US2682523A - Lubricants - Google Patents
Lubricants Download PDFInfo
- 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
- Authority
- US
- 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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- 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
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
- C10M131/14—Halogenated waxes
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M173/00—Lubricating compositions containing more than 10% water
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M173/00—Lubricating compositions containing more than 10% water
- C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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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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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- 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
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/085—Phosphorus oxides, acids or salts
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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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- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/104—Aromatic fractions
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- C10M2203/106—Naphthenic fractions
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- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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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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- C10M2205/14—Synthetic waxes, e.g. polythene waxes
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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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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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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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Description
June 29, 1954 5. K. TALLEY ETAL RICANTS 3 Sheets-Sheet 2 EAST TEXAS SHORT RESIDUE WAX Q) AROMATIC 'HYDROCARBON Q) NAPHTHENlC/AROMATIC HYDROCARBON ISOPARAFFIN/NAPHTHENIC HYDROCARBON @S'TRAIGHT CHAIN PARAFFIN HYDROCARBON I60F L I75F I90 F 0R '00 I I GREATER I I I 2 Q I I; so I i 8 I g I 8 I 60 I 5 I 80% 2' l 40 v i I o I 20 I V 20% I I V I o G) I/ 2O 4O 6O 80 I00 OF wAx (I60F) FIG. ]I INVENTORS:
S.K. TALLEY T.E.. REAMER June 29, 1954 Filed May 24, 1950 APPARENT COEFFICIENT OF FRICTION s. K. TALLEY ETAL 2,682,523
LUBRICANTS 3 Sheets-Sheet 3 Q Low MELTING DISTILLATE. PARAFFIN WAX (MR IZ6F) CHLORINATED LOW MELTING CHLORINATED DISTILLATE PARAFFIN WAX (MP.|26F;2.9%CI) [:I HIGH MELTING POINT azsmur. WAX(M.P.I80-l85F A CHLORINED HIGH MELTING POINT RESlDUE WAX (MP |so|a5r=; 297.0)
4 G I Q 0400 I I I v 00300 D A I 1 v 0-0200 /r 29% o.o\oo
\0 I5 as so NORMAL LOAD ON mas, THOUSAND$ or POUNDS PER 50. m.
FIG. IE
INVENTORS:
5-K. TALLEY T. E.- REAMER k HElR ATTORNEY Patented June 29, 1954 LUBRICANTS Samuel K. Talley, Berkeley, and Thomas, Reamer, Albany, Calif., assignors to Shell De velopment Company, San Francisco, Calif., a
corporation of Delaware Application May 24, 1950, Serial No.163,966 k '15 Claims. 1
use of 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. In order to produce lubricating oils with given viscosity characteristics, 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. In the case of stocks which contain aromatic and resinous materials, these are usually extracted with a selective solvent, such as furfural, phenol, and the like, such extraction being generally carried out before the dewa-xing. The dewaxing may be eifected simply by chilling the waxy oil fraction to crystallize the higher melting hydrocarbons present therein, and pressing, filtering or centrifuging to separate the oil from the wax, which wax is called slack wax or crude wax and which is an oily wax mass of solidified hydrocarbons and liquid hydrocarbons entrained therewith. By the well-known sweating operation, the oils (liquid hydrocarbons) 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. Essentially 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.
The lower melting and lower molecular Weight petroleum base stocks;
, "2 H crystalline and molecular'weight paraflin waxes are obtained from the lower boiling distillate fractions, while thefhigher melting crystalline parafiln waxes are derived from the higher boiling distillate fractions. ,In the case of the residual material from thevacuum distillation used to produce the distillate'lube stocks, the waxes obtained therefromare. of still higher molecular weight, but appear to be of an entirely different character, theirnature being such that a mass thereof is obtained which to the unaided eye appears to have no Crystalline character and to be amorphous, having somewhat plastic characteristics and having refractive indices indicating the principal components to be. 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. Ihese objects will be better understood, other objects will appear and the attainment of them made clear from the description of the invention, which-will be made with reference to the accompanying drawings, wherein: 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 and Figure III disclosescomparative test data of waxes of this invention as against waxes well known in the artf It has now beenfound that a new and novel hydrocarbon wax derivative product can be obtained by halogenating ahydrocarbon wax preferably predominating in straight-chain structure, having a melting pointsabove F, to about 225 F. and a'molecular weight of from about 4'75 to 1000. an'dhigher, said wax being derived from the short residuefractions of waxy base stocks, exemplified'by East Texas, Mid-Continent, Pennsylvania stocks and the like.
The halogenated waxes of the invention are useful as such in metal-working operations and also in certain emulsions as will be described hereinafter.
Briefly stated, 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.
Broadly stated, 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. Generally, 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. Toelncidatefurther, 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. rather elevated temperature and cooling the solution to a suitable temperature so as toprecipitate the waxes while leaving the oily components and portions of the lower melting wax constituents dissolved in the solvent, and filtering the slurry in order to recover a primary microcrystalline' wax having a melting point of above about 160 F. 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. To form the new and novel halogenated products of this invention, 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.
In. order to more clearly set forth the manner in which high melting point waxes, used to form the halogenated products of this invention, are produced, reference is made to Figure I, which 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:
Sp. g1. (20/4" C.) 0.8936
Refractive index C./D.) 1.452 Color (ASTM 13155-451) at C 4 /2 Dropping point (ASTM 11566-42), F 171 Cloud point (methylethyl ketone) F 154 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. to precipitate the Waxes while leaving the oily components, and a portion of the lower melting wax constituents, such as those melting up'to: 117 FL, and recovering aprimary microcrystalline wax (a) 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. Referring to Figure II, it can be seen that the wax (b) or (c) of Figure I is the wax fraction embraced by the bracket 180 F. and consists of approximately 80% of high melting straight-chain paraffin waxes having an average melting point of about 180 F., the melting point of the lowest melting constituent thereof being about 160 F., and about of a mixture of high melting isoparaffinic, naphthenic and aromatic hydrocarbons, while the remainder of the primary microcrystalline wax (a) which remainder is the plastic microcrystalline wax (d) or (e), is essentially all isoparafilnic/naphthenic (about 80%), about 3 being straight-chain paraflinic and the remainder (about 1'7 being a mixture of naphthenic and aromatic hydrocarbons.
The data in 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.
TABLE I indicating that the high melting wax was essentially pure normal paraflin wax; this wax is indicated by thebracketed=190 F. wax in Figure II. At a filtration temperature of 104 F., 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.
-at95 F., as compared with a value of 1 to 2 mm./ 10 g. for the 191 F., melting point wax. It has been found that 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. and the like, in 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. In order to recover hard wax With the highest melting point, 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. For each degree change desired in the melting point of the hard, high melting wax, 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.
A preferred wax from which the halogenated products of this invention can be made is the Fractionation of East Texas short'residue primary microcrystalline wax n-P=normal paraffin.
The values given in the sixth column of Table I are for the deviation between the index of refraction as actually determined for a given wax frachard, high melting hydrocarbon wax represented by (b), or (c) inFigure I, said wax having the following properties:
tion and the index of refraction of the normal 65 a (straight-chain) paraffin hydrocarbon of the a i gfg g g F ii same melting point as the given wax fraction, the 363 g /ml index of refraction being determined at C., Visc (SUS R) m 70.6.
utilizing the D spectral emission line of sodium.
It will be seen that at a filtration temperature of 70 Needle penetratmn at F 1 122 F., the separated high melting wax had a melting point of 191 F. and an index of refracg gg gfi h At lea t 80 h tion which differed only 0.0023 unit from the ins 1g dex of refraction of the normal paraffin hydrocar- In order to clearly show the marked difference bon which has a melting point of 191 F., thus 75 in properties between high melting waxes such as obtained from short residues andidentifled as (a) through (c) in Figure Land paraffin waxes obtained from distillate fractions as shown in steps (7) through (9) in Figure I, an East Texas El Specific. products or utility in accordance. with this invention are:
(1 Chlorinated derivative of crude primary microcrystalline residue hydrocarbon wax having topped crude was subjected to vacuum distilla- 5 a melting point of 160-165" F. and a chlorin'econtion and the waxes from the short residue and tent of from 25 to 60%. waxes from distillate fractions were recovered and (2) Chlorinated derivative of a high melting their properties were determined and found to predominantly straight-chain, residue, parafiin be as. follows: wax originally having a melting point of 180-195 Wax dcn'vcd Wax derived Residue Residue High from. 100 sUs from 250 sUs Plastic Melting at 100 F. at 100 F. lllicrocrystal- Parafiin Wax distillate distillate lino Wax (d (b or c of (fof Fig. I) (fol Fig. I) or e of Fig. I) Fig. I)
Melting Point, F 125 141 145 183 R, I. at 90 1. 4222 1. 4300 1. 4438 1. 4403 Needle Penetration,
mmJlO at 95 F 34 33 29 12 Sp. gr. at 20 C. (by
displacement) 0. 877 0.882 0.921 (1.934 Oil. Content (ASTM),
percent wt 0. 0. 9 l. 7 (soc) 0. 2 sue/210 r 35.8 41.0 76.4 73.5 Mol. Wt 34? 441 665 an In order to produce the halogenated waxes of g F. and to give a product having a chlorine content the present invention, the short residue hydroof from 25 to 60%. carbon waxes having a melting point above about (3) Fluorinated derivative of a primary micro- 160 a molecular weight or" at least 4 75 and crystalline residue hydrocarbon wax having a preferably between 525 and 1000 and consisting melting point of 160-165 F. and a fluorine conpredominantly of straight-chain hydrocarbons 3O tent of from to 60%. are halogenated by conventional means until the l) 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. of a high melting, residue, straight-chain paraffin Instead of chlcrinating waxes of this invention, 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 In all cases it is preferred that 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,
As a specific example, a hard, high-melting (8) 25-50% fluorinated derivative of 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 coning a melting point of MiG-145 F. tent was at least about 30%. 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. They are useful coating and In addition t t halogengtjgn of t wages rust protective agents, for fireproofing materials, of this invention by the method described above, 7 in (1191663116 COmDOBiBiOHS, hydraulic flui s, ythe waxes can be halogenated (with the necespaper coating, as plasticizers, or the like. Addisary modifications in view of the high melting tionally, 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.
In making improved emulsions containing halogenated hydrocarbon waxes of this invention, it is preferable to use as the 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. Specific 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%.
In order to impart good metal wetability and thereby greatly improve the lubricating characteristic and film strength of the halogenated wax emulsion, 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. 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. Additionally, 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.
Excellent drawing lubricants utilizing halogenated waxes of this invention are illustrated by the following examples:
EXAMPLE I Per cent Chlorinated high melting point hydrocarbon wax (ISO-185 F. M. P. of the paraflin wax and 2535% C1) 40 Sorbitan monooleate 4 Polyoxyethylene sorbitan monooleate 4 Lauryl amine 2 Water Balance EXAMPLE II Per cent Chlorinated primary microcrystalline wax (165 F. M. P. of the microcrystalline wax and 30-40% Cl) 40 Sorbitan monooleate 4 Polyoxyethylene sorbitan monooleate 8 Stearyl amine 2 Water Balance EXAMPLE III Per cent Chlorinated high melting point hydrocarbon wax (ISO-185 F. M. P. of the hydrocarbon Wax and 25-35% Cl) 35 Mineral oil 5 Glycerol monooleate 4 Polyoxyethylene sorbitan monooleate 4 Dodecyl amine 2 Water Balance EXAMPLE W Per cent Chlorinated high melting point residue hydrocarbon wax (M. P. of the hydrocarbon wax, -185 F., 40% Cl) 30 Sorbitan monooleate 2 Polyoxyethylene sorbitan monooleate 4 Abietyl amine 3 Water -Balance EXAMPLE V Per cent Chlorinated high melting point residue hydrocarbon wax (M. P. of hydrocarbon wax,
180-185 F., 40% Cl) 35 Mannitan monolaurate 2 Polyoxyethylene mannitan monolaurate 4 Oleyl amine 3 Water Balance EXAMPLE VI Per cent Chlorinated high melting point residue hydrocarbon wax (M. P. 160-165 F., 30% Cl) 40 Pentaerythritoi monocaprylate 4 Polyoxyethylene sorbitan monostearate 4 Stearic acid amide 4 Water Balance 11 dies was measured in conjunction with the known normal force on the dies and from-these values the coefiicient of friction was determined.
COMPOSITION TESTED (1) Chlorinated high melting residue hydrocarbon wax (M. P. of the wax l80185 F., 25-30% Cl) (M. P. of the wax 125 F. and 29% Cl) was substituted 'for the chlorinated residue wax (5) High melting residue hydrocarbon wax (M. P. ISO-185 F.)
(6) Low melting distillate paraifin wax (M. P.
Some or" the 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. In Figure III, low coefiicient of friction athigh normal loads indi cates a superior lubricant.
In actual plant operation, stainless steel tubes 1 having an initial diameter of 1 2 oxidized surface finish, were drawn with the aid of chlorinated waxes of this invention per se or neat, and in emulsion form, and the results compared with commercial lubricants, the results being tabulated below:
l2 phenyl beta naphthylamine, phenyl alpha naphthylamine and dibutylamine.
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).
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.
Depending upon the additional additive used and conditions 'under which it is used, 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.
We claim as our invention:
1. An aqueous emulsion metal-working lubricating concentrate composition containing from Composition 36% Reduction Speed (ft/min.)
(4) Composition: Chlorinated distillate wax (M. P. of wax 124; C1 42%); Remainder same as Ex. IV-Sorbitan monooleate, Polyoxyethylene sorbitan, monooleate, Stearylamine Water.
Smooth draw, no rod chatter, normal deposit in mandrel.
Severe stick-slip, could not be drawn.
Smooth draw, no chat- 'ter in die, normal deposit in mandrel.
Smooth draw for .8 it. then severe chatter noted.
The vehicles to which 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.
To 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.
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.
2. 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. g
3. 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.
4. 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.
5. 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.
6. 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.
7. 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
8. 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.
10. 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 m 2 Polyoxyethylene sorbitan monooleate 4 Stearyl amine 3 Water Balance 11. 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.
13. An emulsion consisting essentially of the composition of claim 2 and additional water in the ratio of from 1:2 to 1:10, respectively.
14. An emulsion consisting essentially of the composition ofclaim 10 and additional water in the ratio of from 1:2 to 1:10, respectively.
15. An emulsion consisting essentially of the composition of claim 11 and additional water in the ratio of from 1:2 to 1:10, respectively.
(References on following page) 15 1'6 References Cited in the me of this patent Number Name Date UNITED 2,560,148 Arabian July 10, 1951 Number Name Date FOREIGN PATENTS 1,948,194 Williams -Ffib. 20, 1934 5 Number Country Date 2,119,149 Bishop May 33, 1338 569,343 Great Britain May 18, 1945 2,130,952 Hardie et a1 Sept. 2 1 38 2,420,328 Shipp et a1. May 13, 1947 OTHER REFERENCES 2 420 329 Shipp t 1 May 13 1947 Atlas spans and Tweens, Atlas Powder 00., 2,496,115 Burford et a1. Jan. 31, 1950 10 Wilmington, Reprinted June PY 2,521,626 Banning Sept. 5, .1950 in 2,524,017 Hance et a1 Sept. 26, 1950
Claims (1)
1. AN AQUEOUS EMULSION METAL-WORKING LUBRICATING CONCENTRATE COMPOSITION CONTAINING FROM 3 TO 50% OF A HALOGENATED HIGH MELTING RESIDUE HYDROCARBON WAX CONTAINING 20-60% HALOGEN, THE HYDROCARBON WAX HAVING A MELTING POINT OF AT LEAST 160* F., A MOLECULAR WEIGHT ABOVE 475, AND CONSISTING OF AT LEAST 60% NORMAL STRAIGHTCHAIN HYDROCARBONS AND THE REMAINING CONSTITUENTS BEING HIGH MELTING ISOPARAFFINIC AND NAPHTHENIC HYDROCARBONX; FROM ABOUT 1% TO ABOUT 25% OF AN ESTER SELECTED ROM 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 THE GROUP CONSISTING OF AN ALIPHATIC AMINE, AND AN ALIPHATIC AMIDE; AND THE BALANCE BEING WATER.
