US3779930A - Fluids - Google Patents

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Publication number
US3779930A
US3779930A US00147231A US3779930DA US3779930A US 3779930 A US3779930 A US 3779930A US 00147231 A US00147231 A US 00147231A US 3779930D A US3779930D A US 3779930DA US 3779930 A US3779930 A US 3779930A
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hydraulic
parts
hydraulic fluid
fluids
fluid
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P Alcorn
K Neill
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Orica Ltd
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ICI Australia Ltd
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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
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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
    • C10M2207/026—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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    • C10M2207/00—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
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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
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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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
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
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    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • 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
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • 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
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • 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
    • C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
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    • 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
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    • 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
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
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    • 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
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/16—Nitriles
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/20—Containing nitrogen-to-oxygen bonds
    • C10M2215/202—Containing nitrogen-to-oxygen bonds containing nitro groups
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/26—Amines
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    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • Alk is an alkylene or aralkylene group containing from 1 to 9 inclusive carbon atoms in a straight or branched chain, R and R separately, is an alkyl, substituted alkyl or aralkyl group containing from 1 to 10 inclusive carbon atoms in a straight or branched chain and n is an integer from 1 to 10 inclusive, said compound having a viscosity at 40 C. of less than 1800 centistokes; and at least one additive.
  • This invention relates to hydraulic fluid.
  • Hydraulic fluids are used in many pressure transmission systems, for example, in hydraulic machinery such as hydraulic presses and rams, and the clutching and braking systems of vehicles.
  • the pressure transmission systems must operate over a wide range of conditions and the hydraulic fluid, to be effective, must not attack the machinery and must also remain a free flowing liquid under the extremes of the external conditions encountered.
  • the hydraulic brake systems of vehicles such as, for example, motor cars and aeroplanes comprise both metal and rubber parts exposed to the liquid employed as the hydraulic fluid. It is necessary that the hydraulic fluid does not attack either the metal or the rubber parts of the brake system, either at ordinary temperatures or at the elevated temperatures such as those caused by prolonged application of the brakes.
  • the hydraulic fluid must also be unaffected by the low temperatures found during cold weather or in the case of aeroplanes in high altitude flight. This means that the freezing point should be below those temperatures likely to be encountered under operating conditions, and in addition the viscosity of the fluid should not increase under these conditions to such an extent that the easy working of the brakes is hindered.
  • the hydraulic fluid should have a high boiling point so as to ensure that the hydraulic fluid will not vaporize and cause vapour locks under operating conditions.
  • the hydraulic fluid should also have a low rate of vaporization and also sufficient lubricating properties to lubricate the moving parts of the system.
  • Conventional hydraulic fluids normally comprise a major proportion of polyalkylene glycols, and/or polyalkylene glycol monoethers together with minor proportions of various additives.
  • hydraulic brake fluids based on polyalkylene glycols and/or polyalkylene glycol monoethers are hygroscopic and in the passage of time water is absorbed from the atmosphere and the boiling point steadily falls. It is not uncommon, for example, for a brake fluid, after several months service, to be found to contain about 1 percent of water and, on prolonged service, up to 3 percent of water may be found in such fluids.
  • hydraulic fluids for typical heavy duty braking systems had a boiling point of about 400F, but with generally increased severity of operation, especially in vehicles fitted with disc brakes, there is now a need for hydraulic fluids having even higher boiling points; and fluids boiling at a temperature greater than 500F. are desired.
  • hydraulic fluids comprising certain diethers have the desirable properties of high boiling point, low freezing point, acceptable rubber swell, and low hygroscopicity.
  • Alk is an alkylene or aralkylene group containing from 1 to 9 inclusive carbon atoms in a straight or branched chain, R, and R separately, is an alkyl, substituted alkyl or aralkyl group containing from I to 10 inclusive carbon atoms in a straight or branched chain and n is an integer from 1 to 10 inclusive, said diether having a viscosity of less than 1800 centistokes at 40C.; and at least one additive.
  • Satisfactory hydraulic fluids may be obtained, for example, when R, is alkyl, aralkyl, beta-cyanoalkyl or beta-alkoxycarbonylalkyl and R is beta-cyanoalkyl or beta-alkoxycarbonylalkyl.
