US3671433A - Lubricant compositions - Google Patents

Lubricant compositions Download PDF

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Publication number
US3671433A
US3671433A US99255A US3671433DA US3671433A US 3671433 A US3671433 A US 3671433A US 99255 A US99255 A US 99255A US 3671433D A US3671433D A US 3671433DA US 3671433 A US3671433 A US 3671433A
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United States
Prior art keywords
lubricant
carbon atoms
sio
formula
fluid
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Expired - Lifetime
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US99255A
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English (en)
Inventor
Bruce C Brenner
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Dow Silicones Corp
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Dow Corning Corp
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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M3/00Liquid 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/22Acids obtained from polymerised unsaturated acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00Organic 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
    • C10M2229/04Siloxanes with specific structure
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00Organic 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
    • C10M2229/04Siloxanes with specific structure
    • C10M2229/041Siloxanes with specific structure containing aliphatic substituents
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00Organic 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
    • C10M2229/04Siloxanes with specific structure
    • C10M2229/043Siloxanes with specific structure containing carbon-to-carbon double bonds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00Organic 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
    • C10M2229/04Siloxanes with specific structure
    • C10M2229/044Siloxanes with specific structure containing silicon-to-hydrogen bonds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01Physico-chemical properties

Definitions

  • Hermann ABSTRACT The lubrication characteristics of alkylmethylpolysiloxanes in which the alkyl radical contains from six1 8 carbon atoms are improved by the addition of from about 0.1 to 3 weight percent dodecenyl succinic acid anhydride.
  • This invention relates to an improved lubricant composition.
  • the invention relates to the use of dodecenyl succinic acid anhydride as a lubricant additive in certain diorganopolysiloxane fluids.
  • a lubricant composition consisting essentially of (a) 97 to 99.9.percent by weight of a fluid organopolysiloxane having a viscosity of from 5 to 500 c.s. (centistokes) as measured at 77 F.
  • alkyl radicals of from one to 18 inclusive carbon atoms the phenyl radical and alkaryl radicals of no more than carbon atoms, at least one R radical being a methyl radical
  • R is an alkyl radical containing from six to 18 inclusive carbon atoms and n has a value of from 1 to 20 inclusive and (b) 0.1 to 3 percent by weight of dodecenyl succinic acid anhydride.
  • the R substituents can be an alkyl radical, such as methyl, ethyl, hexyl, octyl, dodecyl or octadecyl radical; the phenyl radical, or an alkaryl radical of no more than 10 carbon atoms such as the phenylethyl or 2-phenylpropyl radical.
  • the R substituents form the endblocking groups of the polymeric chain, and it is required that at least one R substituent on each of the terminal silicon atoms be'a methyl group.
  • the preferred organosiloxanes are those which are trimethylsilyl-endblocked; i.e., where all of the R radicals are methyl radicals.
  • the R substituents are alkyl radicals including both straightand branched-chain radicals, such as hexyl, octyl, 2- ethylhexyl, decyl, dodecyl, heptadecyl, octadecyl and the like.
  • the octyl and decyl radicals are preferred for fluid applications requiring relatively low viscosity such as hydraulic fluids.
  • the polymeric chain length as defined by the value of n, also has an effect on the viscosity of the fluid.
  • n For low viscosity fluid applications, it is preferred that n have a value of from 2 to 10 while in other lubrication applications higher viscosity fluid, such as obtained when n has a value from 16 to 18, is preferred.
  • the fluid is required to have a viscosity with a range of from 5 to 500 c.s. in order that the enhancement of lubrication properties be observed.
  • organosiloxanes are readily prepared by the reaction of one or more olefinic hydrocarbons with Si- H functional organopolysiloxanes.
  • the olefinic hydrocarbons are specifically alpha-olefins of the fonnula CH CHR"in which R is an alkyl radical of from four to 16 carbon atoms.
  • the organopolysiloxane reactant can be described as having the formula Sim in which R and n are as previously defined.
  • the reaction between the alpha-olefin and the methylhydrogenpolysiloxane can be carried out in the presence of a conventional Sil'l-olefin addition catalyst such as the chloroplatinic acid catalyst described in U.S. Pat. No. 2,823,2 l 8.
  • a conventional Sil'l-olefin addition catalyst such as the chloroplatinic acid catalyst described in U.S. Pat. No. 2,823,2 l 8.
  • Mixed olefins and mixed methylhydrogensiloxanes can be used in the reaction.
  • the fluid may be a homopolymer wherein n varies or it can be a copolymer wherein the R substituents are different.
  • Exemplary of the fluids utilized in the practice of the invention are and
  • the lubricant additive, dodecenyl succinic acid anhydride is mixed with the alkylmethylpolysilox'ane in an amount sufficient to provide at least about 0.1 weight percent of the additive in the lubricant composition.
  • Additive amounts greater than 3 weight percent can be utilized in the. practice of the invention, but as a practical matter, the compositions containing these higher amounts of additive do not show proportionate increase in lubricity.
  • the dodecenyl succinic acid anhydride is uniquein improving the steel on steel lubricity of the defined alkylmethylpolysiloxanes.
  • EXAMPLE 2 Alkylmethylpolysiloxanes were prepared by the method described in Example 1. Fluid A was of the formula (CH- SiO- ⁇ -C,.H, (CH )SiO-]- ,Si(CH:,) and had a viscosity of l6 c.s. as measured at 77 F. Fluid B was of the formula (CH SiO-i-C l-l (CH )SiO+ Si(C]-l and had a viscosity of c.s. as measured at 77 F. Varying amounts of dodecenyl succinic acid anhydride were added to the fluids. The lubrication properties of the additive-fluid mixtures were determined by the Shell four-Ball method.
  • R is selected from the group consisting of alkyl radicals containing from one to 18 inclusive carbon atoms. the phenyl radical and alkaryl radicals of no more than 10 carbon atoms, at least one R radical being a methyl radical;
  • R is an alkyl radical containing from six to 18 inclusive carbon atoms and n has a value of from 1 to 20 inclusive;
  • n has a value of from 1 to 10.
  • the lubricant of claim 3 wherein the R substituent is an alkyl radical containing from six to 10 inclusive carbon atoms.
  • the fluid organopolysiloxane is of the formula (CH SiO ⁇ -C H (Cl-l )SiO- ⁇ -,,Si(CH 6.
  • a method of transmitting power comprising applying pressure to a composition consisting essentially of a. 97 to 99.9 weight percent of an alkylmethylpolysiloxane having a viscosity of from 5 to 100 0.5. as measured at 77 F said polysiloxane being of the formula nasiols'io in which r CIL'gRugSlO SiO SiR-gClI;

