CA1208197A - Friction modifier additive for power transmission shift fluids - Google Patents
Friction modifier additive for power transmission shift fluidsInfo
- Publication number
- CA1208197A CA1208197A CA000446925A CA446925A CA1208197A CA 1208197 A CA1208197 A CA 1208197A CA 000446925 A CA000446925 A CA 000446925A CA 446925 A CA446925 A CA 446925A CA 1208197 A CA1208197 A CA 1208197A
- Authority
- CA
- Canada
- Prior art keywords
- additive
- composition
- power transmission
- fluids
- transmission shift
- 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
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
- 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
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
ABSTRACT OF THE DISCLOSURE
There are disclosed power shift transmission fluids such as automatic transmission fluids containing a friction modifier additive being an oil soluble alkylthio succinic anhydride or acid, such as octadecyl thiosuccinic acid or anhydride.
There are disclosed power shift transmission fluids such as automatic transmission fluids containing a friction modifier additive being an oil soluble alkylthio succinic anhydride or acid, such as octadecyl thiosuccinic acid or anhydride.
Description
~z~
1 This invention relates to power transmission
1 This invention relates to power transmission
2 shift ~luids, such as automatic transmission fluids, which
3 contain an aaditive effective in providing friction modi-
4 fication benefits.
Mineral oil based power transmission shift 6 fluids, or functional fluids, such as automatic transmis-7 sion fluids are required to exhibit a number o properties 8 such as antiwear, friction modification, oxidation inhibi-9 tion, anticorrossion, demulsification and the like in order to qualify for commercial acceptance.
11 Prior art references pertinent to this invention 12 include U.S. Patent 3,852,205,issued December 3, 1974 to 13 Kablaoui et al., which discloses automatic transmission 14 fluid containing either S-carboxy alkylene hydrocarbyl suc-cinimide or hydrocarbylsuccinamic acid. These are prepared 16 in a two-stage process comprising reacting maleic anhydride 17 with a primary amine in a 1:1 mole ratio. The amine and imide 18 product so formed is then contacted with a thiocarboxylic 19 acid to form the desired additive. U.S. Patent 4,129,510, issued December 12, 1978 to Smith, disclosed sul~ur-contain-21 ing additive derived from reacting a hydrocarbyl mercaptan 22 having 1 to 5 SH groups with a C3 to C3g aldehyde or ketone 23 to form an intermediate which is subsequently reacted with 24 an olefinic carboxylic acid or functional derivative. The products are said to be useful as oxidation and rust in-26 hibitors in lubricants and fuels.
27 In accordance with the present invention there 23 have been discovered power transmission shift fluid com-29 positions comprising a major amount of a mineral oil of lubricating viscosity and an oil-soluble alkylthio succinic 31 anhydride or acid additive in an amount to provi~e effective 32 fricti.on modification, the additive being represented by 33 the formulas:
~9 .. . .
~LZ~ 7 2R1 11 R1` 11 3\CHCH25 ~ \ R/2 ~C
C ~OH
Il . Il 7 wherein R' is an alkyl of about 8 to 30 carbon atoms and R
8 is a lower Cl-C4 alkyl or hydrogen. Preferred are those ~ compounds where the total R'(R)CHCH2- group has about 16 to 20, such as 18, carbon atoms.
11 A particularly preferred embodiment of the pre-12 sent invention is the addition product of octadecyl mer-13 captan with maleic anhydride. Compounds of the invention 14 may also be prepared by addition of mercapto diacids to terminal olefins, e.g., R'(R)C=CH2.
16 The compositions of the present invention may 17 contain the additive generally within the range of about 18 0.01 to 1 wt% to provide the effective friction properties.
19 Preferably, the power transmission shift fluids will con-tain about 0.1 to 0. 5 wt~ of the additive of the present ~1 invention. Octadecyl thiosuccinic acid or anhydride are 22 preferred additives of this invention.
23 In addition to use in automatic transmission 2~1 fluids the additive of the present invention will function as a friction modifier in other power transmission shift 26 fluids based on mineral oils such as hydraulic fluids, power 2/ brake and power steering fluids, heavy duty equipment fluids 29 and the like.
2~ Friction modification is one of the most demanding 30 properties to effectively provide in an automatic trans-;; mission fluid and is considered the characteristic which 32 distinguishes ~TF compositions from other categories of ~ ,.. .
