EP0504897A1 - Grease composition - Google Patents
Grease composition Download PDFInfo
- Publication number
- EP0504897A1 EP0504897A1 EP92104809A EP92104809A EP0504897A1 EP 0504897 A1 EP0504897 A1 EP 0504897A1 EP 92104809 A EP92104809 A EP 92104809A EP 92104809 A EP92104809 A EP 92104809A EP 0504897 A1 EP0504897 A1 EP 0504897A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- grease
- grease composition
- antiwear additive
- parts
- 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.)
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- C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
- C10M131/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen and halogen only
- C10M131/04—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen and halogen only aliphatic
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- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
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- C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound containing silicon
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- C10M2229/047—Siloxanes with specific structure containing alkylene oxide groups
- C10M2229/0475—Siloxanes with specific structure containing alkylene oxide groups used as base material
-
- 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
- C10M2229/048—Siloxanes with specific structure containing carboxyl groups
- C10M2229/0485—Siloxanes with specific structure containing carboxyl groups used as base material
-
- 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
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
- C10M2229/0505—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon used as base material
-
- 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
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
- C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
- C10M2229/0515—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen used as base material
-
- 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
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
- C10M2229/052—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing nitrogen
- C10M2229/0525—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing nitrogen used as base material
-
- 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
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
- C10M2229/053—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing sulfur
- C10M2229/0535—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing sulfur used as base material
-
- 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
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
- C10M2229/054—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing phosphorus
- C10M2229/0545—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing phosphorus used as base material
-
- 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
- This invention relates to grease compositions. More particularly, this invention relates to grease compositions containing an additive that imparts excellent low temperature properties and anti-wear performance to the composition.
- One class of additives can be characterized as chlorinated organic compounds and includes the esters of chlorendic acid described in U.S. Patent No. 3,759,857, which issued on September 18, 1973.
- the esters are added to liquid polydiorganosiloxanes to improve the performance of the resultant lubricant composition.
- These compositions exhibit good thermal stability and excellent lubricating characteristics under extremely high pressures, however their low temperature lubricating performance is relatively poor and an additional improvement in the antiwear performance of the compositions would be desirable.
- One objective of this invention is to define a class of compounds that improve the antiwear and low temperature performance of prior art grease compositions, particularly those described in the aforementioned U.S. Patent No. 3,759,857.
- a phenyl substituted hexachlorobicyclo[2,2,1]-hept-2-ene to a conventional grease composition
- a base oil such as an organic oil or a liquid polyorganosiloxane
- a thickener such as an organic oil or a liquid polyorganosiloxane
- This invention provides an improved grease composition
- a base oil selected from the group consisting of organic oils and liquid polyorganosiloxanes, a thickener and at least 1 weight percent, based on the total weight of said composition, of an antiwear additive.
- the improvement consists essentially of selecting as the antiwear additive at least compound of the formula (I), where R1, R2, R3, R4, and R5 are individually selected from the group consisting of hydrogen, bromine and chlorine.
- the chacterizing feature of the present grease compositions is the presence of an antiwear additive represented by formula (I).
- an antiwear additive represented by formula (I).
- one of the substituents represented by R1 - R5 in formula (I) represents a hydrogen atom and the other four substituents represent bromine atoms.
- a particularly preferred additive is 1,2,3,4,7,7-hexachloro-5-(3',4',5',6'-tetrabromophenyl)-bicyclo[2,2,-1]hept-2-ene, represented by formula (II)
- the antiwear additive constitutes at least one percent, preferably from 5 to about 30 percent, of the total weight of the present compositions.
- the present grease compositions comprise a homogeneous blend of a base oil, a thickening agent and, and at least one antiwear additive represented by formula (I).
- the grease composition may optionally contain additional ingredients conventionally present in grease compositions. These additional ingredients include but are not limited to surfactants, dyes, pigments, and dispersing agents.
- the base oil used in the present compositions includes one or more liquid polyorganosiloxanes, also referred to as silicone oils, mineral oils and synthetic organic oils.
- the thickener in the present compositions can be any of those known in the grease art, including but not limited to fatty acid soaps, silica, polytetrafluoroethylene, carbon black, lithium soaps, clay, copper phthalocyanine, ammeline, indanthrene blue, allyl-substituted urea, aromatic ureas, aromatic diureas, aromatic amides, aromatic diamides, cyanuramide, and cyanurodiamide.
