US3671433A - Lubricant compositions - Google Patents
Lubricant compositions Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- lubricant
- carbon atoms
- sio
- formula
- fluid
- 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
Links
Classifications
-
- 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
- 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
- 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
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
-
- 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
- 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
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/22—Acids obtained from polymerised unsaturated acids
-
- 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
-
- 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
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
-
- 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
- C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
-
- 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
- C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
-
- 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
- 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;
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
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 |
Family
ID=22273946
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)
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)
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)
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 |
-
1970
- 1970-12-17 US US99255A patent/US3671433A/en not_active Expired - Lifetime
-
1971
- 1971-09-22 CA CA123,428A patent/CA990267A/en not_active Expired
- 1971-11-04 GB GB5127371A patent/GB1325394A/en not_active Expired
- 1971-11-10 JP JP8974671A patent/JPS5319739B1/ja active Pending
- 1971-12-15 DE DE2162273A patent/DE2162273C3/de not_active Expired
- 1971-12-16 FR FR7145318A patent/FR2118136B1/fr not_active Expired
- 1971-12-16 BE BE776795A patent/BE776795A/xx not_active IP Right Cessation
Patent Citations (5)
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)
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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