US3759827A - Lubricant compositions - Google Patents

Lubricant compositions Download PDF

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Publication number
US3759827A
US3759827A US00076631A US3759827DA US3759827A US 3759827 A US3759827 A US 3759827A US 00076631 A US00076631 A US 00076631A US 3759827D A US3759827D A US 3759827DA US 3759827 A US3759827 A US 3759827A
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United States
Prior art keywords
grease
weight percent
lubricant
additive
siloxane
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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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US00076631A
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English (en)
Inventor
E Groenhof
T Swihart
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 Silicones Corp
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Dow Corning Corp
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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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound containing silicon
    • 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
    • C10M131/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen, halogen and oxygen
    • C10M131/12—Acids; Salts or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04—Elements
    • C10M2201/041—Carbon; Graphite; Carbon black
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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
    • C10M2201/10—Compounds containing silicon
    • C10M2201/102—Silicates
    • C10M2201/103—Clays; Mica; Zeolites
    • C—CHEMISTRY; METALLURGY
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/10—Compounds containing silicon
    • C10M2201/105—Silica
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • 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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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044—Acids; Salts or esters thereof
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • C10M2213/062—Polytetrafluoroethylene [PTFE]
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/068—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
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    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
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    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
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    • C10M2215/16—Nitriles
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    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/227—Phthalocyanines
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    • C10M2215/28—Amides; Imides
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    • C10M2229/02—Unspecified siloxanes; Silicones
    • C10M2229/025—Unspecified siloxanes; Silicones used as base material
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    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/045—Siloxanes with specific structure containing silicon-to-hydroxyl bonds
    • C10M2229/0455—Siloxanes with specific structure containing silicon-to-hydroxyl bonds used as base material
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/046—Siloxanes with specific structure containing silicon-oxygen-carbon bonds
    • C10M2229/0465—Siloxanes with specific structure containing silicon-oxygen-carbon bonds used as base material
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/047—Siloxanes with specific structure containing alkylene oxide groups
    • C10M2229/0475—Siloxanes with specific structure containing alkylene oxide groups used as base material
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/048—Siloxanes with specific structure containing carboxyl groups
    • C10M2229/0485—Siloxanes with specific structure containing carboxyl groups used as base material
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/0505—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon used as base material
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
    • C10M2229/0515—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen used as base material
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/052—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing nitrogen
    • C10M2229/0525—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing nitrogen used as base material
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/053—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing sulfur
    • C10M2229/0535—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing sulfur used as base material
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/054—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing phosphorus
    • C10M2229/0545—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing phosphorus used as base material
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties

Definitions

  • This invention relates to improved lubricating compositions and more particularly to silicone lubricants having high load-carrying capacity.
  • silicone fluids find wide application as lubricants. As discussed by Noll in Chapter 9 of Chemistry and Technology of Silicones, copyright 1968 by Academic Press, silicone fluids cannot be considered general lubricating oils because of their minimal lubrication of steel on steel, especially when sliding friction is involved.
  • Various additives such as chlorinated biphenyls, brominated fatty acids and esters of phosphoric acid, have been proposed for improving the lubricating characteristics of polysiloxanes. While certain additives do enhance the lubrication properties at normal temperatures, the additive effect disappears at extreme high and low temperatures because of inadequate heat stability or because of insolubility at the lower temperatures.
  • lube additives are based on the reaction product of chlorendic acid with various organic compounds such as chlorinated alcohols, lauryl mercaptan and alkanol amines. This class or additives has been recommended for use in both natural lubricants, e.g.: mineral oil, and synthetic lubricants, e.g.: polyesterssee U.S. Pats. 3,426,062, 3,388,191, and 3,234,132. Calcium salts of chlorendic acid are disclosed specifically as lube additives for silicones in U.S. Pat. 3,223,632 which describes the additive as being insoluble, having principal utility as a thickening agent in silicone grease.
  • Another object of the invention is to provide organopolysiloxanes having steel on steel lubricating properties.
  • lubricant compositions comprising a major amount of a liquid diorganosiloxane and a small amount, willcient to improve the load-carrying characteristics of the liquid siloxane, of a diester of the formula in which R is an alkyl radical of from 4 to 8 inclusive carbon atoms.
  • R is an alkyl radical of from 4 to 8 inclusive carbon atoms.
  • the R radical can be a straight or branched alkyl.
  • dibutylchlorendate dihexylchlorendate, dioctylchlorendate, and di-Z-ethylhexylchlorendate and the like are contemplated in the practice of the invention.
  • Chlorendic acid otherwise identified as l,4,5,6,7,7-hexachlorobicyclo(2.2.1)-hept-5-ene-2,3-dicarboxylic acid, is prepared by the Diels-Alder addition of the corresponding chlorinated cyclopentadiene and maleic anhydride. Chlorendic acid is commercially available from the Velsicol Chemical Corporation, Chicago, Ill.
  • silicone fluids utilized in the practice of the invention are described as liquid diorganopolysiloxanes and can be represented by the general formula:
  • each R is selected from the group consisting of the hydrogen atom, alkyl and halogenated alkyl radicals, aryl and halogenated aryl radicals, alkaryl, aralkyl and halogenated derivates thereof.
  • the depicted polymers are triorganosilyl-endblocked the all: C F 3CHgCHg(CH 213i 0 Siloxanes having R substituents of less than 18 carbon atoms are preferred. Most preferred in the practice of the invention are dimethylpolysiloxanes,
  • the silicone fluids have a viscosity of from 0.65- to over 1,000,000 cs. (centistokes) when measured at 77 F.
  • Particularly preferred are those liquid diorganopolysiloxanes having a viscosity in the range of about 20 to 1000 cs. at 77 C. If desired, blends of differviscosity siloxane liquids can be utilized.
  • the lubricant compositions of the invention are prepared by blending the above-described components, the diester being soluble in the siloxane. This solubility has been observed at temperatures as low as -20 F. in concentrations of 5 weight percent in polydimethylsiloxane.
  • the amount of diester additive is sufficient to improve the load-carrying characteristics to the desired degree. This amount will vary with the nature of the organosiloxane and its application, but it will generally be in the range of from 1 to 10 weight percent, based on the weight of the liquid diorganopolysiloxane.
  • the lubricating compositions of the invention may optionally contain corrosion inhibitors, extreme pressure agents, antioxidants, dyes and the like. These additives are generally present in no more than 5-10 weight percent based on the weight of the lubricant compositions.
  • the invention contemplates the use of thickening agents with the lubricant compositions to produce grease formulations having improved load-carrying characteristics.
  • Any suitable thickening agent can be formulated with the diorganopolysiloxane-diester lubricant to produce grease compositions.
  • Suitable thickening agents include fatty acid soaps, carbon black, silica, clay, copper phthalocyanine, ammeline, indantherene blue, aryl-substituted ureas, polytetrafluoroethylene and the like.
  • Nitrogen-containing thickening agents such as aromatic ureas, aromatic di-ureas, aromatic amides, aromatic di-amides, abietyl di-urea, cyanuramide and eyanourodiamide, are especially suitable in the formulation of high temperature greases.
  • These thickeners are well-known in the art, being described in detail in US. Pat. 3,278,435.
  • the lithium soaps of high molecular weight carboxylic acids, for example lithium stearate, are preferred thickeners for grease compositions designed for use in less severe temperature environments.
  • the thickening agent will generally be present in an amount from about to 60 weight percent of the total grease composition, depending upon the consistency desired.
  • Grease compositions containing from 20 to 40 weight percent thickener are preferred because of their varied applications.
  • the grease compositions of the invention can be prepared by mixing the thickener and any other components with the lubricant composition on a three-roll mill, tcol'lodial mill or the like. Other conventional methods can be used to prepare the grease so long as one obtains an intimate mixture of the components.
  • lubricity characteristics were determined by means of 4-Ball test and LFW-l test.
  • the 4-Ball test is conducted on a Roxanna weak testing machine and a Az-inch diameter steel ball is roated against three stationary /z-inch diameter steel balls at a rate of 1200 r.p.m. for one hour at a temperature of 167 F. under loads ranging from 10 to 40 kilograms.
  • the length and width of the scar formed on each stationary ball is measured and the average of the six measurements is taken as the Wear scar diameter. The smaller the wear scar, the better the lubricant.
  • Wear scars for certain grease formulations were also determined on the Alpha LEW-1 test machine in the oscillating mode, using a standard steel ring on a R 30 steel block at a 10 arc and 75 cycles per minute. The wear scar resulting from the oscillations is measured after 500 cycles at 150 pounds load.
  • EXAMPLE 1 Suflicient dibutylchlorendate was blended with trimethylsilyl-endblocked dimethylpolysiloxane to form a 10 Weight percent solution of the diester in the siloxane.
  • the fluid dimethylpolysiloxane had a viscosity of 350 cs. When measured at 77 F.
  • the dibutylchlorendate-siloxane solution was stable at room temperature.
  • This lubricant composition gave a 4-Ball wear scar diameter of 0.73 mm. under 40 kg. load and 0.57 mm. under 10 kg. load.
  • the use of the fluid siloxane without any additive as a lubricant results in a wear scar of 2.33 mm. This data demonstrates that the diester additive does impart steel on steel lubricating properties to dimethylpolysiloxane.
  • a grease formulation contains a 90.7 weight percent of liquid diorganopolysiloxane, 0.7 weight percent dye and 8.6 weight percent of lithium stearate (thickener) was prepared by the in situ reaction of 1.2 weight percent lithium hydroxide with 7.4 weight percent stearic acid in the siloxane vehicle.
  • the liquid diorganopolysiloxane consisted of 84.3 mol percent (CI-I SiO units, 9.8 mol percent C H (CH )SiO units and 5.9 mol percent units and had a viscosity of 100 cs. at 77 F.
  • a portion of this grease was mixed with suflicient dibutylchlorendate 4 to form a grease composition containing 5 weight percent of the additive.
  • a second grease formulation (Grease No. 2) containing 64 weight percent of trimethylsilyl-endblocked 3,3,3- trifluoropropylrnethylpolysiloxane (1000 cs.), 26 weight percent of powdered polytetrafluoroethylene resin and 10 weight percent powdered tetrafluoroethylene-hexafluoropropylene copolymer was prepared by milling of the components. A portion of this grease was mixed with sufficient dibutylchlorendate to form a grease composition containing 5 weight percent of the additive. This grease and the above-described lithium stearate thickened grease were tested by means of the described LFW-1 test. Results are listed below:
  • EXAMPLE 3 Suflicient di-Z-ethylhexylchlorendate was blended with copolymeric siloxane to form a 5 weight percent solution of the diester in the disiloxane.
  • the liquid siloxane consisted of 57 mol percent C H (CH )SiO units, 30.5 mol percent (CH SiO and 12.5 mol percent (CH SiO units and had a viscosity of 135 cs. at 77 F.
  • This lubricant composition gave a 4-Ball wear scar diameter of 2.1 mm. under a 10 kg. load as compared to a wear scar of 2.53 mm. under 10 kg. obtained from the unmodified fluid siloxane.
  • EXAMPLE 4 For purposes of comparison various additives, including the diesters of the invention, were used in combination with trimethylsilyl-endblocked dimethylpolysiloxane having a viscosity of 350 cs. The additives were mixed with portions of the liquid siloxane in amounts sufficient to provide 5 weight percent concentrations of the particular lube addtives. The various additive-siloxane mixtures were tested by the 4-Ball method under 40 kg. load. The coefficient of friction for each lubricant composition was also determined. Descriptions of the additives and test results are tabulated below:
  • Coetfi- 4-bal1 cient of wear seat friction Additive (mm.) f are 1... None 2.33 0.3 2- Dibutylchlorendate 0. 87 0. 065 3. Di-2-ethlhexylchlorendate.-- 0. 0. 058 4. Chlorinated diphenyl conta g 54 w ht percent chlorine. 1. 2 0. 20 5- Chlorinated diphenyl containing 62 weight percent chlorine. 1. 6 0. 24 6 Imide product from reaction of alkylamine with 5, 6, 7, 8, 9, Q-hexachloro-l,2,3,4,4a,5,8, 8a-octahydro-5,8-methano-2,3-napht noiredicarboxylic acid. 1. 9 0.25 7- N-n-butyl chlorondie imide 1. 5 0. 19 8. Dicalcium chlorendate d 1. 7 0. 26
  • Additives 6 through 8 were insoluble in the liquid siloxane at the stated concentration.
  • the cloud point of dibutylchlorendate-containing solution was 20 F. as compared to +45 F. for the solution containing additive No. 4, and +65 F. for the solution containing additive No. 5.
  • the additive-containing siloxanes of the invention are the only species of the above additive-containing lubricants which would not be subject to precipitation or phase separation during shipping and storage.
  • the wear scar values and coeflicients of friction demonstrate the superior lubrication obtained by practice of the invention.
  • the dibutylchlorendate additive is shown to give only one-half the wear resulting from use of dicalcium chlorendate, which is specifically recommended for use in silicone lubricants.
  • a lubricant composition comprising a major amount of a liquid diorganopolysiloxane and a small amount, sufficient to improve the load-carrying characteristics of the liquid siloxane, of a diester of the formula CHC0R in which R is an alkyl radical of from 4 to 8 inclusive carbon atoms.
  • liquid polydiorganosil-oxane is dimethylpolysiloxane having a viscosity in the range of 20 to 1000 cs. as measured at 77 F.
  • a lubricating composition in accordance with claim 1 containing suflicient thickening agent to form a grease.