- the relative amounts of base oil and thickener are not specifically restricted, and are selected to provide a grease of the desired consistency.
- Preferred embodiments of the present compositions contain a silicone oil as the base oil, a lithium salt of a fatty acid, also referred to as a lithium soap, or silica as the thickener and an antiwear additive represented by formula (II)
- compositions can be prepared by either of the following methods:
- the temperature When it is desired to heat the ingredients during the blending operation, the temperature must not exceed the decomposition temperature of the antiwear additive.
- a mixture containing 69.84 parts of a polymethylphenylsiloxane exhibiting a viscosity of 500 centistokes (5 x 10-4 m2/sec), 19.71 parts of lithium stearate and 0.45 percent of a dye was mixed with heating at 200 o C for 10 minutes.
- Ten parts of an antiwear additive of the formula was then added with mixing to produce a grease composition of this invention.
- a grease composition of this invention was prepared as described in Example 1 using the ingredients of Example 1 in the following amounts: 62.08 parts of the polymethylphenylsiloxane, 17.52 parts of lithium stearate, 0.4 parts of dye and 20 parts of the antiwear additive.
- Example 2 For comparative purposes a grease composition was prepared as described in Example 1 but omitting the antiwear additive.
- the composition contained 77.6 weight percent of the polyorganosiloxane, 21.9 weight percent lithium stearate and 0.50 weight percent dye.
- a grease composition was prepared using the ingredients and procedure described in Example 1, but using 10 parts of butyl chlorendate, described as a grease additive in U.S. Patent No. 3,759,827, in place of the antiwear additive of the present invention.
- a grease composition of this invention was prepared by mixing for 30 minutes with heating at 180 o C 83.6 parts of a poly- ⁇ -olefin oil having a viscosity of 28.8 centistokes (2.88 x 10 ⁇ 5 m2/sec.) and 11.41 parts lithium-12-hydroxystearate. 5,.0 parts of the antiwear additive corresponding to formula (II) in Example 1 was added to the resultant mixture with stirring to form the grease composition.
- a grease composition of this invention was prepared as described in Example 3 using 79.2 parts of the poly- ⁇ -olefin oil, 10.89 parts of the lithium compound and 10 parts of the antiwear additive.
- Example 3 For comparative purposes a grease composition was prepared as described in Example 3 without the antiwear additive.
- the composition contained 88.0 weight percent of the poly- ⁇ -olefin oil and 12.0 weight percent lithium 12-hydroxystearate.
- the grease compositions prepared in the preceding examples and comparison examples were subjected to lubrication testing under the following conditions to measure the LFW-1 wear scar and the amount of wear. In addition, the low-temperature performance was examined by measuring the low-temperature torque.
- the low-temperature torque was measured at -40 o C during start up and rotation using the tester specified in Japanese Industrial Standard (JIS) K-2220.
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
The addition of a phenyl- or halophenyl-substituted hexachlorobicyclo-[2.2.1]hept-2-ene to a conventional grease composition comprising a base oil, such as an organic oil or a liquid polyorganosiloxane, and a thickener improves both the antiwear performance and low temperature lubricating properties of the composition.
Description
- This invention relates to grease compositions. More particularly, this invention relates to grease compositions containing an additive that imparts excellent low temperature properties and anti-wear performance to the composition.
- Numerous additives have been proposed to impart antiwear properties to grease composition. One class of additives can be characterized as chlorinated organic compounds and includes the esters of chlorendic acid described in U.S. Patent No. 3,759,857, which issued on September 18, 1973. The esters are added to liquid polydiorganosiloxanes to improve the performance of the resultant lubricant composition. These compositions exhibit good thermal stability and excellent lubricating characteristics under extremely high pressures, however their low temperature lubricating performance is relatively poor and an additional improvement in the antiwear performance of the compositions would be desirable.
- One objective of this invention is to define a class of compounds that improve the antiwear and low temperature performance of prior art grease compositions, particularly those described in the aforementioned U.S. Patent No. 3,759,857.
- The objectives of the present invention are achieved by the addition of a phenyl substituted hexachlorobicyclo[2,2,1]-hept-2-ene to a conventional grease composition comprising a base oil, such as an organic oil or a liquid polyorganosiloxane, and a thickener.
