WO2009095824A1 - Lubrifiant se composant de polyester d'oligosaccharide hautement estérifié pour machinerie - Google Patents

Lubrifiant se composant de polyester d'oligosaccharide hautement estérifié pour machinerie Download PDF

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Publication number
WO2009095824A1
WO2009095824A1 PCT/IB2009/050254 IB2009050254W WO2009095824A1 WO 2009095824 A1 WO2009095824 A1 WO 2009095824A1 IB 2009050254 W IB2009050254 W IB 2009050254W WO 2009095824 A1 WO2009095824 A1 WO 2009095824A1
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WIPO (PCT)
Prior art keywords
lubricant
tert
butyl
partially
metal surfaces
Prior art date
Application number
PCT/IB2009/050254
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English (en)
Inventor
Roger Stephen Berger
Original Assignee
The Procter & Gamble Company
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Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to CA2709964A priority Critical patent/CA2709964A1/fr
Priority to EP09704953A priority patent/EP2240558A1/fr
Publication of WO2009095824A1 publication Critical patent/WO2009095824A1/fr

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    • 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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • 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
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/40—Esters containing free hydroxy or carboxyl groups
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/08—Aldehydes; Ketones
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/124—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • C10M2215/222—Triazines
    • 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
    • C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • 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
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • 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
    • C10N2020/013—Iodine value
    • 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
    • C10N2020/069—Linear chain compounds
    • 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
    • C10N2020/071—Branched chain compounds
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/26—Waterproofing or water resistance
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/30—Anti-misting
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/34—Fragrance or deodorizing 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
    • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
    • 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
    • C10N2040/30—Refrigerators lubricants or compressors lubricants

Definitions

  • This disclosure relates to lubricants for use with the moving parts of various types of machinery, and in particular, with air-driven tools and equipment.
  • Lubricants have been used for parts of machinery that rub or rotate to reduce friction and wear. Metal surfaces can become very hot during use. Lubricants also act as a coolant for the metal. An effective lubricant reduces the abrasion and friction caused by the rotating or rubbing motions of the working parts of machinery. Lubricants are also applied to working machine surfaces to fill in any depressions in uneven surfaces and thereby form a smoother surface thereby reducing the resistance or friction between adjacent surfaces.
  • Lubricants have also been introduced into the air flow of pneumatic tools for lubricating the motor or other parts of the tool.
  • Pneumatic tools generally have a pneumatic motor connected by some kind of coupling to a drive member for driving the operative portion of the tool.
  • the motor housing is typically connected to a source of fluid under pressure, such as compressed air, to drive the motor.
  • a source of fluid under pressure such as compressed air
  • the lubricant is continually fed to the moving parts of the motor when it is in use.
  • Pneumatic or air-driven tools are used in many industries, such as mining, construction, hydro electric facilities, industrial manufacturing and production lines, such as in control valves and moving cylinders.
  • Typical lubricants have consisted of petroleum based oils and greases or vegetable based oils, sometimes in combination with various pulverized metallic, ceramic or organic compounds.
  • Rock drill greases for example, do not lubricate as well as oils in overhead bolting & drilling. They have a moderate viscosity index, which means they thin out rapidly. Rock drill greases have an unpleasant odor and are not biodegradable. Finally, they have poor thermal heat transfer capabilities.
  • Petroleum based products also present problems for workers due to the generation of oil particulate mists, known as fogging. When used in enclosed spaces, such as in mines and tunnels where the air flow is limited to begin with, the particulate material has little opportunity to dissipate.
  • the permissible exposure limit for petroleum based rock drill oils and greases for example, is 5 ppm.
  • Petroleum based oil lubricants can reduce the useful life of the tool.
  • the rotating or sliding parts of machines using such lubricants tend to wear and heat up over long periods of use leading eventually to the deterioration or loss of effectiveness of the lubricant.
  • Water in the compressed air thins out the oil and causes the tool surfaces to wear faster if not frequently replaced.
  • Petroleum based lubricants also leave a slippery deposit on tool surfaces making handling the tools difficult. Like rock drill greases, they are not biodegradable and can pollute water sources. Petroleum based lubricants are also very dirty to use, leaving black deposits on workers' skin and clothing. Further, with rising oil prices, uncertain supplies and the global environmental risks they pose, the cost of petroleum based oils and greases is prohibitive and can only be expected to increase over time.
  • vegetable oil based rock drill oils have been used as lubricants. Examples include castor oil and canola oil. They are not without their own problems. Vegetable oil based rock drill oils have low viscosities, also produce fogging, do not work well or at all in many standard lubricators, have an unusual odor, and have poor oxidative stability.