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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)
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3977986A (en) * 1975-06-02 1976-08-31 The United States Of America As Represented By The Secretary Of The Navy Silicone-base fire resistant hydraulic fluid
DE2614403A1 (de) * 1975-04-02 1976-10-21 Robert Eric Miller Lager und mit einem solchen lager ausgestatteter tragkopf zum drehen und/oder kippen einer vorrichtung
US4039143A (en) * 1975-01-06 1977-08-02 General Electric Company Organic hydrocarbon solvent-based green tire lubricant and process
US4043924A (en) * 1973-06-07 1977-08-23 General Electric Company Water based green tire lubricant
US4049563A (en) * 1973-06-18 1977-09-20 Chevron Research Company Jet engine oils containing extreme pressure additive
DE2714135A1 (de) * 1976-04-02 1977-10-20 Union Carbide Canada Ltd Schmieroel und seine verwendung
US4066560A (en) * 1976-09-20 1978-01-03 General Electric Company Silicone compositions useful as green tire lubricants
US4137189A (en) * 1977-01-19 1979-01-30 Dow Corning Corporation Three component common hydraulic fluid comprising a non-linear siloxane fluid
US4443351A (en) * 1982-11-01 1984-04-17 Dow Corning Corporation Silicone hydraulic fluids and additive concentrates therefor
EP0504897A1 (en) 1991-03-19 1992-09-23 Dow Corning Kabushiki Kaisha Grease composition
US5534173A (en) * 1994-08-30 1996-07-09 Amway Corporation Light duty lubricant composition and method of use
US20070244016A1 (en) * 2006-04-13 2007-10-18 Buck William H Low sap engine lubricant containing silane and zinc dithiophosphate lubricant additive and composition
WO2012018403A1 (en) 2010-08-05 2012-02-09 Biofilm Ip, Llc Cyclosiloxane-substituted polysiloxane compounds, compositions containing the compounds and methods of use thereof
US20130079263A1 (en) * 2010-06-08 2013-03-28 Dow Corning Corporation Silicone Hydraulic Fluids

