerized C4 to C9 unsaturated hydrocarbons and polymerized esters of C4 to Cm alcohols with an acid of the acrylic acid series, said polymer being present in an amount between improving polymer oi the group consisting of following ingredients: 5 2 and 15 parts by weight per 100 parts 01' said major ingredient. Com mm parts by 5.
  • An hydraulic fluid according to claim 4 conweigh taming 0.5-5 parts by weight, per 100 parts of 100 said major ingredient, of a corrosion inhibitor r a compound m of the group consisting of halogenated epoxides, iii?fiieifiiif ifio tfiyiiirifi tdiiiii 2-15 unsaturated epoxides, glycidyl cycloaliphatic g gigg g f Select from the group (Embed H ethers, glycidyl aromatic ethers, phenol-aldehyde Extreme pressure agentsasdcscribed above 0-15 COIIdEIISBJtBS, and metallic Salts Of alkylated aror zi r t i a li l ialogcnated organic compound 81% matic acids I ijexidotign Inhibitors .IIIIIIIIIIIIIIIII 0-5 i6 6.
  • a substantially non-flammable hydraulic fluid consisting essentially of an organic com-
  • S id Compound lowing composition is highly desirable: 233 q v trarilsg Of f om i 0 C.
  • The'iollowing examples are specific composi- I.
  • Cer fluid consisting essentially of an organic comtain data accompany the compositions.
  • the pound containing only halogen and carbon atoms wear test referred to in Example 5 is described as the major ingredient thereof, said compound by Boerlage in Engineering June 13, 1933. so being a liquid over the range C. to 200 0.,
  • Example 1 2 3 4- 5 Hexachlorobutadiene 9o so so 67.5 Hexachloropropylene 90 Chlorinated diphenyl 9 Poly (methacrylic ester) l0 l0 10 10 8. 5 Transformer mineral oil 19 Giyoidylcyclohexyl ether l Trioctyl phosphate. 10 6 Viscosity, cs. at 100 12.33 13.65 14.23 13.37 14.31 Viscosity Index 237 222 222 229 224 Pour Point, "F less than 65 less than -65 Wear test, mm. scar diameter" 0.36
  • a substantially non-flammable hydraulic group consisting of polymerized C4 to C9 unsatflllid Consisting essentially the following urated hydrocarbons and polymerized esters oi gredient in sta y the S d Proportions: C4 to C16 alcohols and an acid of the acrylic acid Parts by weight, series, said polymer being present in an amount Hexachlorobutadiene 100 between 2 and 15 parts by weight per 100 parts Polymerized ester of methacrylic acid 245 of said major ingredient. Glycidyl cyclohexyl ether 0.5-5 8.
  • a substantially non-flammable hydraulic pqlymerized of methacrync 2-15 fluid consisting essentially of hexachlorobuta Mmeml on diene as the major ingredient thereof and from An extreme i i agent selected i 2 to 15 parts by weight, per 100 parts of hexa- 05 the F of Sulfunzed chlorobutadiene, of a viscosity index improving mal Sulfunzed Vegetable polymerized ester of methacrylic acid with an alky 1 p p afndatnary phosphate- 3-15 alcohol having from 4 to 16 carbon atoms.
  • a cormslon i m selected from h 4.
  • a substantially non-flammable hydraulic gr9up conslstmg of halpgenated fluid consisting essentially of an organic com- X1de'a.nm1atumted epoxlde aglycldyl pound containing only chlorine and carbon cycloallphatic ether, a glycidyl aromatic atoms as the major ingredient thereof, said ether a Phenolaldehyde condensate and compound being a liquid over the range of a metallic salt of an alkylated aromatic from 20 c. to 200" 0., and a viscosity index acid II 10.
  • a substantially non-flammable hydraulic 9 fluid consisting essentially of the following ingredients in substantially the stated proportions:
  • Hexachlorobutadiene 100 Polymerized ester of methacrylic acid 2-15 Chlorinated diphenyl -50 Organic phosphate selected from the group consisting of a trialkyl phosphate and a triaryl phosphate 3-15 Metallic salt of an alkylated aromatic acid- 0.5-5
  • a substantially non-flammable hydraulic fluid consisting essentially of the following composition: 80 parts by weight hexachlorobutadiene, 9 parts by weight chlorinated diphenyl, 10 parts by weight of a polymerized ester of methacrylic acid and 1 part by weight of glycidyl cyclohexyl ether.
  • a substantially non-flammable hydraulic fluid consisting essentially of the following com position: 90 parts by weight hexachloropropylene and 10 parts by weight of a polymerized ester of methacrylic acid.
  • a substantially non-flammable hydraulic fluid consisting essentially of hexachlorobutadiene as the major ingredient thereof and from 2 to parts by weight per 100 parts of hexachlorobutadiene of a viscosity index improving polymer 0! the group consisting of (a) polymerized C4 to Co unsaturated hydrocarbons and (b) polymerized esters of C4 to C15 alcohols and an acid of the acrylic acid series, and 0-50 parts by weight per parts of hexachlorobutadiene of chlorinated dlphenyl.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US747844A 1947-05-13 1947-05-13 Nonflammable hydraulic fluid Expired - Lifetime US2509620A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
FR966140D FR966140A (fr) 1947-05-13
US747844A US2509620A (en) 1947-05-13 1947-05-13 Nonflammable hydraulic fluid
GB11798/48A GB656854A (en) 1947-05-13 1948-04-29 Oleaginous compositions particularly suitable for use as hydraulic fluids and/or insulating oils
NL140410A NL71899C (fr) 1947-05-13 1948-05-12
GB186/54A GB759284A (en) 1947-05-13 1954-01-04 Improvements in or relating to lubricating compositions
BE525466D BE525466A (fr) 1947-05-13 1954-01-04
FR1091127D FR1091127A (fr) 1947-05-13 1954-01-04 Compositions lubrifiantes
NL184080A NL91728C (fr) 1947-05-13 1954-01-04
DEN8267A DE939523C (de) 1947-05-13 1954-01-05 Schmiermittel auf Esterbasis