~2~97 1 lubricants. Very specific frictional properties related to 2 transmission parts operation must be met in order to have an 3 acceptable fluid. The additive of the present invention is 4 highly advantageous in that it satisfies at low treat levels the significant friction modification tests, and is ef-6 ficiently prepared at relatively lower costs thereby 7 providing a ~ore effective and economical automatic trans-8 mission fluid. The properties evaluated in ATF tests and 9 specifications are generally applicable to other power shift transmission fluids.
11 Automatic transmission fluids containing the 12 additive of the present invention are the preferred embodi-13 ment. Such ATF compositions contain a number of conven-14 tional additives in amounts providing their normal attendant functions and are typically blended into the mineral oil 1~ base in the following ranges:
17 Components Concentration Range (Vol. %) 18 V.I. Improver 1 _ 15 19 Corrosion Inhibitor 0.01 Oxidation Inhibitor 0.01 - 1 21 Dispersant 0.5 _ 10 22 Pour Point Depressant 0.01 23 Demulsifier 0.001 - 0.1 24 Anti-Foaming Agents 0.001 - 0.1 Anti-Wear Agents 0.001 - 1 26 Seal S~ellant 0.1 - 5 27 Friction Modifier 0.01 28 Mineral Oil Base Balance 29 Typical base oils for automatic transmission 30 fluids and power transmission shift fluids generally 31 include a wide variety of light hydrocarhon mineral oils, 32 such as naphthenic base, paraffin base and mixtures 33 thereof, having a lubricating viscosit~ range of about 34 - 34 to 45 SUS (Saybolt Universal Seconds) at 38C.
The invention is further illustrated by the 36 following examples which are not to be considered as ~IL2~9~
1 limitative of its scope. ATF compositions used in the 2 examples below were formulated in accordance with the components 3 and concentrations noted above (referred to as Base Fluid) 4 except the friction modifier was the compound of this invention used in the amounts reported below.
6 EXAMPLE l 7 About lOOg (0.35 moles) of octadecyl mercaptan 8 were dissolved in 100 ml of tetrahydrofuran (THF). Then, 9 about 34.2g (0.35 moles) of maleic anhydride were added, followed by the addition of 1 ml of triethylamine 11 as catalyst. The reaction mixture was heated to reflux for 12 about one hour. At the end of the hour, the THF solution was 13 poured into a large volume of pentane and a white solid 14 precipitated out of solution. The ~hite solid was filtered, and dried in vacuo until constant weight. The infrared 16 spectrum of the solid revealed no unreacted maleic anhydride 17 present. It analyzed for 68.85% C, 10.52% H and 8.77% S
18 which is consistent with the desired alkylthio succinic 19 anhydride that required 68.70% C, 10.48% H and 8.34% S.
21 About 30g (0.2 mole) of mercapto-succinic acid 22 were dissolved in 200 ml of methanol and cooled to about 23 15C. Thereafter, 56g (0.2 mole, 90%) of l-octadecene were 24 added, followed by the addition of 1.5g of Lucidol 70 radical initiator (Benzoyl peroxide, 70%). The reaction mixture was 26 rapidly stirred for about two hours, while some crystalline 27 white solid formed. The reaction temperature rose to 30C
28 during the first half hour and then about 25C for the rest 29 of the reaction time. The white solid was filtered and 30 collected. The infared spectrum of the solid is consistent 31 with the desired 2-(octadecylthio) succinic acid. The solid 32 analyzed for 66.776 C, 1045% H, and 8.10% S. I~heory requires 33 65.67% C, 10.526 H and 7.97% S.
34 Example 3 To a formulated automatic transmission fluid (Base ~z~
1 Fluid) was added 0.25 wt~ of the octadecylthio succinic 2 anhydride of Example 1 and the fluid was evaluated for its 3 friction properties in the Davison Friction Test utilizing 4 the SAE No.2 Friction Machine; dynamic and static torque values were within the test specification of General Motor 6 Dexron3 II Automatic Transmission Fluid (GM specification 7 G137-~, July, 1980). ~orque values were measured at 3 8 phases: (1) 16,500 lb-ft, 1 sec. lock-up, (2) 7200 lb-ft, 40 9 lb. pressure and (3) 16,500 lb ft, 60 lb pressure. Phase 1 10 friction torque tracings showed results of 102, 91 and 84;
11 phase 2 showed 101, 97 and 88 and phase 3 showed 138, 130 and 12 123 ft-lbs.
Mineral oil based power transmission shift 6 fluids, or functional fluids, such as automatic transmis-7 sion fluids are required to exhibit a number o properties 8 such as antiwear, friction modification, oxidation inhibi-9 tion, anticorrossion, demulsification and the like in order to qualify for commercial acceptance.
