US2682523A - Lubricants - Google Patents

Lubricants Download PDF

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Publication number
US2682523A
US2682523A US163966A US16396650A US2682523A US 2682523 A US2682523 A US 2682523A US 163966 A US163966 A US 163966A US 16396650 A US16396650 A US 16396650A US 2682523 A US2682523 A US 2682523A
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United States
Prior art keywords
wax
melting point
hydrocarbon
waxes
residue
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US163966A
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English (en)
Inventor
Samuel K Talley
Thomas E Reamer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Development Co
Original Assignee
Shell Development Co
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Filing date
Publication date
Priority to BE503495D priority Critical patent/BE503495A/xx
Priority to BE503494D priority patent/BE503494A/xx
Priority to NL81706D priority patent/NL81706C/xx
Priority to US163966A priority patent/US2682523A/en
Application filed by Shell Development Co filed Critical Shell Development Co
Priority to FR1037448D priority patent/FR1037448A/fr
Priority to GB12197/51A priority patent/GB694004A/en
Priority to GB12241/51A priority patent/GB709733A/en
Priority to DEN3951A priority patent/DE967342C/de
Priority to DEN3952A priority patent/DE929208C/de
Application granted granted Critical
Publication of US2682523A publication Critical patent/US2682523A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/01—Acyclic saturated compounds containing halogen atoms containing chlorine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/02—Halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G73/00—Recovery or refining of mineral waxes, e.g. montan wax
    • C10G73/38—Chemical modification of petroleum
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
    • C10M105/52—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen and halogen only
    • C10M105/525—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen and halogen only halogenated waxes
    • 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
    • C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
    • C10M131/14—Halogenated waxes
    • 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
    • C10M173/00—Lubricating compositions containing more than 10% water
    • 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
    • C10M173/00—Lubricating compositions containing more than 10% water
    • C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/20—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils
    • H01B3/22—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils hydrocarbons
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/20—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils
    • H01B3/24—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils containing halogen in the molecules, e.g. halogenated oils
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
    • C—CHEMISTRY; METALLURGY
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04—Elements
    • C10M2201/041—Carbon; Graphite; Carbon black
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    • C10M2201/04—Elements
    • C10M2201/041—Carbon; Graphite; Carbon black
    • C10M2201/042—Carbon; Graphite; Carbon black halogenated, i.e. graphite fluoride
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06—Metal compounds
    • C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06—Metal compounds
    • C10M2201/065—Sulfides; Selenides; Tellurides
    • C10M2201/066—Molybdenum sulfide
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08—Inorganic acids or salts thereof
    • C10M2201/082—Inorganic acids or salts thereof containing nitrogen
    • C10M2201/083—Inorganic acids or salts thereof containing nitrogen nitrites
    • C—CHEMISTRY; METALLURGY
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/085—Phosphorus oxides, acids or salts
    • C—CHEMISTRY; METALLURGY
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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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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
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    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
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    • C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
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    • C10M2205/17—Fisher Tropsch reaction products
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    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10N2040/247—Stainless steel

Definitions

  • halogenated derivatives of high melting point hydrocarbon waxes derived from petroleum distillation residues It especially involves the production of halogenated petroleum wax obtained from distillation residues of petroleum petroleum lubricating oil base stocks during the' treatment of such lubricating oil stocks to remove therefrom materials which markedly'reduce the fluidity of the oil when it is cooled to low temperatures, such as C. and the like.
  • the base stock is generally first separated into different fractions by distillation, under reduced pressure, and-the distillate fractions, as well as the residual fraction, are subsequently dewaxed to remove the higher melting hydrocarbons present and to produce an oil with a suitable pour point.
  • oils liquid hydrocarbons
  • the oils may be at least partially removed from the slack or crude wax, thereby yielding a harder wax product, the so-called scale wax,' and a still more oily wax product, so-called slop wax, which is a soft wax.