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US747844A US2509620A (en) 1947-05-13 1947-05-13 Nonflammable hydraulic fluid
US759284XA 1953-01-05 1953-01-05

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US2509620A true US2509620A (en) 1950-05-30

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Country Status (6)

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US (1) US2509620A (fr)
BE (1) BE525466A (fr)
DE (1) DE939523C (fr)
FR (2) FR1091127A (fr)
GB (2) GB656854A (fr)
NL (2) NL71899C (fr)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2636861A (en) * 1950-06-09 1953-04-28 Shell Dev Hydraulic fluid
US2683120A (en) * 1950-08-29 1954-07-06 Standard Oil Dev Co Hydraulic transmission fluids
US2686760A (en) * 1951-10-27 1954-08-17 Shell Dev Hydraulic fluids and lubricating compositions
US2707176A (en) * 1951-01-15 1955-04-26 Monsanto Chemicals Tricresyl phosphate-chlorinated biphenyl functional fluid improved by alkylated polystyrene
DE950805C (de) * 1953-07-17 1956-10-18 Shell Res Ltd Nichtentflammbare hydraulische Fluessigkeit
US2842497A (en) * 1953-01-05 1958-07-08 Shell Dev Phosphorus esters containing diarylamines and polyepoxypolyhydroxy polyethers
US2851421A (en) * 1951-08-07 1958-09-09 Pure Oil Co Power transmission fluids
US2933449A (en) * 1956-09-21 1960-04-19 Douglas Aircraft Co Inc Functional fluid and lubricant
US2934501A (en) * 1952-10-20 1960-04-26 Douglas Aircraft Co Inc Fire-resistant functional fluid and lubricant composition
US2961408A (en) * 1957-06-14 1960-11-22 Shell Oil Co Power transmission mineral oil base fluids
US3031410A (en) * 1958-06-10 1962-04-24 Detrex Chem Ind Composition and method of inhibiting corrosion of ferrous metals by amine-stabilized unsaturated chlorinated hydrocarbons
US3075040A (en) * 1957-07-26 1963-01-22 Siemens Ag Method for improving the electric strength and flash-over or glowdischarge resistance of olefine polymers
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
US3496107A (en) * 1969-03-13 1970-02-17 Fmc Corp Fire-resistant functional fluids
US3793207A (en) * 1971-11-05 1974-02-19 Chevron Res Fire-resistant hydraulic fluid
US3862048A (en) * 1972-05-01 1975-01-21 Mc Donnell Douglas Corp Functional fluid compositions
US3865743A (en) * 1972-05-01 1975-02-11 Mc Donnell Douglas Corp Functional fluids
US3873464A (en) * 1970-12-28 1975-03-25 Mobil Oil Corp Flame resistant hydraulic fluid
US6156228A (en) * 1994-11-16 2000-12-05 Houghton International, Inc. Trialkoxyalkylphosphate-based fire resistant fluid containing triglyceride

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3127353A (en) * 1958-07-15 1964-03-31 Lubricating compositions
DE1218097B (de) * 1961-04-01 1966-06-02 Bayer Ag Hydraulikoele
US3637507A (en) * 1968-02-12 1972-01-25 Stauffer Chemical Co Aircraft hydraulic fluid and method of controlling acid buildup therein with acid acceptor

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1082528A (en) * 1913-08-08 1913-12-30 Matthew Albert Hunter Low-freezing liquid.
GB418230A (en) * 1932-04-22 1934-10-22 Ig Farbenindustrie Ag New or improved compositions comprising chlorinated organic substances
US2017089A (en) * 1934-07-16 1935-10-15 Wagner Electric Corp Operating fluid for hydraulic transmission
US2102825A (en) * 1935-03-06 1937-12-21 Du Pont Hydraulic fluids
US2408983A (en) * 1943-01-25 1946-10-08 Union Oil Co Composition of matter suitable as a hydraulic fluid
US2413170A (en) * 1943-04-01 1946-12-24 Gen Electric Liquid stable at low temperatures
US2423927A (en) * 1942-05-22 1947-07-15 Standard Oil Co Constant viscosity hydraulic fluid compositions
US2438446A (en) * 1945-05-25 1948-03-23 Standard Oil Dev Co Lubricant and hydraulic fluid composition