  • a new lubricating composition has been discovered in the form of partially-esterified oligosaccharide.
  • a method for reducing friction between at least two metal surfaces which are in a frictional relationship with each other is described herein which includes contacting the metal surfaces with an effective amount of a lubricant composition comprised of partially- esterified oligosaccharide molecules.
  • the metal surfaces are contacted by introducing the lubricant into the flow of compressed air in the pneumatic tool, or equipment.
  • the metal surfaces are contacted by applying the lubricant directly to the metal surfaces in need of lubrication.
  • An embodiment of the lubricant may comprise partially-esterified sucrose.
  • Each partially-esterified sucrose molecule of this embodiment of the lubricating composition comprises a sucrose backbone having from 5 to 7 fatty acids bound thereto.
  • Each fatty acid bound to the sucrose backbone may have from 2 to 28, and preferably from 4 to 22, carbon atoms in unbranched or branched chains saturated and unsaturated and mixtures thereof.
  • the partially-esterified sucrose molecules have an average distribution of five to six or six to seven fatty acids bound thereto.
  • the partially-esterified sucrose molecules have an average distribution of six fatty acids bound thereto.
  • the lubricating composition may further include an amount of an antioxidant effective for reducing the rate of oxidation of the lubricant.
  • the amount useful in some embodiments of the lubricant may range from about 20 ppm to about 10,000 ppm. Other embodiment may use from about 100 ppm to about 5000 ppm, or from about 500 ppm to about 2500 ppm of the antioxidant.
  • An amount found to be useful in at least one embodiment of the lubricant is about 1000 ppm of the antioxidant.
  • at least half of the antioxidant is an active tocopherol.
  • FIG. 1 is a schematic comparison of the applicant' s understanding of the behavior of the lubricating film of the present invention and that of a prior art petroleum-based oil lubricant.
  • FIG. 2 is a schematic of an exemplary process for making an embodiment of the partially-esterified lubricant of the invention. DETAILED DESCRIPTION OF THE INVENTION
  • the term “comprising” means various components conjointly employed in the preparation of the compositions of the present disclosure. Accordingly, the terms “consisting essentially of and “consisting of are embodied in the term “comprising”.
  • the term "partially-esterified sucrose” represents a commercially distinct chemical class (chemical compound) known as sucrose esters of fatty acids (SEFA).
  • SEFA compounds are high molecular weight compounds formed by esterifying fatty acids to a sucrose molecule backbone, which contains eight potential esterification sites.
  • a fully esterified sucrose has eight esters bound to the sucrose backbone.
  • a partially esterified-sucrose has fewer than eight esters bound thereto.
  • the fatty acids used to form these esters include those containing about four to 28 or more carbon atoms, and preferably containing from 8 to about 22 carbon atoms, and mixtures of such esters.
  • Suitable esters can be prepared by the reaction of diazoalkanes and fatty acids, or derived by alcoholysis from the fatty acids naturally occurring in fats and oils.
  • Fatty acid esters suitable for use herein may be derived from either saturated or unsaturated fatty acids.
  • Suitable preferred saturated fatty acids include, for example, capric, lauric, palmitic, stearic, behenic, isomyristic, isomargaric, myristic, caprylic, and anteisoarachadic.
  • Suitable preferred unsaturated fatty acids include, for example, maleic, linoleic, licanic, oleic, linolenic, and erydiogenic acids.
  • Methyl esters are the preferred fatty acid esters for use herein, since their use in the lubricant described herein tends to result in high yields of sucrose fatty acid partially-esterified reaction products.
  • Sucrose is an oligosaccharide.
  • Other oligosaccharides believed to be suitable for use herein include, for example, maltose, kojibiose, nigerose, cellobiose, lactose, melibiose, gentiobiose, turanose, rutinose, trehalose, and raffinose.
  • the polyols which include for example, sorbitol and others.
  • average distribution with respect to fatty acids, means the average frequency of fatty acids bound to the sucrose backbone of a quantity of partially-esterified sucrose molecules, which includes individual sucrose molecules having a lesser or greater number of esters bound thereto, but when taken together, have a number of fatty acids bound to the sucrose backbone, which on average equal the range or number stated herein.
  • the lubricant of the present invention is made of a partially-esterified oligosaccharide composition, preferably in combination with an antioxidant additive.
  • Machine parts and particularly pneumatic, or air-driven, machine parts are coated with the lubricant to reduce friction and wear.
  • the lubricant has been found to be particularly advantageous in pneumatic equipment where the lubricant is introduced into the compressed air flow for lubricating the motor or other parts of the tool.