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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)
US99255A 1970-12-17 1970-12-17 Lubricant compositions Expired - Lifetime US3671433A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US9925570A 1970-12-17 1970-12-17

Publications (1)

Publication Number Publication Date
US3671433A true US3671433A (en) 1972-06-20

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Family Applications (1)

Application Number Title Priority Date Filing Date
US99255A Expired - Lifetime US3671433A (en) 1970-12-17 1970-12-17 Lubricant compositions

Country Status (7)

Country Link
US (1) US3671433A (de)
JP (1) JPS5319739B1 (de)
BE (1) BE776795A (de)
CA (1) CA990267A (de)
DE (1) DE2162273C3 (de)
FR (1) FR2118136B1 (de)
GB (1) GB1325394A (de)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3919097A (en) * 1974-09-06 1975-11-11 Union Carbide Corp Lubricant composition
US4005023A (en) * 1973-06-11 1977-01-25 General Electric Company Silicone fluid useful as a brake fluid
US4564467A (en) * 1982-12-31 1986-01-14 Exxon Research And Engineering Co. Oil composition
US4640792A (en) * 1985-11-25 1987-02-03 Dow Corning Corporation Silicone brake fluid having reduced air solubility
EP0245046A2 (de) * 1986-05-05 1987-11-11 Dow Corning Corporation Methylalkylcyclosiloxane
US20070166264A1 (en) * 2004-02-17 2007-07-19 Dow Corning Toray Company, Ltd. Method of manufacturing purified products of liquid medium-chain alkyl-modified polydimethysiloxane and cosmetics prepared therefrom