11 Prior art references pertinent to this invention 12 include U.S. Patent 3,852,205,issued December 3, 1974 to 13 Kablaoui et al., which discloses automatic transmission 14 fluid containing either S-carboxy alkylene hydrocarbyl suc-cinimide or hydrocarbylsuccinamic acid. These are prepared 16 in a two-stage process comprising reacting maleic anhydride 17 with a primary amine in a 1:1 mole ratio. The amine and imide 18 product so formed is then contacted with a thiocarboxylic 19 acid to form the desired additive. U.S. Patent 4,129,510, issued December 12, 1978 to Smith, disclosed sul~ur-contain-21 ing additive derived from reacting a hydrocarbyl mercaptan 22 having 1 to 5 SH groups with a C3 to C3g aldehyde or ketone 23 to form an intermediate which is subsequently reacted with 24 an olefinic carboxylic acid or functional derivative. The products are said to be useful as oxidation and rust in-26 hibitors in lubricants and fuels.
27 In accordance with the present invention there 23 have been discovered power transmission shift fluid com-29 positions comprising a major amount of a mineral oil of lubricating viscosity and an oil-soluble alkylthio succinic 31 anhydride or acid additive in an amount to provi~e effective 32 fricti.on modification, the additive being represented by 33 the formulas:
~9 .. . .
~LZ~ 7 2R1 11 R1` 11 3\CHCH25 ~ \ R/2 ~C
C ~OH
Il . Il 7 wherein R' is an alkyl of about 8 to 30 carbon atoms and R
8 is a lower Cl-C4 alkyl or hydrogen. Preferred are those ~ compounds where the total R'(R)CHCH2- group has about 16 to 20, such as 18, carbon atoms.
11 A particularly preferred embodiment of the pre-12 sent invention is the addition product of octadecyl mer-13 captan with maleic anhydride. Compounds of the invention 14 may also be prepared by addition of mercapto diacids to terminal olefins, e.g., R'(R)C=CH2.
16 The compositions of the present invention may 17 contain the additive generally within the range of about 18 0.01 to 1 wt% to provide the effective friction properties.
19 Preferably, the power transmission shift fluids will con-tain about 0.1 to 0. 5 wt~ of the additive of the present ~1 invention. Octadecyl thiosuccinic acid or anhydride are 22 preferred additives of this invention.
23 In addition to use in automatic transmission 2~1 fluids the additive of the present invention will function as a friction modifier in other power transmission shift 26 fluids based on mineral oils such as hydraulic fluids, power 2/ brake and power steering fluids, heavy duty equipment fluids 29 and the like.
2~ Friction modification is one of the most demanding 30 properties to effectively provide in an automatic trans-;; mission fluid and is considered the characteristic which 32 distinguishes ~TF compositions from other categories of ~ ,.. .
~2~97 1 lubricants. Very specific frictional properties related to 2 transmission parts operation must be met in order to have an 3 acceptable fluid. The additive of the present invention is 4 highly advantageous in that it satisfies at low treat levels the significant friction modification tests, and is ef-6 ficiently prepared at relatively lower costs thereby 7 providing a ~ore effective and economical automatic trans-8 mission fluid. The properties evaluated in ATF tests and 9 specifications are generally applicable to other power shift transmission fluids.
11 Automatic transmission fluids containing the 12 additive of the present invention are the preferred embodi-13 ment. Such ATF compositions contain a number of conven-14 tional additives in amounts providing their normal attendant functions and are typically blended into the mineral oil 1~ base in the following ranges:
17 Components Concentration Range (Vol. %) 18 V.I. Improver 1 _ 15 19 Corrosion Inhibitor 0.01 Oxidation Inhibitor 0.01 - 1 21 Dispersant 0.5 _ 10 22 Pour Point Depressant 0.01 23 Demulsifier 0.001 - 0.1 24 Anti-Foaming Agents 0.001 - 0.1 Anti-Wear Agents 0.001 - 1 26 Seal S~ellant 0.1 - 5 27 Friction Modifier 0.01 28 Mineral Oil Base Balance 29 Typical base oils for automatic transmission 30 fluids and power transmission shift fluids generally 31 include a wide variety of light hydrocarhon mineral oils, 32 such as naphthenic base, paraffin base and mixtures 33 thereof, having a lubricating viscosit~ range of about 34 - 34 to 45 SUS (Saybolt Universal Seconds) at 38C.