  • the same separations may be effected in the presence of an inert diluent, such as a light hydrocarbon, propane, butane, and the like, or in the presence of various organic solvents which may exert preferential solvent action for one type of hydrocarbons present over another type present, such as methylethyl ketone, acetone, benzene, toluene, and the like, and mixtures thereof, as is well known and practiced in the art, with appropriate selection of dewaxing temperatures for the waxy oil and of deoiling temperatures for de-oiling the oily wax.
  • an inert diluent such as a light hydrocarbon, propane, butane, and the like
  • organic solvents which may exert preferential solvent action for one type of hydrocarbons present over another type present, such as methylethyl ketone, acetone, benzene, toluene, and the like, and mixtures thereof, as is well known and practiced in the art, with appropriate selection of
  • non-straight chain hydrocarbons and to, be for the most part a mixture of isoparaffiniqnaphthenic and. aromatic hydrocarbons. f Magnification reveals a microcrystalline structure, hence the name microcrystalline waxr .It is an object of -this invention to produce halogenated-high,melting point waxes obtained from particularpetroleum hydrocarbon fractions.
  • a further object is to produce a chlorinated high molecular weight and high melting point wax material from short residue fractions of waxy
  • a still further object is to produce aqueous andnon-aqueous emulsions containing as an essentialingredient a new halogenated, high molecular weight and high melting point hydrocarbonwax derived from short residue fractions ofwaxy petroleum base stocks, said emulsions having. wide applicability for industrial uses.
  • Figure'I is a flow sheet for the process of preparing waxes of this invention
  • Figure II discloses the composition ofwaxes of this invention from which the halogenated derivatives are obtained
  • Figure III disclosescomparative test data of waxes of this invention as against waxes well known in the artf
  • halogenated waxes of the invention are useful as such in metal-working operations and also in certain emulsions as will be described hereinafter.
  • the hydrocarbon waxes and fractions thereof, from. which the halogenated waxy products of this invention are. made are derived from the short residue fractions of Waxy petroleum base stocks such as East Texas, Mid- Oontinent and Pennsylvania crudes, said waxes having a paraflinicity corresponding to a content of at least 60%, and preferably at least 80% by weight or more, thereof of straightechain paraffin hydrocarbons, the hydrocarbon wax. having a melting point of at least 160 F., and preferably above 180 F., and a molecular weight around 475 and preferably ranging from 525 to 1000.
  • the hydrocarbon waxes from which the novel halogenated waxes are produced, can be obtained from petroleum oils derived from different sources or localities and having different specific characteristics, the only requirement being, that the oil be of. a paraflinic or parafli'nicnaphtheni'c character; that is, that it is a waxy oil and that it contain paraffinic hydrocarbons of high molecular weight, including normal and isoparaifinic hydrocarbons, with or without naphthenic. hydrocarbons.
  • the stock material is preferably a. so-called mixed base oil in that it is largely paraffinic and naphthenic in character, the East Texas crudes being particularly valuable for recovering therefrom hydrocarbon waxes used to form the halogenated products of this invention.
  • the high molecular weight, high melting point parafiin hydrocarbon waxes useful in this invention can be recovered from a suitable base crude stock in the following manner.
  • a crude oil such as an East Texas crude is topped to remove the lighter fractions and the topped crude oil is subjected to vacuum distillation to recover the distillate lubricating oil base stock in one or more fractions which contains the crystalline parafiin waxes well known in the art.
  • the short residue fraction is further processed in order to recover the wax fraction thereof used to form the halogenated products of this invention by deasphaltizing if necessary, solvent extracting to produce a waxy, raflinate residual stock, d'ewaxing the deasphalted andsolvent extractedshort residue utilized for a specific purpose such as for water proofing and coating materials, electrical insulation, fire proofing, lubricating oil such as. drawing oil and the like.
  • the short residue can besubjected to propane deasp'haltizing treatment and the deasphalted' short residue subjected to solvent extraction treatment with phenol or the like, and the waxy raffinate fraction furtherprocessedh Thiswaxy raffinateis subjected to a dewaxing? solvent treatment in order to recover from the waxy raffinate the so-called short residue.- slack or crude wax.
  • This short residue crude wax. is: de-oiled as by dissolving the wax in a typical waxde-oiling solvent or solvent mixture. at. a.