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4075115A (en) * 1972-09-18 1978-02-21 General Electric Company Silicone fluid useful as a brake fluid
US4048084A (en) * 1975-09-24 1977-09-13 Olin Corporation Functional fluid systems containing alkoxysilane cluster compounds
US4137189A (en) * 1977-01-19 1979-01-30 Dow Corning Corporation Three component common hydraulic fluid comprising a non-linear siloxane fluid
DE3039736C2 (de) * 1980-10-21 1986-06-12 Wacker-Chemie GmbH, 8000 München Verwendung von Organopolysiloxan als Bremsflüssigkeit bzw. Bestandteil von Bremsflüssigkeiten

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2133734A (en) * 1936-07-24 1938-10-18 Shell Dev Noncorrosive lubricating oil
US2471850A (en) * 1946-09-25 1949-05-31 Gen Electric Liquid polysiloxane lubricants
US2823218A (en) * 1955-12-05 1958-02-11 Dow Corning Process for the production of organo-silicon compounds
US2970150A (en) * 1957-12-17 1961-01-31 Union Carbide Corp Processes for the reaction of silanic hydrogen-bonded siloxanes with unsaturated organic compounds with a platinum catalyst
US3291736A (en) * 1964-11-20 1966-12-13 Mobil Oil Corp Grease compositions containing alkyl succinic partial esters

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2133734A (en) * 1936-07-24 1938-10-18 Shell Dev Noncorrosive lubricating oil
US2471850A (en) * 1946-09-25 1949-05-31 Gen Electric Liquid polysiloxane lubricants
US2823218A (en) * 1955-12-05 1958-02-11 Dow Corning Process for the production of organo-silicon compounds
US2970150A (en) * 1957-12-17 1961-01-31 Union Carbide Corp Processes for the reaction of silanic hydrogen-bonded siloxanes with unsaturated organic compounds with a platinum catalyst
US3291736A (en) * 1964-11-20 1966-12-13 Mobil Oil Corp Grease compositions containing alkyl succinic partial esters

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4005023A (en) * 1973-06-11 1977-01-25 General Electric Company Silicone fluid useful as a brake fluid
US3919097A (en) * 1974-09-06 1975-11-11 Union Carbide Corp Lubricant composition
US4564467A (en) * 1982-12-31 1986-01-14 Exxon Research And Engineering Co. Oil composition
US4640792A (en) * 1985-11-25 1987-02-03 Dow Corning Corporation Silicone brake fluid having reduced air solubility
EP0225071A2 (de) * 1985-11-25 1987-06-10 Dow Corning Corporation Silikon-Hydraulikflüssigkeit mit reduzierter Löslichkeit in Luft
EP0225071A3 (en) * 1985-11-25 1987-10-21 Dow Corning Corporation Silicone hydraulic fluid having reduced air solubility
EP0245046A2 (de) * 1986-05-05 1987-11-11 Dow Corning Corporation Methylalkylcyclosiloxane
US4719024A (en) * 1986-05-05 1988-01-12 Dow Corning Corporation Methylalkylcyclosiloxanes
EP0245046A3 (en) * 1986-05-05 1988-04-20 Dow Corning Corporation Methylalkylcyclosiloxanes
US20070166264A1 (en) * 2004-02-17 2007-07-19 Dow Corning Toray Company, Ltd. Method of manufacturing purified products of liquid medium-chain alkyl-modified polydimethysiloxane and cosmetics prepared therefrom
US7943720B2 (en) * 2004-02-17 2011-05-17 Dow Corning Toray Company, Ltd. Method of manufacturing purified products of liquid medium-chain alkyl-modified polydimethysiloxane and cosmetics prepared therefrom

Also Published As

Publication number Publication date
DE2162273B2 (de) 1973-10-25
DE2162273A1 (de) 1972-07-06
DE2162273C3 (de) 1974-06-12
CA990267A (en) 1976-06-01
FR2118136B1 (de) 1975-08-29
GB1325394A (en) 1973-08-01
BE776795A (fr) 1972-06-16
FR2118136A1 (de) 1972-07-28
JPS5319739B1 (de) 1978-06-22

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