  • a lubricant comprised of partially-esterified sucrose in addition to providing excellent lubrication for metal surfaces, also provides surprising and unexpected benefits to the environment and to the safety of workers whose jobs require them to use, or be in the vicinity of, lubricated machinery.
  • Other advantages of the various embodiments of the lubricant of the present invention will be apparent to those skilled in the art.
  • a preferred partially-esterified sucrose has an average distribution of fatty acid esters on the sucrose backbone of 5 to 7, wherein the fatty acid moieties each contain 4 or more, and preferably from 4 to about 28 carbon atoms, more preferably from 8 to 22 carbon atoms and most preferably contain 18 carbon atoms.
  • a particularly preferred partially-esterified sucrose is the hexa-ester of sucrose in which there are 6 fatty acid moieties in the molecule.
  • the partially-esterified sucrose may be combined with an anti-oxidant.
  • the antioxidants useful for the lubricant additive include tocopherols, alkylated monophenols, alkylthiomethylphenols, alkylidenebisphenols, hydroxylated thiodiphenyl ethers, hydroquinones and alkylated hydroquinones, hydroxybenzylated malonates, benzyl compounds, aromatic hydroxybenzyl compounds, triazine compounds, benzyl phosphonates, acylaminophenols, ascorbic acid, certain esters, and aminic antioxidants.
  • the antioxidant is a tocopherol.
  • tocopherols include ⁇ - tocopherol, ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocopherol and mixtures thereof (vitamin E).
  • alkylated monophenols examples include 2,6-di-tert-butyl-4-methylphenol, 2-tert- butyl-4,6-di- methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-( ⁇ -methylcyclohexyl)- 4,6-dimethyl- phenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert- butyl-4-methoxymethylphenol, nonylphenols which are linear or branched in the side chains, for example, 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6-(l -methylundec- 1 -yl)phenol
  • alkylthiomethylphenols examples include 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4- dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-di- dodecylthiomethyl-4-nonylphenol.
  • hydroquinones and alkylated hydroquinones examples include 2,6-di-tert-butyl-4- methoxy- phenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4- octade- cyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di- tert- butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4- hydroxyphenyl) adipate.
  • hydroxylated thiodiphenyl ethers examples include 2,2'-thiobis(6-tert-butyl-4- methylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'- thiobis(6-tert-butyl- 2-methyl phenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4-bis(2,6- dimethyl-4- hydroxyphenyl)disulfide.
  • alkylidenebisphenols examples include 2,2'-methylenebis(6-tert-butyl-4- methylphenol), 2,2'- methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-( ⁇ - methylcyclohexyl)- phenol], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'- methylenebis(6-nonyl-4- methyl phenol), 2,2'-methylenebis(4,6-di-tert-butylphenol), 2,2'- ethylidenebis(4,6-di-tert-butyl- phenol), 2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2'- methylenebis[6-( ⁇ -methylbenzyl)-4-nonylphenol], 2,2'-methylenebis[6-( ⁇ , ⁇ -dimethyl
  • benzyl compounds include 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydi- benzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecyl-4-hydroxy- 3,5- di-tert-butylbenzylmercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4- tert- butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxy- benzyl)sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate.
  • hydroxybenzylated malonates include dioctadecyl-2,2-bis(3,5-di-tert-butyl- 2-hydroxybenzyl)malonate, di-octadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate, di- dodecylmercaptoethyl-2,2-bis (3,5-di-tert-butyl-4-hydroxybenzyl)malonate, bis[4-(l,l ,3, 3- tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate.
  • aromatic hydroxybenzyl compounds include 1 ,3,5-tris(3,5-di-tert-butyl-4- hydroxy- benzyl)-2,4,6-trimethylbenzene, 1 ,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6- tetrame- thylbenzene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol.
  • triazine compounds examples include 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4- hydroxy- anilino)-l,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)- 1,3,5-tri- azine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-l ,3,5-triazine, 2,4,6-tris- (3,5-di-tert-butyl-4-hydroxyphenoxy)-l,2,3-triazine, l,3,5-tris(3,5-di-tert-butyl-4- hydroxybenzyl)isocyanurate, l,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)iso
  • benzyl phosphonates include dimethyl-2,5-di-tert-butyl-4- hydroxybenzylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3- methylbenzylphosphonate, the calcium salt of the monoethyl ester of 3,5-di-tert-butyl-4- hydroxybenzylphosphonic acid.
  • acylaminophenols include 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N- (3,5-di-tert-butyl-4-hydroxyphenyl)carbamate.