The invention is further illustrated by the 36 following examples which are not to be considered as ~IL2~9~
1 limitative of its scope. ATF compositions used in the 2 examples below were formulated in accordance with the components 3 and concentrations noted above (referred to as Base Fluid) 4 except the friction modifier was the compound of this invention used in the amounts reported below.
6 EXAMPLE l 7 About lOOg (0.35 moles) of octadecyl mercaptan 8 were dissolved in 100 ml of tetrahydrofuran (THF). Then, 9 about 34.2g (0.35 moles) of maleic anhydride were added, followed by the addition of 1 ml of triethylamine 11 as catalyst. The reaction mixture was heated to reflux for 12 about one hour. At the end of the hour, the THF solution was 13 poured into a large volume of pentane and a white solid 14 precipitated out of solution. The ~hite solid was filtered, and dried in vacuo until constant weight. The infrared 16 spectrum of the solid revealed no unreacted maleic anhydride 17 present. It analyzed for 68.85% C, 10.52% H and 8.77% S
18 which is consistent with the desired alkylthio succinic 19 anhydride that required 68.70% C, 10.48% H and 8.34% S.
21 About 30g (0.2 mole) of mercapto-succinic acid 22 were dissolved in 200 ml of methanol and cooled to about 23 15C. Thereafter, 56g (0.2 mole, 90%) of l-octadecene were 24 added, followed by the addition of 1.5g of Lucidol 70 radical initiator (Benzoyl peroxide, 70%). The reaction mixture was 26 rapidly stirred for about two hours, while some crystalline 27 white solid formed. The reaction temperature rose to 30C
28 during the first half hour and then about 25C for the rest 29 of the reaction time. The white solid was filtered and 30 collected. The infared spectrum of the solid is consistent 31 with the desired 2-(octadecylthio) succinic acid. The solid 32 analyzed for 66.776 C, 1045% H, and 8.10% S. I~heory requires 33 65.67% C, 10.526 H and 7.97% S.
34 Example 3 To a formulated automatic transmission fluid (Base ~z~
1 Fluid) was added 0.25 wt~ of the octadecylthio succinic 2 anhydride of Example 1 and the fluid was evaluated for its 3 friction properties in the Davison Friction Test utilizing 4 the SAE No.2 Friction Machine; dynamic and static torque values were within the test specification of General Motor 6 Dexron3 II Automatic Transmission Fluid (GM specification 7 G137-~, July, 1980). ~orque values were measured at 3 8 phases: (1) 16,500 lb-ft, 1 sec. lock-up, (2) 7200 lb-ft, 40 9 lb. pressure and (3) 16,500 lb ft, 60 lb pressure. Phase 1 10 friction torque tracings showed results of 102, 91 and 84;
11 phase 2 showed 101, 97 and 88 and phase 3 showed 138, 130 and 12 123 ft-lbs.
Claims (5)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A power transmission shift fluid composition 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 formu-las:
wherein R' is an alkyl of about 8 to 30 carbon atoms and R is a lower C1-C4 alkyl or hydrogen.
wherein R' is an alkyl of about 8 to 30 carbon atoms and R is a lower C1-C4 alkyl or hydrogen.
2. The composition of claim 1 where there is present about 0.01 to 1 wt% of said additive.
3. The composition of claim 2 wherein said composition is an automatic transmission fluid.
4. The composition of claim 3 wherein said additive is octadecyl thiosuccinic anhydride or acid present in an amount of about 0.1 to 0.5 wt%.
5. The composition of claim 1 wherein the R'(R)CHCH2 group has a total of about 16 to 20 carbon atoms.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46495083A | 1983-02-08 | 1983-02-08 | |
| US464,950 | 1983-02-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1208197A true CA1208197A (en) | 1986-07-22 |
Family
ID=23845920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000446925A Expired CA1208197A (en) | 1983-02-08 | 1984-02-07 | 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) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2599045B1 (en) * | 1986-05-26 | 1988-07-29 | Elf France | ADDITIVES WITH ANTICORROSION EFFECT FOR AQUEOUS FLUIDS AND COMPOSITIONS CONTAINING 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 |
| JPH11181460A (en) * | 1997-12-25 | 1999-07-06 | Tonen Corp | Lubricating oil composition |
Family Cites Families (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 EP EP84300788A patent/EP0116460B1/en not_active Expired
- 1984-02-08 DE DE8484300788T patent/DE3465332D1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3465332D1 (en) | 1987-09-17 |
| EP0116460A3 (en) | 1985-05-22 |
| EP0116460A2 (en) | 1984-08-22 |
| EP0116460B1 (en) | 1987-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |