CA1336185C - Phosphate ester lubricants - Google Patents
Phosphate ester lubricantsInfo
- Publication number
- CA1336185C CA1336185C CA000603216A CA603216A CA1336185C CA 1336185 C CA1336185 C CA 1336185C CA 000603216 A CA000603216 A CA 000603216A CA 603216 A CA603216 A CA 603216A CA 1336185 C CA1336185 C CA 1336185C
- Authority
- CA
- Canada
- Prior art keywords
- traction
- lubricants
- compounds
- phosphate
- methylcyclohexyl
- 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 - Fee Related
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
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/002—Traction fluids
-
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/74—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing phosphorus
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
-
- 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
- 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
-
- 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
- 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
- C10M2223/042—Metal salts 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Friction Gearing (AREA)
Abstract
Use as lubricants, especially for traction drives, of organophosphate esters of the general formula I:
I
wherein R1 and R2 are independently selected from 2-methylcyclo-hexyl and 3-methylcyclohexyl groups. The compounds of the invention have good viscosity characteristics and can be used as lubricants in various engineering applications, either per se or in admixture with other lubricants, such as mineral or synthetic oils.
I
wherein R1 and R2 are independently selected from 2-methylcyclo-hexyl and 3-methylcyclohexyl groups. The compounds of the invention have good viscosity characteristics and can be used as lubricants in various engineering applications, either per se or in admixture with other lubricants, such as mineral or synthetic oils.
Description
PHOSPHATE ESTER LUBRICANTS
The present process relates to the use of certain phosphate ester compounds as lubricants, in p~rticular their use in traction drives.
These lubricants can be used in a variety of engineering applications, being of particular value in traction drives. Traction is broadly defined as the adhesive friction of a body on a surface on which it moves. A traction drive is a device in which torque is transmitted from an input element to an output element through nominal point or line contact typically with a rolling action by virtue of the traction between the contacting elements. While traction elements are commonly spoken of as being in contact, it is generally accepted that a fluid film is present therebetween. Almost all traction drives r~quire fluids to remove heat, to prevent wear at the contact surfaces and to lubricate bearings and other moving parts associated with the drive. Thus, ihstead of metal to metal rolling contact there is a film of fluid introduced into the contact zone and interposed between the metal elements. The nature of this fluid determines to a large extent the limits in pçrformance and the capacity of the drive. Most traction drives are designed to operate with a traction fluid which preferably has a coefficient of traction above about 0.06, a viscosity in the range of about 4-20,000 mPa.s over a temperature range of 40C to -20C and good thermal and oxidative stability. The fluid should also be noncorrosive to common materials of construction and have good load-bearing and low wear-rate properties.
Mineral base oils are rather unsatisfactory lubricants for traction drives since in general their traction (friction) coefficient is low, which means that for any given load applied to the gears the maximal tangential force that may be trans-mitted by the friction wheels is low.
Accordingly, the present invention provides the use aslubricants, and especially as traction fluids, or organophosphate esters of the general formula I
1 ll 2 IR O)2-P-(OR ) wherein Rl and R2 are independently selected from 2-methylcyclo-hexyl and 3-methylcyclohexyl groups.
Organophosphate esters are known compounds, and there-fore may be prepared by known procedures, such as the reaction of phosphoryl chloride with the appropriate alcohol in the presence of a base, such as pyridine or triethylamine, and suitably also a solvent.
It has been found that the viscosity characteristics of the above ester compounds are very suitable for use in e.g.
friction wheel gears (traction drives) in which application they may be admixed with conventional grease thickeners. Such thickeners can be of any number of materials commonly used to ` _ 3 _ 1336185 ~ 63293-3123 thicken mineral oils to lubricating viscosity, including both organic and inorganic compositions such as metallic soaps, synthetic polymers, organosiloxanes, clays, bentonite, and colloidal silica. Suitably, the viscosity properties of compounds to be used in traction drives are such that the compounds are operable between -30 and 150C.
The compounds can be used as lubricants in various engineering applications. Since the above ester compounds show excellent lubricating performance in traction drives, the invent~ion in particular provides the use of these ester compounds as traction fluids, and also the operation of a traction drive wherein such esters form the traction fluid.