- This invention provides an improved grease composition comprising a base oil selected from the group consisting of organic oils and liquid polyorganosiloxanes, a thickener and at least 1 weight percent, based on the total weight of said composition, of an antiwear additive. The improvement consists essentially of selecting as the antiwear additive at least compound of the formula (I),
where R¹, R², R³, R⁴, and R⁵ are individually selected from the group consisting of hydrogen, bromine and chlorine. - The chacterizing feature of the present grease compositions is the presence of an antiwear additive represented by formula (I). In preferred embodiments of this additive, one of the substituents represented by R¹ - R⁵ in formula (I) represents a hydrogen atom and the other four substituents represent bromine atoms. A particularly preferred additive is 1,2,3,4,7,7-hexachloro-5-(3',4',5',6'-tetrabromophenyl)-bicyclo[2,2,-1]hept-2-ene, represented by formula (II)
- The antiwear additive constitutes at least one percent, preferably from 5 to about 30 percent, of the total weight of the present compositions.
- The present grease compositions comprise a homogeneous blend of a base oil, a thickening agent and, and at least one antiwear additive represented by formula (I). The grease composition may optionally contain additional ingredients conventionally present in grease compositions. These additional ingredients include but are not limited to surfactants, dyes, pigments, and dispersing agents.
- The base oil used in the present compositions includes one or more liquid polyorganosiloxanes, also referred to as silicone oils, mineral oils and synthetic organic oils.
- The thickener in the present compositions can be any of those known in the grease art, including but not limited to fatty acid soaps, silica, polytetrafluoroethylene, carbon black, lithium soaps, clay, copper phthalocyanine, ammeline, indanthrene blue, allyl-substituted urea, aromatic ureas, aromatic diureas, aromatic amides, aromatic diamides, cyanuramide, and cyanurodiamide.
- The relative amounts of base oil and thickener are not specifically restricted, and are selected to provide a grease of the desired consistency.
- Preferred embodiments of the present compositions contain a silicone oil as the base oil, a lithium salt of a fatty acid, also referred to as a lithium soap, or silica as the thickener and an antiwear additive represented by formula (II)
- The present compositions can be prepared by either of the following methods:
- (1) the present antiwear additive is blended into a grease base of the desired consistency that has been previously prepared from a base oil of the appropriate viscosity and a suitable thickener; or
- (2) the antiwear additive, base oil and thickener are blended in a single operation.
- When it is desired to heat the ingredients during the blending operation, the temperature must not exceed the decomposition temperature of the antiwear additive.
- The following examples describe preferred embodiments of the present grease compositions, and should not be interpreted as limiting the scope of the invention defined in the accompanying claims. All parts and percentages are by weight and viscosities were measured at 25o C.
- A mixture containing 69.84 parts of a polymethylphenylsiloxane exhibiting a viscosity of 500 centistokes (5 x 10-4 m²/sec), 19.71 parts of lithium stearate and 0.45 percent of a dye was mixed with heating at 200o C for 10 minutes. Ten parts of an antiwear additive of the formula
was then added with mixing to produce a grease composition of this invention. - A grease composition of this invention was prepared as described in Example 1 using the ingredients of Example 1 in the following amounts:
62.08 parts of the polymethylphenylsiloxane,
17.52 parts of lithium stearate,
0.4 parts of dye and
20 parts of the antiwear additive. - For comparative purposes a grease composition was prepared as described in Example 1 but omitting the antiwear additive. The composition contained 77.6 weight percent of the polyorganosiloxane, 21.9 weight percent lithium stearate and 0.50 weight percent dye.
- For comparative purposes a grease composition was prepared using the ingredients and procedure described in Example 1, but using 10 parts of butyl chlorendate, described as a grease additive in U.S. Patent No. 3,759,827, in place of the antiwear additive of the present invention.
- A grease composition of this invention was prepared by mixing for 30 minutes with heating at 180o C 83.6 parts of a poly-α -olefin oil having a viscosity of 28.8 centistokes (2.88 x 10⁻⁵ m²/sec.) and 11.41 parts lithium-12-hydroxystearate. 5,.0 parts of the antiwear additive corresponding to formula (II) in Example 1 was added to the resultant mixture with stirring to form the grease composition.
- A grease composition of this invention was prepared as described in Example 3 using 79.2 parts of the poly-α-olefin oil, 10.89 parts of the lithium compound and 10 parts of the antiwear additive.
- For comparative purposes a grease composition was prepared as described in Example 3 without the antiwear additive. The composition contained 88.0 weight percent of the poly-α-olefin oil and 12.0 weight percent lithium 12-hydroxystearate.
- The grease compositions prepared in the preceding examples and comparison examples were subjected to lubrication testing under the following conditions to measure the LFW-1 wear scar and the amount of wear. In addition, the low-temperature performance was examined by measuring the low-temperature torque.
- To measure LFW-1 wear amount the testing machine specified in ASTM D 2714-68 was used. The measurement conditions were as follows: speed = 1,200 rpm, sliding velocity = 2.2 m/second, test time = 240 seconds, load = 13.59 kg, type of contact = line contact. To measure wear scar the 4-ball wear tester specified in ASTM D 2266 was used. The measurement conditions were as follows: speed = 1,200 rpm, sliding velocity = 2.2 m/second, test time = 1 hour, load = 40 kg, type of contact = point contact.
- The low-temperature torque was measured at -40o C during start up and rotation using the tester specified in Japanese Industrial Standard (JIS) K-2220.
- The test results are reported in Table 1.
Table 1 grease composition LFW-1 wear amount (mg) wear scar (mm) low-temperature during start-up torque (gfm) during rotation Example 1 3.8 - 1,100 360 Example 2 2.9 - - - Comparison Example 1 6.1 - 940 300 Comparison Example 2 4.1 - 2,340 1,270 Example 3 - 0.46 - - Example 4 - 0.43 - - Comparison Example 3 - 0.70 - -
Claims (1)
- In an improved grease composition comprising a base oil selected from the group consisting of organic oils and liquid polyorganosiloxanes, a thickener and at least 1 weight percent, based on the total weight of said composition, of an antiwear additive, the improvement comprising the presence in said composition of an antiwear additive of the formula
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP78340/91 | 1991-03-19 | ||
JP3078340A JPH07113114B2 (en) | 1991-03-19 | 1991-03-19 | Grease composition |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0504897A1 true EP0504897A1 (en) | 1992-09-23 |
Family
ID=13659255
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92104809A Withdrawn EP0504897A1 (en) | 1991-03-19 | 1992-03-19 | Grease composition |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP0504897A1 (en) |
JP (1) | JPH07113114B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2869911A1 (en) * | 2004-05-05 | 2005-11-11 | Rhodia Chimie Sa | HIGH COHESION SILICONE GREASE WITH COLD |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3072571A (en) * | 1958-06-13 | 1963-01-08 | Texaco Inc | Calcium base greases containing chlorinated bicycloheptene compounds |
US3759827A (en) | 1970-09-29 | 1973-09-18 | Dow Corning | Lubricant compositions |
US3759857A (en) | 1970-06-23 | 1973-09-18 | Labofina Sa | Cross linking of acrylamide polymers |
EP0248641A2 (en) * | 1986-06-02 | 1987-12-09 | Shin-Etsu Chemical Co., Ltd. | Silicone grease composition |
-
1991
- 1991-03-19 JP JP3078340A patent/JPH07113114B2/en not_active Expired - Lifetime
-
1992
- 1992-03-19 EP EP92104809A patent/EP0504897A1/en not_active Withdrawn
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3072571A (en) * | 1958-06-13 | 1963-01-08 | Texaco Inc | Calcium base greases containing chlorinated bicycloheptene compounds |
US3759857A (en) | 1970-06-23 | 1973-09-18 | Labofina Sa | Cross linking of acrylamide polymers |
US3759827A (en) | 1970-09-29 | 1973-09-18 | Dow Corning | Lubricant compositions |
EP0248641A2 (en) * | 1986-06-02 | 1987-12-09 | Shin-Etsu Chemical Co., Ltd. | Silicone grease composition |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2869911A1 (en) * | 2004-05-05 | 2005-11-11 | Rhodia Chimie Sa | HIGH COHESION SILICONE GREASE WITH COLD |
WO2005121287A1 (en) * | 2004-05-05 | 2005-12-22 | Rhodia Chimie | High cold cohesion silicone-based grease composition |
Also Published As
Publication number | Publication date |
---|---|
JPH0586384A (en) | 1993-04-06 |
JPH07113114B2 (en) | 1995-12-06 |
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