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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
  • C07D285/01—Five-membered rings
  • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
  • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
  • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
  • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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  • C08K5/00—Use of organic ingredients
  • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
  • C08K5/39—Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates
  • C08K5/405—Thioureas; Derivatives thereof
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  • 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
  • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
  • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
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  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/102—Aliphatic fractions
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  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/108—Residual fractions, e.g. bright stocks
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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
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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
  • C10M2207/10—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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  • 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
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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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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
  • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
  • C10M2219/106—Thiadiazoles
• • 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
  • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
• • 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
  • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
• • 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
• • 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
  • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
  • C10N2050/015—Dispersions of solid lubricants
  • C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating

Definitions

• Oxidation stability is one of the most important properties of hydraulic oils.
• the term oxidation stability, as applied to hydraulic oils, means that the oil does not become non-operational in a hydraulic system after a reasonable period of time even though certain difierenccs in the oil properties resulting from oxidation have occurred.
• Resins and other oxidation products begin to form almost immediately after an oil is put in use; the rate of formation can be extremely low or exceedingly high, depending on the oil and operating conditions.
• Certain resins which are formed are soluble in the oil. This formation causes a darkening in color (not inherently an undesirable property) and an increase in viscosity of the oil.
• When the resins come in contact with very hot surfaces there is a tendency for some types to be changed into insoluble compounds that may either bake out on the hot surface or circulate as solids suspended in the oil.
• varnishes or lacquers other forms, which often settle out at some low point in a hydraulic system, are called sludges. Frequently, these sludges, together with small bits of metal, and other types of dirt, form even more obje'ction able mixtures that might be called super-sludges.
• a composition has now been found which when subjected to the D-943 test has a rating of from 2-4 times subjected to vacuum fractional distillation.
• the novel composition of this invention comprises a major amount of amineral oil, and minor amounts of (a) A hindered phenol having the general formula I OH wherein R and R are alkyl radicals containing from 1 to 8 carbon atoms,
• the mineral oil component comprising the major proportion of the composition of this invention is any refined mineral oil and is preferably a solvent refined paraffinic oil.
• Such oils are prepared by a variety of processes.
• a particularly preferred oil which can be used in this invention is obtained by first subjecting a parafiinic crude oil to distillation under atmospheric pressures. There is obtained a long residue which is a fraction which does not distill under the conditions used without undue decomposition. The long residue is then subjected to steam distillation, usually under a vacuum. Under these conditions gas oil and waxy lubricant fractions distill over leaving a bottoms which is conventionally termed a short residue or a steam refined stock also known as a cylinder stock. The distillate and bottoms fractions are then solvent extracted with furfural and a countercurrent propane-cresylic acid system respectively.