  • Suitable diethers used in our invention may be prepared by known means from condensates of ethylene oxide, propylene oxide, butylene oxide, styrene oxide, alpha-methyl styrene oxide or mixtures thereof, with water or an alkyl or aralkyl alcohol containing from 1 to 10 inclusive carbon atoms.
  • ethylene glycol ethylene glycol monomethylether, ethylene glycol monoethyl ether, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, dipropylene glycol, dipropylene glycol monobutyl ether, dipropylene glycol monoethyl ether, tripropylene glycol, tripropylene glycol monomethyl ether and tripropylene glycol monoethyl ether.
  • Particularly suitable hydraulic fluids may be prepared when R is a beta-cyanoalkyl group.
  • R is a beta-cyanoalkyl group.
  • Such a group may be introduced into the diethers used in our hydraulic fluid by reacting suitable condensates as illustrated above with beta-cyano-olefines such as for example acrylonitrile or methacrylonitrile.
  • Alk is an alkylene or aralkylene group containing from 1 to 9 inclusive carbon atoms in a straight or branched chain
  • R is an alkyl, substituted alkyl or aralkyl group containing from 1 to 10 inclusive carbon atoms in a straight or branched chain
  • R and R separately is a hydrogen atom or an alkyl group containing from 1 to 4 inclusive carbon atoms and n is an integer from 1 to 10 inclusive, said diether having a viscosity of less than l800 centistokes at 40C; and at least one additive.
  • the additives are selected from those known in the art to be effective for improving the properties of hyhaving a viscosity at 40C of 260 centistokes with 0.3 parts of Topanol A.
  • Hydraulic fluid D was prepared by mixing 997 parts of tripropylene glycolmethyl ether beta-methyl-betadraulic fluids. Hydraulic fluids normally contain 5 cyanoethyl ether having a viscosity at 40C. of 1570 amongst other ingredients various additives such as lucentistokes with 0.3 parts of Topanol A. bricating additives, corrosion inhibitors, antioxidants The total reflux boiling point, freezing point (nonand the like. The exact nature of the additives required stirrable) rubber swell and the water uptake of hydrauto obtain a hydraulic fluid of optimum performance he fluid A. B. C and D were measured.
  • the water up may be found by the meth d ll d b those take was measured in the following manner.
  • a weighed skilled in the an, sample (5 g) of the hydraulic fluid was exposed, in a Lubricity additives which a b d i our shallow dish, in a humidity chamber under a constant tion include, for example, Ucon lubri ant (Trad atmosphere of 75 percent relative humidity at 75F. Mark for polyalkylene glycols), alkoxylated a t oil
  • Ucon lubri ant Trad atmosphere of 75 percent relative humidity at 75F. Mark for polyalkylene glycols
  • alkoxylated a t oil The samples were weighed after being kept under these or borate esters. Certain of the diethers described here- Conditions for 96 hours.
  • the water uptake was the perinabove may also be used as lubricity additives.
  • Corro- Cemage increase in Weight P Unit Weight of the g sion inhibitors which may be used in our invention inha] p clude, for example, heterocyclic nitrogen containing
  • the rubber Swell was measured y measuring the compounds, amines or derivativ s f i organic crease of diameter in inches of the base of a styrene phosphates or certain inorganic salts known in the art.
  • Rubber Piston C P aft th Cup had n imm rsed in Certain compounds may be used both as corrosion ina hydraulic fluid at temperature of 120C for 70 hibitors and as lubricity additives, these include, for exhoursample, orthophosphate salts of primary or secondary
  • the rubber cups used in this test were of a standard aromatic amines, dialkyl citrates, aliphatic dicarboxylic Size having a base diameter in the range cm to acids and es er her f, A i id hi h may b cm. inclusive.
  • EXAMPLE 3 M EXAMPLE 8 7' v i A hydraulic fluid was prepared by mixing diethylene glycol methylether 2-cyanoethyl ether 80 parts) with Ucon 50 H3660 (20 parts) (Ucon 50 H8660 is a Trade Mark for polyalkylene glycols).
  • the hydraulic fluid was found to have a viscosity at 40C of 1640 centistokes and the rubber swell as measured in Example 1 was 0.018.
  • EXAMPLE 4 xxiim A hydraulic fluid was prepared by mixing diethyleneglycol 'methylether 2-cyanoethyl ether (60 parts), diethylene-glycol n-butylether 2-cyanoethyl ether parts) and Ucon 50 HB260 (20 parts).
  • the hydraulic fluid was' found to have a viscosity at 40C of 1090 centistokes and the rubber swell mea- 'EXKMP'LE 6
  • a hydraulic fluid was prepared by mixing diethyleneglycol methylether 2-cyanoethylether (50 parts) with propyleneglycol bis-2-cyanoethyl ether (50 parts).
  • the hydraulic fluid was found to have a viscosity at 40C of 1290 centistokes and the rubber swell measured by the method of Example 1 was 0.007.
  • EXAMPLE 7 A hydraulic fluid was prepared by mixing diethyle'neglycol ethylether 2-cyanoethylether (60 parts) with propyleneglycol bis-2-cyanoethyl ether (40 parts).
  • the hydraulic fluid was found to have a viscosity at 40C of 1500 centistokes and the rubber swell measured by the method of Example 1 was 0.012.
  • a hydraulic fluid was prepared by mixing diethyleneglycol methylether 2-cyanoethylether (79.7 parts) Ucon 50 H8660 (20 parts), Topanol A (0.3 parts) benzotriazole (0.02 parts), di-n-butylamine (0.30 parts) and m-dinitro-benzene (0.05 parts).
  • the hydraulic fluid was found to have the properties shown in Table 3.
  • the hydraulic fluid was found to have acceptably low corrosive action on tinned iron, steel, cast iron, brass, copper and aluminium.
  • Alk is an alkylene group containing from 1 to 4 inclusive carbon atoms in a straight or branched chain
  • R is alkyl containing from 1 to 10 inclusive car- .bon atoms in a straight or branched chain
  • R is a betacyanoalkyl group containing from 1 to 10 inclusive carbon atoms and n is from 1 to 10 inclusive, said diether having a viscosity of less than 1800 centistokes at 40C.
  • betacyanoalkyl R is the group CHR CHR, CN wherein R and R are each selected from the group consisting of hydrogen and alkyl containing from 1 to 4 inclusive carbon atoms.
  • each of R and R separately, is hydrogen or methyl.