  • This microcrystalline wax can be segregated into two wax products by dissolving it in dewaxing or de-oiling solvents at an elevated temperature and cooling the solution just sufficiently to precipitate a hard parafiin wax having a melting point above 160 F. and generally above 180 F; a plastic microcrystalline wax with a melting point above 140 F. is recoverable from the filtrate.
  • the primary microcrystalline wax having a melting point above 160 F., or the plastic mi'crocrystalline wax, or the high melting point paraffin wax recovered from the primary microcrystalline wax, as well as fractions and mixtures thereof, can be used.
  • Figure I is a schematic flow diagram illustrating a process of recovering waxes of this invention from suitable base stocks, For example, a topped. East Texas crude oil is subject to vacuum distillation (I) to recover the distillate lubricating oil base stock contained therein, including all material which is removable at about 650 F; and 130 mm. of mercury absolute pressure. From this lubricating cil distillate can be recovered the conventional or commercial. crystalline hydrocarbon wax known in the art as paraihn wax, in the manner indicated in the flow diagram by steps (7), (8), and (9)..
  • This paraffin wax is a low melting wax having a melting point range from 113 to less than 140 F.
  • This type of low melting parafiin wax, and particularly the halogen derivatives, is clearly distinct in properties and utility to the high melting, point waxes of this invention and particularly to the halogenated products thereof.
  • the residue fraction if necessary, is given a propane deasphalting treatment (2') yielding a deasphalted short residue.
  • the deasphalted short residue is then given solvent extraction treatment with any suitable selective solvent, suchas phenol, (3)- which results in the formation of a short residue deasphaltized extract and a short residue deasphaltized' waxy raffinate-fraction'.
  • the waxy raflinate is dissolved in a dewa-xing solvent or solvent mixture (4) such as the usual mixture of methylethyl ketone, benzene and toluene, the solution is chilled to about l-0 F. to precipitate the Waxes and filtered to recover wax from the oil.
  • the wax is usually thoroughly washed on the filter, after which it is recovered as an oily wax, so-called short residue crude or slack wax.
  • a representative crude wax thus produced had the following properties:
  • This short residue crude wax is de-oiled as by dissolving the wax in a typical wax de-oiling solvent or solvent mixture such as methyl isobutyl ketone or the usual dewaxing solvent mixture of methylethyl ketone, benzene and toluene (5). for example, 7 volumes of solvent to 1 volume of wax at a solution temperature of about F., cooling the solution to a suitable temperature such as about 60 F.
  • a primary microcrystalline wax having a melting point of about 160 F., the component parts of which are shown graphically in Figure II by areas (1), (2), (3) and (4), the molecular weights of which are above 475 and range from about 525 to 1000.
  • the primary microcrystalline wax (a) is segregated into two wax products by fractional crystallization (6). This is suitably accomplished by dissolving wax (a) in from about 5 to about 10, preferably 7, volumes of a suitable dewaxing or de-oiling solvent, as already described, at a. suitable elevated temperature, such as about 160 F., and chilling the solution suflicient to precipitate substantially only the higher melting point waxes (b), or (c) if subsequently clay treated, and filtering the precipitated high melting point, hard parafiin wax having a melting point above about 180 F., the component parts of which are represented graphically in Figure II by the area bracketed by 180 F.
  • the wax fraction in the solution is recovered by distilling off the solvent, or by precipitation at a still lower temperature, to produce a plastic microcrystalline wax (d), or (e) if subsequently clay treated, said wax having a melting point above 140 F.
  • a plastic microcrystalline wax (d) or (e) if subsequently clay treated, said wax having a melting point above 140 F.
  • the wax (b) or (c) of Figure I is the wax fraction embraced by the bracket 180 F.
  • Table I show the yields and properties of various high melting, essentially straight-chain paraffin waxes and of the complementary plastic waxes obtained from the de-oiled primary microcrystalline wax at various filtration temperatures.
  • the high melting wax had a melting point of 182 F., and its index of refraction differed from that of the normal paraffin hydrocarbon of the same melting point by only 0.0042 unit at 90 C.
  • the penetration of this latter'high melting wax was 4 to 6 mm./ 10 g.
  • the high-melting waxes of relatively low index of refraction comprising essentially and substantially only high melting point, normal paraffin hydrocarbons, are recoverable from the primary microcrystalline wax, or from the entire residual slack wax, by dissolving the wax in a suitable wax (or so-called dewaxing) solvent, such as methylethyl ketone, methyl isobutyl ketone, acetone, dichloro-diethyl ether, methyl isobutyl carbinol, and the like, or mixtures thereof, as well as mixtures of such solvents with aromatic hydrocarbons such as benzene, toluene.
  • a suitable wax or so-called dewaxing solvent
  • a solvent to wax weight ratio of from about 2:1 to about 10:1, preferably from about 5:1 to about 9: 1, at a temperature at least as high as about the normal melting point of the wax being treated, and generally about 150 F. to 170 F., and cooling the solvent-wax solution to a temperature from about F. to about F., below the desired melting point of the high melting, hard, paraffin wax which it is desired to precipitate from the solution and to recover as high melting wax.
  • the difference between the melting point of said wax and the filtration temperature must be at a minimum, being of the order of about 65 F. or less.
  • the filtration temperature should be changedby about two degrees. In general, the filtration temperature should be about 100 F. or higher, depending on the specific properties desired for the separated wax.
  • Fluorinated derivative of a high melting, wax has a halogen content of at least 20% and residue, straight-chain paraffin wax having 2. preferably so that the wax contains a halogen melting point of 180-195 F. and a fluorine concontent of from to about 60%. tent of from 25 to 60%.
  • the preferred halogenating agent is gaseous (5) 25-60% chl'orinated-fiuorinated derivative chlorine and the waxes of this invention can be of a crude primary microcrystalline residue hychlorinated by passing gaseous chlorine through drocarbon Wax having a melting oint of 160165 the wax at just above its melting point, with or F., the chlorine content being at least 80% of the Without the use of a catalyst, After chlorinatotal halogen content of the wax. tion it is preferable to blow the chlorinated wax 4n (6') 25-60% chlorinated-fiuorinated derivative with an inert gas such as nitrogen and the like.
  • wax having a. melting point of 180-195 Ft. the they can be fiuorinated, brominated, or the wax chlorine content being at least 80% of the total can be halogenated in such a manner as to conhalogen content of the wax. tain dissimilar halogen atoms in the molecule. ('7) 25-60% chlorinated derivative of a mixed
  • the halogen conresidue hydrocarbon wax consisting of 60%80% tent of the halogenated high melting, high moof residue, straight-chain paraffin wax having a lecular weight residue hydrocarbon waxes be melting. point. of 180-195" F. and 4070-2070 of above 20% and preferably range from 25 to 60 a plastic microcrystalline wax having a melting by weight. point of lid-1&5" F,
  • a mixed (184 F.) high molecular weight (640-660) preresidue hydrocarbon Wax consisting of 60%-80% dominantly straight-chain paraffin wax was of residue, predominantly straight-chain pararfin heated to about 230-248 F. and maintained at wax having a melting point of 180-195 F. and said temperature while chlorine gas was passed 40%-20% of a plastic microcrystalline wax havthrough the molten wax until the chlorine
  • the chlorinated The new and novel halogenated (preferably wax was blown with nitrogen in order to remove chlorinated) derivatives of high melting, high impurities and the resulting product was. a dark molecular weight, hydrocarbon waxes of this inbrown, highly viscous mass and had the followvention can beused, per se, or as components in ing properties: various aqueous or non-aqueous media.
  • Chlorino ated hydrocarbon waxes of this invention are (20/4 useful, per so, as industrial metal-working lubricmorme (percent) cants such as rolling, drawing, stamping, forging Vlsc' at 139 F (centlstokes) 5061 lubricants or the like and 3.376 ar'fiinulqrl uit- Visc. at 210 F. (centistokes) 300.6 p "1 T able for working metals which have a negative '2 surface charge such as stainless and other high chromium steels.