The ester compounds of the present invention can be used se as lubricants. They can be mixed with other lubricants such as mineral or synthetic oils, and various additives can be added to the ester compounds, such as VI-improvers, pour point depressants, dispersants, detergents, anti-oxidants and the like. A mixture that can be of particular interest for traction fluid applications is a blend with a polyolefin, in particular a poly-alpha-olefin, especially polyisobutylene, since the presence of the polymer can usefully enh~e the traction coefficient of the fluid blend. The molecular weight of such polyolefin blend components is conveniently in the range 500-10,000, a specific example of a suitable polyisobutylene being "Hyvis", and the proportion of polyolefin may vary from zero to 70~ by weight.
The following Examples illustrate the preparation of compounds used in the present invention (III and IV), and of - 1 33 6 18~3293-3l23 comparative compounds (I, II and V), together with their frictional and other physical properties.
Example 1 - TricyclohèXyl phosphate A solution of cyclohexanol (751.2g, 7.5m) and pyridine (595.0g, 7.5m) in dichloromethane (3.5L) was stirred under an atmosphere of dry nitrogen and phosphoryl chloride (382.5g, 2.5m) was added dropwise over 1-2 hours, whilst maintaining the temperature of the reaction mixture at between 15 and 25C
throughout the addition period. On completion of the addition, stirring was continued at ambient temperature fora further 18 hours, and then the resultant mixture was filtered. The organic solution was washed with water (3 x SL) and dried (over MgSO4), and the solvent was evaporated off ln-vacuo at 30C to give a pale-yellow viscous oil (730.3g) which slowly solidifed on standing. The crude oil was dissolved with stirring in diethyl ether ~750ml) and cooled with stirring to -40 to -50C in a dry ice/acetone cooling bath. The precipitate was filtered and dried in vacuo at 25C to give tri(cyclohexyl) phosphate (520.0g) as an off-white solid, m.p. 48-50C.
Example II - Tri(methylcyclohexyl) phosphate A solution of methylcyclohexanol (technical grade, containing a mixture of isomers; 2.08 kg, 18.2m) and pyridine (1.44 kg, 18.2m) in dichloromethane (lOL) was stirred under an atmosphere of dry nitrogen and phosphoryl chloride (930.2g, 6.07m) added dropwise over 1.5 hours, whilst maintaining the temperature of the stirred reaction mixture at between 15 and 25C throughout the addition period. On completion of the addition, stirring was continued at ambient temperature for a ~ 5 ~ 1336185 further 18 hours, and then the resuItant mixture was filtered, washed with water (4 x 6L) and dried (over MgSO4), and the solvent was evaporated off in vacuo at 30C to give the crude product as a viscous oil. The crude oil was allowed to stand at room temperature overnight, was then filtered and unreacted methyl-cyclohexanol and other volatile impurities were removed by evaporation on a KDL-4 thin-film evaporator (at 85C and 0.8mmHg (107 Pa)) to give the product as a clear viscous oil (1.75 kg) containing a mixture of different isomers.
Examples III to V
By using the process of Example II, but substituting respectively 2-methylcyclohexanol, 3-methylcyclohexanol and 4-meth~lcyclohexanol (in each case mixtures of CiS- and trans-isomers) in place of the technical grade methylcyclohexanol, there were prepared:
III - Tri-(2-methylcyclohexyl)phosphate (oil) IV - Tri-(3-methylcyclohexyl)phosphate (oil) V - Tri-(4-methylcyclohexyl)phosphate (oil) Example VI - Friction coefficient measurement All friction measurements were performed on a two-disc machine. Hardened steel discs are fixed on the ends of two shafts so as to make tangential contact with each other. Radial forces may be applied to press the discs together with loads of 0-200 kgf. Each disc is driven by an electric motor. The speeds of rotation of the two discs are different, such that there is a slip .
Between the electric motor and the shaft carrying the lower test specimen, a measuring device is fitted which indicates A
_ 1 336185 63293-3123 the transmitted friction torque. The measuring device is a gear dynamo~eter with a pendulum which is swung out of its vertical balanced position when power is transmitted, the sine of the angle of inclination being a measure of the torque. The torque measurement is pre-calibrated through the design and dimensions of the instrument. The friction coefficient is defined by the torque measured divided by the product of the radial force times the radius of the lower disc.
Both discs used had a diameter of 50.Omm, the upper disc having a width of 3mm, the lower one having a width of lOmm.
