US2628941A - Extreme pressure lubricant - Google Patents

Extreme pressure lubricant Download PDF

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Publication number
US2628941A
US2628941A US142536A US14253650A US2628941A US 2628941 A US2628941 A US 2628941A US 142536 A US142536 A US 142536A US 14253650 A US14253650 A US 14253650A US 2628941 A US2628941 A US 2628941A
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United States
Prior art keywords
acid
reaction
extreme pressure
organic
oil
Prior art date
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Expired - Lifetime
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US142536A
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English (en)
Inventor
David E Adelson
George L Perry
George G Pritzker
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Shell Development Co
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Shell Development Co
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Publication date
Priority to NL79051D priority Critical patent/NL79051C/xx
Priority to BE504651D priority patent/BE504651A/xx
Application filed by Shell Development Co filed Critical Shell Development Co
Priority to US142536A priority patent/US2628941A/en
Priority to US173754A priority patent/US2648634A/en
Priority to GB2638/51A priority patent/GB705273A/en
Priority to DEN3458A priority patent/DE872624C/de
Priority to FR1047896D priority patent/FR1047896A/fr
Priority to DEN4161A priority patent/DE872626C/de
Priority to GB16804/51A priority patent/GB704019A/en
Application granted granted Critical
Publication of US2628941A publication Critical patent/US2628941A/en
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    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
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    • C10M2201/02—Water
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
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    • 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
    • C10N2040/20—Metal working
    • C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
    • 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
    • C10N2040/20—Metal working
    • C10N2040/241—Manufacturing joint-less pipes
    • 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
    • C10N2040/20—Metal working
    • C10N2040/242—Hot working
    • 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
    • C10N2040/20—Metal working
    • C10N2040/243—Cold working
    • 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
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • 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
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/245—Soft metals, e.g. aluminum
    • 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
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/246—Iron or steel
    • 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
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/247—Stainless steel
    • 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—Semi-solids; greasy
    • 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
    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/04—Oxidation, e.g. ozonisation
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • This invention rel-ates to extreme pressure lubricants capable of withstanding high pressures at elevated temperatures under severe and adverse operating conditions. More specifically this invention pertains to improvement of extreme pressure lubricants by enhancing their extreme pressure properties and at the same time rendering them substantially non-corrosive and stable, by addition of a novel additive thereto, in relatively minor amounts.
  • Natural and/or synthetic lubricants per so are not capable of withstanding extreme pressures at high temperatures, high speeds and under severe loading conditions as generally encountered in present-day lubricating such as internal combustion engines of various ty es, transmission devices, certain types of gears, e. g. hypoid gears, metal fabrication such as in cutting and drawing and the like. Under such conditions of lubrication, the protective film formed between contactr ing surfaces, by the lubricant, so as to prevent direct metal-to-metal contact, breaks down or ruptures and seizure or even welding of metal parts occurs, resulting in serious damage to the elements being lubricated.
  • extreme pressure agents are largely a physiochemical phenomenon and this accounts primarily for their effectiveness as extreme pres sure agents.
  • These agents or materials in addition to increasing the film strength of lubricants, become reactive with contacting surfaces forming thereon an alloying protective coating or film of great strength and thermal stability.
  • This tenaioiously adhering adsorbed protective film not only reduces friction between relatively moving parts suohas encountered in internal combustion around about 150 C. and higher, the performance of a given lubricant must depend upon its composition, the composition of the contacting surface being lubricated, as well as the conditions to which the combination is subjected.
