US3758407A - Lithium soap grease containing monolithium borate - Google Patents

Lithium soap grease containing monolithium borate Download PDF

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Publication number
US3758407A
US3758407A US00201140A US3758407DA US3758407A US 3758407 A US3758407 A US 3758407A US 00201140 A US00201140 A US 00201140A US 3758407D A US3758407D A US 3758407DA US 3758407 A US3758407 A US 3758407A
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Prior art keywords
acid
grease
lithium
hydroxy
greases
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US00201140A
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G Harting
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • 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
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • a grease composition that combines good water resistance, good mechanical stability and high oil retention with excellent oxidation stability and high dropping point is prepared by the use of a novel thickener system whose essential components include a combination of the monolithium salt of boric acid; and a lithium soap of a 9-, 10-, or 12-hydroxy C to C fatty acid, e.g., lithium 12- hydroxystearate.
  • a third thickener component is included, this being a lithium salt formed in situ in the grease from a second hydroxy carboxylic acid of from 3 to 14 carbon atoms wherein the OH group is attached to a carbon atom not more than 6 carbon atoms removed from the carboxyl group, and wherein either of those groups may be attached to either aliphatic or aromatic portions of a molecule.
  • This invention concerns a modified lithium soap grease of premium quality with outstanding properties which include a high dropping point, excellent oxidation stability, long lubrication life and water resistance.
  • Lithium greases have been known and widely used for many years.
  • the lithium soaps that are used as thickening agents for these greases are ordinarily prepared by reaction of lithium hydroxide or other suitable lithium base with a conventional high molecular weight acid or acids.
  • the principal advantages of lithium greases have been high water resistance and ease of dispersion of the soaps in all types of lubricating oil base stocks.
  • Particularly useful have been greases prepared from lithium hydroxystearate, since the soaps of the hydroxystearic acids and related hydroxy fatty acids have been found to be more mechanically stable than the corresponding soaps of the conventional fatty acids.
  • a lithium base grease having excellent oxidation and mechanical stability and desirably high dropping points is prepared from a 9-hydroxy, 10-hydroxy, or 12-hydroxy C to C preferably C to C fatty acid, and boric acid. Additionally, for further improvement in dropping point, there may advantageously be used a second hydroxycarboxylic acid of from 3 to 14 carbon atoms, wherein the hydroxy group is attached to a carbon atom not more than 6 carbon atoms removed from the carboxyl group.
  • the presence of a glycol is undesirable because it renders the grease prone to oxidation and makes the water resistance of the grease undesirably low in some applications.
  • the present invention makes possible the preparation of high dropping point greases from hydroxy fatty acids without the necessity of incorporating a glycol.
  • the hydroxy fatty acid employed in preparing the greases of this invention will have from about 12 to 24, or more usually about 16 to 20 carbon atoms, and will preferably be a hydroxystearic acid, e.g., 9-hydroxy, 10- hydroxy, or l2-hydroxystearic acid, more preferably the latter.
  • Ricinoleic acid which is an unsaturated form of 12-hydroxystearic acid, having a double bond in the 9- 10 position, can also be used.
  • Other hydroxy fatty acids include 12-hydroxybehenic acid and IO-hydroxypalmitic acid.
  • a second hydroxycarboxylic acid When a second hydroxycarboxylic acid is used along with the boric acid and hydroxy fatty acid, it will be one having an OH group attached to a carbon atom that is not more than 6 carbon atoms removed from the carboxyl group.
  • This acid has from 3 to 14 carbon atoms and can be either an aliphatic acid such as lactic acid, -hydroxydecanoic acid, 3-hydroxybutanoic acid, l-hydroxycaproic acid, 4 hydroxybutanoic acid, 6-hydroxy-alphahydroxystearic acid, etc.
  • an aromatic acid such as parahydroxybenzoic acid, salicylic acid, 2-hydroxy-4-hexylbenzoic acid, metahydroxybenzoic acid, 2,5-dihydroxybenzoic acid (gentisic acid); 2,6-dihydroxybenzoic acid (gamma resorcylic acid); (4-hydroxy-4-methoxybenzoic acid, etc. or a hydroxyaromatic aliphatic acid such as orthohydroxyphenyl, metahydroxyphenyl, or parahydroxyphenyl acetic acid.
  • a cycloaliphatic hydroxy acid such as hydroxycyclopentyl carboxylic acid or hydroxynaphthenic acid could also be used. Particularly useful hydroxy acids are lactic acid, salicylic acid, and parah'ydroxybenzoic acid.
  • a lower alcohol ester e.g., the methyl, ethyl, or propyl, isopropyl, or sec-butyl ester of the acid, e.g., methyl salicylate
  • the amount of lithium salt of the hydroxy acid will range from about 0.1 to about 10 wt. percent of the finished grease, or preferably from about 0.2 to about 5 wt. percent.