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2600879A1 (de) * 1975-01-13 1976-07-15 Maruzen Oil Co Ltd Hydraulikfluessigkeit fuer zentrale fahrzeug-hydrauliksysteme
US4088590A (en) * 1973-10-09 1978-05-09 Hoechst Aktiengesellschaft Hydraulic fluid containing tertiary butyl ethers
US4320024A (en) * 1980-06-16 1982-03-16 The Dow Chemical Company Hydraulic fluids containing cyano derivatives of cyclic ketals and acetals
US4331549A (en) * 1980-04-21 1982-05-25 The Dow Chemical Company Hydraulic fluids containing cyano derivatives of ketones
US4371448A (en) * 1979-11-08 1983-02-01 Hoechst Aktiengesellschaft Hydraulic fluid composition with improved properties based on boric acid esters, glycol mono-ethers and bis-(glycolether) formals
EP0080530A1 (en) * 1981-11-25 1983-06-08 The Dow Chemical Company Hydraulic fluids containing cyano derivatives of cyclic ketals and acetals
US4659861A (en) * 1981-11-03 1987-04-21 The Dow Chemical Company Novel nitrile functional glycol ether acetals
JP2009120489A (ja) * 2007-11-12 2009-06-04 Idemitsu Kosan Co Ltd レジスト剥離剤用化合物及びそれを用いたレジスト剥離剤

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2350569C2 (de) * 1973-10-09 1982-04-08 Alfred Teves Gmbh, 6000 Frankfurt Verwendung von Alkyl-polyäthylenglykol - tert.- butyläthern als Bestandteil eines hydraulischen Mittels.