  • extreme pressure additives to be effective should be reactive with contacting surfaces, this reactivity should not be corrosive to the reactive surface. This is generally a serious draw-back of known extreme pressure agents, for serious damage to metal surfaces, particularly such as alloy bearings and the like, might result. Such additive should also not tend to promote oxidation which generally prompts formation of corrosive acidic materials, sludge, lacquer and varnish which results in sticking and fouling of movable engine parts and the like.
  • this invention is directed tov the use in liquid hydrocarbon compositions such as lubricants, fuels, greases, rust-inhibiting; compositions and the like, as well as synthetic lubricatingbases, of: a reaction productobt-ained taining: at least;;0ne XR;radical, whichcompound can be representedqby theegeneralformula:
  • an :integer j of at :least 2.;a-ndrj-represents the numberof acidic radicalsrQ which -areqattachedto A one: of the; acid; radicals represented by a- -C iXR radical andthe other; acid radicals represented by-Q canrbe th'eisame as CXXR or: may be: selectedfrom1 oxy inorganic acids such as sulfonic; sulfinic; nitric and; acids of phosphorus; 'X.,is antelement-selected from the group; consistingofO,'- S , Se and: Te and 'inithe radical-(IXXRthe Xscanjoezthe sameor different?
  • R can be hydrogen, alkyl, cycloalkyl, aralk-yl alkylaryl', aryl radicals ora cationic portionof :a molecule such asNaiLi, Ca Ba; Sr, Sn; Ni, A1,Zn, P1) or organic amines, at :least-one of the-Rs either the acid .or polar radical XR beingrhydrogen; Y is-apol-ar selected from the group consisting of'nitro, nitroso, amino, sulfo and-halo groups; m'isan' integerof-at least l" 'andpreferably l'to 3;"and p can be a .whole number varying from zero to one.
  • droxy adipic acid, chloromalic” acid, mercapto' B,-sulfenicu acid ofw-hydroxy decyl carboxylic acid Na salt of;B-sulfonic-;acid-of w-hydroxyl hexyl carboxyliclacid naphthol 3-.-carboxylic 6-' 4 sulfon-icacid; etc. Any of: these acidszcan be partially esterifiedto form partial esters, which partial esters can be used to form the condensation reaction product of this invention.
  • Esters/which are particularly preferred to form condensation reaction products of this invention include acid ester of oleyl malate, acid ester of "oleyl tartarate, acid ester of oleyl citrate, acid ester'of-ste'aryl citrate, acid ester of cetyl citrate, 9,10 octa-decenyl acid citrate, dodecyl acid, hydroxy succinate, oc-tyl mercapto acid phthalate, acid ester of methylene disalicylate, dihydroxy dithiomonostearate of butyl alcohol, acid ester of oleyl dihydroxyl thiophene carboxylate, B-sulfonic acid of oleyl w-hydroxyl decanate; etc: In: addition; theifullestersran be -used-to form'condensation products of this,
  • dioleyltartarate dioctyl tartarate, dibenzyl tartarate; di'phenyl; tartarate, dioleyl. malate; trioleylcitrate; dioleyl ester of methylene salicylic acid,:.distearyl esterof-methylene salicylic acid,
  • dioleyl ester-of propyl dihydroxy thiophene dicarboxylic acid, etc. mixtures thereof can be partially neutralized with -a metal compound or organic bases to form salts; which salts can be used to form condensation products'ofth-is invention: Preferredexamples of such saltsare sodium salt" ofacid ester of oleyl'malate, sodium-or potassium salt of'acidtesterof oleyl tartarate, calcium saltof acid ester of oleyl citrate, calciumsalt of methyl ene' disalicylate, triethanolamine salt of acid ester of stearyl" citrate, dibutyla-mine "salt of acid ester 'ofioctyl 'tartarate, etc. If 'desired, the saltsof thisinvention can' be produced after the condensation products of thisinvent-ion haveb'een formed.
  • the above polar-substituted organie-polyacidic compounds, their ester and/or-salts are'reacted with'alkylene oxide, sulfide-and/or-imine to form the desired condensation reaction product of this invention;
  • the alkyleneoxides which can be-- used are:- ethyleneoxide, propylene oxide; butylene oxide, amylene oxide, epichlorhydrin, glycide, alkyl glycides, glycidyl compounds, e. g:, glycidyl isopropyl ether, and the like; Instead of the alkylene oxides as enumeratedabove; ,the'
  • Sulfide andimine analogues can be used,v of which particularly preferred areethylene sulfide, propylene sulfide, ethylene imine; propylene W imine and the like.
  • the imine to the polar-containing organic polyacidic compound canvary over wide limits in order to produce the desired reaction product.
  • the pre-'- ferred'ratio of oxide-to the'polyacidic organic compound or itsderivative is 4:1 to 12:1, respectively. varied over wide'dimits and primarily depends upon the reacants-used in .forming the condensation product of-thi-sinvention.
  • the reaction temperature lies between.50 C. and 350"CL, and generally the reaction temperature lies between 75C. and200 C.
  • the reaction can be carried out underpressure in.-a, suitable reaction vessel, with thepressure varying from 50-pound gauge pressure to over LOGO-pound gauge pressure.
  • condensation reaction need not be-carried out under pressure, but it is preferredthat it be carried out in an enclosed "vessel.