  • the monolithium salt or the dilithium salt of the second hydroxy acid can be used, but the dilithium salt is preferred.
  • the total soap and salt content of the grease will be in the range of from about 2 to 30 wt. percent and preferably about 5 to 20 wt. percent.
  • the proportion of the C to C hydroxy fatty acid to boric acid will be in the range of a weight ratio of about 3 to 100 parts, or more usually about 5 to parts, of hydroxy fatty acid per part by weight of boric acid.
  • the lubricating oil base that is used in preparing the grease compositions of this invention can be any of the conventionally used mineral oils, synthetic hydrocarbon oils, or synthetic ester oils, and will generally have a viscosity within the range of about 35 to 200 SUS at 210 F.
  • Synthetic lubrictaing oils that can be used include esters of dibasic acids such as di-Z-ethylhexyl sebacate, esters of glycols' such as the C oxo acid diester of tetraethylene glycol, or complex esters such as a complex ester formed by reacting l mole of sebacic acid with 2 moles of tetraethylene glycol and 2 moles of 2-ethylhexanoic acid.
  • Other synthetic oils that can be used include synthetic hydrocarclude the polyphenyl ethers, e.g., those having from about 3 to 7 ether linkages and about 4 to 8 phenyl groups. (See US. Pat. 3,424,678, column 3.)
  • the greases can be prepared by coneutralizing all three types of acid, or alternatively by first neutralizing the boric acid and hydroxy fatty acid together and then forming the lithium salt of the second hydroxycarboxylic acid.
  • Example 1 (including comparative greases) A grease designated grease A was prepared using as the thickener system a combination of lithium 12-hydroxystearate and monolithium borate.
  • the base oil used in preparing this grease was a solvent-refined Mid-Continent lubricating oil distillate known as Solvent 450 Neutral, having a viscosity at 100 F. of about 450 SUS.
  • Solvent 450 Neutral having a viscosity at 100 F. of about 450 SUS.
  • the 12- hydroxystearic acid was added to a portion of the base oil (about /2 of the total oil used in the complete grease) and the mixture was heated to a temperature sufliciently high to melt the 12-hydroxystearic acid, this temperature being about 180 F. to 190 F.
  • Example 2 Two greases were prepared using as the thickener system a combination of dilithium salicylate, lithium 12-hydroxy-stearate and monolithium borate, the proportions of the thickener components being varied as between the two greases.
  • the base oil used in preparing these greases was a solvent refined Mid-Continent lubricating oil distillate known as Solvent 600 Neutral, having a viscosity at F. of about 600 SUS.
  • Solvent 600 Neutral having a viscosity at F. of about 600 SUS.
  • Methyl salicylate and 12-hydroxystearic acid were added to a portion of the base oil and the mixture was heated. After it was observed that the 12-hydroxystearic acid had melted, the temperature being then about F.
  • Comparative example Using the same procedure as in Examaple 2, comparative greases were prepared in which one case the methyl salicylate was omitted, in a second case the boric acid was omitted and in the third case both the boric acid and methyl salicylate were omitted. In each instance the corresponding quantity of lithium hydroxide needed to form the soap or salt of the omitted component was also omitted.
  • the phenyl alpha naphthylamine referred to was used as an antioxidant.
  • the Na-Sul-BSN is a trademarked product which serves as a rust inhibitor; it is a 50 wt. percent concentrate, in a light mineral oil, of a neutral bar-' ium salt of dinonyl naphthalene sulfonic acid derived from naphthalene alkylated with tripropylene.
  • additives can be incorporated into the grease compositions of this invention, as is understood by those skilled in the art.
  • additives include antioxidants, rust inhibitors, tackiness agents, odor modifiers, dyes, extreme pressure agents, etc.
  • a lubricating grease composition of high dropping point which comprises a major proportion of a lubricating oil and from about 2 to 30 wt. percent of a thickener system whose essential components include a lithium soap of a C to C hydroxy fatty acid and a monolithium salt of boric acid, wherein there are from 3 to 100 parts by weight of hydroxy fatty acid per part by weight of boHc acid.
  • composition as defined by claim 1 wherein the thickener system also includes as a third component a lithium salt of a second hydroxycarboxylic acid of from 3 to 14 carbon atoms, wherein the hydroxy group is attached to a carbon atom not more than 6 carbon atoms removed from the carboxy group, and wherein there is a weight ratio of from about 0.1 to about 10 parts of said second hydroxycarboxylic acid per part of boric acid.
  • Grease composition as defined by claim 1 wherein said hydroxy fatty acid is 12-hydroxystearic acid.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US00201140A 1971-11-11 1971-11-22 Lithium soap grease containing monolithium borate Expired - Lifetime US3758407A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU35624/71A AU457980B2 (en) 1970-11-18 1971-11-11 Lithium soap grease
US20114071A 1971-11-22 1971-11-22