The top shaft speed was 606rpm, and the mean tangential (or surface) velocity was 1.48ms . The slip employed was 9.1%.
All experiments were run at ambient temperature (21C+2C). The friction readings are provided at loadings equivalent to Hertzian stresses of 0.69, 0.97, 1.19 and 1.38 GPa.
The friction coefficients of the compounds are indicated in the following Table. For the compound of Example I, whose m.pt. is 48-50C, these coefficients were determined on a supercooled fluid at 21(+2)C.
Example VIII - Friction coefficient measurement The kinematic viscosity properties of the compounds are also included in this Table.
It will be noted that the friction coefficients of the compounds are all good, but that those of Examples III and IV are very surprisingly superior.
r ~' ~
1 3 3 6 1 8 5 63293-3l23 ~ a~ o o r~ r o o o ,~
~1_1 I . . . .
,1 a~ O o o o ~D ~ O O ~
~1~ u7 o o o o t~ ~ o ~
~ N _I ~1 ~ _I
O . ~
O O
O I O O~
--I 1~ O O O O
_I O
1~ '~5 N 1-1 ~ U-) 11~ a~ CD ~ CO
~--1~0 O N--~ ~ G t` tl~ 0~ O
tS~ ~ U') ~ ~ O O O _~
~3 o u~ , O O O 'r O O O O
N N N
O O U
o ~ a~
O O O O O
_ _ _ I I I
6 ~
U O
8 X ~ ~ ~, _ O U
o .
~r ~ ~ ~ ~ t~ r- t, _ c , O O
U
r~
a a ~ ~ ~ 6~ ~
The present process relates to the use of certain phosphate ester compounds as lubricants, in p~rticular their use in traction drives.
These lubricants can be used in a variety of engineering applications, being of particular value in traction drives. Traction is broadly defined as the adhesive friction of a body on a surface on which it moves. A traction drive is a device in which torque is transmitted from an input element to an output element through nominal point or line contact typically with a rolling action by virtue of the traction between the contacting elements. While traction elements are commonly spoken of as being in contact, it is generally accepted that a fluid film is present therebetween. Almost all traction drives r~quire fluids to remove heat, to prevent wear at the contact surfaces and to lubricate bearings and other moving parts associated with the drive. Thus, ihstead of metal to metal rolling contact there is a film of fluid introduced into the contact zone and interposed between the metal elements. The nature of this fluid determines to a large extent the limits in pçrformance and the capacity of the drive. Most traction drives are designed to operate with a traction fluid which preferably has a coefficient of traction above about 0.06, a viscosity in the range of about 4-20,000 mPa.s over a temperature range of 40C to -20C and good thermal and oxidative stability. The fluid should also be noncorrosive to common materials of construction and have good load-bearing and low wear-rate properties.
Mineral base oils are rather unsatisfactory lubricants for traction drives since in general their traction (friction) coefficient is low, which means that for any given load applied to the gears the maximal tangential force that may be trans-mitted by the friction wheels is low.
Accordingly, the present invention provides the use aslubricants, and especially as traction fluids, or organophosphate esters of the general formula I
1 ll 2 IR O)2-P-(OR ) wherein Rl and R2 are independently selected from 2-methylcyclo-hexyl and 3-methylcyclohexyl groups.
Organophosphate esters are known compounds, and there-fore may be prepared by known procedures, such as the reaction of phosphoryl chloride with the appropriate alcohol in the presence of a base, such as pyridine or triethylamine, and suitably also a solvent.
It has been found that the viscosity characteristics of the above ester compounds are very suitable for use in e.g.
friction wheel gears (traction drives) in which application they may be admixed with conventional grease thickeners. Such thickeners can be of any number of materials commonly used to ` _ 3 _ 1336185 ~ 63293-3123 thicken mineral oils to lubricating viscosity, including both organic and inorganic compositions such as metallic soaps, synthetic polymers, organosiloxanes, clays, bentonite, and colloidal silica. Suitably, the viscosity properties of compounds to be used in traction drives are such that the compounds are operable between -30 and 150C.
The compounds can be used as lubricants in various engineering applications. Since the above ester compounds show excellent lubricating performance in traction drives, the invent~ion in particular provides the use of these ester compounds as traction fluids, and also the operation of a traction drive wherein such esters form the traction fluid.
The ester compounds of the present invention can be used se as lubricants. They can be mixed with other lubricants such as mineral or synthetic oils, and various additives can be added to the ester compounds, such as VI-improvers, pour point depressants, dispersants, detergents, anti-oxidants and the like. A mixture that can be of particular interest for traction fluid applications is a blend with a polyolefin, in particular a poly-alpha-olefin, especially polyisobutylene, since the presence of the polymer can usefully enh~e the traction coefficient of the fluid blend. The molecular weight of such polyolefin blend components is conveniently in the range 500-10,000, a specific example of a suitable polyisobutylene being "Hyvis", and the proportion of polyolefin may vary from zero to 70~ by weight.
The following Examples illustrate the preparation of compounds used in the present invention (III and IV), and of - 1 33 6 18~3293-3l23 comparative compounds (I, II and V), together with their frictional and other physical properties.
Example 1 - TricyclohèXyl phosphate A solution of cyclohexanol (751.2g, 7.5m) and pyridine (595.0g, 7.5m) in dichloromethane (3.5L) was stirred under an atmosphere of dry nitrogen and phosphoryl chloride (382.5g, 2.5m) was added dropwise over 1-2 hours, whilst maintaining the temperature of the reaction mixture at between 15 and 25C
throughout the addition period. On completion of the addition, stirring was continued at ambient temperature fora further 18 hours, and then the resultant mixture was filtered. The organic solution was washed with water (3 x SL) and dried (over MgSO4), and the solvent was evaporated off ln-vacuo at 30C to give a pale-yellow viscous oil (730.3g) which slowly solidifed on standing. The crude oil was dissolved with stirring in diethyl ether ~750ml) and cooled with stirring to -40 to -50C in a dry ice/acetone cooling bath. The precipitate was filtered and dried in vacuo at 25C to give tri(cyclohexyl) phosphate (520.0g) as an off-white solid, m.p. 48-50C.
Example II - Tri(methylcyclohexyl) phosphate A solution of methylcyclohexanol (technical grade, containing a mixture of isomers; 2.08 kg, 18.2m) and pyridine (1.44 kg, 18.2m) in dichloromethane (lOL) was stirred under an atmosphere of dry nitrogen and phosphoryl chloride (930.2g, 6.07m) added dropwise over 1.5 hours, whilst maintaining the temperature of the stirred reaction mixture at between 15 and 25C throughout the addition period. On completion of the addition, stirring was continued at ambient temperature for a ~ 5 ~ 1336185 further 18 hours, and then the resuItant mixture was filtered, washed with water (4 x 6L) and dried (over MgSO4), and the solvent was evaporated off in vacuo at 30C to give the crude product as a viscous oil. The crude oil was allowed to stand at room temperature overnight, was then filtered and unreacted methyl-cyclohexanol and other volatile impurities were removed by evaporation on a KDL-4 thin-film evaporator (at 85C and 0.8mmHg (107 Pa)) to give the product as a clear viscous oil (1.75 kg) containing a mixture of different isomers.
Examples III to V
By using the process of Example II, but substituting respectively 2-methylcyclohexanol, 3-methylcyclohexanol and 4-meth~lcyclohexanol (in each case mixtures of CiS- and trans-isomers) in place of the technical grade methylcyclohexanol, there were prepared:
III - Tri-(2-methylcyclohexyl)phosphate (oil) IV - Tri-(3-methylcyclohexyl)phosphate (oil) V - Tri-(4-methylcyclohexyl)phosphate (oil) Example VI - Friction coefficient measurement All friction measurements were performed on a two-disc machine. Hardened steel discs are fixed on the ends of two shafts so as to make tangential contact with each other. Radial forces may be applied to press the discs together with loads of 0-200 kgf. Each disc is driven by an electric motor. The speeds of rotation of the two discs are different, such that there is a slip .
Between the electric motor and the shaft carrying the lower test specimen, a measuring device is fitted which indicates A
_ 1 336185 63293-3123 the transmitted friction torque. The measuring device is a gear dynamo~eter with a pendulum which is swung out of its vertical balanced position when power is transmitted, the sine of the angle of inclination being a measure of the torque. The torque measurement is pre-calibrated through the design and dimensions of the instrument. The friction coefficient is defined by the torque measured divided by the product of the radial force times the radius of the lower disc.
Both discs used had a diameter of 50.Omm, the upper disc having a width of 3mm, the lower one having a width of lOmm.
The top shaft speed was 606rpm, and the mean tangential (or surface) velocity was 1.48ms . The slip employed was 9.1%.
All experiments were run at ambient temperature (21C+2C). The friction readings are provided at loadings equivalent to Hertzian stresses of 0.69, 0.97, 1.19 and 1.38 GPa.
The friction coefficients of the compounds are indicated in the following Table. For the compound of Example I, whose m.pt. is 48-50C, these coefficients were determined on a supercooled fluid at 21(+2)C.
Example VIII - Friction coefficient measurement The kinematic viscosity properties of the compounds are also included in this Table.
It will be noted that the friction coefficients of the compounds are all good, but that those of Examples III and IV are very surprisingly superior.
r ~' ~
1 3 3 6 1 8 5 63293-3l23 ~ a~ o o r~ r o o o ,~
~1_1 I . . . .
,1 a~ O o o o ~D ~ O O ~
~1~ u7 o o o o t~ ~ o ~
~ N _I ~1 ~ _I
O . ~
O O
O I O O~
--I 1~ O O O O
_I O
1~ '~5 N 1-1 ~ U-) 11~ a~ CD ~ CO
~--1~0 O N--~ ~ G t` tl~ 0~ O
tS~ ~ U') ~ ~ O O O _~
~3 o u~ , O O O 'r O O O O
N N N
O O U
o ~ a~
O O O O O
_ _ _ I I I
6 ~
U O
8 X ~ ~ ~, _ O U
o .
~r ~ ~ ~ ~ t~ r- t, _ c , O O
U
r~
a a ~ ~ ~ 6~ ~
Claims (5)
1. Use as lubricants of organophosphate esters of the general formula I:
I
wherein R1 and R2 are independently selected from 2-methylcyclo-hexyl and 3-methylcyclohexyl groups.
I
wherein R1 and R2 are independently selected from 2-methylcyclo-hexyl and 3-methylcyclohexyl groups.
2. Use according to claim 1, wherein the organophosphate ester of formula I is tri-(2-methylcyclohexyl)phosphate or tri-(3-methylcyclohexyl)phosphate.
3. Lubricant composition which contains as the major component an organophosphate ester as defined in claim 1.
4. Use as a traction fluid of an organophosphate ester as defined in claim 1 or 2 or a composition as defined in claim 3.
5. Method of operating a traction drive wherein the traction fluid is an organophosphate ester as defined in claim 1 or 2 or a composition as defined in claim 3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8815754 | 1988-07-01 | ||
| GB888815754A GB8815754D0 (en) | 1988-07-01 | 1988-07-01 | Phosphate ester lubricants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1336185C true CA1336185C (en) | 1995-07-04 |
Family
ID=10639747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000603216A Expired - Fee Related CA1336185C (en) | 1988-07-01 | 1989-06-19 | Phosphate ester lubricants |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0349093B1 (en) |
| JP (1) | JP2749878B2 (en) |
| KR (1) | KR0134774B1 (en) |
| CN (1) | CN1019021B (en) |
| AT (1) | ATE73839T1 (en) |
| AU (1) | AU613207B2 (en) |
| BR (1) | BR8903177A (en) |
| CA (1) | CA1336185C (en) |
| DE (1) | DE68901010D1 (en) |
| ES (1) | ES2030262T3 (en) |
| FI (1) | FI95594C (en) |
| GB (1) | GB8815754D0 (en) |
| GR (1) | GR3004107T3 (en) |
| MY (1) | MY106974A (en) |
| PT (1) | PT91001B (en) |
| SG (1) | SG45393G (en) |
| ZA (1) | ZA894897B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5817606A (en) * | 1996-08-08 | 1998-10-06 | Rohm And Haas Company | Viscosity index improving additives for phosphate ester-containing hydraulic fluids |
| JP5188309B2 (en) * | 2008-07-30 | 2013-04-24 | コスモ石油ルブリカンツ株式会社 | Flame retardant gear oil composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2285854A (en) * | 1934-02-23 | 1942-06-09 | Du Pont | Lubrication |
-
1988
- 1988-07-01 GB GB888815754A patent/GB8815754D0/en active Pending
-
1989
- 1989-06-19 CA CA000603216A patent/CA1336185C/en not_active Expired - Fee Related