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1217013B (it) * 1987-02-05 1990-03-14 Tecnochimica Srl Emulsione siliconica per la lubrificazione e la sigillatura dei tappi in sughero destinati alla chiusura di contenitori di bevande e prodotti a lunga conservazione
JP3040618B2 (ja) * 1992-11-20 2000-05-15 コスモ石油株式会社 新規ビスカスカップリング用流体組成物

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4043924A (en) * 1973-06-07 1977-08-23 General Electric Company Water based green tire lubricant
US4049563A (en) * 1973-06-18 1977-09-20 Chevron Research Company Jet engine oils containing extreme pressure additive
US4039143A (en) * 1975-01-06 1977-08-02 General Electric Company Organic hydrocarbon solvent-based green tire lubricant and process
DE2614403A1 (de) * 1975-04-02 1976-10-21 Robert Eric Miller Lager und mit einem solchen lager ausgestatteter tragkopf zum drehen und/oder kippen einer vorrichtung
US3977986A (en) * 1975-06-02 1976-08-31 The United States Of America As Represented By The Secretary Of The Navy Silicone-base fire resistant hydraulic fluid
DE2714135A1 (de) * 1976-04-02 1977-10-20 Union Carbide Canada Ltd Schmieroel und seine verwendung
US4066560A (en) * 1976-09-20 1978-01-03 General Electric Company Silicone compositions useful as green tire lubricants
US4137189A (en) * 1977-01-19 1979-01-30 Dow Corning Corporation Three component common hydraulic fluid comprising a non-linear siloxane fluid
US4443351A (en) * 1982-11-01 1984-04-17 Dow Corning Corporation Silicone hydraulic fluids and additive concentrates therefor
EP0504897A1 (en) 1991-03-19 1992-09-23 Dow Corning Kabushiki Kaisha Grease composition
US5534173A (en) * 1994-08-30 1996-07-09 Amway Corporation Light duty lubricant composition and method of use
US20070244016A1 (en) * 2006-04-13 2007-10-18 Buck William H Low sap engine lubricant containing silane and zinc dithiophosphate lubricant additive and composition
US20130079263A1 (en) * 2010-06-08 2013-03-28 Dow Corning Corporation Silicone Hydraulic Fluids
WO2012018403A1 (en) 2010-08-05 2012-02-09 Biofilm Ip, Llc Cyclosiloxane-substituted polysiloxane compounds, compositions containing the compounds and methods of use thereof
US9175141B2 (en) 2010-08-05 2015-11-03 Biofilm Ip, Llc Cyclosiloxane-substituted polysiloxane compounds, compositions containing the compounds and methods of use thereof

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FR2108065A1 (xx) 1972-05-12
NL7113282A (xx) 1972-04-04
DE2148664A1 (de) 1972-04-06
FR2108065B1 (xx) 1974-03-29
DE2148664B2 (de) 1975-01-09
AT310911B (de) 1973-10-25
CH559770A5 (xx) 1975-03-14
GB1309032A (en) 1973-03-07
BE773171A (fr) 1972-03-28
JPS5138864B1 (xx) 1976-10-25
SE365816B (xx) 1974-04-01
BR7103060D0 (pt) 1973-04-10
CA946370A (en) 1974-04-30
DE2148664C3 (de) 1975-08-28

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