  • Catalysts may be used in carryingout the condensation reaction, and the catalyst may be either acid or basic.
  • a few examples of'such-cat-alystg areboric acid, caustic The acids or the esters or The reaction temperature can. be-
  • the reaction can be carried out in a suitable solvent or diluent.
  • the diluents can be light or heavy hydrocarbons such as benzene, kerosene, gas oil, mineral oil or dioxane (purified by distillation with alkylene reagents), or any other suitable organic diluent which is substantially non-reactive with the constituents comprising the condensation reaction product of this invention and from which products of this invention can be easily removed.
  • the mechanism of the present invention is complex. ucts form in which the alkylene oxide, sulfide or. imine attaches to both the carboxyl and hydroxyl radicals, provided both are free, although the reaction can be controlled so that only the carboxyl or hydroxyl groups are attacked.
  • the complexity of the reaction it is desired to cover within the scope of the present invention all possible condensation products and mixtures thereof which are formed from reaction products of this invention.
  • the reaction is carried out under conditions.
  • the method of preparing condensation reaction products of this invention can be accomplished by employing the following procedure.
  • About one mole of an organic polarcontaining polycarboxylic acid or derivative thereof such as tartaric acid, oleyl tar'tarate, acidv ester of methylene disalicyclic acid, etc. is slowly heated in a suitable reaction vessel, such as an autoclave, and the product heated to above about 75 C. and higher, depending upon the organic polyacidic material used.
  • the material can be I heated per se or dispersed in a diluent su'ch as mineral oil and heated therein.
  • reaction is then added from 1 to and generally 2, to 12 moles of an alkylene oxide, sulfide or imine and the reaction allowed to proceed, varying the reaction temperature by either cooling or heating above the. temperature indicated above, in order to form a smooth reaction, and the ingredient allowed to react for from 4 to 48 hours.
  • the reaction is preferably carried out under pressure and in the presence of a basic catalyst and is regarded as being completed when the average molecular weight of the organic polyacidic starting material has increased by at least 44 weight units and higher.
  • Example I Approximately 1 mole of tartaric, acid was slowly heated to a temperature between C.'
  • Example III Following the procedure and'conditions as outlined in Example II, malic acid was reacted with ethylene oxide. The condensation product thus formed had good extreme pressure properties.
  • Example IV Approximately 1 mole of hydroxy glutamic acid was reacted with 4 to 10 moles of propylene oxide under conditions set forth in Example I. At the end of the reaction period, the hydroxy .glutamic acid indicated an average increase in molecular weight between 348 and 580 weight units. The condensation product when added to an oil imparted extreme pressure properties thereto.
  • Example V Approximately 1 mole of z-propyl dihydroxythiophene 3-4 dicarboxylic acid was reacted with 5 to 15 moles of ethylene oxide in the presence of sodium methylate in purified dioxane at be.- tween 100 and C. for about 48 hours. At the end of the reaction, the condensation product was removed from the solvent and on analysis indicated an increase in average molecular weight over the acid of from 220 to 660 weight units.
  • Example VII 1 Approximately 1 mole of tartaric acid was reacted with 4 to 10 moles of ethylene sulfide under conditions set forth in Example II. On analysis, the tartaric acid indicated an average molecular weight increase between 240 and 600 weight units. The condensation product was soluble in oil.
  • the sulfur-containing condensation productwhen added to oil imparted extreme pressure properties toit.
  • tartaric acid Approximately 1 mole of tartaric acid' was heated with 4 to moles ethyleneimine under conditions as set forth in Example WI on analysis, the tartaric acid indicated an increase in molecular weight between .168 and 420 weight units.
  • the nitrogen-containing condensation product was oil-soluble and possesses good antioxidant properties.
  • Example XI Following the procedure of Example X, ap-
  • Example XII Approximately 1 mole of dibenzyl tartarate and between 2 and 10 moles of amylene oxide were reacted under-conditions set forth in Example .X, while maintaining the reaction temperature above C. increase in molecular-weight between 175 and 345' weight units.
  • Example XIII Approximately :1 mole of Jdihydroxydithiobutyl monostearate was reacted, with.4 .to.110.moles1of ethylene sulfide under conditions set forth. in Example X.
  • the ester-indicated an average increase-in molecular.weight of around 2.40 weight units...
  • the condensationproduct.contained. a substantiallincreasein sulfur content and.the product possessed good extreme pressure proper-- ties.
  • the ester indicated an average EmamplaXl/T Followingtheprocedure setforth in Example XIV. but-using 'glycidyl isopropyl ether, thecondensation product formed indicated that the ester" increased in average molecular weight b'y about"1,000 weight units:
  • Example XVII Followingthe;procedure :set forth in Example XIV. but using ethylene sulfide," the: condensation productiformed containedtsubstantial amount-of sulfur; and the i ester: indicated an average increaselin molecular.- weight ofover 240.-weight units ⁇ .
  • Example XVIII Following; the procedureset forth in'Example XIV butusing ethylene imine, the condensation product formed contained substantial amount of nitrogen and the "ester indicated an average in-. crease in molecular weight of over 168 weight units;
  • Example XIX Acondensationproduct was. prepared by reacting potassium. salt: ofv acid ester: of oleyl tartarate with ethyleneoxide underthe reaction condition setforth in ExampleXEV; The product obtained indicated .an .average molecular weight increase overthesalt of around 220 weight units.
  • Example XX A..condensation product was preparedby reacting calcium. methylene disalicylate with .eth-. ylene oxide. under. conditions set forth .in ExamplaXIV. except.that. the reaction. temperature wasincreasedto. to 200? C..
  • Emample XXI Approximately" 1 mole of B-sulfonic acid of w-hydroxyjdecyl carboxylic acid was dispersedin 7 purified dioxane and between .4 and 12 moles of ethylene oxide added andthe'mixtureslowly re acted in-the presence of sodium methylate at between:.7'5 and125C. forabout 48 hours. At the endof the reactionperiod, the condensation product was: recovered and the ester indicated anaverage increase in molecular weight between 176 and 440 weight units. The condensation product was oil soluble and imparted extreme pressure properties to the oil.
  • Example XIV and 4 to 8 moles of PzSs were reacted at 125 to 250 C. for about 24 hours.
  • the phosphorized-sulfurized condensation product was extracted with a ketone and the solvent thereafter removed. On analysis, the product indicated the presence of reacted sulfur and phosphorus in the molecule.
  • Example XXIII About 1 mole of the condensation product of Example XIV and 4 moles of sulfur were reacted atabout 160 C. for about 24 hours. The sulfurizedproduct was isolated by means of toluene to yield a product containing sulfur in the molecule. Any of the above condensation products can be admixed with from 1 to 8 parts of the acid or acid'ester from which the condensation products are derived. Thus, for example, one part of the condensation product of Example II when admixed with four parts of tartaric acid and the mixture added to a base mineral oil the resultant composition (A) possesses excellent extreme pressure properties.
  • Base lubricants which may be improved by addition of minor amounts of condensation re- 1' action products of this invention may be selected from a wide variety of natural oils such as mineral oil, vegetable oil, animal oil, marine oil and mixtures thereof.
  • synthetic lubricants may be used such as polymerized olefins, organic esters, e. g., 2-ethylhexyl sebaeate, dioctyl phthalate, trioctyl phosphate, silicon polymers, e. g., dimethyl silicone polymer; mixtures of natural and synthetic lubricants; lubrieating emulsion bases and the like.
  • General formulation of compositions of invention can be'represented by:
  • Brimary additive Condensation reaction product of this invention 0.01 to 10% Secondary additive: Detergents,
  • compositions of this invention e. g., sulfonates, solubilizers, e, g., esters of polyhydric acids (sorbitan monooleate, glycerol monooleate, etc.), corrosion inhibitors, etc. to 2% l (0.01 to 1%)
  • Base Nature oil such as mineral oil and/or fixed oils and derivatives thereof and/or synthetic lubricants Balance
  • compositions of this invention e. g., sulfonates, solubilizers, e, g., esters of polyhydric acids (sorbitan monooleate, glycerol monooleate, etc.), corrosion inhibitors, etc. to 2% l (0.01 to 1%)
  • Base Nature oil such as mineral oil and/or fixed oils and derivatives thereof and/or synthetic lubricants Balance
  • compositions of this invention e. g., sulfonates, solubilizers, e, g., esters of polyhydric acids (
  • compositions of this invention were evaluated for their extreme pressure properties on a spurgear machine, which essentially consists of two geometrically similar pairs of gears connected by two parallel shafts.
  • the gear pairs are placed in separate gear boxes, which also contain the supporting ball bearings.
  • One of the shafts con sists of two sections connected by a coupling. Loading is accomplished by locking one side of the coupling and applying torque to the other.
  • the conditions of the test were:
  • Mineral oil 5 Mineral oil containing 1% sorbitol 25 Mineral oil containing 1% sorbitan monooleate g 25 Mineral oil containing 2% salicylic acid 20 Mineral oil containing 5% polyethylene oxide polymer (M. W. 1500) Mineral oil containing 1% methylene disalicylic acid lVlZineral oil containing 1% glycerol monooleate Composition 3 (as in table) 70+ Composition 4 (as in table) 70+ Composition 1 (as in table) 70+ Composition 2 (as in table) 70+ Composition 6 (as in table) 70+ Composition 7 (as in table) Composition 13 (as in table) Composition 17 (as in table) Composition A 75+ Because of its synergistic effect the reaction product of this invention can be combined with other additives in lubricants, such as blooming agents, pour point depressants or viscosity improvers, extreme pressure agents, antifoaming agents and the like.
  • other additives in lubricants
  • oil-soluble detergents which include oil-solube salts of various bases with detergent forming acids.
  • bases include metal as well as organic bases.
  • Metallic bases include those of the alkali metals and of Cu, Mg, Ca, Sr, Ba, Zn, Cd, Al, Sn, Pb, Cr, Mn, Fe, Ni, Co, etc.
  • Organic bases include various nitrogen bases as primary, secondary and tertiary amines and quaternary ammonium bases.
  • detergent forming acids are the various fatty acids of, say, 10 to 30 carbon atoms, wool fat acids, paraffin wax acids (produced by oxidation of paraffin wax), chlorinated fatty Compositions Components Composition of Ex. Composition of Ex. Composition of Ex.
  • composition of Ex. Composition of Ex. Composition of Ex. Composition of Ex. Composition of Ex. X Composition of Ex. Composition of Ex. Composition of Ex. Composition of Ex. Ca petroleum sulfonate Sorbitan monooleate Sorbitol monooleate Glycerol monooleate High molecular wt. aliphatic am Mineral oil Mineral oil alkyl naphthalene -- Dimethyl silicone fluid 1
  • the additives were present in amounts varying from 0.5 to to 5%.
  • acids such'as' may be produced by treatment of alkyl aryl hydrocarbons or high boiling petroleum oils with sulfuric acid; sulfuric acid monoester's; phosphoric, arsonic and antimony 'acid mono and diesters, including thecorresponding thiophosphoric, arsenic-and antimony acids,-phosphonic and arsonic acids and the like.
  • Additional detergents are the alkaline earth phosphate diesters, including the thio'ph'o'sphate diester the alkaline earthdiphenolates, specifically'the calcium and barium'saltsof diphenol mono and p'olysulfides.
  • Non m etallic detergents include coinpounds such "as r the ph-osphatides, P such -a-s lecithin and cephalin; certain fatty oils-as rapeseed oils, oltolized fattyor mineral oils and thelike.
  • Antioxidants-comprise several'-types, for example; alkyl phenols such as 2 ,4,6 tr'i'methylphenol, pentamethyl phenol, YZA-d-imethyI-G-tertiarybutyl phenol, '2 i4 -dimethyl-fi-oc'tyl phenol, 2,6 ditertiary-butyl 4-methyl phenol, -'2,4,6-tritertiary-butyl phenol and the like ;aminc phenols asbenzyl amino phenols z-amines such asdibutylphenylene dia-mine, diphenyl amine, phenylbeta naphthylamine, :phenyl-alpha-naphthylamine; dinaphthyl amine.
  • alkyl phenols such as 2 ,4,6 tr'i'methylphenol, pentamethyl phenol, YZA-d-imethy
  • diphenylsulfidadiphenol sulfide, dicresol sulfide, dixylenol sulfide,- methyl butyl 'diphenol sulfide, dibenzyl sulfide, corresponding diand tri-sulfides, and the like; sulfurized fatty oils' or esters of fatty acids and monohydric alcohols, e. g.
  • sulfurized long chain olefins such as may be obtained by dehydrogenation or cracking of wax
  • chlorinated hydrocarbons such as chlorinated paraffin, aromatic hydrocarbons, terpenes, mineral lubricating oil, etc.; or
  • chlorinated esters of fatty acids containing the chlorine in position other than alpha position.
  • Additional ingredients may compriseoil-soluble urea or thiourea derivatives, e. g. urethanes, allophanates, carbazides,"carbazones;etc.; polyisobutylene polymers, unsaturated polymerized 1'2 esters of fatty acidsandmonohydric-alcohols and other :high molecular weight *oil soluble compounds.
  • urea or thiourea derivatives e. g. urethanes, allophanates, carbazides,"carbazones;etc.
  • polyisobutylene polymers unsaturated polymerized 1'2 esters of fatty acidsandmonohydric-alcohols and other :high molecular weight *oil soluble compounds.
  • the amount of additive used may vary from 0.1to 2%or higher.
  • novel reactionaproductsof this invention in addition to being excellent lubricating oil improving agents, are potent oxidation inhibitors for fu'els,-' natural and-synthetic rubber, wax coatingc'ompositions and other or'ganic materials.
  • a lubricating composition comprising a major amountof a liquid organiclubricating base having incorporated therein from about 0.01 to 10% of reaction productobtained by reacting an aliphatic compound selected from-thegroup consisting'of C2-C5 alkylene oxide, C2'C5 alkylene sulfide, andzC -alkylene imine' 'withan organicpolyacidic compouncl containing: from 1 -to'3 freecarboxylicacid groups and-at least one hydroxy' group, said reaction being carried out at atemperatu're -'of:at-' least"7-5 C. in the mole ratio of iro'm4 1' to 12 1 respectively.
  • a lubricating composition comprising a major amount of liquidorganiclubricating base having incorporated therein from"0.01% to of a reaction product obtaine'dby reacting C2-C5 alkylene' oxide with an organic polyhydroxy carboxylic acid containing from -1 to 3 carboxylic acidgroups at a temperature of at least C. and in the mole ratio'of 4i1 to 2:1 respectively.
  • a lubricating composition comprising a, major amount of liquid organic lubricating base having incorporated therein'from-0;01'% tol0% of a reaction product obtained by reacting ethylene oxide with an organicp'olyhydroxy carboxylic acid containing froml' to 3 carboxylic acid-groups at a temperature of at least 75 C. and in the mole ratio of 4:1 to 2:1"respectively.
  • a lubricating composition comprising a major amount "of liquid organic lubricating base having incorporated therein from 0.01% to 10% of a reaction product obtained by reacting C2'-C5 alkylene oxide with an aliphatic polyhydroxy poly-carboxylidacid, said carboxylic acid radical being'not more than three in number, at a temperature of from 75 -C. to- 200.C. and in the mole ratio of 4:1 to 251 respectively.
  • a lubricating composition comprising a major amountof mineral oil having incorporated therein in an amount sufiicient to impart extreme pressure properties of a condensation reaction product obtained by reacting ethylene oxide and tartaric acid at a temperature of from '75 to C. in the mole ratio of about 10:1, respectively.
  • a lubricating composition comprising a major amount of mineral oil having incorporated therein in'an amount sufiicient to impart extreme pressure properties of a condensation reaction product obtained by reacting ethylene oxide and malic acid at a temperature of from 75 to 100 C. in the mole ratio of about 10:1, respectively.
  • a lubricating composition comprising a major amount of mineraloil having incorporated product obtained by reacting'ethylene sulfide and 13 tartaric acid at a temperature of from 75 to 100 C. in the mole ratio of about 10:1, respectively.
  • a lubricating composition comprising a major amount of a liquid organic lubricating base having incorporated therein from about 0.01 to 10% of a reaction product obtained by reacting an organic compound selected from the group consisting of C2-C5 alkylene oxide, C2-C5 alkylene sulfide, and C2-C5 alkylene imine with an organic poly acidic compound containing from 1 to 3 free carboxylic acid groups and at least one hydroxy group, said reaction being reacted at a temperature of at least 75 C.
  • a lubricating composition comprising a major amount of a liquid organic lubricating base having incorporated therein from about 0.01 to 10% of a reaction product obtained by reacting an organic compound selected from the group consisting of C2-C5 alkylene oxide, C2-C5 alkylone sulfide, and C2-C alkylene irnine with an organic poly acidic compound containing from 1 to 3 free carboxylic acid groups and at least one hydroxy group, said reaction being carried out at a temperature of at least 75 C. in the mole ratio of from 4: 1 to 12:1 respectively and treating about 1 mole of the condensation product thus formed with'about 4 moles of a sulfurizing agent at a temperature of around 160 C.
  • a lubricating composition comprising a major amount of a liquid organic lubricating base having incorporated therein from about 0.01 to of a reaction product obtained by reacting an organic compound selected from the group consisting of C2-C5 alkylene oxide, C2-C5 alkylene sulfide, and C2-C5 alkylene imine with an organic poly acidic compound containing from 1 to 3 free carboxylic acid groups and at least one hydroxy group, said reaction being carried out at a temperature of at least 75 C. in the mole ratio of from 4:1 to 12:1 respectively and treating about 1 mole of the condensation product thus formed with about 4 moles of a phosphorous sulfide at a temperature of around 250 C.
  • a lubricating composition comprising a major amount of a liquid organic lubricating base having incorporated therein from about 0.01 to 10% of a reaction product obtained by reacting a C2C5 alkylene oxide with an organic poly acidic compound containing from 1 to 3 carboxylic acid groups and at least one hydroxy group, said reaction being carried out at a temperature of at least C. in the mole ratio of from 4:1 to 12:1, respectively.
  • a lubricating composition comprising a. major amount of a liquid organic lubricating base having incorporated therein from about 0.01 to 10% of a reaction product obtained by reacting an ethylene oxide with-an organic poly acidic compound containing from 1 to 3 carboxylic acid groups and at least one hydroxy group, said reaction being carried out at a temperature of at least 75 C. in the mole ratio of from 4:1 to 12:1, respectively.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US142536A 1950-02-04 1950-02-04 Extreme pressure lubricant Expired - Lifetime US2628941A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
NL79051D NL79051C (xx) 1950-02-04
BE504651D BE504651A (xx) 1950-02-04
US142536A US2628941A (en) 1950-02-04 1950-02-04 Extreme pressure lubricant
US173754A US2648634A (en) 1950-02-04 1950-07-14 Method of preparing lubricating grease compositions
GB2638/51A GB705273A (en) 1950-02-04 1951-02-02 Lubricating compositions
DEN3458A DE872624C (de) 1950-02-04 1951-02-02 Zusammengesetzte Schmiermittel, insbesondere auf Mineraloelbasis
FR1047896D FR1047896A (fr) 1950-02-04 1951-07-13 Procédé de préparation de compositions de graisses lubrifiantes
DEN4161A DE872626C (de) 1950-02-04 1951-07-15 Verfahren zur Herstellung von Schmierfetten
GB16804/51A GB704019A (en) 1950-02-04 1951-07-16 Improvements in and relating to the preparation of lubricating greases

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US142536A US2628941A (en) 1950-02-04 1950-02-04 Extreme pressure lubricant

Publications (1)

Publication Number Publication Date
US2628941A true US2628941A (en) 1953-02-17

Family

ID=22500222

Family Applications (1)

Application Number Title Priority Date Filing Date
US142536A Expired - Lifetime US2628941A (en) 1950-02-04 1950-02-04 Extreme pressure lubricant

Country Status (6)

Country Link
US (1) US2628941A (xx)
BE (1) BE504651A (xx)
DE (2) DE872624C (xx)
FR (1) FR1047896A (xx)
GB (2) GB705273A (xx)
NL (1) NL79051C (xx)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2774733A (en) * 1953-05-12 1956-12-18 Shell Dev Lubricating composition
US2780642A (en) * 1953-05-07 1957-02-05 Monsanto Chemicals Reaction of aryloxyacetic acids and unsymmetrical epoxides
US3130161A (en) * 1958-11-18 1964-04-21 Shell Oil Co Lubricating oil and anti-wear additives therefor
US3236771A (en) * 1964-11-02 1966-02-22 Sinclair Research Inc Anti-chatter gear lubrication
US3301783A (en) * 1960-08-04 1967-01-31 Petrolite Corp Lubricating composition
US4957651A (en) * 1988-01-15 1990-09-18 The Lubrizol Corporation Mixtures of partial fatty acid esters of polyhydric alcohols and sulfurized compositions, and use as lubricant additives
WO2011075403A1 (en) * 2009-12-14 2011-06-23 The Lubrizol Corporation Lubricating composition containing an antiwear agent

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1113358A (fr) * 1953-10-05 1956-03-28 Bataafsche Petroleum Compositions de graisses
DE1024658B (de) * 1954-10-08 1958-02-20 Alpha Molykote Corp Verfahren zum nachtraeglichen Einbau von chemisch bzw. thermisch beeinflussbaren Substanzen in Schmierfette
FR1206242A (fr) * 1958-06-11 1960-02-08 Exxon Research Engineering Co Perfectionnements aux huiles lubrifiantes pour moteurs à combustion interne
NL108694C (xx) * 1959-02-11
DE1128069B (de) * 1959-02-11 1962-04-19 Shell Int Research Schmierfett
GB1266214A (xx) * 1969-10-24 1972-03-08

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1463092A (en) * 1921-07-07 1923-07-24 Technical Res Works Ltd Lubricant and process of preparing same
US1810318A (en) * 1925-10-21 1931-06-16 Ig Farbenindustrie Ag Production of esters of glycols
US2134736A (en) * 1935-04-19 1938-11-01 Atlantic Refining Co Lubricant
US2341846A (en) * 1941-06-24 1944-02-15 American Cyanamid Co Polyhydric alcohol ethers of aliphatic polycarboxylic acid esters and their preparation
US2370300A (en) * 1937-12-03 1945-02-27 Standard Oil Co California Lubricant
US2457139A (en) * 1946-02-26 1948-12-28 Carbide & Carbon Chem Corp Esters of polyoxyalkylene diols
US2481278A (en) * 1946-08-31 1949-09-06 Shell Dev Polyoxyalkylene compounds
US2491432A (en) * 1946-08-12 1949-12-13 Shell Dev Stabilized lubricant
US2536684A (en) * 1947-06-02 1951-01-02 Shell Dev Sulfurized product and preparation thereof
US2542550A (en) * 1947-12-31 1951-02-20 Standard Oil Dev Co Esters of polyether acids and process

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1463092A (en) * 1921-07-07 1923-07-24 Technical Res Works Ltd Lubricant and process of preparing same
US1810318A (en) * 1925-10-21 1931-06-16 Ig Farbenindustrie Ag Production of esters of glycols
US2134736A (en) * 1935-04-19 1938-11-01 Atlantic Refining Co Lubricant
US2370300A (en) * 1937-12-03 1945-02-27 Standard Oil Co California Lubricant
US2341846A (en) * 1941-06-24 1944-02-15 American Cyanamid Co Polyhydric alcohol ethers of aliphatic polycarboxylic acid esters and their preparation
US2457139A (en) * 1946-02-26 1948-12-28 Carbide & Carbon Chem Corp Esters of polyoxyalkylene diols
US2491432A (en) * 1946-08-12 1949-12-13 Shell Dev Stabilized lubricant
US2481278A (en) * 1946-08-31 1949-09-06 Shell Dev Polyoxyalkylene compounds
US2536684A (en) * 1947-06-02 1951-01-02 Shell Dev Sulfurized product and preparation thereof
US2542550A (en) * 1947-12-31 1951-02-20 Standard Oil Dev Co Esters of polyether acids and process

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2780642A (en) * 1953-05-07 1957-02-05 Monsanto Chemicals Reaction of aryloxyacetic acids and unsymmetrical epoxides
US2774733A (en) * 1953-05-12 1956-12-18 Shell Dev Lubricating composition
US3130161A (en) * 1958-11-18 1964-04-21 Shell Oil Co Lubricating oil and anti-wear additives therefor
US3301783A (en) * 1960-08-04 1967-01-31 Petrolite Corp Lubricating composition
US3236771A (en) * 1964-11-02 1966-02-22 Sinclair Research Inc Anti-chatter gear lubrication
US4957651A (en) * 1988-01-15 1990-09-18 The Lubrizol Corporation Mixtures of partial fatty acid esters of polyhydric alcohols and sulfurized compositions, and use as lubricant additives
WO2011075403A1 (en) * 2009-12-14 2011-06-23 The Lubrizol Corporation Lubricating composition containing an antiwear agent
US9708563B2 (en) 2009-12-14 2017-07-18 The Lubrizol Corporation Lubricating composition containing an antiwear agent

Also Published As

Publication number Publication date
BE504651A (xx)
FR1047896A (fr) 1953-12-17
GB705273A (en) 1954-03-10
DE872624C (de) 1953-04-02
GB704019A (en) 1954-02-17
NL79051C (xx)
DE872626C (de) 1953-04-02

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