EP0116460A2 - Friction modifier additive for power transmission shift fluids - Google Patents
Friction modifier additive for power transmission shift fluids Download PDFInfo
- Publication number
- EP0116460A2 EP0116460A2 EP84300788A EP84300788A EP0116460A2 EP 0116460 A2 EP0116460 A2 EP 0116460A2 EP 84300788 A EP84300788 A EP 84300788A EP 84300788 A EP84300788 A EP 84300788A EP 0116460 A2 EP0116460 A2 EP 0116460A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- additive
- composition
- power transmission
- fluids
- alkyl
- 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.)
- Granted
Links
- 0 *C*(C(C*=O)N)=O Chemical compound *C*(C(C*=O)N)=O 0.000 description 1
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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M135/26—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives 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
- 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
- C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Definitions
- This invention relates to power transmission shift fluids, such as automatic transmission fluids; which contain an additive effective in providing friction modification benefits.
- Mineral oil based power transmission shift fluids, or functional fluids, such as automatic transmission fluids are required to exhibit a number of properties such as antiwear, friction modification, oxidation inhibition, anticorrossion, demulsification and the like in order to qualify for commercial acceptance.
- Patent 4,129,510 issued December 12, 1978 to Smith', disclosed sulfur-containing additive derived from reacting a hydrocarbyl mercaptan having 1 to 5 SH groups with a C 3 to C 38 aldehyde or ketone to form an intermediate which is subsequently reacted with an olefinic carboxylic acid or functional derivative.
- the products are said to be useful as oxidation and rust inhibitors in lubricants and fuels.
- power transmission shift fluid compositions comprising a major amount of a mineral oil of lubricating viscosity and an oil-soluble alkylthio succinic anhydride or acid additive in an amount to provide effective friction modification, the additive being represented by the formulas: wherein R' is an alkyl of about 8 to 30 carbon atoms and R is a lower C l -C 4 alkyl or hydrogen. Preferred are those compounds where the total R' (R)CHCH 2 - group has about 16 to 20, such as 18, carbon atoms.
- a particularly preferred embodiment of the present invention is the addition product of octadecyl mercaptan with maleic anhydride.
- compositions of the present invention may contain the additive generally within the range of about 0.01 to 1 wt% to provide the effective friction properties.
- the power transmission shift fluids will contain about 0.1 to 0.5 wt% of the additive of the present invention.
- Octadecyl thiosuccinic acid or anhydride are preferred additives of this invention.
- the additive of the present invention will function. as a friction modifier in other power transmission shift fluids based on mineral oils such as hydraulic fluids, power brake and power steering fluids, heavy duty equipment fluids and the like.
- Friction modification is one of the most demanding properties to effectively provide in an automatic transmission fluid and is considered the characteristic which distinguishes ATF compositions from other categories of lubricants. Very specific frictional properties related to transmission parts operation must be met in order to have an acceptable fluid.
- the additive of the present invention is highly advantageous in that it satisfies at low treat levels the significant friction modification tests, and is efficiently prepared at relatively lower costs thereby. providing a more effective and economical automatic trans-' mission fluid.
- the properties evaluated in ATF tests and specifications are generally applicable to other power shift transmission fluids.
- ATF compositions contain a number of conventional additives in amounts providing their normal attendant functions and are typically blended into the mineral oil base in the following ranges:
- Typical base oils for automatic transmission fluids and power transmission shift fluids generally include a wide variety of light hydrocarbon mineral oils, such as naphthenic base, paraffin base and mixtures thereof, having a lubricating viscosity range of about 34 to 45 SUS (Saybolt Universal Seconds) at 38°C.
- ATF compositions used in the examples below were formulated in accordance with the components and concentrations noted above (referred to as Base Fluid) except the friction modifier was the compound of this invention used in the amounts reported below.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Abstract
Description
- This invention relates to power transmission shift fluids, such as automatic transmission fluids; which contain an additive effective in providing friction modification benefits.
- Mineral oil based power transmission shift fluids, or functional fluids, such as automatic transmission fluids are required to exhibit a number of properties such as antiwear, friction modification, oxidation inhibition, anticorrossion, demulsification and the like in order to qualify for commercial acceptance.
- Prior art references pertinent to this invention include U.S. Patent 3,852,205, issued December 3, 1974 to Kablaoui et al.,which discloses automatic transmission fluid containing either S-carboxy alkylene hydrocarbyl succinimide or hydrocarbylsuccinamic acid. These are prepared in a two-stage process comprising reacting maleic anhydride with a primary amine in a 1: 1 mole ratio. The amine and imide product so formed is then contacted with a thiocarboxylic acid to form the desired additive. U.S. Patent 4,129,510, issued December 12, 1978 to Smith', disclosed sulfur-containing additive derived from reacting a hydrocarbyl mercaptan having 1 to 5 SH groups with a C3 to C38 aldehyde or ketone to form an intermediate which is subsequently reacted with an olefinic carboxylic acid or functional derivative. The products are said to be useful as oxidation and rust inhibitors in lubricants and fuels.
- In accordance with the present invention there have been discovered power transmission shift fluid compositions comprising a major amount of a mineral oil of lubricating viscosity and an oil-soluble alkylthio succinic anhydride or acid additive in an amount to provide effective friction modification, the additive being represented by the formulas:
- A particularly preferred embodiment of the present invention is the addition product of octadecyl mercaptan with maleic anhydride. Compounds of the invention may also be prepared by addition of mercapto diacids to terminal olefins, e.g., R'(R)C=CH2.
- The compositions of the present invention may contain the additive generally within the range of about 0.01 to 1 wt% to provide the effective friction properties. Preferably, the power transmission shift fluids will contain about 0.1 to 0.5 wt% of the additive of the present invention. Octadecyl thiosuccinic acid or anhydride are preferred additives of this invention.
- In addition to use in automatic transmission fluids the additive of the present invention will function. as a friction modifier in other power transmission shift fluids based on mineral oils such as hydraulic fluids, power brake and power steering fluids, heavy duty equipment fluids and the like.
- Friction modification is one of the most demanding properties to effectively provide in an automatic transmission fluid and is considered the characteristic which distinguishes ATF compositions from other categories of lubricants. Very specific frictional properties related to transmission parts operation must be met in order to have an acceptable fluid. The additive of the present invention is highly advantageous in that it satisfies at low treat levels the significant friction modification tests, and is efficiently prepared at relatively lower costs thereby. providing a more effective and economical automatic trans-' mission fluid. The properties evaluated in ATF tests and specifications are generally applicable to other power shift transmission fluids.
- Automatic transmission fluids containing the additive of the present invention are the preferred embodiment. Such ATF compositions contain a number of conventional additives in amounts providing their normal attendant functions and are typically blended into the mineral oil base in the following ranges:
- Typical base oils for automatic transmission fluids and power transmission shift fluids generally include a wide variety of light hydrocarbon mineral oils, such as naphthenic base, paraffin base and mixtures thereof, having a lubricating viscosity range of about 34 to 45 SUS (Saybolt Universal Seconds) at 38°C.
- The invention is further illustrated by the following examples which are not to be considered as limitative of its scope. ATF compositions used in the examples below were formulated in accordance with the components and concentrations noted above (referred to as Base Fluid) except the friction modifier was the compound of this invention used in the amounts reported below.
- About 100g (0.35 moles) of octadecyl mercaptan were dissolved in 100 ml of tetrahydrofuran (THF). Then, about 34.2g (0.35 moles) of maleic anhydride were added, followed by the addition of 1 ml of triethylamine as catalyst. The reaction mixture was heated to reflux for about one hour. At the end of the hour, the THF solution was poured into a large volume of pentane and a white solid precipitated out of solution. The white solid was filtered, and dried in vacuo until constant weight. The infrared spectrum of the solid revealed no unreacted maleic anhydride present. It analyzed for 68.85% C, 10.52% H and 8.77% S which is consistent with the desired alkylthio succinic anhydride that required 68.70% C, 10.48% H and 8.34% S.