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US2200495A (en) * 1937-07-30 1940-05-14 Carbide & Carbon Chem Corp Fluid pressure transmission media
US2226599A (en) * 1937-11-17 1940-12-31 Zellhoefer Esters of glycol ethers and process for preparing them
US2350964A (en) * 1940-06-14 1944-06-06 Du Pont Esters
US2520612A (en) * 1947-01-08 1950-08-29 Union Carbide & Carbon Corp Diethers of polyoxyalkylene diols
US2836613A (en) * 1956-03-14 1958-05-27 Monsanto Chemicals 3, 3'-(alkylenedioxy) dipropionitriles
US2886600A (en) * 1957-03-29 1959-05-12 Dow Chemical Co Process for producing isobutyl ethers
US2942033A (en) * 1960-06-21 Stabilization of polyoxyalkylene
US2998389A (en) * 1958-06-11 1961-08-29 Olin Mathieson Hydraulic pressure transmitting fluid
US3137737A (en) * 1959-09-04 1964-06-16 Standard Oil Co Telomerization of unsaturated hydrocarbons with polyoxyalkylene compounds and telomeric products and synthetic lubricants obtained thereby
US3278585A (en) * 1962-08-08 1966-10-11 Shell Oil Co Process for esterification of secondary alcohols containing an ether group by reaction in the presence of a cation exchange resin catalyst
GB1188825A (en) * 1966-07-27 1970-04-22 Basf Ag Brake Fluids.
US3623987A (en) * 1964-06-18 1971-11-30 Costrol Ltd Functional fluids

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US2942033A (en) * 1960-06-21 Stabilization of polyoxyalkylene
US2200495A (en) * 1937-07-30 1940-05-14 Carbide & Carbon Chem Corp Fluid pressure transmission media
US2226599A (en) * 1937-11-17 1940-12-31 Zellhoefer Esters of glycol ethers and process for preparing them
US2350964A (en) * 1940-06-14 1944-06-06 Du Pont Esters
US2520612A (en) * 1947-01-08 1950-08-29 Union Carbide & Carbon Corp Diethers of polyoxyalkylene diols
US2836613A (en) * 1956-03-14 1958-05-27 Monsanto Chemicals 3, 3'-(alkylenedioxy) dipropionitriles
US2886600A (en) * 1957-03-29 1959-05-12 Dow Chemical Co Process for producing isobutyl ethers
US2998389A (en) * 1958-06-11 1961-08-29 Olin Mathieson Hydraulic pressure transmitting fluid
US3137737A (en) * 1959-09-04 1964-06-16 Standard Oil Co Telomerization of unsaturated hydrocarbons with polyoxyalkylene compounds and telomeric products and synthetic lubricants obtained thereby
US3278585A (en) * 1962-08-08 1966-10-11 Shell Oil Co Process for esterification of secondary alcohols containing an ether group by reaction in the presence of a cation exchange resin catalyst
US3623987A (en) * 1964-06-18 1971-11-30 Costrol Ltd Functional fluids
GB1188825A (en) * 1966-07-27 1970-04-22 Basf Ag Brake Fluids.
US3538003A (en) * 1966-07-27 1970-11-03 Basf Ag Brake fluids

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4088590A (en) * 1973-10-09 1978-05-09 Hoechst Aktiengesellschaft Hydraulic fluid containing tertiary butyl ethers
DE2600879A1 (de) * 1975-01-13 1976-07-15 Maruzen Oil Co Ltd Hydraulikfluessigkeit fuer zentrale fahrzeug-hydrauliksysteme
US4371448A (en) * 1979-11-08 1983-02-01 Hoechst Aktiengesellschaft Hydraulic fluid composition with improved properties based on boric acid esters, glycol mono-ethers and bis-(glycolether) formals
US4331549A (en) * 1980-04-21 1982-05-25 The Dow Chemical Company Hydraulic fluids containing cyano derivatives of ketones
US4320024A (en) * 1980-06-16 1982-03-16 The Dow Chemical Company Hydraulic fluids containing cyano derivatives of cyclic ketals and acetals
US4659861A (en) * 1981-11-03 1987-04-21 The Dow Chemical Company Novel nitrile functional glycol ether acetals
EP0080530A1 (en) * 1981-11-25 1983-06-08 The Dow Chemical Company Hydraulic fluids containing cyano derivatives of cyclic ketals and acetals
JP2009120489A (ja) * 2007-11-12 2009-06-04 Idemitsu Kosan Co Ltd レジスト剥離剤用化合物及びそれを用いたレジスト剥離剤

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FR2095290B1 (enExample) 1976-02-06
NL7108108A (enExample) 1971-12-20
FR2095290A1 (enExample) 1972-02-11
GB1347290A (en) 1974-02-20
CA955918A (en) 1974-10-08
DE2129932B2 (de) 1975-09-25
DE2129932A1 (de) 1971-12-23

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