- 1989-06-27 KR KR1019890008901A patent/KR0134774B1/en not_active IP Right Cessation
- 1989-06-28 AU AU37132/89A patent/AU613207B2/en not_active Ceased
- 1989-06-28 FI FI893169A patent/FI95594C/en not_active IP Right Cessation
- 1989-06-28 ZA ZA894897A patent/ZA894897B/en unknown
- 1989-06-28 CN CN89106346A patent/CN1019021B/en not_active Expired
- 1989-06-28 BR BR898903177A patent/BR8903177A/en not_active IP Right Cessation
- 1989-06-28 PT PT91001A patent/PT91001B/en not_active IP Right Cessation
- 1989-06-28 JP JP1166471A patent/JP2749878B2/en not_active Expired - Lifetime
- 1989-06-28 MY MYPI89000871A patent/MY106974A/en unknown
- 1989-06-30 AT AT89201758T patent/ATE73839T1/en not_active IP Right Cessation
- 1989-06-30 ES ES198989201758T patent/ES2030262T3/en not_active Expired - Lifetime
- 1989-06-30 EP EP89201758A patent/EP0349093B1/en not_active Expired - Lifetime
- 1989-06-30 DE DE8989201758T patent/DE68901010D1/en not_active Expired - Fee Related
-
1992
- 1992-03-19 GR GR920400462T patent/GR3004107T3/el unknown
-
1993
- 1993-04-14 SG SG45393A patent/SG45393G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI95594B (en) | 1995-11-15 |
| ZA894897B (en) | 1990-06-27 |
| KR0134774B1 (en) | 1998-04-18 |
| GB8815754D0 (en) | 1988-08-10 |
| GR3004107T3 (en) | 1993-03-31 |
| EP0349093B1 (en) | 1992-03-18 |
| PT91001B (en) | 1995-01-31 |
| JP2749878B2 (en) | 1998-05-13 |
| AU3713289A (en) | 1990-01-04 |
| KR900001826A (en) | 1990-02-27 |
| CN1019021B (en) | 1992-11-11 |
| FI95594C (en) | 1996-02-26 |
| DE68901010D1 (en) | 1992-04-23 |
| ATE73839T1 (en) | 1992-04-15 |
| MY106974A (en) | 1995-08-30 |
| SG45393G (en) | 1993-06-25 |
| FI893169A0 (en) | 1989-06-28 |
| FI893169A (en) | 1990-01-02 |
| CN1039053A (en) | 1990-01-24 |
| ES2030262T3 (en) | 1992-10-16 |
| BR8903177A (en) | 1990-02-13 |
| EP0349093A1 (en) | 1990-01-03 |
| JPH0253893A (en) | 1990-02-22 |
| AU613207B2 (en) | 1991-07-25 |
| PT91001A (en) | 1990-02-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1291984C (en) | Ester compound lubricants | |
| US3440894A (en) | Tractants and method of use | |
| US4374032A (en) | Lubricant composition containing borated oxazoline friction reducer | |
| Kržan et al. | Tribological properties of an environmentally adopted universal tractor transmission oil based on vegetable oil | |
| JP5916916B2 (en) | Lubricating compound and lubricant composition containing the same | |
| US4886614A (en) | Synthetic traction fluid | |
| CA1336185C (en) | Phosphate ester lubricants | |
| EP0361347A1 (en) | Lubricating oil for traction drives | |
| Murphy et al. | Structural guides for synthetic lubricant development | |
| US4886613A (en) | Traction fluid | |
| EP0350125B1 (en) | Traction fluid lubricants | |
| US4392973A (en) | Method for transmitting power by traction utilizing borate esters as traction fluids and a device for using the method | |
| EP0275313B1 (en) | Synthetic traction fluid | |
| RO116413B1 (en) | Method for lubricating metal-metal contact systems in metal working operations | |
| CA1293499C (en) | Synthetic lubricating fluid | |
| WO2006059687A1 (en) | Bearing lubricant | |
| Novikov et al. | Effect of mesomorphism on lubricating efficiency of nanomaterials under boundary friction | |
| CA1287617C (en) | Traction fluid | |
| Kolesnikov et al. | Phosphate Ceramics as a Multifunctional Grease Additive | |
| CA1280403C (en) | Synthetic tractor fluid | |
| CA1289550C (en) | Traction fluid | |
| JPS6261637B2 (en) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |