US3649538A - Diol-containing aluminum lubricant - Google Patents

Diol-containing aluminum lubricant Download PDF

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Publication number
US3649538A
US3649538A US888806A US3649538DA US3649538A US 3649538 A US3649538 A US 3649538A US 888806 A US888806 A US 888806A US 3649538D A US3649538D A US 3649538DA US 3649538 A US3649538 A US 3649538A
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diol
aluminum
diols
lubricant
carbon atoms
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US888806A
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Bruce W Hotten
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Chevron USA Inc
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Chevron Research and Technology Co
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    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/245—Soft metals, e.g. aluminum
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/246—Iron or steel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/247—Stainless steel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01—Emulsions, colloids, or micelles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/04—Oxidation, e.g. ozonisation

Definitions

  • the present invention relates to the use of diols in the lubrication of the surface of aluminum or aluminum alloys during cold forming processes, machining, including tapping and drilling, or in mechanical devices.
  • lubricants are used to decrease friction between the metal and rolls of the rolling mill and to promote good surface finish. These lubricants also serve as heat transfer fluids to remove heat generated in the rolls and metal during rolling.
  • Lubricants used for rolling of aluminum are almost always mixtures of polar or oiliness additives with a light mineral oil, synthetic hydrocarbon oil, petroleum distillate, or water.
  • the effect of the additives in rolling lubricants is to improve the lubricating ability of the oil or water, thus decreasing friction in the roll bite between rolls and metal. By resultant effects, a decrease in friction allows more efficient reduction in thickness of the metal being rolled.
  • These additives also, through their chemical or polar action, serve to decrease the tendency of the metal to Weld to or pickup on the surface of the rolls during rolling.
  • Machining aluminum also requires lubricants. Lack of adequate lubrication during drilling, tapping, or other machining of aluminum seriously shortens the useful life of tools such as drills and taps.
  • the process of this invention is a process for lubricating aluminum and aluminum alloys during cold working, machining, or other mechanical operation which comprises applying to the surface of the material a lubricant comprising a major portion of a carrier fluid and a minor portion of a C -C diol having a structure such that the two hydroxy groups are attached to carbon atoms which are either directly bonded together or are separated by one other carbon atom.
  • the carrier tfluid may be a mineral oil, synthetic hydrocarbon oil, petroleum distillate, halogenated or oxygenated hydrocarbon, or water.
  • the process of this invention is a process for lubricating aluminum and aluminum alloys which comprises applying to the surface of the aluminum or aluminum alloy a lubricant comprising a major portion of a carrier fiuid and a minor portion of a C -C diol having a structure such that the two hydroxy groups are attached to carbon atoms which are either directly bonded together or are separated by one other carbon atom.
  • a lubricant comprising a major portion of a carrier fiuid and a minor portion of a C -C diol having a structure such that the two hydroxy groups are attached to carbon atoms which are either directly bonded together or are separated by one other carbon atom.
  • the diols used in the process of this invention are C C diols containing any one of the following saturated or aromatically unsaturated structural units:
  • n represents the number 0 or 1;
  • R R and when 11:1, R each represents hydrogen or a hydrocarbon group of from 1 to 28 carbon atoms, with at least one being hydrocarbon, and the total number of carbon atoms in the hydrocarbon groups being of from 7 to 28;
  • R R and R are each hydrogen or a hydrocarbon group of from 1 to 12, preferably 1 to 6, carbon atoms, or two may be taken together with adjacent carbon atoms to form a carbomonocyclic structure of from 4 to 30, preferably 6 to 30, carbon atoms.
  • the total number of annular carbon atoms in the carbocyclic structure will range from 4 to 8, preferably 5 to 7. and usually 6.
  • n 0 and the fl-diols by 11:1.
  • the carbon atoms may be arranged as straightor branched-chain aliphatic, cycloaliphatic, aryl, or ali phatic-substituted aryl configurations.
  • R and R can be joined with the carbon atoms to which they are attached to form a carbocyclic (i.e., alicyclic or aromatic) or substituted carbocyclic structure.
  • carbocyclic i.e., alicyclic or aromatic
  • R and [R may be taken together with the carbon atoms to which they are attached to form carbocyclic or aliphatic-substituted carbocyclic structures.
  • Preferred structures include (1) R R and R are as previously defined; and
  • R R R and R are each hydrogen or a hydrocarbon group of from 1 to 24 carbon atoms, preferably 4 to carbon atoms.
  • structure VI may be referred to as an aliphatic u-diOl
  • structure VII as an aliphatic fi-diol
  • structure VIII as a catechol
  • structure IX as a mixed alkylaryl diol
  • the diols of this invention will contain no atoms other than carbon, hydrogen, and oxygen.
  • the carrier fluid should contain no atoms other than carbon, hydrogen, oxygen, and halogen.
  • diols are those wherein R R and R are all hydrogen and which have the formula It is important that there be no more than one carbon atom in the chain between the carbon atom to which one of the hydroxy group is attached and the chain carbon atom to which the second hydroxy group is attached; i.e., that n in the above Formula V be 0 or 1. Since there will be no more than one carbon atom between the points of attachment of the hydroxy groups, the B-diols represent the maximum hydroxy group separation. It has been found that diols having greater hydroxy group separation do not exhibit the superior lubricating properties of the diols of the process of this invention. Rather, the diols having more widely separated hydroxy groups exhibit the properties associated with monohydric alcohols which, as will be shown below, are significantly inferior to the uand fi-diols in the process of this invention.
  • the diol must contain at least ten carbon atoms and, preferably, at least twelve carbon atoms. It has been found that diols having less than ten carbon atoms do not exhibit the superior anti-wear and lubricating properties of the C -C diols. The lower carbon number diols rather tend to have approximately the same lubricating capacity as the C -C monohydric alcohols. Similarly, diols having more than 30 carbon atoms have not been found to be the equivalent of the C -C diols.
  • the carrier fluid which comprises the major portion of the lubricant of this invention may be a mineral oil, bydrocarbon oil, hydrocarbon distillate, halogenated or oxygenated hydrocarbon, or water.
  • Water is the preferred carrier fluid because of its high heat removal properties.
  • emulsifier may be ionic or nonionic. Suitable emulsifiers include alkylarylpolyethoxy alcohols, sorbitan monooleate, polyethoxylated amines, amides or fatty acids, sugar esters, soaps, and sulfonates.
  • Oils suitable as carrier fluids in the process of this invention are generally hydrocarbon oils produced by distillation, cracking, hydrogenation, or other refining processes. They typically have boiling points of 500 to 1,000 P. and viscosities of 50 to 500 SSU at F. A typical example of a suitable oil is a hydrocarbon neutral oil having a viscosity of SSU at 100 F. These may provide a minor amount of lubrication themselves.
  • carrier fluids are halogenated and oxyginated hydrocarbons. These are particularly preferred as carrier fluids for the a-diols, for the latter often have greater solubility in these non-hydrocarbon fluids than they do in the hydrocarbon fluids.
  • the oxygenated hydrocarbon fluids useful in this invention include carboxylic acid esters, alcohols, ketones, ethers, and aldehydes.
  • the halogen-substituted hydrocarbons include haloalkyls and haloaryls.
  • the fluids may have both substituents, as in the case of a haloether.
  • Typical non-hydrocarbon fluids which may be used include carbon tetrachloride, 1,1,1-trichloroethane, chloroform, bromoform, 1,2-dichloroethane, chlorobenzene, ethanol, methanol, isopropanol, allyl alcohol, benzyl alcohol, n-butyraldehyde, benzaldehyde, acetone, methyl ethyl ketone, 2-hexanone, methyl isobutyl ketone, ethyl ether, n-propyl ether, ethyl phenyl ether, 1,4-dioxane, and propylene oxide.
  • any suitable hydrocarbon, halogenated hydrocarbon, or oxygenated hydrocarbon may be used which can, by the use of suitable emulsifiers, be made miscible with the particular aor fi-diol in question.
  • the carrier fluid may be a mixture of two or more of the above materials. All materials so combined should be mutually miscible or should be capable of being made so by use of appropriate emulsifiers.
  • the diol comprises a minor portion.
  • the diol comprises no more than 30 percent by volume of the diol-carrier fluid mixture.
  • the diol is no more than 15 volume percent of the mixture and more preferably, no more than volume percent.
  • the minimum diol concentration is 0.1 volume percent.
  • the diol is first dispersed in a polyolefin, such as polybutene having a number average molecular weight of about 300- to 1,000. The mixture is then emulsified in water. Such materials are readily volatilized during the annealing of the aluminum following cold rolling, and thus leave little surface residue on the aluminum.
  • the volumetric ratio of diol to polyolefin is 1:1 to 1:10.
  • the lubricant composition of this invention may also contain conventional additives, such as anti-rust agents, oxidation inhibitors, and lubricity agents.
  • a typical lubricity agent is lard oil. These additives will normally be present as 5-25 weight percent of the lubricant.
  • Table 1 below illustrates the lubricating properties of the diol lubricants of this invention.
  • the data in this table were derived from a Falex Machine test. This is a well-known test in which a cylindrical shaft of steel is rotated between and in contact with two V-shaped aluminum blocks. The shaft is connected to a motor by a small shear-pin. The shaft and blocks are immersed in the lubricant to be tested. An increasing load is placed on the blocks, forcing them against the shaft. The point at which the shaft seizes against the blocks and shears the shear-pin is measured, and the pounds of force being exerted against the blocks at that point is recorded as the failure load of the lubricant.
  • the aqueous lubricating fluid is of the type described immediately above; 90 percent water, 2 percent diol or comparative test compound, 7.6 percent polybutene (molecular weight of approximately 330) and 0.4 percent commercial nonionic emulsifiers.
  • the nonaqueous lubricating fluid is the 130 SUS neutral oil described above, containing the indicated percentage of diol or comparative test material.
  • Table II illustrates the superiority of the 01- and ,B-diols over similar materials such as diols having wide hydroxy group separation or monohydric alcohols. All materials listed in the following table were present as 2 volume percent of an aqueous lubricant.
  • the diols used in the process of this invention also have excellent anti-wear characteristics when used as aluminum lubricants. That they are far superior to the corresponding monohydric alcohols in this regard is illustrated below in Table III.
  • Table III The data in Table HI were derived from a modified version of the Falex Machine test described above. In this modification of the test, a constant force was put on the aluminum blocks and the steel shaft rotated between them for a set period of time. At the end of this time, the amount of aluminum worn off the blocks was measured and the milligrams of aluminum lost reported.
  • an aluminum; machining lubricant was formulated consisting of weight percent 1,1,1-trichloroethane, 16 Weight percent lard oil, 4 weight percent 1,2- (C C )alkanediol mixture, and a small additional amount of an odorant. This was used in the tapping of aluminum, and was found to increase the tap life more than tenfold over the life (i.e., time to tap breakage) obtained with a lubricant formulated as above but without the diol present.
  • the diols used in this invention may, in some cases, be obtained commercially, or in other cases may be synthesized. Syntheses of typical aand fl-diols are described below.
  • EXAMPLE 1 A mixture of 245 g. (1 mole) of Nedox 1518, a commercially available mixture of C C terminal epoxides made from cracked wax olefins and supplied by Ashland Oil and Refining Co., 90 g. moles) of water, and 2 g. of concentrated sulfuric acid catalyst were refluxed for 8 hours at 100 C., washed free of acid, and dried. The product was a waxy white solid, melting point 52 0., containing 1,2-(C -C )alkanediols.
  • EXAMPLE 4 A solution containing 270 g. (1 mole) of a mixture of C -C cracked wax olefins, 30 g. (1 mole) paraformaldehyde, 120 g. (2 moles) acetic acid, and 30 g. sulfuric acid catalyst was heated at LOO-120 C. for 24 hours, then washed with dilute NaOH solution and water, to form crude esters. The crude esters were reacted with KOH solution to form a mixture of 1,3(C C )alkanedio1s.
  • the ocand p-diols are superior aluminum lubricants and anti-wear additives. They have superior load-carrying capacity and the ability to reduce aluminum wear significantly.
  • a process for lubricating aluminum and aluminum alloys which comprises applying to the surface of the aluminum or aluminum alloys a lubricant comprising a major portion of a carrier fluid and a minor portion sufiicient to provide lubrication of a C -C diol having a structure in which the two hydroxy groups are attached to carbon atoms which are either directly bonded together or are separated by one other carbon atom and containing only carbon, hydrogen, and oxygen atoms.
  • said carrier fluid is a mixture of two or more materials selected from the group consisting of water, mineral oils, hydrocarbon oils, halogenated hydrocarbons, and oxygenated hydrocarbons.
  • R R and when n 1, R each represents hydrogen or a hydrocarbon group of from 1 to 28 carbon atoms, with at least one being hydrogen, and the total number of carbon atoms in the hydrocarbon groups being of from 7 to 28;
  • R R and R are each hydrogen or a hydrocarbon group of from 1 to 12 carbon atoms, or two may be taken together with the carbon atoms to which they are attached to form a carbocyclic structure of from 4 to 30 carbon atoms having of from 4 to 8 annular carbon atoms.
  • R R R and R are each hydrogen or a hydrocarbon group of from 1 to 6 carbon atoms.
  • R are each hydrogen or a hydrocarbon group of from 1 to 24 carbon atoms.
  • An aqueous lubricating composition useful for lubricating aluminum which comprises:

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Shaping Metal By Deep-Drawing, Or The Like (AREA)
US888806A 1969-08-27 1969-12-29 Diol-containing aluminum lubricant Expired - Lifetime US3649538A (en)

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US85347469A 1969-08-27 1969-08-27
US88880669A 1969-12-29 1969-12-29

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JP (1) JPS4827868B1 (enrdf_load_stackoverflow)
BE (1) BE754672A (enrdf_load_stackoverflow)
CA (1) CA923488A (enrdf_load_stackoverflow)
CH (1) CH567566A5 (enrdf_load_stackoverflow)
DE (1) DE2042279A1 (enrdf_load_stackoverflow)
FR (1) FR2059697B1 (enrdf_load_stackoverflow)
GB (1) GB1288879A (enrdf_load_stackoverflow)
NL (1) NL7012714A (enrdf_load_stackoverflow)
SE (1) SE362658B (enrdf_load_stackoverflow)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3755168A (en) * 1971-12-03 1973-08-28 Phillips Petroleum Co Lubricant for extrusion of thermoplastics
US3846319A (en) * 1973-03-27 1974-11-05 Chevron Res Dioxan-containing aluminum lubricant
US3855136A (en) * 1971-11-15 1974-12-17 Kaiser Aluminium Chem Corp Dispersion for hot rolling aluminum products
FR2439815A1 (fr) * 1978-10-27 1980-05-23 Pennwalt Corp Procede pour diminuer les residus de produits carbones non volatils resultant du traitement, a temperature elevee, d'un substrat metallique par une composition de traitement
US4326974A (en) * 1980-09-12 1982-04-27 Swiss Aluminium Ltd. Oil-in-water emulsion for cold rolling light metals
US4331222A (en) * 1980-07-07 1982-05-25 Chevron Research Company Method for reducing brake noise in oil-immersed disc brakes
US4371447A (en) * 1981-07-06 1983-02-01 Standard Oil Company Low viscosity water-in-oil microemulsions
US4406803A (en) * 1980-11-24 1983-09-27 Chevron Research Company Method for improving fuel economy of internal combustion engines
DE3529192A1 (de) * 1984-08-17 1986-02-27 Chevron Research Co., San Francisco, Calif. Fluessiges alkylkatechin, dieses enthaltendes schmieroel und dessen verwendung
US4704218A (en) * 1985-12-16 1987-11-03 Horodysky Andrew G Reaction products of sulfur containing vicinal diols and hydrogen phosphites as lubricant and fuel additives
US4781848A (en) * 1987-05-21 1988-11-01 Aluminum Company Of America Metalworking lubricant comprising an oil-in-water microemulsion
US4781849A (en) * 1987-05-21 1988-11-01 Aluminum Company Of America Lyotropic liquid crystal metalworking lubricant composition
US4927553A (en) * 1983-05-06 1990-05-22 Ethyl Corporation Haze-free boronated antioxidant
US6004911A (en) * 1995-12-27 1999-12-21 Denso Corporation Processing oil suitable for aluminum materials and removable via heating
WO2010115864A1 (en) * 2009-04-10 2010-10-14 Shell Internationale Research Maatschappij B.V. Lubricating oil compositions
US10414964B2 (en) 2015-06-30 2019-09-17 Exxonmobil Chemical Patents Inc. Lubricant compositions containing phosphates and/or phosphites and methods of making and using same
US10844264B2 (en) 2015-06-30 2020-11-24 Exxonmobil Chemical Patents Inc. Lubricant compositions comprising diol functional groups and methods of making and using same
US10927283B2 (en) 2016-12-28 2021-02-23 Exxonmobil Chemical Patents Inc. Friction-reducing compositions for use in drilling operations

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB629139A (en) * 1947-06-23 1949-09-13 Shell Refining & Marketing Co Improvements in or relating to emulsification and emulsifying compositions
US3400083A (en) * 1964-07-10 1968-09-03 Exxon Research Engineering Co Lubricating films

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3855136A (en) * 1971-11-15 1974-12-17 Kaiser Aluminium Chem Corp Dispersion for hot rolling aluminum products
US3755168A (en) * 1971-12-03 1973-08-28 Phillips Petroleum Co Lubricant for extrusion of thermoplastics
US3846319A (en) * 1973-03-27 1974-11-05 Chevron Res Dioxan-containing aluminum lubricant
FR2439815A1 (fr) * 1978-10-27 1980-05-23 Pennwalt Corp Procede pour diminuer les residus de produits carbones non volatils resultant du traitement, a temperature elevee, d'un substrat metallique par une composition de traitement
US4214924A (en) * 1978-10-27 1980-07-29 Pennwalt Corporation Method of improving surface characteristic of heat-treated metal
US4331222A (en) * 1980-07-07 1982-05-25 Chevron Research Company Method for reducing brake noise in oil-immersed disc brakes
US4326974A (en) * 1980-09-12 1982-04-27 Swiss Aluminium Ltd. Oil-in-water emulsion for cold rolling light metals
US4406803A (en) * 1980-11-24 1983-09-27 Chevron Research Company Method for improving fuel economy of internal combustion engines
US4371447A (en) * 1981-07-06 1983-02-01 Standard Oil Company Low viscosity water-in-oil microemulsions
US4927553A (en) * 1983-05-06 1990-05-22 Ethyl Corporation Haze-free boronated antioxidant
US4632771A (en) * 1984-08-17 1986-12-30 Chevron Research Company Normally liquid C14 to C18 monoalkyl catechols
DE3529192A1 (de) * 1984-08-17 1986-02-27 Chevron Research Co., San Francisco, Calif. Fluessiges alkylkatechin, dieses enthaltendes schmieroel und dessen verwendung
DE3546844C2 (de) * 1984-08-17 1994-01-27 Chevron Res & Tech Verfahren zum Vermindern des Treibstoffverbrauchs von Verbrennungsmotoren
US4704218A (en) * 1985-12-16 1987-11-03 Horodysky Andrew G Reaction products of sulfur containing vicinal diols and hydrogen phosphites as lubricant and fuel additives
US4781848A (en) * 1987-05-21 1988-11-01 Aluminum Company Of America Metalworking lubricant comprising an oil-in-water microemulsion
US4781849A (en) * 1987-05-21 1988-11-01 Aluminum Company Of America Lyotropic liquid crystal metalworking lubricant composition
AU610250B2 (en) * 1987-05-21 1991-05-16 Aluminum Company Of America Metalworking lubricant comprimising an oil-in-water microemulsion
US6004911A (en) * 1995-12-27 1999-12-21 Denso Corporation Processing oil suitable for aluminum materials and removable via heating
WO2010115864A1 (en) * 2009-04-10 2010-10-14 Shell Internationale Research Maatschappij B.V. Lubricating oil compositions
US10414964B2 (en) 2015-06-30 2019-09-17 Exxonmobil Chemical Patents Inc. Lubricant compositions containing phosphates and/or phosphites and methods of making and using same
US10844264B2 (en) 2015-06-30 2020-11-24 Exxonmobil Chemical Patents Inc. Lubricant compositions comprising diol functional groups and methods of making and using same
US10927283B2 (en) 2016-12-28 2021-02-23 Exxonmobil Chemical Patents Inc. Friction-reducing compositions for use in drilling operations

Also Published As

Publication number Publication date
FR2059697B1 (enrdf_load_stackoverflow) 1974-08-23
FR2059697A1 (enrdf_load_stackoverflow) 1971-06-04
CH567566A5 (enrdf_load_stackoverflow) 1975-10-15
DE2042279A1 (de) 1971-03-04
CA923488A (en) 1973-03-27
JPS4827868B1 (enrdf_load_stackoverflow) 1973-08-27
GB1288879A (enrdf_load_stackoverflow) 1972-09-13
SE362658B (enrdf_load_stackoverflow) 1973-12-17
NL7012714A (enrdf_load_stackoverflow) 1971-03-02
BE754672A (fr) 1971-01-18

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