• the separate raflinates typically have the physical properties as set forth in Table I.
• the separate rafiinates are combined and solvent dewaxed with a suitable solvent such as methyl ethyl ketone by methods which are well known in the art.
• a suitable solvent such as methyl ethyl ketone
• the dewaxed product is conventionally known as a total pressed oil.
• the total pressed oil is then Three separate distillate fractions and a bottoms material are recovered. The bottoms is commonly known as a bright stock. Typical properties for the total pressed oil and the distillate fractions are set forth in Table II.
• the hindered phenols are used in the novel composition of this invention in an amount in .the range of from 0.1 to 2.0 preferably 0.2 to 1.0 percent by weight.
• these compounds have the following general formula wherein R and R are alkyl radicals containing from 1 to 8 carbon atoms. It is preferred that at least one of the alkyl radicals be of branched configuration.
• Suitable substituted phenols which can be used in this invention include 2,4,6-trimethylphenol; 2,6-ditertiarybutyl-4-rnethyliphenotl; 2, 6 dineopentyl-4-methylphenol; 2-ethyl-4-methyl-o-t-butylphenol; 2 isopr-opyl-4-methyl- 6-neopentylphenol, etc.
• the most preferred hindered phenol to be used in this invention is 2,6-ditertiarybutyl- 4-methylphenol.
• the oil soluble a'l kylated sucoinic anhydrides used in this invention are present in an amount in the range of from 0.001 to 0.5 preferably 0.005 to 0.05 percent by weight. As stated above, these compounds have the general formula wherein R is an alkyl radical containing from 8 to 20 carbon atoms.
• suitable alkylated succinic anhydrides which can be used in this invention include the isomeric octyl swccinic anhydrides, nonly succinic anhydrides, decyl succinic anhydrides, dodecyl succinic anhydrides, pentadecyl :succinic anhydrides, etc.
• the most preferred alkyl succinic anhydrides to be used in this invention are those in which the alkyl radical contains at least 12 carbon atoms.
• R and R are selected from the group consisting of hydrogen and an alkyl radical containing from 1 to 20 carbon atoms.
• suitable amines which 'can be used in this invention include diphenylamine; ethylphenylamine, N-phenyl-; t-butylphenylamine, N- phenyl-; di(hexylphenyl)amine; hexylphenylamine, N-tbutylphenyl-; di(octylphenyl) amine; dodecylphenylaminm,
• the most preferred amines to be used in this invention are the isomeric di(octylphenyl) amines.
• Sulfurized terpenes are well known. Those which can be used in this invention are oil soluble and can be prepared by any of the accepted methods of sulfurizing unsaturated hydrocarbons. Among the sulfurization processes which can suitably be employed is that of treating the terpene with sulfur and hydrogen sulfide in the presence of water or steam at temperatures within the range of about 250 F. to 450 F. and at pressures up to about 1500 pounds per square inch for a period of 1 to 10 hours. The sulfurized terpene can also be prepared by treating the desired terpene with a sulfur chloride, such as S Cl or SCl at a temperature within the range of about 60 F. to about 250 F.
• a sulfur chloride such as S Cl or SCl
• the chlorine present in the sulfurized material can be removed by treating the sulfurized material in a bomb at a temperature of about 300 F. to about 400 F. with ammonia or other aqueous or alcoholic alkalies, alkali metal sulfides and polysulfides, such as a sodium sulfide, or other bases.
• the sulfurized terpenes which are best suited or use in the instant invention are those which have a sulfur content of from about 5% to about 45%.
• oil-soluble sulfurized derivatives of terpinolene alpha, beta and gamma terpinene; limonene; dipentene; alpha and beta phel landrene; sylvestrene; carvestrene; methene; carvomenthene; and isomers thereof.
• the 1,3,4-thiadiazole polysulfides useful in this invention have the general formula wherein R and R are the same or different hydrocarbon radicals, x and y are numbers 0 to about 8, the sum of x and y is at least 1, and preferably 2 to about 16.
• the radicals R and R can be aliphatic or aromatic, including talkyl, aralkyl, aryl and talkaryl radicals.
• the acylic radicals can contain from 2 to about 30 carbon atoms, and preferably from about 4 to about 16 carbons atoms.
• hydrocarbon radicals examples include ethyl, propyl, butyl, hexyl, octyl, nonyl, decyl dodecyl, tridecyl, hexadecyl, octadecyl, cyclohexyl, phenyl, tolyl, benzyl, styryl, naphthyl, etc.
• the polysulfide derivatives can be suitably prepared by several methods. For example, they can be prepared by reacting 2,5-dimercapto-1,3,4-thiadiazole with a suitable sulfenyl chloride, or by reacting the dimeroaptan with chlorine and reacting the result-ant disulfenyl chloride,
• N N ClS(") -s-cr with a primary or tertiary mercaptan.
• Bis-trisulfide derivatives are obtained by reacting the dimercaptan with a mercaptan and a sulfur chloride in molar ratios of from 122:2 to 1:224 at a temperature of from about 50l00 C.
• Higher polysulfides can be prepared by reacting the thiadiazole dior trisulfides with sulfur at temperatures of about ZOO-400 F.
• Another method of preparing the polysulfides involves reacting 2,5-dimercapto-1,3,4- thiadiazole with a mercaptan and sulfur in the molar ratio of from 1:1:1 to 1:4:16 at temperatures of from about 75 C. to about 150 C.
• R and R are selected from the group consisting of hydrogen and alkyl radicals containing 1 to 20 carbon atoms, a sulfurized terpene and a 1,3,4-thiadiazole polysulfide having the general formula Table IV G i H J K L M N Oil 99. 1 99. 99 4 99. 85 99. 65 99v 6 99. 65 2,6-di-t-butyl-4-methylphenol 0.6 0. 6 0 5 0. 1 Hexadecyl succinic anhydride 0. 03 0. 03 0. 03 0. 03 0. 03
• x and y are integers in the range of from 0 to 8 and wherein the sum of x and y is at least 1 and ranges up to about 16.
• the oxidation resistant hydraulic oil of claim 1 wherein said hindered phenol is present in an amount in the range of from 0.1 to 2.0 weight percent, said oil soluble alkylated succinic anhydride is present in an amount in the range of from 0.001 to 0.5 weight percent and wherein the oil soluble material is said aromatic secondary amine and which is present in an amount in the range of from 0.001 to 2.0 weight percent.
• the oxidation resistant hydraulic oil of claim 1 wherein said hindered phenol is present in an amount in the range of from 0.1 to 2.0 weight percent, said oil soluble alkylated succinic anhydride is present in an amount in the range of from 0.001 to 0.5 weight percent and wherein the oil soluble material is said sulfurized terpene and which is present in an amount in the range of from 0.001 to 2.0 weight percent.
• the oxidation resistant hydraulic oil of claim 1 wherein said hindered phenol is present in an amount in the range of from 0.1 to 2.0 weight percent, said oil soluble alkylated succinic anhydride is present in an amount in the range of from 0.001 to 0.5 weight percent and wherein the oil soluble material is said 1,3,4-thiadiazole polysulfide and which is present in an amount in the range of from 0.001 to 2.0 weight percent.
• the oxidation resistant hydraulic oil of claim 1 wherein said hindered phenol is present in an amount in the range of from 0.2 to 1.0 weight percent, said oil soluble alkylated succinic anhydride is present in an amount in the range of from 0.005 to 0.05 weight percent and wherein the oil soluble material is said aromatic secondary amine and which is present in an amount in the range of from 0.005 to 0.2 Weight percent.
• the oxidation resistant hydraulic oil of claim 1 wherein said hindered phenol is present in an amount in the range of from 0.2 to 1.0 weight percent, said oil soluble alkylated succinic anhydride is present in an amount in the range of from 0.005 to 0.05 weight percent and wherein the oil soluble material is said sulfurized terpene and which is present in an amount in the range of from 0.005 to 0.2 weight percent.
• the oxidation resistant hydraulic oil of claim 1 wherein said hindered phenol is present in an amount in the range of from 0.2 to 1.0 weight percent, said oil soluble alkylated succinic anhydride is present in an amount in the range of from 0.005 to 0.05 weight percent and wherein the oil soluble material is said 1,3,4-thiadiazole polysulfide and which is present in an amount in the range of from 0.005 to 0.2 weight percent.
• An oxidation resistant hydraulic oil comprising a major amount of a solvent refined paraifinic oil and from 0.2 to 1.0 weight percent of 2,6-ditertiarybutyl-4-methylphenol, 0.005 to 0.05 weight percent hexadecyl succinic anhydride and 0.005 to 0.2 weight percent 2,5-dioctyldithiothiadiazole.
• An oxidation resistant hydraulic oil comprising a References Cited by the Examiner UNITED STATES PATENTS 2,459,717 1/1949 Perry. 2,877,184 3/1959 Ragborg 25278 2,913,415 11/1959 Schmitz 252-78 LEON D. ROSDOL, Primary Examiner.

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• Chemical & Material Sciences (AREA)
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• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Engineering & Computer Science (AREA)
• General Chemical & Material Sciences (AREA)
• Lubricants (AREA)

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Cited By (11)

Citations (3)

• 1963
  • 1963-08-28 US US305213A patent/US3274113A/en not_active Expired - Lifetime
• 1966
  • 1966-01-28 GB GB3961/66A patent/GB1096920A/en not_active Expired
  • 1966-02-03 DE DE1966S0101796 patent/DE1594603A1/de active Pending
  • 1966-02-11 CH CH194266A patent/CH473888A/de not_active IP Right Cessation
  • 1966-04-25 BE BE680024A patent/BE680024A/xx unknown

Patent Citations (3)

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