Publications (1)

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US3758407A true US3758407A (en) 1973-09-11

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ID=25623379

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Country Status (7)

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US (1) US3758407A (enrdf_load_stackoverflow)
JP (1) JPS5747235B2 (enrdf_load_stackoverflow)
CA (1) CA971545A (enrdf_load_stackoverflow)
DE (1) DE2235098C2 (enrdf_load_stackoverflow)
FR (1) FR2159251B2 (enrdf_load_stackoverflow)
GB (1) GB1370947A (enrdf_load_stackoverflow)
MY (1) MY7500155A (enrdf_load_stackoverflow)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3940339A (en) * 1975-01-21 1976-02-24 Exxon Research & Engineering Co. Lithium borate complex grease exhibiting salt water corrosion resistance
US3988248A (en) * 1973-12-20 1976-10-26 Deutsche Texaco Aktiengesellschaft Lithium soap lubricating grease
US4100081A (en) * 1977-03-14 1978-07-11 Chevron Research Company Polyurea-based extreme pressure grease
US4138348A (en) * 1973-06-16 1979-02-06 Deutsche Texaco Aktiengesellschaft Lubricant for use in non-chip metal forming
US4156655A (en) * 1978-01-30 1979-05-29 Exxon Research & Engineering Co. Grease composition resistant to salt water corrosion
US4253979A (en) * 1979-02-05 1981-03-03 Exxon Research & Engineering Co. Lubricating grease composition containing pyrrolidone derivative as grease thickener
US4376060A (en) * 1981-11-04 1983-03-08 Exxon Research And Engineering Co. Process for preparing lithium soap greases containing borate salt with high dropping point
US4582616A (en) * 1983-08-23 1986-04-15 Idemitsu Kosan Company Limited General-purpose grease composition
US4780227A (en) * 1984-08-22 1988-10-25 Mobil Oil Corporation Grease composition containing borated alkoxylated alcohols
US4802999A (en) * 1986-04-30 1989-02-07 Shell Oil Company Lubricating grease
US4822503A (en) * 1986-04-11 1989-04-18 Exxon Research And Engineering Company Method of manufacturing an improved multi-grade lubricating grease
US4828734A (en) * 1985-08-27 1989-05-09 Mobil Oil Corporation Grease compositions containing borated oxazoline compounds and hydroxy-containing soap thickeners
US4961868A (en) * 1983-01-10 1990-10-09 Mobil Oil Corporation Grease composition
US5064545A (en) * 1986-12-17 1991-11-12 The Lubrizol Corporation Process for overbasing via metal borate formation
US5084194A (en) * 1984-03-07 1992-01-28 Mobil Oil Corporation Grease composition
US5242608A (en) * 1986-12-17 1993-09-07 The Lubrizol Corporation Process for overbasing via metal borate formation
EP1275707A1 (en) * 2001-06-29 2003-01-15 King Industries, Inc. N-alkylsubstituted naphthalenesulfonic acid derivatives in fluids compositions
US20060052261A1 (en) * 2004-08-11 2006-03-09 Bernd Kray Process for the preparation of pulverulent (poly)ureas by means of spray drying
US20060058203A1 (en) * 2004-08-11 2006-03-16 Wilhelm Laufer Process for the preparation of pulverulent (poly)ureas
US20150148274A1 (en) * 2013-11-27 2015-05-28 Chevron U.S.A. Inc. Continuous lithium complex grease manufacturing process with a borated additive
WO2020106553A1 (en) 2018-11-20 2020-05-28 Nch Corporation Composition and method of manufacturing sulfonate-based greases using a glycerol derivative
US11661563B2 (en) 2020-02-11 2023-05-30 Nch Corporation Composition and method of manufacturing and using extremely rheopectic sulfonate-based greases

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2425161C2 (de) * 1974-05-24 1983-03-24 Deutsche Texaco Ag, 2000 Hamburg Lithiumseifenschmierfett
BR112012033761A2 (pt) * 2010-07-05 2016-11-22 Shell Int Research processo para a fabricação de uma composição de graxa de complexo metálico, e, composição de graxa.

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB717453A (en) * 1952-01-02 1954-10-27 Standard Oil Dev Co Improvements in or relating to lubricating grease composition
US2940930A (en) * 1956-05-15 1960-06-14 Exxon Research Engineering Co Lubricating grease compositions
BE633058A (enrdf_load_stackoverflow) * 1960-07-01
US3223624A (en) * 1962-12-07 1965-12-14 Exxon Research Engineering Co Lubricating grease
US3223633A (en) * 1963-07-01 1965-12-14 Exxon Research Engineering Co Lubricant
US3433743A (en) * 1967-04-03 1969-03-18 Exxon Research Engineering Co Lubricating grease containing colloidal asbestos
JPS542205A (en) * 1977-06-08 1979-01-09 Hosokura Kougiyou Kk Insulating of electrolytic cathode electrode plate

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4138348A (en) * 1973-06-16 1979-02-06 Deutsche Texaco Aktiengesellschaft Lubricant for use in non-chip metal forming
US3988248A (en) * 1973-12-20 1976-10-26 Deutsche Texaco Aktiengesellschaft Lithium soap lubricating grease
US3940339A (en) * 1975-01-21 1976-02-24 Exxon Research & Engineering Co. Lithium borate complex grease exhibiting salt water corrosion resistance
US4100081A (en) * 1977-03-14 1978-07-11 Chevron Research Company Polyurea-based extreme pressure grease
US4156655A (en) * 1978-01-30 1979-05-29 Exxon Research & Engineering Co. Grease composition resistant to salt water corrosion
US4253979A (en) * 1979-02-05 1981-03-03 Exxon Research & Engineering Co. Lubricating grease composition containing pyrrolidone derivative as grease thickener
US4376060A (en) * 1981-11-04 1983-03-08 Exxon Research And Engineering Co. Process for preparing lithium soap greases containing borate salt with high dropping point
US4961868A (en) * 1983-01-10 1990-10-09 Mobil Oil Corporation Grease composition
US4582616A (en) * 1983-08-23 1986-04-15 Idemitsu Kosan Company Limited General-purpose grease composition
US5084194A (en) * 1984-03-07 1992-01-28 Mobil Oil Corporation Grease composition
US4780227A (en) * 1984-08-22 1988-10-25 Mobil Oil Corporation Grease composition containing borated alkoxylated alcohols
US4828734A (en) * 1985-08-27 1989-05-09 Mobil Oil Corporation Grease compositions containing borated oxazoline compounds and hydroxy-containing soap thickeners
US4822503A (en) * 1986-04-11 1989-04-18 Exxon Research And Engineering Company Method of manufacturing an improved multi-grade lubricating grease
US4802999A (en) * 1986-04-30 1989-02-07 Shell Oil Company Lubricating grease
US6090757A (en) * 1986-12-17 2000-07-18 The Lubrizol Corporation Process for overbasing via metal borate formation
US5242608A (en) * 1986-12-17 1993-09-07 The Lubrizol Corporation Process for overbasing via metal borate formation
US5064545A (en) * 1986-12-17 1991-11-12 The Lubrizol Corporation Process for overbasing via metal borate formation
EP1275707A1 (en) * 2001-06-29 2003-01-15 King Industries, Inc. N-alkylsubstituted naphthalenesulfonic acid derivatives in fluids compositions
US20060052261A1 (en) * 2004-08-11 2006-03-09 Bernd Kray Process for the preparation of pulverulent (poly)ureas by means of spray drying
US20060058203A1 (en) * 2004-08-11 2006-03-16 Wilhelm Laufer Process for the preparation of pulverulent (poly)ureas
US20150148274A1 (en) * 2013-11-27 2015-05-28 Chevron U.S.A. Inc. Continuous lithium complex grease manufacturing process with a borated additive
US9157045B2 (en) * 2013-11-27 2015-10-13 Chevron U.S.A. Inc. Continuous lithium complex grease manufacturing process with a borated additive
WO2020106553A1 (en) 2018-11-20 2020-05-28 Nch Corporation Composition and method of manufacturing sulfonate-based greases using a glycerol derivative
US12331261B2 (en) 2018-11-20 2025-06-17 Nch Corporation Composition and method of manufacturing sulfonate-based greases using a glycerol derivative
US11661563B2 (en) 2020-02-11 2023-05-30 Nch Corporation Composition and method of manufacturing and using extremely rheopectic sulfonate-based greases
US12146114B2 (en) 2020-02-11 2024-11-19 Nch Corporation Composition and method of manufacturing and using extremely rheopectic sulfonate-based greases

Also Published As

Publication number Publication date
MY7500155A (en) 1975-12-31
DE2235098C2 (de) 1982-12-02
JPS4856203A (enrdf_load_stackoverflow) 1973-08-07
JPS5747235B2 (enrdf_load_stackoverflow) 1982-10-07
FR2159251A2 (enrdf_load_stackoverflow) 1973-06-22
DE2235098A1 (de) 1973-05-17
CA971545A (en) 1975-07-22
FR2159251B2 (enrdf_load_stackoverflow) 1976-06-11
GB1370947A (en) 1974-10-16

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