  • halogenated waxes of this invention are wax of this invention) under conditions substanuseful as additives in cutting oil compositions, tially described in U. S. Patents 2,186,916, extreme pressure lubricants, grease compositions 2,340,968, 2,372,414, 2,370,787, and 2,403,179. '15 and the like.
  • emulsifying agent neutral partial esters of polyhydric alcohols and carboxylic acids, although other emulsifying agents are suitable.
  • the partial ester may be derived from glycerine, erythritol, pentaerythritol, mannitol, sorbitol, sorbitan, etc.
  • the acid forming the ester with the polyhydric alcohol should have at least about 10 and preferably from about 10 to 40 carbon atoms, in the form of an aliphatic or cyclo aliphatic radical.
  • Suitable radicals comprise, for example, those of acids such as capric, lauric, myristic, palmitic, oleic, stearic radicals, etc. Radicals such as are contained in the acids obtained from rosin or tall oil as well as naphthenic acids having the requisite number of carbon atoms are also applicable.
  • esters are: glyceryl monoand di-oleate, glyceryl monoand di-stearate, sorbitan mono-, and tri-oleate, sorbitan mono-, diand tri-stearate, glyceryl monoand di-ricinoleate, pentaerythritol mono-stearate, gylcerol mono-ester of soya bean fatty acids, pentaerythritol monocaprylate, polymerized partial esters of glycol laurate, oleylricinoleate, and stearate, etc. These esters may be modified by hydrogenation condensed with alkylene oxide and the like, if desired.
  • the amount of said partial ester alcohol which is suitably used in compositions of this invention varies from about 1 to about 25% and'preferably between about 5 and 20%.
  • cationic agents containing an oleophilic group should be added to the emulsion in minor amounts, such as organic amines, am,- ides or salts of such organic nitrogen bases.
  • organic amines, am,- ides or salts of such organic nitrogen bases Specifically preferred are long-chain aliphatic amines or amides having 8 or more carbon atoms, for instance, up to about 40 carbon atoms, in the hydrocarbon chain, such as octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, octadecenyl amines or amides.
  • cyclic amines and alkylol amines can be used such as cyclohexyl amine, ethanolamine, diethanolamine, N-lauryl hydroxylamine, mono-oleicamide of diethylene triamine, and the like.
  • Quaternary ammonium compounds such as trimethyl benzyl ammonium hydroxide, cetyl piperidinium chloride, are also useful.
  • the general formulation of wax emulsions of this invention may be represented by:
  • the emulsions can be prepared by any suitable means such as by heating the chlorinated residue wax until suitably fluid, adding the emulsifler and cationic wetting agent and heating the mixture under constant agitation. The required amount of water is added with constant agitation and the mixture cooled to room temperature. Instead of adding the emulsifier to the 10 molten chlorinated wax, it can be admixed with the water and introduced into the fluid chlorinated wax in that manner. The product is dispersible in water and other aqueous media and excellent lubricants are obtained when the base emulsion is used with water in the ratio of 1:2 to 1:10.
  • test results are represented graphically in Figure III and the superiority for compositions of this invention over those containing the conventional halogenated parafiin waxes can be clearly noted.
  • Figure III low coefiicient of friction athigh normal loads indi cates a superior lubricant.
  • Corrosion inhibitors or anti-rusting compounds may also be combined with the halogen waxes, such as dicarboxylic acids of 16 and more carbon atoms, 6. g., octadecenyland octadecylsuccinic acid, alkali metal and alkaline earth metal salts of sulfonic acids (petroleum sulfonic acids) and fatty acids, organic compounds containing an acidic radical in close proximity to a mercapto, nitrile, nitro or nitroso group (e. g., alpha cyano stearic acid).
  • halogen waxes such as dicarboxylic acids of 16 and more carbon atoms, 6. g., octadecenyland octadecylsuccinic acid, alkali metal and alkaline earth metal salts of sulfonic acids (petroleum sulfonic acids) and fatty acids, organic compounds containing an acidic
  • Additional ingredients may comprise oilsoluble urea or thiourea derivatives, e. g., urethanes, allophanates, carbazides, carbazones, etc., polyisobutylenepolymers, unsaturated polymerized esters of fatty acids and monohydric alcohols and other high molecular weight oilsoluble compounds.
  • oilsoluble urea or thiourea derivatives e. g., urethanes, allophanates, carbazides, carbazones, etc.
  • polyisobutylenepolymers unsaturated polymerized esters of fatty acids and monohydric alcohols and other high molecular weight oilsoluble compounds.
  • the amount of additive used may vary from 0.1% to 2% or higher. However, substantial improvement is obtained by using amounts ranging from 0.1% to 0.5% in combination with the halogenated high melting point waxes of this invention.
  • compositions of this invention can be applied to and removed fromthe surfaces to which they have been applied by any suitable means such as are well known in commercial practice.
  • An aqueous emulsion metal-working lubricating concentrate composition containing from Composition 36% Reduction Speed (ft/min.)
  • Chlorinated distillate wax (M. P. of wax 124; C1 42%); Remainder same as Ex. IV-Sorbitan monooleate, Polyoxyethylene sorbitan, monooleate, Stearylamine Water.
  • halogenated waxes of this invention can be added, generally in minor amounts of from 3 to 49% andpreferably from 5 to are suitably any substantially neutral vehicle of polar and non-polar character such as water, water emulsions, natural, synthetic and/or mineral oils, erg. castor oil,-lard oil,-mineral oil, greases, polymeric olefins and copolymers such as alkylene glycolalkylene oxide copolymer, natural and synthetic resins, etc.
  • polar and non-polar character such as water, water emulsions, natural, synthetic and/or mineral oils, erg. castor oil,-lard oil,-mineral oil, greases, polymeric olefins and copolymers such as alkylene glycolalkylene oxide copolymer, natural and synthetic resins, etc.
  • compositions containing the "halogenated derivative of a high melting point wax of this invention can be added, e. g., non-metallic detergents such as the phosphatides, lecithin and cephalin, certain fatty oils as rapeseed oils, voltolized fatty or mineral oils or lanolin, sulfonates, metal stearate e. g. Ca or Al stearate, phenates (halo-waxes), and the like.
  • non-metallic detergents such as the phosphatides, lecithin and cephalin, certain fatty oils as rapeseed oils, voltolized fatty or mineral oils or lanolin, sulfonates, metal stearate e. g. Ca or Al stearate, phenates (halo-waxes), and the like.
  • Anti-oxidants can be added to halogen-waxes of this invention such as, for example, alkyl phenols such as 2,4,6-trimethyl phenol, 2,4--dimethyl-fi-tertiary-butyl phenol, 2,6-ditertiarybutyl--methyl-phenol, and the like; amino phenols as benzyl amino phenols; amines such as dibutyl-phenylene diamine, diphenyl amine,
  • At least F. a molecular weight above 475, and consisting of at least-60% normal straightchain hydrocarbons and the remaining constituents being highmelting isoparamnic and naphthenic hydrocarbons; from about 1% to about 25% of an ester selected from the group consisting of an ester of a polyhydric alcohol and a carboxylic acid and a polyalkylene glycol ether of a partial ester of a polyhydric alcohol and a carboxylic acid; from about 0.7% to 10% of an organic nitrogen-containing compound having a hydrocarbon .chain of from 8 to 18 carbon atoms selected from thegroup consisting-of an aliphatic amine, and an aliphatic amide; and the balance being water.
  • An aqueous emulsion metal-working lubricating concentrate composition containing from 3 to 50% of a halogenated high melting-residue hydrocarbon wax containing 20-50% halogen, the hydrocarbon wax having a melting point-of at least F., a molecular weight above 600, and consisting of at least 80% normal straight-chain hydrocarbons and the remaining constituents being isoparaii'inic and naphthenic hydrocarbons; from about 1% to about 25% of an ester of a 13 polyhydric alcohol and an aliphatic monocarboxylic acid; from about 0.7% to 1% of a longchain aliphatic amine having a hydrocarbon chain of from 8 to 18 carbon atoms; and the balance being water.
  • An aqueous emulsion metal-working lubricating concentrate composition containing from 3 to 50% of a chlorinated high melting residue hydrocarbon wax containing -60% chlorine, the hydrocarbon wax having a melting point of at least 180 F., a molecular weight above 600, and consisting of at least 80% normal straightchain hydrocarbons and the remaining constituents being isopararfinic and naphthenic hydrocarbons; from about 1% to about of an ester of a polyhydric alcohol and an aliphatic monocarboxylic acid; from about 0.7% to 1% of a long-chain aliphatic amine having a hydrocarbon chain of from 8 to 18 carbon atoms; and the balance being water.
  • An aqueous emulsion metal-working lubricating concentrate composition containing from 3 to 50% of a fiuorinated high melting residue hydrocarbon wax containing 20-60% fluorine, the hydrocarbon wax having a melting point of at least 180 F., a molecular weight above 600, and consisting of at least 80% normal straight-chain hydrocarbons and the remaining constituents being isoparaflinic and naphthenic hydrocarbons; from about 1% to about 25% of an ester of a polyhydric alcohol and an aliphatic monocarboxylic acid; from about 0.7% to 1% of a longchain aliphatic amine having a hydrocarbon chain of from 8 to 18 carbon atoms; and the balance being water.
  • An aqueous emulsion metal-working lubricating concentrate composition containing from about 5 to of a chlorinated high melting residue hydrocarbon wax containing approximately 20-40% chlorine, the hydrocarbon wax having a melting point above 180 F., a molecular weight above 600, and consisting essentially of a mixture of normal straight-chain hydrocarbons and isoparaffinic hydrocarbons, the normal straight-chain hydrocarbons constituting about 80% of the wax mixture; from 5 to 20% of sorbitan monooleate, from 0.5 to 5% of a longchain aliphatic amine having a hydrocarbon chain of from 8 to 18 carbon atoms; and the balance being water.
  • An aqueous emulsion metal-working lubricating concentrate composition containing from about 5 to 40% of a chlorinated high melting residue hydrocarbon wax containing approximately 20-40% chlorine, the hydrocarbon wax having a melting point above 180 F., a molecular weight above 600, and consisting essentially of a mixture of normal straight-chain hydrocarbons and isoparafiinic hydrocarbons, the normal straight-chain hydrocarbons constituting about 80% of the wax mixture; from 5 to 20% of sorbitan monooleate, from 0.5 to 5% of laurylamine; and the balance being water.
  • An aqueous emulsion metal-working lubricating concentrate composition containing from about 5 to 40% of a chlorinated-high melting residue hydrocarbon wax containing approximately 20-40% chlorine, the hydrocarbon wax having a melting point above 180 F., a molecular weight above 600, and consisting essentially of a mixture of normal straight-chain hydrocarbons and isoparafiinic hydrocarbons, the normal straight-chain hydrocarbons constituting about 80% of the wax mixture and the balance of said wax mixture consisting predominantly of a mixture of naphthenic and aromatic hydrocarbons; from 5 to 20 of polyoxyethylene sorbitan monooleate, from 0.5 to 5% of laurylamine; andthe balance being water.
  • H a chlorinated-high melting residue hydrocarbon wax containing approximately 20-40% chlorine
  • the hydrocarbon wax having a melting point above 180 F., a molecular weight above 600, and consisting essentially of a mixture of normal straight-chain hydrocarbons and isoparafiinic hydrocarbons, the normal straight
  • An aqueous emulsion metal-working lubricating concentrate composition containing from about 5 to 40% of a chlorinated high melting residue hydrocarbon wax containing approxiabout 5 to 40% of a chlorinated high melting residue hydrocarbon wax containing approximately 20-40% chlorine, the hydrocarbon wax having a melting point above 180 F., a molecular weight above 600, and consisting essentially of a mixture of normal straight-chain hydrocarbons and isoparafiinic hydrocarbons, the normal straightchain hydrocarbon constituting about of the wax mixture and the balance of said wax mixture consisting predominantly of a mixture of naphthenic and aromatic hydrocarbons; from 5 to 20% of polyoxyethylene sorbitan monooleate, from 0.5 to 5% of stea-rylamine; and the balance being water.
  • An aqueous emulsion metal-working lubricating concentrate containing the following constituents in approximately the following proportions:
  • Per cent Hydrocarbon wax residue as defined in claim 5 30 Sorbitan monooleate 2 Polyoxyethylene sorbitan monooleate 4 Abietylamine 3 Water Balance 12.
  • An emulsion consisting essentially of the composition of claim 1 and additional water in the ratio of from 1:2 to- 1:10, respectively.
  • An emulsion consisting essentially of the composition of claim 2 and additional water in the ratio of from 1:2 to 1:10, respectively.
  • An emulsion consisting essentially of the composition ofclaim 10 and additional water in the ratio of from 1:2 to 1:10, respectively.
  • An emulsion consisting essentially of the composition of claim 11 and additional water in the ratio of from 1:2 to 1:10, respectively.

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FR1037448D FR1037448A (fr) 1950-05-24 1951-05-23 Paraffine halogénée
GB12197/51A GB694004A (en) 1950-05-24 1951-05-24 Improvements in or relating to halogenated petroleum waxes
GB12241/51A GB709733A (en) 1950-05-24 1951-05-24 Improvements in and relating to aqueous emulsions of paraffin wax or halogenated derivatives thereof
DEN3951A DE967342C (de) 1950-05-24 1951-05-26 Verfahren zur Herstellung eines halogenierten Paraffins
DEN3952A DE929208C (de) 1950-05-24 1951-05-26 Waessrige Emulsion, insbesondere fuer die Metallbearbeitung

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US3011972A (en) * 1957-02-25 1961-12-05 Sinclair Refining Co Method for the manufacture of an oxidation stable bright stock
US3012960A (en) * 1959-07-28 1961-12-12 Shell Oil Co Manufacture of lubricating oils and waxes
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US3201349A (en) * 1960-11-18 1965-08-17 Sinclair Research Inc Emulsifiable oil composition
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US6291407B1 (en) 1999-09-08 2001-09-18 Lafrance Manufacturing Co. Agglomerated die casting lubricant
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US9200230B2 (en) 2013-03-01 2015-12-01 VORA Inc. Lubricating compositions and methods of use thereof
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US3526596A (en) * 1968-06-05 1970-09-01 Quaker Chem Corp Lubricants for metalworking operations
FR2501526A1 (fr) * 1981-03-13 1982-09-17 Montagne Noire Produits Chimiq Nouveaux emulsionnants et leur application pour la production de vaccins
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US3011972A (en) * 1957-02-25 1961-12-05 Sinclair Refining Co Method for the manufacture of an oxidation stable bright stock
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US2956001A (en) * 1958-12-03 1960-10-11 Exxon Research Engineering Co Refining of microcrystalline wax
US3005768A (en) * 1958-12-19 1961-10-24 Exxon Research Engineering Co Dehazing process
US3012960A (en) * 1959-07-28 1961-12-12 Shell Oil Co Manufacture of lubricating oils and waxes
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USRE33124E (en) * 1976-08-04 1989-12-05 Singer and Hersch Industrial Development (PTY) Ltd. Water-based industrial fluids
US6291407B1 (en) 1999-09-08 2001-09-18 Lafrance Manufacturing Co. Agglomerated die casting lubricant
US6432886B1 (en) 1999-09-08 2002-08-13 Mary R. Reidmeyer Agglomerated lubricant
WO2014134506A1 (fr) * 2013-03-01 2014-09-04 VORA Inc. Compositions lubrifiantes et procédés d'utilisation associés
US9200230B2 (en) 2013-03-01 2015-12-01 VORA Inc. Lubricating compositions and methods of use thereof
CN110283640A (zh) * 2019-03-07 2019-09-27 山东小松油品有限公司 一种高性能不锈钢拉拔油的制备方法

Also Published As

Publication number Publication date
GB694004A (en) 1953-07-08
FR1037448A (fr) 1953-09-16
DE929208C (de) 1955-06-20
NL81706C (fr)
BE503495A (fr)
GB709733A (en) 1954-06-02
BE503494A (fr)
DE967342C (de) 1957-11-07

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