- About 30g (0.2 mole) of mercapto-succinic acid were dissolved in 200 ml of methanol and cooled to about 15°C. Thereafter, 56g (0.2 mole, 90%) of I-octadecene were added, followed by the addition of 1.5g of Lucidol 70 radical initiator (Benzoyl peroxide, 70%). The reaction mixture was rapidly stirred for about two hours, while some crystalline white solid formed. The reaction temperature rose to 30°C during the first half hour and then about 25°C for the rest of the reaction time. The white solid was filtered and collected. The infared spectrum of the solid is consistent with the desired 2-(octadecylthio) succinic acid. The solid analyzed for 66.77% C, 1045% H, and 8.10% S. Theory requires 65.67% C, 10.52% H and 7.97% S.
- To a formulated automatic transmission fluid (Base Fluid) was added 0.25 wt% of the octadecylthio succinic anhydride of Example 1 and the fluid was evaluated for its friction properties in the Davison Friction Test utilizing the SAE No.2 Friction Machine; dynamic and static torque values were within the test specification of General Motor Dexron® II Automatic Transmission Fluid (GM specification G137-M, July, 1980). Torque values were measured at 3 phases: (1) 16,500 lb-ft, 1 sec. lock-up, (2) 7200 lb-ft, 40 lb. pressure and (3) 16,500 lb ft, 60 lb pressure. Phase 1 friction torque tracings showed results of 102, 91 and 84; phase 2 showed 101, 97 and 88 and phase 3 showed 138, 130 and 123 ft-lbs.
Claims (6)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US46495083A | 1983-02-08 | 1983-02-08 | |
US464950 | 1983-02-08 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0116460A2 true EP0116460A2 (en) | 1984-08-22 |
EP0116460A3 EP0116460A3 (en) | 1985-05-22 |
EP0116460B1 EP0116460B1 (en) | 1987-08-12 |
Family
ID=23845920
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP84300788A Expired EP0116460B1 (en) | 1983-02-08 | 1984-02-08 | Friction modifier additive for power transmission shift fluids |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0116460B1 (en) |
CA (1) | CA1208197A (en) |
DE (1) | DE3465332D1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2599045A1 (en) * | 1986-05-26 | 1987-11-27 | Elf France | Additives with an anticorrosion effect for aqueous fluids and compositions containing the said additives |
US5582760A (en) * | 1995-12-22 | 1996-12-10 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and alkylthiosuccinic acid |
US5585029A (en) * | 1995-12-22 | 1996-12-17 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and 2-alkylthio-1,3,4-thiadiazole-5-alkanoic acid |
EP0926224A2 (en) * | 1997-12-25 | 1999-06-30 | Tonen Corporation | Lubricating oil composition |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2371142A (en) * | 1945-03-13 | Anticoerosive | ||
US2496798A (en) * | 1946-05-14 | 1950-02-07 | Texas Co | Rust-inhibiting lubricating composition |
-
1984
- 1984-02-07 CA CA000446925A patent/CA1208197A/en not_active Expired
- 1984-02-08 DE DE8484300788T patent/DE3465332D1/en not_active Expired
- 1984-02-08 EP EP84300788A patent/EP0116460B1/en not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2371142A (en) * | 1945-03-13 | Anticoerosive | ||
US2496798A (en) * | 1946-05-14 | 1950-02-07 | Texas Co | Rust-inhibiting lubricating composition |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2599045A1 (en) * | 1986-05-26 | 1987-11-27 | Elf France | Additives with an anticorrosion effect for aqueous fluids and compositions containing the said additives |
US5582760A (en) * | 1995-12-22 | 1996-12-10 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and alkylthiosuccinic acid |
US5585029A (en) * | 1995-12-22 | 1996-12-17 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and 2-alkylthio-1,3,4-thiadiazole-5-alkanoic acid |
EP0926224A2 (en) * | 1997-12-25 | 1999-06-30 | Tonen Corporation | Lubricating oil composition |
EP0926224A3 (en) * | 1997-12-25 | 2000-06-28 | Tonen Corporation | Lubricating oil composition |
Also Published As
Publication number | Publication date |
---|---|
EP0116460A3 (en) | 1985-05-22 |
EP0116460B1 (en) | 1987-08-12 |
DE3465332D1 (en) | 1987-09-17 |
CA1208197A (en) | 1986-07-22 |
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