US3376224A - Lubricating compositions and antioxidants therefor - Google Patents

Lubricating compositions and antioxidants therefor Download PDF

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Publication number
US3376224A
US3376224A US368407A US36840764A US3376224A US 3376224 A US3376224 A US 3376224A US 368407 A US368407 A US 368407A US 36840764 A US36840764 A US 36840764A US 3376224 A US3376224 A US 3376224A
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Prior art keywords
phenothiazine
ester
esters
percent
phenyl
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Elliott John Scotchford
Edwards Eric Descamp
Brazier Anthony David
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Castrol Ltd
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Castrol Ltd
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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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
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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
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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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    • C10M2203/104—Aromatic fractions
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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    • 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
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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
    • 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
    • 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2215/24—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
    • C10M2215/30—Heterocyclic 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • 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
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • 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
    • 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
    • C10M2219/108—Phenothiazine
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines
    • 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
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • Phenothiazine derivatives have been disclosed which have the formula:
  • R represents an alkyl or cycloalkyl radical which may carry an alkoxy or other non-reactive substituent. It has further been disclosed that such new compounds and solutions in oil are useful for pharmaceutical veterinary and pest control purposes. However, there has been no disclosure of the use of compounds of this type as ingredients of lubricating compositions.
  • a lubricating composition comprising a major amount of lubricating oil, i.e., an oil of lubricating viscosity, or grease together with a phenothiazine derivative having the general formula where Ar and Ar are benzene or naphthalene nuclei and R is an alkyl, aryl, alkaryl, aralkyl, cycloalkyl, alkoxy alkyl, cycloalkoxy alkyl or aryloxy alkyl radical.
  • the phenothiazine derivative may carry alkyl or alkoxy substituents attached to the aromatic nuclei if desired.
  • phenothiazine derivative has the general formula:
  • R and R are H or alkyl radicals, the sum of the carbon atoms in R and R being from 4-24.
  • phenothiazine derivatives are particularly useful as antioxidants in lubricating compositions based on mineral lubricating oils as well as in synthetic lubricants of various types, e.g., in the wellknown neutral organic dicarboxylic acid diesters or in the so-called hindred esters which are derived from dior polyhydric alcohols having no hydrogen atoms on the carbon atom in the ,8-position to the hydroxyl groups. They are also effective antioxidants in lubricating compositions based on polyglycol ethers.
  • phenothiazine derivatives are effective antioxidants for synthetic ester-based lubricants when used on their own, their efficiency may be considerably enhanced by employing them in conjunction with one or more secondary aromatic amines containing two aromatic groups directly attached to nitrogen, the two additives acting synergistically to provide greater resistance to oxidation at elevated temperatures than would be provided by either additive used by itself in comparable proportions.
  • Synthetic diester-based lubricants containing additive combinations of the foregoing type have given very satisfactory performance at maximum bulk oil temperatures of up to 350-375 F, and have been extremely clean in operation. With the advent of supersonic aircraft, however, and the considerably higher maximum bulk oil temperatures attained (e.g., 450 F. for the so-called Type II oils) it is necessary to provide not only base stocks of higher thermal and oxidation stability but also superior antioxidants.
  • phenothiazine derivatives of the present invention when used in conjunction with secondary aromatic amines of the type described, in hindered ester base stocks, are capable of providing lubricants having superior oxidation resistance at temperatures of the order of 450 F. to similar lubricants containing phenothiazine or phenothiazine derivatives of the prior art.
  • phenothiazine derivatives of the present invention function by means of a two-stage break down mechanism, initially furnishing (llH radicals, these two radicals together providing the oxidation resistance required.
  • the compounds of the present invention are more effective antioxidants in the range 400-4 50 F. than phenothiazine or nuclear alkylated phenothiazines because the NCH bond is more resistant to oxidation than the NH bond and therefore the side reactions involving the direct oxidation of the compound take place to a lesser degree.
  • R is an alkyl radical, and R is H or an alkyl radical, the sum of the carbon atoms in R and R being at least 4 and preferably at least 8.
  • the present invention therefore includes, as new compounds, thiazines having the general formula:
  • R is an alkyl, aryl, alkaryl, aralkyl, cycloalkyl, alkoxyalkyl, cycloalkoxyalkyl or aryloxyalkyl radical, R is an alkyl radical, R is H or an alkyl radical and the sum of the carbon atoms in R and R is from 8 to 24.
  • Ar and Ar are both benzene nuclei
  • R and R are both tertiary octyl radicals and R is an alkyl or cycloalkyl radical having from 1-20 carbon atoms, the compounds being derived from 3,7-dioctyl phenothiazine.
  • a preferred form of the invention relates to lubricating compositions which are suitable for use as high temperature gas turbine lubricants, such compositions being based upon synthetic organic carboxylic esters.
  • a lubricating composition comprises a major proportion of a synthetic organic lubricating oil based upon neutral organic carboxylic esters, which esters are preferably of the so-called hindered ester type and a minor proportion of two additives (a) and (b), additive (a) being a phenothiazine derivative as defined above and additive (b) being a secondary aromatic amine which contains two aromatic groups directly attached to nitrogen.
  • the secondary aromatic amine which is preferred is phenyl-u-naphthylamine but alternative amines which may be used are phenyl-B-naphthylamine, pp-dioctyl diphenylamine, pmono-octyl diphenylamine, mixed heptyl diphenylamines or compounds having the formula:
  • Ar represents a benzene neucleus
  • Ar represents a benzene or naphthalene nucleus (both Ar and Ar may contain alkyl substituents)
  • R and R" are saturated alkyl radicals preferably containing a total of from 8 to 20 carbon atoms
  • m is 1 or 2
  • n is zero or 1. It may be desirable to employ more than one secondary aromatic amine.
  • group R of the phenothiazine derivative is derived from a primary alcohol ROH having from 1 to 12 carbon atoms.
  • a lubricating composition comprises a major proportion of a synthetic organic lubricating oil based upon one or more neutral esters of trimethylol propane, pentaerythritol or dipentaerythritol and monocarboxylic acids having from four to ten carbon atoms together with a minor proportion of two additives (a) and (b), additive (a) being a phenothiazine derivative as defined present in an amount sufficient to provide from 0.04 to 0.15% of sulphur in the composition and additive (b) being a secondary aromatic amine which contains two aromatic groups directly attached to nitrogen present in an amount sufficient to provide from 0.1 to 0.2% of nitrogen in the composition.
  • additive (a) is an N-alkoxymethyl or N- cycloalkoxymethyl derivative of 3,7 dioctyl phenothiazine derived from a primary alcohol ROH having from 1-20 carbon atoms in the radical R and additive (b) is phenyl-u-naphthylamine.
  • phenothiazine derivatives in accordance with the invention are N-ethoxymethyl phenothiazine N-n-butoxymethyl phenothiazine N-n-hexoxymethyl phenothiazine N-1,3,dimethyl butoxymethyl phenothiazine N-n-decoxymethyl phenothiazine N-n-dodecoxymethyl phenothiazine N-methoxy-methyl 3-n-butoxy phenothiazine N-n-hexoxymethyl S-n-decoxy phenothiazine.
  • additives (b) are Phenyl-a-naphthylamine Phenyl-fl-naphthylamine pp-Dioctyl diphenylamine p-Monooctyl diphenylamine Mixed octylated diphenylamines Mixed heptylated diphenylamines p-Isopropoxydiphenylamine p-n-Butoxydiphenylamine Diphenyl-p-phenylene diarnine p-n-octoxy diphenylamine p-n-decoxy diphenylamine p-n-dodecoxy diphenylamine p-n-hexadecoxy diphenylamine p-(3 15:5 trimethyl hexoxy) diphenylamine p-n-octoxy phenyl-fl-naphthylamine pp'-di-n-decoxy diphenylamine
  • the composition is a so-called Type II gas turbine lubricant, i.e. suitable for use at bulk oil temperatures of about 450 F.
  • the ester is one of the so-called hindered esters which are derived from primary mono-, or poly-hydric (e.g. alcohols having from 2 to 10 or more OH groups),
  • R and R are alkyl, hydroxyalkyl or etherified hydroxyalkyl radicals.
  • a particularly suitable class of hindered etsers are those derived from tri-methylolpropane, or pentaerythritol, substantially completely esterfied with one or more straight chain saturated monocarboxylic acids having from 4 to carbon atoms.
  • hindered esters which may be employed as the lubricating oil in compositions according to this invention are:
  • dicarboxylic acids examples include adipic, azelaic, and sebacic acids and of the monocarboxylic acids butyric, valeric, caproic, caprylic, capric and pelargonic acids.
  • the acids have to be chosen so that the resulting ester possesses the requisite physical properties, e.g. viscosity, pour point, and often mixtures of acids must be selected to provide a synthetic oil which will be suitable for the most exacting military specifications.
  • branched-chain mono carboxylic acids may be employed in the synthesis of the esters. Alternatively, blends of several different esters can be used.
  • hindered esters are:
  • blends of mixed esters may be prepared by esterifying a hindered alcohol with a mixture of acids in a wide range of proportions.
  • trimethylol propane 0.4 mol
  • caproic acid 0.5 mol
  • capric acid 0.5 mol
  • sebacic acid 0.1 mol
  • esters derived from pentaerythritol are available commercially from the Hercules Powder Company under the registered trademarks Hercoflex and Hercolube. These esters are useful for blending in lubricating compositions for use at high temperatures.
  • esters of trimethylol propane or pentaerythritol with straight chain monocarboxylic acids having from 4 to 10 carbon atoms.
  • One very suitable base fluid comprises a major proportion of a mixture of esters of trimethylol propane with straight chain monocarboxylic acids having from 4 to 9 carbon atoms together with a minor proportion, preferably from 530%, of a mixture of esters of dipentaerythritol with straight chain monocarboxylic acids having from 2-10 carbon atoms.
  • Lubricants based on such blends have been found to be less prone to sludging than lubricants based wholly on trimethylol propane esters,
  • compositions according to the invention may be based upon a synthetic lubricating oil comprising one or more of the conventional-type diesters.
  • diesters which may be employed are:
  • Type I compositions Di-2-ethyl hexyl sebacate Di-3,5,5-tri methyl hexyl sebacate Di-iso octyl sebacate Di-Z-ethyl hexyl azelate Di-iso octyl azelate Di-iso octyl adipate Di-iso tri decyl adipate
  • Type I compositions may contain from 1 to by weight of a substantially water-insoluble polyoxyalkylene glycol ether.
  • polyoxyalkylene glycol ethers have the general formula RO(R O) R where R represents an alkyl group, R an alkylene radical, R is H or another alkyl group, and n is an integer.
  • R represents a propylene radical or a mixture of propylene and ethylene radicals, suitable products being obtained by reacting propylene oxide or a mixture of propylene and ethylene oxides with an aliphatic monohydric alcohol or with a monoether of a glycol.
  • the polyoxyalkylene chain may be composed, therefore, of alkylene radicals R of more than one kind.
  • R is hydrogen
  • LB series of synthetic lubricants sold under the registered trademark Ucon, these, it is understood, consisting of mixed polyoxypropylene glycol ethers containing one free hydroxyl group per molecule.
  • Ucon fluids of the socalled D series may be employed, e.g. Ucon DLB 20-E, these materials being diethers in which both R and R are alkyl groups. Similar materials to the Ucon D series are the Dow Ambiflo C series.
  • compositions which are specifically designed as high temperature lubricants may be employed; such compounds may be employed in compositions which are specifically designed as high temperature lubricants.
  • composition it may be desirable to have present in the composition one or more additives designed to increase the load-carrying capacity of the lubricant.
  • compositions according to the invention may also contain copolymers which are well-known in the art as additives having sludge dispersant properties.
  • additives are copolymers of alkyl methacrylates, e.g. lauryl or higher methacrylates or mixtures of such methacrylates, with N-vinyl pyrrolidone and copolymers of long chain alkyl furnarates with vinyl acetate and N-vinyl pyrrolidone.
  • These copolymers not only serve to disperse sludge and maintain the oil and the engine in a cleaner condition than would otherwise be obtained, but also in some cases appear to cooperate synergistically with the antioxidants giving overall better oxidation resistance.
  • These copolymers may be used in the present invention in amounts of from about 0.2 to about 1.5% by weight on the weight of the composition.
  • a preferred composition in accordance with this inventi-on is a lubricating composition comprising an ester which has the formula:
  • R, R and R' are the same or difierent straight or branched chain alkyl radicals having an average of from 6 to 9 carbon atoms, said ester having a viscosity at 210 F. from about 3.0 to about 5.0 es. and remaining free from crystallisation on storage at -40 F.
  • ester having dissolved therein an N-alkoxymethyl or an N-cycloalkoxymethyl 3,7-dioctyl phenothiazine in an amount sufiicient to provide from 0.04 to 0.15 percent of sulphur together with from 1.5 to 2.5 percent of phenyl-a-naphthylamine.
  • a sludge dispersant copolymer is preferably also present.
  • the preferred phenothiazine derivatives in which Ar and Ar are substituted by alkyl groups having a total of at least 8 carbon atoms, the use of sludge dispersant copolymers is rendered unnecessary. This is a considerable advantage since the copolymers are prone to both shear and thermal breakdown with a consequent reduction in viscosity of the lubricant.
  • This composition was of a type suitable for use as an ashless dispersant oil for piston-engined aircraft.
  • This composition was of a type suitable for use as a synthetic Worm gear lubricant conforming to S.A.E. (Society of Automotive Engineers) viscosity requirements.
  • Ucon LB 1145 was a polyoxypropylene glycol ether having a viscosity of about 38 cs. at 210 F.
  • EXAMPLE 7 Percent Di (2-ethylhexyl)sebacate 66.25 Ucon LB 1145 28.0 N-methoxymethyl 3,7 dioctyl phenothiazine 1.5 pp-Dioctyl diphenylamine 1.5 Aroclor 1254 2.4 CPS. concentrate 0.25 Benzotriazole 0.1
  • CPS. concentrate was a mineral oil solution containing approximately 20% of calcium petroleum sulphonate.
  • Aroclor 1254 was a chlorinated diphenyl containing 54% chlorine.
  • Ester C was a dipentaerythritol ester of mixed straight chain carboxylic acids having from 2 to 10 (average 6) carbon atoms.
  • This composition was of a type designed to meet the requirements of Pratt & Whitney Aircraft specification PWA 521-13 for a Type 11 gas turbine lubricant.
  • CioHnO *Further information as to the structure of the radical R is given in certain cases, as follows:
  • R 1, 3 dimethyl butyl.
  • B7 R oleyl, derived from commercial oleyl alcohol.
  • B8 R 2-ethyl hexyl.
  • B9 R 2,2,4 trimethyl pentyl.
  • B10 R 3,5,5 trimethyl hexyl.
  • I311 R derived from mixed branched-chain primary decanols.
  • B12 R derived from mixed branched-chain primary tridecanols.
  • Table IV demonstrates the effectiveness of a selection of the additives of the present invention when used in concentration] conjunction with phenyl-a-naphthylamine and shows that Additive Percent Induction Period equivalent proportions of the additives give similar re- (minutes) sults. It was noteworthy that the first four blends gave NM? 15 4 much drrtier tubes than the remarnder. Addmve o 7 15 TABLE IV.-OXIDATION 'rns'rs AT 450 F.18 hours duration A5 3 (AIR FLOW RATE 19s LITRES/HOUR) B2. 1.2 188 [Ester A was used throughout as base fluid and all blends contained B3 1.
  • the bomb was ro- 1 63 tated in an oil bath at 160 C., the drop in pressure in 47 bolnb 'f recorded Contlnuously f f y-
  • the All additives except B1 were present in sutficient amount to provide induction period was taken as that period of time over 65 about O the blendwhich a 25 lb./sq. in. pressure drop from the maximum pressure initially reached was recorded. Obviously the longer the induction period, the better the oxidation resistance of the oil under these test conditions.
  • Table III demonstrates the effectiveness of a typical preferred additive of this invention when used in conjunction with phenyl-a-naphthylamine (PAN).
  • PAN phenyl-a-naphthylamine
  • Ester D was a trimetiiylol propane ester of mixed straight chain carboxylic acids having predominantly from 7 to 10 carbon atoms.
  • Ester E was a trimethylol propane ester of mixed carboxylic acids having a viscosity of about'5.0 cs. at 210 F.
  • Ester F was a dipentaerythritol ester of mixed straight chain carboxylic acids, predominantly nbutyric, n-octanoic and n-decanoic acids.
  • a lubricating composition consisting essentially of a major proportion of synthetic neutral organic carboxylic ester lubricating oil and a minor proportion of additives (a) and (b) as follows:
  • N n decoxymethyl-3,7-dioctyl phenothiazine in such proportion to provide from 0.04 to 0.15% of sulphur by weight of the composition
  • composition as claimed in claim 1 wherein the lubricating oil is selected from the group consisting of TABLE V II.OXIDATION/CORROSI0N TESTS AT 450 F (48 HOURS) [All blends were based on ester A] Change in wt. of metal specimens Percent Acidity Thiazine Amines Dispersant Other (mg/sq. cm.) Vise. Increase (Percent) (Percent) (Percent) Additives Increase (mg. KOH/ (Percent) Ti Ag Cu Steel Mg A1 (cs. gm.)
  • Phenothiazinc 1.0 PAN, 1.0 Plexo1917, 2.0 Nil Nil -0 35 +0, 03 0 77 +0,04 1 7,2 Additive A2, 0.7. PAN, 0.5; Acryloid HF 866, Benzotriazole, 0.2; Nil +0.02 +0.03 +0.01 Nil Nil 16 5. 3
  • DODP 1 0. 2.0. gtgacic acid, Additive A3, 0.8 PAN, 1.0. Acryloid HF 866, Benzotriazole, 0.2; Nil Nil +0.10 +0. 05 +0. 06 +0.03 21 9.8
  • PAN Phenyl-a-naphthylamine.
  • D CDP p-n-deooxy diphenylamine.
  • composition as claimed in claim 1 wherein the lubricating oil is selected from the group consisting of esters derived from trimethylol propane, pentaerythritol and dipentaerythritol substantially completely esterified with at least one saturated monocarboxylic acid having from 4 to 10 carbon atoms and mixtures of such esters, the ester and mixture of esters having a viscosity at 210 F. of from 3.0 to 6.5 centistokes.
  • composition as claimed in claim 1 wherein the lubricating oil is selected from the group consisting of pentaerythritol tetravalerate, trimethylol propane tri-n- 15 heptanoate, trimethylol propane tripelargonate, trimethylol propane tricaprylate, pentaerythritol tetra-caproate, dipentaerythritol hexacaproate and mixtures thereof.
  • composition as claimed in claim 1 wherein the lubricating oil consists essentially of at least one substantially neutral ester of a member selected from the group consisting of trimethylol propane, pentaerythritol and dipentaerythritol and monocarboxylic acids having from 4 to 10 carbon atoms.
  • a lubricating composition consisting essentially of a major proportion of an ester which has the formula:
  • R, R" and R' are the same or difierent straight or branched chain alkyl radicals having an average of from 6 to 9 carbon atoms, said ester having a viscosity at 210 C. from about 3.0 to about 5.0 es. and remaining free from crystallisation on storage at 40 F. for at least 72 hours, said ester having dissolved therein N-ndecoxymethyl-3,7-dioctyl phenothiazine in an amount suflicient to provide from 0.04 to 0.15 percent of sulphur together with from 1.5 to 2.5 percent of phenyl-oi-naphthylamine.
  • a lubricating composition consisting essentially of a major portion of an ester which has the formula wherein R, R", R and R" are the same or different straight or branched chain alkyl radicals having an average of from 4 to 9 carbon atoms, said ester having a viscosity of from 4.0 to 6.5 centistokes at 210 F. and said ester having dissolved therein N-n-decoxymethyl 3,7 dioctyl phenothiazine in an amount sufiicient to provide from 0.04 to 0.15 percent of sulphur together with from 1.5 to 2.5 percent of phenyl-a-naphthylamine.
  • a lubricating composition as claimed in claim 1 wherein the lubricating oil is selected from the group consisting of esters having the formula:
  • R and R are the same 'or difiereut and are branched-chain alkyl radicals having at least six carbon atoms, and x is from 4 to 8, and mixtures of such esters.
  • a lubricating composition which consists essentially of a mixture of from to 95 percent by weight of an ester of trirnethylol propane with straight chain carboxylic acids comprising from 70 to by weight of pelargonic acid; from 5 to 25% by weight of an ester of dipentaerythritol with mixed straight chain carboxylic acids having from 2 to 10 carbon atoms; from 2 to 3% by weight of phenyl-wnaphthylamine; from 1.5 to 2.5% by weight of N-n-decoxymethyl 3,7 dioctyl phenothiazine; from 0.05 to 0.15% by weight of benzotriazole and from 0.005 to .02% by weight of sebacic acid.

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  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US368407A 1963-05-24 1964-05-18 Lubricating compositions and antioxidants therefor Expired - Lifetime US3376224A (en)

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GB20934/63A GB1023380A (en) 1963-05-24 1963-05-24 Improvements in or relating to lubricating compositions containing phenothiazine derivatives

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US3376224A true US3376224A (en) 1968-04-02

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BE (1) BE648377A (is")
DE (1) DE1594370B2 (is")
DK (1) DK114008B (is")
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NL (2) NL6405729A (is")

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3523910A (en) * 1966-05-06 1970-08-11 Geigy Chem Corp Method of use of a 1-t-butyl-3:7-dialkyl phenothiazine as antioxidant and stabilized compositions containing same
US3539515A (en) * 1968-04-03 1970-11-10 Mobil Oil Corp Lubricating oil compositions containing peroxide-treated phenothiazine as an antioxidant
US3912640A (en) * 1972-08-07 1975-10-14 Stauffer Chemical Co Gas turbine lubricants
US4072619A (en) * 1976-08-30 1978-02-07 The Dow Chemical Company Ester lubricants containing polyoxyalkylene phenothiazines
EP0275835A1 (en) * 1986-12-31 1988-07-27 Ciba-Geigy Ag Substituted phenothiazines as lubricant stabilizers
US4785095A (en) * 1986-09-16 1988-11-15 The Lubrizol Corporation N-substituted thio alkyl phenothiazines
US4798684A (en) * 1987-06-09 1989-01-17 The Lubrizol Corporation Nitrogen containing anti-oxidant compositions
US4915858A (en) * 1987-06-09 1990-04-10 The Lubrizol Corporation Nitrogen containing anti-oxidant compositions
US5024774A (en) * 1987-06-09 1991-06-18 The Lubrizol Corporation Nitrogen containing anti-oxidant compositions
US5034019A (en) * 1988-06-23 1991-07-23 The Lubrizol Corporation N-substituted thio alkyl phenothiazines
US5157118A (en) * 1986-09-16 1992-10-20 The Lubrizol Corporation N-substituted thio alkyl phenothiazines
US5178784A (en) * 1986-09-16 1993-01-12 The Lubrizol Corporation N-substituted thio alkyl phenothiazines
US5211862A (en) * 1986-12-31 1993-05-18 Ciba-Geigy Corporation Substituted N-thiomethylphenothiazines as lubricant stabilizers
US5269954A (en) * 1988-12-05 1993-12-14 Elf France Nitrogenous additives with an antioxidant action and lubricating compositions containing the said additives
US6797677B2 (en) 2002-05-30 2004-09-28 Afton Chemical Corporation Antioxidant combination for oxidation and deposit control in lubricants containing molybdenum and alkylated phenothiazine
US20040192563A1 (en) * 2003-03-28 2004-09-30 Exxonmobil Research And Engineering Company Lubricant containing a synergistic combination of rust inhibitors, antiwear agents, and a phenothiazine antioxidant
US20080064616A1 (en) * 2004-10-25 2008-03-13 Huntsman Petrochemical Corporation Fuel And Oil Detergents
US20110245364A1 (en) * 2008-12-25 2011-10-06 Cheong Hun Song Adhesive composition and optical member using the same
JP2016062028A (ja) * 2014-09-19 2016-04-25 日東電工株式会社 粘着剤層付き偏光板

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2415252A (en) * 1947-02-04 Phenothiazine derivatives
US2461460A (en) * 1949-02-08 N-acixphenothiazines
US2526118A (en) * 1950-10-17 Paul chabpentier
US2836564A (en) * 1954-10-28 1958-05-27 Standard Oil Co Corrosion inhibitors and compositions containing the same
US2897152A (en) * 1956-03-08 1959-07-28 Wakefield & Co Ltd C C Lubricating oils
US2930758A (en) * 1956-09-28 1960-03-29 Texaco Inc Ester-base lubricant containing anti-oxidant mixtures
GB860675A (en) * 1957-04-29 1961-02-08 Castrol Ltd Improvements in or relating to lubricating compositions
US3148147A (en) * 1961-01-31 1964-09-08 Eastman Kodak Co 2, 2-dialkyl-1, 3-propanediol diesters as functional fluids
US3218256A (en) * 1959-01-14 1965-11-16 Castrol Ltd Lubricating compositions

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2415252A (en) * 1947-02-04 Phenothiazine derivatives
US2461460A (en) * 1949-02-08 N-acixphenothiazines
US2526118A (en) * 1950-10-17 Paul chabpentier
US2836564A (en) * 1954-10-28 1958-05-27 Standard Oil Co Corrosion inhibitors and compositions containing the same
US2897152A (en) * 1956-03-08 1959-07-28 Wakefield & Co Ltd C C Lubricating oils
US2930758A (en) * 1956-09-28 1960-03-29 Texaco Inc Ester-base lubricant containing anti-oxidant mixtures
GB860675A (en) * 1957-04-29 1961-02-08 Castrol Ltd Improvements in or relating to lubricating compositions
US3218256A (en) * 1959-01-14 1965-11-16 Castrol Ltd Lubricating compositions
US3148147A (en) * 1961-01-31 1964-09-08 Eastman Kodak Co 2, 2-dialkyl-1, 3-propanediol diesters as functional fluids

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3523910A (en) * 1966-05-06 1970-08-11 Geigy Chem Corp Method of use of a 1-t-butyl-3:7-dialkyl phenothiazine as antioxidant and stabilized compositions containing same
US3539515A (en) * 1968-04-03 1970-11-10 Mobil Oil Corp Lubricating oil compositions containing peroxide-treated phenothiazine as an antioxidant
US3912640A (en) * 1972-08-07 1975-10-14 Stauffer Chemical Co Gas turbine lubricants
US4072619A (en) * 1976-08-30 1978-02-07 The Dow Chemical Company Ester lubricants containing polyoxyalkylene phenothiazines
US5157118A (en) * 1986-09-16 1992-10-20 The Lubrizol Corporation N-substituted thio alkyl phenothiazines
US5178784A (en) * 1986-09-16 1993-01-12 The Lubrizol Corporation N-substituted thio alkyl phenothiazines
US4785095A (en) * 1986-09-16 1988-11-15 The Lubrizol Corporation N-substituted thio alkyl phenothiazines
US5319081A (en) * 1986-12-31 1994-06-07 Ciba-Geigy Corporation Substituted N-thiomethyl phenothiazines as lubricant stabilizers
EP0275835A1 (en) * 1986-12-31 1988-07-27 Ciba-Geigy Ag Substituted phenothiazines as lubricant stabilizers
US5211862A (en) * 1986-12-31 1993-05-18 Ciba-Geigy Corporation Substituted N-thiomethylphenothiazines as lubricant stabilizers
US4798684A (en) * 1987-06-09 1989-01-17 The Lubrizol Corporation Nitrogen containing anti-oxidant compositions
US4915858A (en) * 1987-06-09 1990-04-10 The Lubrizol Corporation Nitrogen containing anti-oxidant compositions
US5024774A (en) * 1987-06-09 1991-06-18 The Lubrizol Corporation Nitrogen containing anti-oxidant compositions
US5034019A (en) * 1988-06-23 1991-07-23 The Lubrizol Corporation N-substituted thio alkyl phenothiazines
US5269954A (en) * 1988-12-05 1993-12-14 Elf France Nitrogenous additives with an antioxidant action and lubricating compositions containing the said additives
US6797677B2 (en) 2002-05-30 2004-09-28 Afton Chemical Corporation Antioxidant combination for oxidation and deposit control in lubricants containing molybdenum and alkylated phenothiazine
US20040192563A1 (en) * 2003-03-28 2004-09-30 Exxonmobil Research And Engineering Company Lubricant containing a synergistic combination of rust inhibitors, antiwear agents, and a phenothiazine antioxidant
US7176168B2 (en) 2003-03-28 2007-02-13 Exxonmobil Research And Engineering Company Lubricant containing a synergistic combination of rust inhibitors, antiwear agents, and a phenothiazine antioxidant
US20080064616A1 (en) * 2004-10-25 2008-03-13 Huntsman Petrochemical Corporation Fuel And Oil Detergents
US20110245364A1 (en) * 2008-12-25 2011-10-06 Cheong Hun Song Adhesive composition and optical member using the same
US8288450B2 (en) * 2008-12-25 2012-10-16 Cheil Industries, Inc. Adhesive composition and optical member using the same
JP2016062028A (ja) * 2014-09-19 2016-04-25 日東電工株式会社 粘着剤層付き偏光板

Also Published As

Publication number Publication date
NL6405729A (is") 1964-11-25
DK114008B (da) 1969-05-19
BE648377A (is") 1964-09-16
DE1594370B2 (de) 1976-11-18
DE1594370A1 (de) 1970-01-29
GB1023380A (en) 1966-03-23
NL129113C (is")

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