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
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NL81706D NL81706C (en) | 1950-05-24 | ||
BE503494D BE503494A (en) | 1950-05-24 | ||
BE503495D BE503495A (en) | 1950-05-24 | ||
US163966A US2682523A (en) | 1950-05-24 | 1950-05-24 | Lubricants |
FR1037448D FR1037448A (en) | 1950-05-24 | 1951-05-23 | Halogenated paraffin |
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 |
DEN3952A DE929208C (en) | 1950-05-24 | 1951-05-26 | Aqueous emulsion, especially for metalworking |
DEN3951A DE967342C (en) | 1950-05-24 | 1951-05-26 | Process for the production of a halogenated paraffin |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US163966A US2682523A (en) | 1950-05-24 | 1950-05-24 | Lubricants |
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US2682523A true US2682523A (en) | 1954-06-29 |
Family
ID=22592398
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US163966A Expired - Lifetime US2682523A (en) | 1950-05-24 | 1950-05-24 | Lubricants |
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US (1) | US2682523A (en) |
BE (2) | BE503494A (en) |
DE (2) | DE929208C (en) |
FR (1) | FR1037448A (en) |
GB (2) | GB694004A (en) |
NL (1) | NL81706C (en) |
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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 |
US3085868A (en) * | 1960-08-01 | 1963-04-16 | British Petroleum Co | Fuel oil composition |
US3167511A (en) * | 1961-04-13 | 1965-01-26 | Socony Mobil Oil Co Inc | Metal working lubricant |
US3201349A (en) * | 1960-11-18 | 1965-08-17 | Sinclair Research Inc | Emulsifiable oil composition |
US3244614A (en) * | 1963-04-22 | 1966-04-05 | Gulf Oil Corp | Solvent refining and dewaxing process |
US3275545A (en) * | 1963-04-16 | 1966-09-27 | Exxon Research Engineering Co | Hydrofining of microcrystalline wax |
USRE33124E (en) * | 1976-08-04 | 1989-12-05 | Singer and Hersch Industrial Development (PTY) Ltd. | Water-based industrial fluids |
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US6432886B1 (en) | 1999-09-08 | 2002-08-13 | Mary R. Reidmeyer | Agglomerated 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 |
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US5518639A (en) * | 1994-08-12 | 1996-05-21 | Hoeganaes Corp. | Powder metallurgy lubricant composition and methods for using same |
US5555756A (en) * | 1995-01-24 | 1996-09-17 | Inland Steel Company | Method of lubricating steel strip for cold rolling, particularly temper rolling |
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US1948194A (en) * | 1931-11-17 | 1934-02-20 | Ironsides Company | Metal-forming lubricants |
US2119149A (en) * | 1935-04-09 | 1938-05-31 | Hercules Powder Co Ltd | Stabilized chlorinated paraffin wax and method of producing |
US2130952A (en) * | 1936-07-01 | 1938-09-20 | Ici Ltd | Manufacture of derivatives of paraffin wax |
GB569348A (en) * | 1943-02-05 | 1945-05-18 | Wakefield & Co Ltd C C | Improvements in lubricants and cooling emulsions particularly for wire-working |
US2420328A (en) * | 1945-05-26 | 1947-05-13 | Du Pont | Lubricant for processing metals |
US2420329A (en) * | 1945-06-01 | 1947-05-13 | Du Pont | Lubricant for processing metals |
US2496115A (en) * | 1948-02-02 | 1950-01-31 | William B Burford | Stabilization of perfluoro oils |
US2521626A (en) * | 1944-11-30 | 1950-09-05 | Anthony F Benning | Process for fluorinating hydrocarbons |
US2524017A (en) * | 1950-09-26 | Metalworking lubricant | ||
