US3609079A - Silicone lubricants - Google Patents

Silicone lubricants Download PDF

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US3609079A
US3609079A US783537A US3609079DA US3609079A US 3609079 A US3609079 A US 3609079A US 783537 A US783537 A US 783537A US 3609079D A US3609079D A US 3609079DA US 3609079 A US3609079 A US 3609079A
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silicone
sulfur
lubricant
percent
polysulfide
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Martin J Devine
Edward R Lamson
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EDWARD R LAMSON
MARTIN J DEVINE
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EDWARD R LAMSON
MARTIN J DEVINE
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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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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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
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C10M2219/068—Thiocarbamate metal salts
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
    • C—CHEMISTRY; METALLURGY
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
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    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
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    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
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    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
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    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043—Polyoxyalkylene ethers with a thioether group
    • C—CHEMISTRY; METALLURGY
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • C—CHEMISTRY; METALLURGY
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/02—Esters of silicic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
    • C—CHEMISTRY; METALLURGY
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    • C10M2229/04—Siloxanes with specific structure
    • C—CHEMISTRY; METALLURGY
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    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/042—Siloxanes with specific structure containing aromatic substituents
    • C—CHEMISTRY; METALLURGY
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    • C10M2229/04—Siloxanes with specific structure
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    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
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    • C10M2229/04—Siloxanes with specific structure
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    • C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
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    • C10M2229/052—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing nitrogen
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/10—Groups 5 or 15
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • Lubricant compositions having increased lubricity are obtained by forming a mixture of a major amount of a silicone lubricant and a minor amount of a sulfur containing compound dissolved in the silicone and including at least two sulfur atoms per molecule.
  • from 1 to 10 parts by weight of ditertiarynonyl polysulfide are admixed with from 99-90 parts by weight of a silicone oil to provide a new composition which functions properly as a lubricant under loads as high as 240 kilograms when employing the Shell 4-Ball EP machine.
  • a silicone oil is not useful as a lubricant under loads exceeding about 40 kilograms when employing the Shell 4-Ball EP machine.
  • Silicone oils and lubricants compounded from them are well-known, commercially available materials which have presented numerous advantages over other types of lubricant compositions.
  • silicone lubricants have (1) lower evaporation rates, (2) smaller changes in viscosity with unit change in temperature, (3) lower freezing or solidification points, and (4) better oxidation and thermal degradation resistance than other types of lubricants.
  • a major disadvantage of such silicone lubricants is their poor load-carrying capacities. In this respect, the silicone lubricants are considerably less useful than most other classes of lubricants, including the commonly used petroleum and diester lubricants.
  • This invention relates to silicone lubricant compositions and has for an object greatly increasing the wear-prevention properties of a silicone lubricant, especially under conditions of sliding motion, by adding thereto a sulfur containing compound soluble in the silicone and including at least two sulfur atoms per molecule.
  • silicone lubricant in general, any of the well-known silicone fluids and greases may be used to provide the lubricant compositions of the invention.
  • Such silicone lubricants generally are liquids, or solids liquifiable on warming.
  • silicone lubricant includes the well-known organopolysiloxanes and organosilanes, silicate esters, silarylene-type compounds, such as silphenylene, as well as alkyl and aryl disilazane such as hexamethyl disilazane, for example.
  • organopolysiloxanes which may be used to provide the lubricant compositions of the invention are those having the formula I nr nmm where R represents a member selected from the class consist ing of alkyl radicals (e.g., methyl, ethyl, propyl, isopropyl, butyl, octyl, etc.
  • radicals ); cycloalkyl radicals (e.g., cyclohexyl, cycloheptyl, etc., radicals); aryl radicals (e.g., phenyl, diphenyl, naphthyl, etc., radicals); alkaryl radicals (e.g., tolyl, xylyl, ethylphenyl, etc., radicals); aralkyl radicals (e.g., benzyl, phenylethyl, etc., radicals); haloaryl radicals (e.g., monochlorophenyl, dibromophenyl, tetrachlorophenyl, monofluorophenyl, etc., radicals); cyanoalkyl radicals (e.g., cyanomethyl, Bcyanomethyl, rcyanopropyl, etc., radicals).
  • cycloalkyl radicals e.g., cyclohexy
  • At least 50 mole percent of the R groups are lower alkyl groups having from one to two carbon atoms, preferably the methyl radical, and m has a value from 1.98 to 3.
  • organopolysiloxanes are given in Patnode U.S. Pat. Nos. 2,469,888 and 2,469,890, and in Pfeifer U.S. Pat. No. 2,704,748, wherein are disclosed linear as well as branchchuined organopolysiloxanes coming within the above formula as well as cyclic organopolysiloxanes, e.g., hexamethylcyclotetrusiloxune. octamethylcyclotetrasiloxane, tetraphenyltetramethylcyclotetrasiloxane, octaethylcyclotetrasiloxane, etc.
  • silicate ester lubricants which can be used to provide the compositions of the invention will generally correspond to the formula where R,, R R and K, may be the same or different and are selected from the same class of radicals as designated for R in formula I above.
  • the silarylene-type materials useful to provide the lubricant compositions of the invention will generally comprise polymeric materials characterized by recurring structural units of the formula where R R R and R are the same or different and are selected from the same class of radicals as R above, and A is an arylene radical (e.g., phenylene, diphenylene, naphthylene, etc. radicals); alkarylene radicals (e.g., tolylene, xylylene, ethylphenylene, etc. radicals); haloarylene radicals e.g., monocholorophenylene, dibromophenylene, tetrachlorophenylene, monofluorophenylene, etc., radicals).
  • arylene radical e.g., phenylene, diphenylene, naphthylene, etc. radicals
  • alkarylene radicals e.g., tolylene, xylylene, ethylphenylene, etc.
  • any sulfur-containing compound soluble in the silicone lubricant with which it is to be admixed, and including at least two atoms of sulfur per molecule, may be employed to provide the improved silicone lubricants of the invention.
  • sulfur containing compounds which may be used are those having the formula where R,, and R are hydrocarbon radicals which can be the same or different, and which are selected from the same class of radicals as R above, and x is a number from 1 to about 20.
  • One particular group of sulfur compounds which can advantageously be used are those corresponding to the general formula where R and R are the same or different hydrocarbon radicals selected from the same class of radicals as R above, a and b are whole numbers from 0 to about 8, the sum of a and b being at least I, and preferably 2 to about 16.
  • R and R are the same or different hydrocarbon radicals selected from the same class of radicals as R above, a and b are whole numbers from 0 to about 8, the sum of a and b being at least I, and preferably 2 to about 16.
  • suitable polysulfides which are soluble in the silicone lubricant with which they are to be admixed and which include at least two sulfur atoms per molecule will readily occur to those skilled in the art.
  • the amount of the sulfur-containing compound used in the practice of the present invention can be varied within wide limits. Satisfactory results can be obtained in improving the wear-resistant properties of the silicone lubricant by adding to the silicone from as low as about one-tenth of 1 percent to as high as 25 percent or more, based upon the total weight of the silicone lubricant plus sulfur compound employed.
  • the amount of the sulfur compound advantageously employed is the minimum required to impart the desired load-carrying characteristics to the silicone lubricant that is used. It is essential in this connection that the sulfur compound used be dissolved in the silicone in the amount employed so as to form a homogeneous solution therewith. Preferably, therefore sulfur compounds which are soluble in the silicone should be employed.
  • FIGS. I-6 respectively present the results of test of a plurality of silicone lubricants with and without soluble sulfur additives which include two or more sulfur atoms per molecule.
  • a Shell 4-Ball Extreme Pressure Tester was used for the comparison presented in the graphs of FIGS. 1-6, inclusive.
  • the pressure tester used to compile the data shown in FIGS. [-3, 5 and 6 is an accepted testing device comprising three balls which are maintained stationary and located 120 apart. A fourth ball is supported by the three stationary balls, all of them being of steel. In the test, the steel balls were of the composition of specification AISI-C52 100.
  • the ball supported by the other three was rotated with an initial load of about 20 kilograms.
  • the four-ball tester includes a cup within which the balls are located, and which is filled with the lubricant whose lubricity is to be tested.
  • Curve 10 was drawn from data acquired when the cup was filled with a poly(methyl-phenyl)siloxane containing no additive.
  • the four balls, or test specimens are one-half inch in diameter and the reference to wear scar diameter is the width of the brightened and worn circular area produced on the stationary ball. With initial loading (kg), this wear scar diameter had a width of 0.75 millimeters.
  • the four balls were then replaced and the load was increased to kilograms.
  • the wear scar diameter had increased to about 1.42 millimeters. At 75 kilograms load, the wear scar diameter had further increased to 2.15.
  • the initial scar diameter at 40 kilograms load had not increased beyond its magnitude at 20 kilograms (see curve 12). There was then the unexpected decrease in scar diameter to 75 kilograms load with a gradual rise in scar diameter until a loading of 240 kilograms was reached. At this heavy loading, the scar diameter was only 1.35 in contrast with the scar diameter for the silicone liquid without additive of 2.27 at kilograms of load, and as compared with a scar diameter of about 1.9 for the 1 percent of additive at a load of 220 kilograms.
  • Curve 13 shows the results obtained by the addition of 10 percent by weight of di-tertiary-nonyl polysulfide to the silicone employed.
  • the scar diameter was depressed throughout the loading with the final scar diameter at 240 kilograms about the same as that for the 5 percent addition.
  • curve 14 illustrates the relationship between load and wear scar diameter for a chlorinated silicone available on the market as Dow Corning 560.
  • the scar diameter rapidly increased to 1.65, at which time seizure occurred.
  • the addition of 10 percent of di-tertiarynonyl polysulfide completely changed the wear characteristics.
  • the initial scar diameter was less, and at a loading of 240 kilograms, it has increased to 1.25, the scar diameter without the additive having been attained as shown by curve 14, at about 55 kilograms load.
  • Table I sets forth the wear scar diameters (in millimeters) obtained from testing, at various load levels, poly(methyl-phenyl)siloxane alone, and in admixture with 5 percent by weight of various alkyl polysulfides corresponding to the formula in which R was an alkyl from four to 12 carbon atoms.
  • FIG. 3 shows a comparison of wear scar diameters attained at various loads in the test apparatus using silphenylene lubricant alone, and silphenylene lubricant including 10 percent by weight of di-tertiary-nonyl polysulfide.
  • FIG. 3 thus demonstrates that the silphenylene fluid afiords little wear resistance since the wear scar diameter rapidly increases from a value of just below 0.7 millimeters at 20 kilograms load to over 2.2 millimeters at 80 kilograms load.
  • the addition of 10 weight percent of di-tertiary-nonyl polysulfide extended the permissible load to 240 kilograms with a scar diameter of only 1.2 millimeters.
  • FIG. 4 illustrates the effect on lubricity of increased addition to the silicone lubricant of a sulfur-containing compound in accordance with the invention.
  • the Shell 4- Ball Wear Test was conducted.
  • FIG. 1 demonstrates that the addition of only one-half of 1 percent of the sulfur additive (di-tertiary-nonyl polysulfide) materially decreases the scar diameter.
  • the chart shown in FIG. 4 also demonstrates that the optimum amount of sulfur compound addition is at about 8 percent, based on the weight of the silicone liquid used.
  • FIG. 5 shows the results of tests made on a fluorosilicone lubricant alone, compared to the fluorosilicone lubricant containing percent by weight of the di-tertiary-nonyl polysultide. It will be observed that the fluorosilicone without the additive is useful as a lubricant up to about 130 kilograms load, at which point, any additional loading greatly increases the scar diameter. In contrast, the composition of the invention comprising the fluorosilicone including 10 weight percent of di-tertiary-nonyl polysulfide extends the usefulness of the lubricant to a loading in excess of 280 kilograms and with a scar diameter of only 1.25 millimeters.
  • FIG. 6 illustrates the unexpected results achieved by adding to the silicone lubricant 10 weight percent of a polysulfide comprising an alkyl derivative of 2,5-di-mercapto-1,3,4- thiadiazole.
  • the following table 11 sets forth the data obtained from an oscillator motion test conducted with an organic dye thickened p0ly(methyl-pheny1)siloxane with, and without, a sulfur compound additive (alkyl derivative of 2, S-di-mercapto-b 1, 3, 4Thiadiazole of the type disclosed in US Pat. No. 2,719,125).
  • Test Conditions A1514620 steel ring oscillation against a stationary A1S14l30 steel block. Grease Properties Penetration (worked 60 strokes) 297 Dropping point 450 F. Oscillations/Min. 87.5
  • the following table 111 sets forth the wear scar diameters (in mm.) obtained at various load levels using a poly(methylphenyl)silicone modified with 15 percent di-tertiary-nonyl polysulfide and with 25 percent of said polysulfide.
  • the Shell 4-Ball EP Tester was used.
  • Table IV below sets forth the wear scar diameters (in mm.) obtained at various load levels using (a) poly(methyl-phem yl)siloxane plus 10 percent by weight di-tertiarynonyl polysulfide, (b) poly(methyl-phenyl)siloxane siloxane plus 10 percent by weight of an alkyl derivative of 2,5-di-mercapto- 1,3 ,4-thiadiazole; and (c) poly(methyl-phenyl)siloxane plus 5 percent by weight of di-tertiary-nonyl polysulfide and 5 percent by weight of an alkyl derivative of 2,5-di-mercapto-l ,3,4- thiadiazole.
  • the Shell 4-Ball EP Tester was used.
  • the following table VI sets forth the values of wear scar diameters (in mm.) at various loads using, as a lubricant, (a) poly(methyl-phenyl)siloxane; (b) poly(methyl-phenyl)silox ane plus 10 percent by weight of di-2-ethyl hexyl sebacate (a well-known and widely used diestcr fluid); (c) poly(methylphenyl)siloxane with 9.5 weight percent di-Z-ethyl sebacate and 5 percent by weight of di-tertiary-nonyl polysulfide; and (d) 85.05 weight percent poly(methyl-phenyl)siloxane, 9.45 weight percent di-2-ethyl hexyl sebacate, 5 percent di-tertiarynonyl polysulfide and 0.5 percent phenyl alphanaphthylamine (a well-known antioxidant).
  • the Shell 4-Ball EP Tester was used.
  • a lubricant composition consisting essentially of a major proportion of an organic silicon-containing lubricant selected from the class consisting of organopolysiloxanes, organosilanes, silicate esters, silarylenes, and alkyl and aryl disilazanes, having dissolved therein a minor proportion, sufficient to improve the load-carrying properties of said organic silicon-containing lubricant, of a sulfur-containing compound selected from the group consisting of:
  • a a di-tertiary alkyl polysulfide wherein the alkyl group includes from four to 12 atoms;
  • a hydrocarbon polysulfide derivative of 2,5dimercaptol,3,4,-thiadiazo1e having the general formula wherein R and R are the same or different hydrocarbon radicals selected from the class consisting of alkyl, cycloalkyl, aryl, alkaryl, aralkyl, haloaryl, and cyanoalkyl radicals; and a and b are whole numbers from O to about 8, the sum of a and b are whole numbers from to about 8, the sum of a and b being at least 1.
  • the lubricant composition of claim I wherein the sulfurcontaining compound comprises a compound having the general formula H--S(C H -OCH -O-C H -S C H,0CH OC,H -S-H wherein x is 6 or 23.
  • the lubricant composition of claim 1 wherein the sulfurcontaining compound comprises a di-tertiary alkyl polysulfide wherein the alkyl group includes from four to 12 carbon atoms.

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  • General Chemical & Material Sciences (AREA)
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US783537A 1968-12-13 1968-12-13 Silicone lubricants Expired - Lifetime US3609079A (en)

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US78353768A 1968-12-13 1968-12-13
CA107,100A CA965403A (en) 1968-12-13 1971-03-08 Silicone lubricants
DE2113861A DE2113861C3 (de) 1968-12-13 1971-03-23 Silicon-Schmiermittel
FR7110934A FR2131827B1 (de) 1968-12-13 1971-03-29
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Cited By (9)

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US4059534A (en) * 1976-04-07 1977-11-22 Union Carbide Canada Limited Hydrocarbon/silicon oil lubricating compositions for low temperature use
US4310715A (en) * 1975-11-03 1982-01-12 Texaco, Inc. Steam dealkylation process
US4419254A (en) * 1980-05-09 1983-12-06 Toshiba Silicones Limited Method of protecting silver contacts
US4517103A (en) * 1983-04-18 1985-05-14 R. T. Vanderbilt Company, Inc. Lubricating compositions containing 5,5'-dithiobis(1,3,4-thiadiazole-2-thiol)
US4761482A (en) * 1987-04-23 1988-08-02 R. T. Vanderbilt Company, Inc. Terpene derivatives of 2,5-dimercapto-1,3,4-thiadiazoles and lubricating compositions containing same
US4795479A (en) * 1988-05-02 1989-01-03 R. T. Vanderbilt Company, Inc. Fuel compositions containing terpene derivatives of 2,5-dimercapto-1,3,4-thiadiazole
EP0636682A1 (de) * 1993-07-30 1995-02-01 Tonen Corporation Flüssige Zusammensetzung für Flüssigkeitsreibungskupplung
US5391621A (en) * 1993-10-15 1995-02-21 R. T. Vanderbilt Company, Inc. 1,3,4-thiadiazole curing systems for chlorine containing polymers
US20090084512A1 (en) * 2007-10-02 2009-04-02 Moffett Robert H Process to produce substrate resistant to alkaline starch

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US4140643A (en) * 1974-05-16 1979-02-20 The Lubrizol Corporation Nitrogen- and sulfur-containing lubricant additive compositions of improved compatibility
US4210544A (en) * 1976-08-18 1980-07-01 Texaco Inc. Dual purpose cutting oil composition
JPH0631389B2 (ja) * 1987-05-30 1994-04-27 コスモ石油株式会社 ビスカスカップリング用流体組成物
EP0397507B1 (de) * 1989-05-10 1995-03-15 Tonen Corporation Silikonflüssigkeiten für Visco-Kupplungen
EP0462777B1 (de) * 1990-06-18 1995-01-18 Tonen Corporation Hydraulik-, Schmier- und Kupplungsmittelzusammensetzung

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4310715A (en) * 1975-11-03 1982-01-12 Texaco, Inc. Steam dealkylation process
US4059534A (en) * 1976-04-07 1977-11-22 Union Carbide Canada Limited Hydrocarbon/silicon oil lubricating compositions for low temperature use
US4419254A (en) * 1980-05-09 1983-12-06 Toshiba Silicones Limited Method of protecting silver contacts
US4517103A (en) * 1983-04-18 1985-05-14 R. T. Vanderbilt Company, Inc. Lubricating compositions containing 5,5'-dithiobis(1,3,4-thiadiazole-2-thiol)
US4761482A (en) * 1987-04-23 1988-08-02 R. T. Vanderbilt Company, Inc. Terpene derivatives of 2,5-dimercapto-1,3,4-thiadiazoles and lubricating compositions containing same
US4795479A (en) * 1988-05-02 1989-01-03 R. T. Vanderbilt Company, Inc. Fuel compositions containing terpene derivatives of 2,5-dimercapto-1,3,4-thiadiazole
EP0636682A1 (de) * 1993-07-30 1995-02-01 Tonen Corporation Flüssige Zusammensetzung für Flüssigkeitsreibungskupplung
US5656577A (en) * 1993-07-30 1997-08-12 Tonen Corporation Fluid composition for fluid coupling
US5391621A (en) * 1993-10-15 1995-02-21 R. T. Vanderbilt Company, Inc. 1,3,4-thiadiazole curing systems for chlorine containing polymers
US20090084512A1 (en) * 2007-10-02 2009-04-02 Moffett Robert H Process to produce substrate resistant to alkaline starch

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GB1296163A (de) 1972-11-15
FR2131827A1 (de) 1972-11-17
CA965403A (en) 1975-04-01

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