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL66836C (fr) * 1943-09-15
NL142969B (nl) * 1947-10-28 Monsanto Co Werkwijze voor het bereiden van een mengsel, dat polyvinylchloride en/of een of meer vinylchloridevinylacetaatcopolymeren en een ftalaat als weekmaker bevat.

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1082528A (en) * 1913-08-08 1913-12-30 Matthew Albert Hunter Low-freezing liquid.
GB418230A (en) * 1932-04-22 1934-10-22 Ig Farbenindustrie Ag New or improved compositions comprising chlorinated organic substances
US2017089A (en) * 1934-07-16 1935-10-15 Wagner Electric Corp Operating fluid for hydraulic transmission
US2102825A (en) * 1935-03-06 1937-12-21 Du Pont Hydraulic fluids
US2423927A (en) * 1942-05-22 1947-07-15 Standard Oil Co Constant viscosity hydraulic fluid compositions
US2408983A (en) * 1943-01-25 1946-10-08 Union Oil Co Composition of matter suitable as a hydraulic fluid
US2413170A (en) * 1943-04-01 1946-12-24 Gen Electric Liquid stable at low temperatures
US2438446A (en) * 1945-05-25 1948-03-23 Standard Oil Dev Co Lubricant and hydraulic fluid composition

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2636861A (en) * 1950-06-09 1953-04-28 Shell Dev Hydraulic fluid
US2683120A (en) * 1950-08-29 1954-07-06 Standard Oil Dev Co Hydraulic transmission fluids
US2707176A (en) * 1951-01-15 1955-04-26 Monsanto Chemicals Tricresyl phosphate-chlorinated biphenyl functional fluid improved by alkylated polystyrene
US2851421A (en) * 1951-08-07 1958-09-09 Pure Oil Co Power transmission fluids
US2686760A (en) * 1951-10-27 1954-08-17 Shell Dev Hydraulic fluids and lubricating compositions
US2934501A (en) * 1952-10-20 1960-04-26 Douglas Aircraft Co Inc Fire-resistant functional fluid and lubricant composition
US2842497A (en) * 1953-01-05 1958-07-08 Shell Dev Phosphorus esters containing diarylamines and polyepoxypolyhydroxy polyethers
DE950805C (de) * 1953-07-17 1956-10-18 Shell Res Ltd Nichtentflammbare hydraulische Fluessigkeit
US2933449A (en) * 1956-09-21 1960-04-19 Douglas Aircraft Co Inc Functional fluid and lubricant
US2961408A (en) * 1957-06-14 1960-11-22 Shell Oil Co Power transmission mineral oil base fluids
US3136726A (en) * 1957-06-28 1964-06-09 Douglas Aircraft Co Inc Fire-resistant hydraulic fluid and lubricant
US3075040A (en) * 1957-07-26 1963-01-22 Siemens Ag Method for improving the electric strength and flash-over or glowdischarge resistance of olefine polymers
US3031410A (en) * 1958-06-10 1962-04-24 Detrex Chem Ind Composition and method of inhibiting corrosion of ferrous metals by amine-stabilized unsaturated chlorinated hydrocarbons
US3129186A (en) * 1961-03-24 1964-04-14 Westinghouse Electric Corp Damping and flotation fluid
US3496107A (en) * 1969-03-13 1970-02-17 Fmc Corp Fire-resistant functional fluids
US3873464A (en) * 1970-12-28 1975-03-25 Mobil Oil Corp Flame resistant hydraulic fluid
US3793207A (en) * 1971-11-05 1974-02-19 Chevron Res Fire-resistant hydraulic fluid
US3862048A (en) * 1972-05-01 1975-01-21 Mc Donnell Douglas Corp Functional fluid compositions
US3865743A (en) * 1972-05-01 1975-02-11 Mc Donnell Douglas Corp Functional fluids
US6156228A (en) * 1994-11-16 2000-12-05 Houghton International, Inc. Trialkoxyalkylphosphate-based fire resistant fluid containing triglyceride
US6521142B1 (en) 1994-11-16 2003-02-18 Houghton Technical Corp. Fire-resistant hydraulic fluid compositions

Also Published As

Publication number Publication date
DE939523C (de) 1956-02-23
NL71899C (fr) 1953-03-16
NL91728C (fr) 1959-08-15
FR966140A (fr) 1950-09-30
BE525466A (fr) 1956-05-25
FR1091127A (fr) 1955-04-07
GB656854A (en) 1951-09-05
GB759284A (en) 1956-10-17

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