US2560148A (en) * | 1949-02-08 | 1951-07-10 | Shell Dev | Wax emulsion |
-
0
- BE BE503495D patent/BE503495A/xx unknown
- NL NL81706D patent/NL81706C/xx active
- BE BE503494D patent/BE503494A/xx unknown
-
1950
- 1950-05-24 US US163966A patent/US2682523A/en not_active Expired - Lifetime
-
1951
- 1951-05-23 FR FR1037448D patent/FR1037448A/en not_active Expired
- 1951-05-24 GB GB12197/51A patent/GB694004A/en not_active Expired
- 1951-05-24 GB GB12241/51A patent/GB709733A/en not_active Expired
- 1951-05-26 DE DEN3952A patent/DE929208C/en not_active Expired
- 1951-05-26 DE DEN3951A patent/DE967342C/en not_active Expired
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Publication number | Priority date | Publication date | Assignee | Title |
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US2524017A (en) * | 1950-09-26 | Metalworking lubricant | ||
US1948194A (en) * | 1931-11-17 | 1934-02-20 | Ironsides Company | Metal-forming lubricants |
US2119149A (en) * | 1935-04-09 | 1938-05-31 | Hercules Powder Co Ltd | Stabilized chlorinated paraffin wax and method of producing |
US2130952A (en) * | 1936-07-01 | 1938-09-20 | Ici Ltd | Manufacture of derivatives of paraffin wax |
GB569348A (en) * | 1943-02-05 | 1945-05-18 | Wakefield & Co Ltd C C | Improvements in lubricants and cooling emulsions particularly for wire-working |
US2521626A (en) * | 1944-11-30 | 1950-09-05 | Anthony F Benning | Process for fluorinating hydrocarbons |
US2420328A (en) * | 1945-05-26 | 1947-05-13 | Du Pont | Lubricant for processing metals |
US2420329A (en) * | 1945-06-01 | 1947-05-13 | Du Pont | Lubricant for processing metals |
US2496115A (en) * | 1948-02-02 | 1950-01-31 | William B Burford | Stabilization of perfluoro oils |
US2560148A (en) * | 1949-02-08 | 1951-07-10 | Shell Dev | Wax emulsion |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2874194A (en) * | 1953-03-18 | 1959-02-17 | Ruhrchemie Ag | Elastic high molecular weight hydroxyl group containing materials |
US3011972A (en) * | 1957-02-25 | 1961-12-05 | Sinclair Refining Co | Method for the manufacture of an oxidation stable bright stock |
US2995508A (en) * | 1958-07-21 | 1961-08-08 | Pure Oil Co | Production of waxes of improved quality |
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 |
US3085868A (en) * | 1960-08-01 | 1963-04-16 | British Petroleum Co | Fuel oil composition |
US3201349A (en) * | 1960-11-18 | 1965-08-17 | Sinclair Research Inc | Emulsifiable oil composition |
US3167511A (en) * | 1961-04-13 | 1965-01-26 | Socony Mobil Oil Co Inc | Metal working lubricant |
US3275545A (en) * | 1963-04-16 | 1966-09-27 | Exxon Research Engineering Co | Hydrofining of microcrystalline wax |
US3244614A (en) * | 1963-04-22 | 1966-04-05 | Gulf Oil Corp | Solvent refining and dewaxing process |
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 (en) * | 2013-03-01 | 2014-09-04 | VORA Inc. | Lubricating compositions and methods of use thereof |
US9200230B2 (en) | 2013-03-01 | 2015-12-01 | VORA Inc. | Lubricating compositions and methods of use thereof |
CN110283640A (en) * | 2019-03-07 | 2019-09-27 | 山东小松油品有限公司 | A kind of preparation method of high-performance stainless steel drawing oil |
Also Published As
Publication number | Publication date |
---|---|
DE967342C (en) | 1957-11-07 |
NL81706C (en) | |
DE929208C (en) | 1955-06-20 |
GB709733A (en) | 1954-06-02 |
GB694004A (en) | 1953-07-08 |
FR1037448A (en) | 1953-09-16 |
BE503494A (en) | |
BE503495A (en) |
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