US3288710A - High load capacity dry film lubricants - Google Patents

High load capacity dry film lubricants Download PDF

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Publication number
US3288710A
US3288710A US346409A US34640964A US3288710A US 3288710 A US3288710 A US 3288710A US 346409 A US346409 A US 346409A US 34640964 A US34640964 A US 34640964A US 3288710 A US3288710 A US 3288710A
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United States
Prior art keywords
lubricant
weight
composition
dry film
dry
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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US346409A
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English (en)
Inventor
Rhynie F Hollitz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Corning Canada Inc
Original Assignee
Dow Corning Silicones Ltd
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Publication date
Application filed by Dow Corning Silicones Ltd filed Critical Dow Corning Silicones Ltd
Priority to US346409A priority Critical patent/US3288710A/en
Priority to GB40555/64A priority patent/GB1036078A/en
Priority to CH1346864A priority patent/CH468458A/de
Priority to NO155508A priority patent/NO122328B/no
Priority to DK554164AA priority patent/DK111630C/da
Priority to DEP1271A priority patent/DE1271875B/de
Priority to NL6502095A priority patent/NL6502095A/xx
Priority to FR6355A priority patent/FR1431139A/fr
Application granted granted Critical
Publication of US3288710A publication Critical patent/US3288710A/en
Anticipated expiration legal-status Critical
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M7/00—Solid or semi-solid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single solid or semi-solid substances
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
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    • C10M2201/041—Carbon; Graphite; Carbon black
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04—Elements
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    • 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
    • C10M2201/061—Carbides; Hydrides; Nitrides
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    • C10M2201/066—Molybdenum sulfide
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    • C10M2201/16—Carbon dioxide
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    • C10M2201/18—Ammonia
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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
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
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    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
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    • C10M2209/102—Polyesters
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • Dry film lubricants are commonly used to give metal surfaces a permanent, dry coating that serves as a lubricant, in that it greatly reduces the coeificient of friction of the metal contacting surfaces. In many applications dry film lubricants eliminate the need for the oiling of bearings, sliding surfaces, etc.
  • Dry film lubricants generally consist of a solid lubricant, such as molybdenum disulfide or graphite, plus a resin that is capable of forming a cured film.
  • a solid lubricant such as molybdenum disulfide or graphite
  • the mixture of solid lubricant and resin is applied as a film over the metal surface that is to be lubricated, and the film is cured by air drying, baking, etc.
  • the result of this is a dry lubricating film; the solid lubricant does the lubricating, and it is held in place by the resin film, making the lubricating action long lasting.
  • compositions of this invention are described in the following manner:
  • a lubricating composition consisting essentially of (1) from 40 to 85 weight percent of a dry lubricant, and (2) from to 60 weight percent of a resinous composition consisting of an epoxy resin which is a condensation product (a) from 40 to 100% by Weight of an aromatic epoxy resin; and, (b) from 0 to 60% by weight of an organo silicon compound of the formula where R is selected from the group consisting of monovalent aromatic hydrocarbon radicals and lower alkyl radicals, R is a hydrolyzable radical, n has an average value of 0.8 to 3, and m has an average value of 0.1 to 3.2, the sum of n+m being not greater than 4.
  • composition of this invention is operative as a dry film lubricant without any silicone ingredient, but it is generally preferred for ingredient (2) to contain from 5 to 40% by weight of silicone.
  • the silicone appears to enhance the load-bearing ability and the heat stability of the film.
  • Example 5 shows a composition that contains no silicone, but works very well.
  • Ingredient (1) can be any dry lubricant such as molyb- Patented Nov. 29, 1965 ICC denum disulfide, graphite, antimony trioxide, titanium disulfide, tungsten disulfide, bismuth, lead sulfide, lead oxide, polytetrafiuoroethylene, magnesium oxide, boron nitride, calcium fluoride, zirconium disulfide, colloidal silver, etc.
  • Suitable combinations of dry lubricants can also be used, such as the combination of graphite and molybdenum disulfide, and combinations of calcium fluoride, molybdenum disulfide, and boron nitride.
  • aromatic epoxide resin as used in the description of ingredient (2) it is meant those resins that are produced by the reaction of polyhydric phenols with either polyfunctional halohydrins or polyepoxides or mixtures thereof to form complex reaction products containing terminal epoxide groups By consisting essentially of, it is implied that other ingredients can be present in the compositions of this invention.
  • solvents to plasticize or dissolve the uncured composition and modifiers for the aromatic epoxy resin such as non-aromatic epoxy resins to make the cured composition softer, and fatty acids and mixtures thereof such as octanoic acid, stearic acid, linseed oil acid, tung oil acid, caster oil acid, etc., which fatty acids tend to enhance the cure, and the lubricity of the compositions of this invention at low loads.
  • aromatic epoxy resin such as non-aromatic epoxy resins to make the cured composition softer
  • fatty acids and mixtures thereof such as octanoic acid, stearic acid, linseed oil acid, tung oil acid, caster oil acid, etc., which fatty acids tend to enhance the cure, and the lubricity of the compositions of this invention at low loads.
  • the polyhydric phenols used in making the epoxide resins employed herein include any of the phenols containing two or more phenolic hydroxyl groups, which can be on one phenyl ring as in resorcinol, or in different, fused ring systems, as in 1,5-dihydroxy naphthalene, or in different ring systems which are attached by chains composed of one or more atoms, in which case the chains should be free from elements which interfere with the reaction of the polyepoxides with the phenolic hydroxyl groups.
  • the phenolic nuclei can contain substituents (such as ring substituted halogen atoms) providing that they also do not interfere with the aforesaid reaction.
  • polyhydric phenols which can be used in making the epoxide resin copolymers are monophenyl phenols such as resorcinol, hydroquinone, catechol, phloroglucinol; polyphenyl phenols such as bisphenol(p, p-dihydroxydiphenyl dimethylmethane), p,p-dihydroxy benzophenone, p,p-dihydroxydiphenyl, p,p-dihydroxydibenzyl, bis(4-hydroxyphenyl)sulfone, 2,2-dihydroxy-l,ldinaphthylmethane, polyhydroxynaphthalenes and anthracenes, 0,p,o,p-tetrahydroxydiphenyldimethylmethane, ctc.
  • monophenyl phenols such as resorcinol, hydroquinone, catechol, phloroglucinol
  • polyphenyl phenols such as bisphenol(p, p
  • polyhydric phenols which are condensation products of simpler polyhydric phenols with dichlorides such as dichlorodiethyl ether and dichlorobutene and are assumed to have one of the following general formulae:
  • a special case of interest and operative herein involves the condensation of complex polyhydric phenols with dibasic acids.
  • condensation of adipic acid with a polyhydric phenol produces a polymer of the general formula in which R is the residue from the phenol and n is at least 1.
  • One of the best known and preferred of the polyhydric phenols operative herein is bis-phenol-(p,p'-dihydroxydiphenyldimethyl methane).
  • the polyepoxides which are operative herein as reactants with the polyhydric phenols contain two or more epoxide groups.
  • the simplest diepoxides contain at least 4 carbon atoms such as 1,2-epoxy-3,4-epoxy butane.
  • the epoxy groups can be separated from each other by ether groups or linkages as in the case of bis-(2-3-epoxypropyl)- ether and bis-(2,3-epoxy-2-methylpropyl)ether.
  • Polyepoxides derived from polyhydric alcohols such as mannitol, sorbitol, erythritol or polyallyl alcohol can also be used.
  • the polyepoxy compounds used herein can have varying structures and can be of complex structure so long as they do not contain groups which interfere with the reaction between the epoxide groups and the phenolic hydroxyl groups.
  • the polyepoxide reactants employed herein should be substantially free from reactive groups other than epoxide and aliphatic hydroxyl groups.
  • Simple diepoxides of a high degree of purity can be prepared and obtained by fractional distillation to separate them from byproducts formed during their manufacture.
  • bis-(2,3-epoxypropyl)ether or diglycid ether can be produced and separated by fractional distillation to give products of high purity.
  • More complex polyepoxides of higher molecular weight are generally difficult to isolate by fractional distillation, but they can be employed herein after purification to remove objectionable inorganic impurities and catalysts such as caustic alkali.
  • the high molecular weight diepoxide or polyepoxide with admixed byproducts such as monoepoxides is operative herein.
  • Particularly well known and useful herein are the reactive products of, for example, epichlorohydrin with a polyhydric alcohol.
  • a specific example of this reaction involves 1 mol of a trihydric alcohol reacted with 3 mols of epichlorohydrin and a catalyst.
  • the epoxide group of the epichlorohydrin reacts with a hydroxyl group of the alcohol and subsequent treatment removes chlorine from the reaction product thus producing the desired polyepoxide.
  • Such polyepoxides can contain less than 3 epoxy groups per molecule even though 3 mols of epichlorohydrin are reacted with 1 mol of a trihydric alcohol.
  • the polyepoxides can contain varying small amounts of admixed monoepoxides. To the extent that monoepoxides are present they will react with the polyhydric phenols to form terminal groups or residues containing hydroxyl groups and to the extent that such terminal hydroxyl groups are present the complex polyepoxide compositions will contain complex epoxy-hydroxyl compounds containing both terminal epoxide-containing residues and terminal hydroxyl-containing residues. The presence of monoepoxides or of monoepoxy-hydroxyl compounds does not interfere with the desired reaction provided a sufficient amount of polyepoxides is present to serve as polyfunctional reactants With polyhydric phenols.
  • the polyhydric phenol can be reacted with a polyfunctional chlorohydrin such as monochlorohydrins, for example, epichlorohydrin, dichlorohydrins, for example, glycerol dichlorohydrin, bis-(3-chloro, 2-hydroxypropyl)ether, 1,4-dichloro-2,3-dihydroxy butane, 2-methyl- 2-hydroxy-l,3-dichloropropane, bis(3-chloro, 2-methyl, 2- hydroxypropyDether, and other mono and dichlorohydrins derived from aliphatic olefins, mannitol, sorbitol and other alcohols.
  • a polyfunctional chlorohydrin such as monochlorohydrins, for example, epichlorohydrin, dichlorohydrins, for example, glycerol dichlorohydrin, bis-(3-chloro, 2-hydroxypropyl)ether, 1,4-dichloro-2,3-di
  • polyfunctional chlorohydrin as employed herein includes all compounds which contain at least one epoxide and at least one chlorine atom in the molecule and all compounds containing a chlorine atom and an OH group on adjacent carbon atoms and at least one other chlorine atom in the molecule. It is preferred that the chlorohydrin be substantially free of other functional groups. Epichlorohydrin and/or glycerol dichlorohydrin are particularly useful in this invention.
  • the uncondensed silicone portion of ingredients (2) is a silane or silanol of the formula R SiR' or a siloxane containing R and R groups.
  • R can be any monovalent aromatic hydrocarbon radical, such as phenyl, tolyl, biphenyl, naphthyl, n,n-diethylphenyl, anthracenyl, chrysenyl, etc.; or any lower alkyl radical such as methyl, ethyl, hexyl, isobutyl, etc.
  • R can be OH or any hydrolyzable group; e.g. halogens such as fluorine, chlorine, and bromine; alkoxy groups such as methoxy, ethoxy, isopropoxy, decoxy, etc.; polyalkoxy such as beta-ethoxyethoxy, beta-methoxyethoxy, and CH OC H 0C I-I O-; haloalkoxy groups such as beta-chloroethoxy, 3,3-difluoropropoxy,
  • acyloxy groups such as acetate, propionate, isobutyrate and octoate; haloacyloxy such as beta-chloroacetate, 3,3- difluoropropionate, etc.; the isocyanate group; amino groups such as NH NHCH NHC H NHC H N 3 2 and groups of the ketoxime class such as etc.
  • the condensation should be carried out at low temperatures and under anhydrous conditions in order to minimize reaction of the HR byproduct with the oxirane groups on the epoxide resin.
  • the preferred hydrolyzable groups are alkoxy.
  • ingredients that make up ingredient (2) can be cocondensed by heating in a manner that is well known to the art (e.g. see Canadian Patent 662,941).
  • the condensation can be carried out at room temperature in those cases where the R group is very reactive.
  • Ingredients (1) and (2) are then mixed intimately, the best way being to dissolve them in the presence of a solvent, and apply them to the metal surface for curing.
  • This composition was milled in a colloid mill, and diluted with toluene until it was sprayable.
  • This composition was sprayed on two vapor-blasted steel V blocks and a pin that fits into the V block, and cured for one hour at 300 F.
  • the frictional characteristics of the pin rotating in the blocks were determined'by means of a Falex lubricant testing machine, using a step test.
  • the load on the pin and block is increased stepwise at periodic intervals, the torque of the rotating pin being constantly measured.
  • composition was run through a colloid mill, and to it was added enough of a mixture of 50% ethylene glycol and 5 0% xylene to make the composition sprayable.
  • Example 1 The composition was sprayed on a block and pin set, cured, and step-tested in the manner of Example 1.
  • Example 3 The composition of Example 1 was reformulated, replacing the graphite with 7% of boron nitride.
  • composition was run through a colloid mill, and to it was added enough of a mixture of 50% ethylene glycol and 50% xylene to make the composition sprayable.
  • Example 4 The composition of Example 1 was reformulated, replacing the of MOS- and the 7% of graphite with 60% of M08 10% of antimony trioxide, and 7% of zirconium sulfide.
  • composition was run through a colloid mill, and to it was added enough of a mixture of 50% ethylene glycol and 50% xylene to make the composition sprayable.
  • composition was sprayed on four block and pin sets, cured, and tested in the manner of Example 1, except that the block and pin sets had received the commerciallyavailable phosphate-manganese anticorrosion treatment, and except that the test runs were at a constant load of 1000 pounds.
  • The' four block and pin sets endured an average of 2 hours and 9 minutes of continuous operation at the 1000 pound load before failure of the dry film lubricant.
  • the first block and pin set failed after two hours of operation, and the last set failed after 2 hours and 14 minutes of operation.
  • Example 5 A composition was prepared consisting of 70% by weight M08 7% graphite, and 23% of a material is formed that cures on metal as a film by heating and imparts good lubricating qualities to the metal surface.
  • Example 8 When 60 parts by weight of polytetrafluoroethylene are intimately mixed in diethyl ether with 40 parts by weight of a cocondensate of (a) 70 weight percent of the condensation product of 40 mol percent of phloroglucinol and where n equals approximately 2.
  • a small amount of a solvent which was a mixture of 50% methyl isobutyl ketone and 50% toluene was added to plasticize the composition, which was then run through a colloid mill.
  • Example 6 Eighteen commercial dry film lubricants were applied to V blocks and pins by methods in accordance with the manufacturers recommendations, and tested on the Falex machine by the step test as described in Example 1. The best of the eighteen compositions failed at a load of 3250 pounds, i.e. the point where a rapid rise of torque to the point of welding of the pin to the blocks were observed. The two second best compositions failed at a load of 2750 pounds. The approximate mean failing load was 1750 pounds.
  • Example 7 When 40 parts by weight of magnesium oxide are intimately mixed in toluene with 60 parts by weight of a cocondensate of 95 weight per-cent of When parts by weight of lead sulfide are intimately mixed with 30 parts of a cocondensate of (a) 60 weight percent of the condensation product of 40 mol percent of l,3,7-trihydroxynaphthylene, 10 mol per cent of 40 mol percent of bis(2,3-epoxy-2-methylpropyl)ether, and 10 mol percent of 1,2-epoxypropane; and (b) 40 weight percent of 0 CH3 CH3 0 ll L l CH3 -OS1 081 0 CH3 a material is formed that cures on metal as a film upon heating, and imparts lubricating qualities to the metal surface.
  • Example 11 When parts by weight of colloidal silver are intimately mixed in benzene with 20 parts of a composition where m equals approximately and 5 weight percent of a silicone of the average formula:
  • Example 12 where a is an integer of 0 through 100.
  • a dry film lubricant consisting essentially of 70 (CHa)1.5SiO- weight percent of M08 7% of graphite; 13.8% of a (OCH2CH2C1) 5]n composition consisting of 75 weight percent of and 1,4-dichloro-2,3-dihydroxy butane, and 60 weight percent of a polymer of the average formula 0 OH, OH OH, 0
  • a material is formed that cures on metal as a film on heatwhere a has an average value of 2, and Weight percent ing, and imparts lubricating qualities to the metal surface.
  • the lubricant of claim 8 where the M08 and Ll graphite ingredients are replaced with 60% by weight of for the silicone ingredient of Example 11, a material is 40 M082 10% antimony tnoxlde and 7% of Zlrcomum formed that cures on metal as a film on heating, and imsulfideparts lubricating qualities to the metal surface.
  • I R is selected from the group consisting of monovalent aromatic hydrocarbon radicals and lower alkyl radicals, is a y m y radical, DANIEL E. WYMAN, Prlmary Examiner. n has an average value of 0.8 to 2, and I. VAUGHN, Assistant Examiner.

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US346409A 1964-02-21 1964-02-21 High load capacity dry film lubricants Expired - Lifetime US3288710A (en)

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GB40555/64A GB1036078A (en) 1964-02-21 1964-10-05 High load capacity dry film lubricants
CH1346864A CH468458A (de) 1964-02-21 1964-10-16 Trockenfilm-Gleitmittel
DK554164AA DK111630C (da) 1964-02-21 1964-11-10 Tørt smøremiddel til anvendelse ved høje tryk.
NO155508A NO122328B (enrdf_load_stackoverflow) 1964-02-21 1964-11-10
DEP1271A DE1271875B (de) 1964-02-21 1965-02-18 Trockenschmiermittel
NL6502095A NL6502095A (enrdf_load_stackoverflow) 1964-02-21 1965-02-19
FR6355A FR1431139A (fr) 1964-02-21 1965-02-19 Lubrifiants à film sec susceptibles de résister à des pressions élevées

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3371038A (en) * 1966-10-10 1968-02-27 Air Force Usa Solid lubricant composition and method of manufacturing same
US3405063A (en) * 1966-03-16 1968-10-08 Westinghouse Electric Corp Solid lubricant composition and process for its preparation
US3639237A (en) * 1969-05-14 1972-02-01 Exxon Research Engineering Co Extreme pressure greases
US3674690A (en) * 1969-07-08 1972-07-04 Us Air Force Air drying silicone resin bonded dry film lubricant
US3833408A (en) * 1972-04-19 1974-09-03 Rca Corp Video discs having a methyl alkyl silicone coating
US3844953A (en) * 1971-04-19 1974-10-29 Midwest Research Inst Solid film lubricant with polyamide binder
US3881048A (en) * 1972-08-10 1975-04-29 Dow Corning Metal coated with a lubricant composition
US4584115A (en) * 1982-02-11 1986-04-22 The Lubrizol Corporation Method of preparing boron-containing compositions useful as lubricant additives

Families Citing this family (5)

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Publication number Priority date Publication date Assignee Title
US4115606A (en) * 1976-06-11 1978-09-19 Continental Oil Company Method for retarding scale formation
DE2923579C2 (de) * 1979-06-11 1984-07-26 Geb. Zaprudskaja Alla Kronidovna Mitrofanova Antifriktionspaste
DE3046012A1 (de) * 1980-12-05 1982-07-15 Omnikote GmbH Spezialschmierstoffe, 8000 München Festschmierstoff und seine verwendung
GB2131828B (en) * 1982-12-10 1985-10-09 Kobe Steel Ltd Lubricant film for preventing galling of sliding metal surfaces
WO2001012344A1 (en) * 1999-08-12 2001-02-22 Alliedsignal Inc. Tungsten disulfide modified epoxy, high temperature/low friction/machinable

Citations (5)

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Publication number Priority date Publication date Assignee Title
US2592560A (en) * 1945-11-02 1952-04-15 Devoe & Raynolds Co Polyepoxide compositions
US2615008A (en) * 1945-09-18 1952-10-21 Devoe & Raynolds Co Epoxide resin compositions
US2615007A (en) * 1950-12-08 1952-10-21 Devoe & Raynolds Co Epoxide resins
US3079338A (en) * 1959-01-26 1963-02-26 Caubet Jacques Jean Anti-friction material
CA662941A (en) * 1963-05-14 Dow Corning Corporation Organosilicon - epoxy resins

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
FR1183959A (fr) * 1959-02-03 1959-07-16 Matériau de frottement

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA662941A (en) * 1963-05-14 Dow Corning Corporation Organosilicon - epoxy resins
US2615008A (en) * 1945-09-18 1952-10-21 Devoe & Raynolds Co Epoxide resin compositions
US2592560A (en) * 1945-11-02 1952-04-15 Devoe & Raynolds Co Polyepoxide compositions
US2615007A (en) * 1950-12-08 1952-10-21 Devoe & Raynolds Co Epoxide resins
US3079338A (en) * 1959-01-26 1963-02-26 Caubet Jacques Jean Anti-friction material

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3405063A (en) * 1966-03-16 1968-10-08 Westinghouse Electric Corp Solid lubricant composition and process for its preparation
US3371038A (en) * 1966-10-10 1968-02-27 Air Force Usa Solid lubricant composition and method of manufacturing same
US3639237A (en) * 1969-05-14 1972-02-01 Exxon Research Engineering Co Extreme pressure greases
US3674690A (en) * 1969-07-08 1972-07-04 Us Air Force Air drying silicone resin bonded dry film lubricant
US3844953A (en) * 1971-04-19 1974-10-29 Midwest Research Inst Solid film lubricant with polyamide binder
US3833408A (en) * 1972-04-19 1974-09-03 Rca Corp Video discs having a methyl alkyl silicone coating
US3881048A (en) * 1972-08-10 1975-04-29 Dow Corning Metal coated with a lubricant composition
US4584115A (en) * 1982-02-11 1986-04-22 The Lubrizol Corporation Method of preparing boron-containing compositions useful as lubricant additives

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NL6502095A (enrdf_load_stackoverflow) 1965-08-23
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GB1036078A (en) 1966-07-13
DE1271875B (de) 1968-07-04
DK111630B (enrdf_load_stackoverflow) 1968-09-23

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