  • esters of ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, e.g. with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9- nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethy- lene glycol, Methylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3- thiapentadecanol, trimethylhexanediol, trimethylol- propane, 4-hydroxymethyl-l-phospha-2,6,7-
  • Esters of ⁇ -(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid with mono- or polyhydric alcohols e.g. with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6- hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, Methylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3- thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-l-phospha- 2,6,7- trioxabicyclo[2.2.2
  • Esters of ⁇ -(3,5-dicyclohexyl-4-hvdroxyphenyl)propionic acid with mono- or polyhydric alcohols e.g. with methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)ox- amide, 3- thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl- l-phospha-2,6,7-trioxabicyclo[2.2.2]octane
  • Esters of 3,5-di-tert-butyl-4-hydroxyphenyl acetic acid with mono- or polyhydric alcohols e.g. with methanol, ethanol, octanol, octadecanol, 1 ,6- hexanediol, 1 ,9-nonanediol, ethylene glycol, 1 ,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, Methylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)ox- amide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-l-phospha-2,6,7-trioxabicyclo[2.2.2]octane.
  • amides of ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid examples include N,N'-bis(3,5-di-tert- butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di- tert-butyl-4-hydroxy- phenylpropionyl)trimethylenediamide, N,N'-bis(3,5-di-tert-butyl-4- hydroxyphenylpropionyl)hydrazide, N,N'-bis[2-(3-[3,5-di-tert-butyl-4- hydroxyphenyl]propionyloxy)ethyl]oxamide.
  • aminic antioxidants include N,N'-di-isopropyl-p-phenylenediamine, N,N'- di-sec- butyl-p-phenylenediamine, N,N'-bis(l ,4-dimethylpentyl)-p-phenylenediamine, N,N'- bis(l- ethyl-3-methylpentyl)-p-phenylenediamine, N,N'-bis(l-methylheptyl)-p- phenylenediamine, N,N'-dicyclohexyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, N,N'-bis(2- naphthyl)-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-(I ,3- dimethylbutyl)-N'-phenyl-p-pheny
  • the lubricant of the present invention may be made according to the procedure shown in Figure 2.
  • the partially-esterified sucrose is produced with sucrose and refined vegetable oils, such as soybean oil or cotton seed oil.
  • a sucrose molecule contains eight potential esterification sites, each of which may support a fatty acid of up to about 28 carbon atoms.
  • the average distribution found to be beneficial for the method of lubricating described herein has from 5-7 esters, and preferably from 6-7 esters.
  • the average distribution is most preferably a 6 ester sucrose polyester, i.e, on average, six fatty acid molecules are bound through an ester linkage to a sucrose molecule backbone.
  • SE sucrose ester
  • the number following SE means the number of fatty acid chains bound to the sucrose
  • I-BAR means the average degree of esterification.
  • Ester distribution can be obtained by Supercritical Fluid Chromatography (SFC) or HPLC with SE representing the Sucrose Esters with 1-8 fatty chains attached and I-BAR being a calculated average number of fatty chains.
  • SFC Supercritical Fluid Chromatography
  • HPLC HPLC with SE representing the Sucrose Esters with 1-8 fatty chains attached and I-BAR being a calculated average number of fatty chains.
  • the 6-ester sucrose polyester has been found to provide the best overall viscosity and the best bonding to the metal surfaces in use.
  • an antioxidant as described above may be added to the partially-esterified sucrose. From about 20 ppm to about 10,000 ppm of one or more of the antioxidants described above may be added to the partially-esterified sucrose composition. For example, about half of the added antioxidant may be an active tocopherol in combination with one or more additional antioxidants.
  • an antioxidant increases the oxidative stability of the lubricant. Fats and oils are susceptible to oxidative degradation. Thus, the addition of an amount of an antioxidant effective for minimizing oxidation of the partially-esterified sucrose increases the useful life of the lubricant.
  • the lubricant is applied to the surfaces of machinery in need of lubrication by any suitable known means, including without limitation application by hand using, for example, a cloth, sponge or brush applicator, application by spraying or squirting onto the desired surface.
  • suitable known means including without limitation application by hand using, for example, a cloth, sponge or brush applicator, application by spraying or squirting onto the desired surface.
  • the amount of lubricant applied will vary depending on the tool, the intended period of use and the environment in which the tool is used.
  • the lubricant When used to lubricate pneumatic tools, the lubricant may be added to a reservoir in fluid communication through a venturi or another valve, with the compressed air flow. In some tools, the lubricant may be pre-loaded into a lubricator, essentially, a replaceable reservoir for the lubricant.
  • the boundary lubrication in a dynamic mechanical system is primarily governed by the formation of a stable tribochemical film.
  • the lubricant of the present invention appears to line up in a uniform fashion along exposed surfaces of the metal and the orientation of the lubricant is believed to be responsible, at least in part, for the significant improvement in wear resistance and lubrication under extreme pressure demonstrated by the lubricant composition of the present invention.
  • the orientation of the lubricant may also be responsible for there not being a greasy feel to the lubricant when applied to metal surfaces due, it is believed, to better metal adhesion over conventional lubricants obtained by the lubricant of the present invention.
  • Copper Tapping Tests conducted on tapping elemental copper demonstrated that one embodiment of the partially-esterified sucrose based lubricant, SEFA 1618S, outperformed Tapping Fluids based on chlorine extreme pressure additives. Copper Tapping tests are based on the Cincinnati Machine Thermal Stability Test wherein polished, pre-weighed steel and copper rods are immersed in a beaker containing 200 cc of oil and heated to 135°C for 168 hours. The rods are weighed and examined for discoloration and weight loss. Elemental copper is extremely ductile, and poor lubricity results in torn threads (rejects). SEFA excelled in all tests. The comparison is shown in Table 3 below. TABLE 3 Comparative Copper Weight Change of SEFA with those of Other Esters & Base Oils
  • the partially-esterified sucrose based lubricant was tested as the sole lubricant for two drills in a mine to determine how it would perform in an enclosed environment on actual equipment.
  • the drills were used to create a vent raise to the surface. Drilling was overhead and blasting of the material was carried out above the drills. When the ceiling was blasted down, comparative drilling resumed on the blasted rock to drill. There is virtually no ventilation in this environment, arguably the worst condition possible to test in.
  • Two drills were lubricated with partially-esterified sucrose based lubricant. Additional drills were lubricated with a conventional lubricant, Petro Canada's Ardee 150 Rock Drill Oil. The tests were conducted over a period of 3-5 months.
  • the amount of lubricant was reduced to even lower levels compared to the conventional lubricant amounts needed during the same period. It is believed that a reduction to 25% consumption for the partially-esterified sucrose based lubricant as compared to Petro Canada's Ardee 150 Rock Drill Oil will provide effective lubrication.
  • Viscosity Index is an arbitrary numbering scale that indicates the changes in oil viscosity with changes in temperature. Viscosity index can be classified as follows.
  • TLV - Threshold Limit Value is a measure of the weighted average concentration to which it is believed that nearly all workers may be repeatedly exposed, day after day, without adverse effects.
  • Fogging and odor were evaluated subjectively using a scale of 1-4, with 4 being the worst and 1 the best observed results.
  • Tool life was determined by field test comparison and is based on a scale of 1-4, wherein 1 means longest wear life and 4 means shortest wear life.
  • Washout means cleaning of the tool using water and was determined by the amount of residue left on the tool.
  • Consumption means the amount of lubricant used in the tool and was determined by the amount of times the lubricator needed to be refilled.
  • the partially-esterified sucrose based lubricant of the present invention has been found to reduce product consumption by as much as 75% compared to the conventional lubricants tested.
  • the partially-esterified sucrose based lubricant has a high threshold limit value (TLV) of 10 ppm, making it much safer for workers than the conventional lubricants.
  • TLV threshold limit value
  • the partially- esterified sucrose based lubricant has better lubricity and tool protection than any petroleum based lubricant. It reduces tool rebuild costs for end user.
  • the partially-esterified sucrose based lubricant is non fogging, a factor that is very important to worker safety and comfort as well as to avoidance of work stoppage to compensate for slippery tool surfaces.
  • the partially-esterified sucrose based lubricant biodegradable and has considerably lower production costs than petroleum based oils and some vegetable based oils.
  • the partially-esterified sucrose based lubricant is useful as a chain saw oil, conveyor chain lubricant, wire rope lubricant for elevating devices, metalworking, such as tapping, threading and drilling, saw guide oil, such as those used for band saws in lumber production, form release oil for the construction industry, water pump gear case oil, gear oil, and a railroad rail oil used on curves to minimize wear.

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)

Abstract

L'invention porte sur un procédé pour réduire le frottement entre au moins deux surfaces métalliques qui sont en relation de frottement l'une avec l'autre ou sinon qui nécessitent une lubrification. Le procédé comprend la mise en contact des surfaces métalliques avec une quantité efficace d'une composition de lubrifiant se composant de molécules de saccharose partiellement estérifiées ayant, dans un mode de réalisation, une distribution moyenne de 5 à 7 acides gras liés à un squelette de saccharose. Le lubrifiant peut également comprendre entre environ 20 ppm et environ 10 000 ppm d'un antioxydant, dont environ la moitié peut être un tocophérol actif.
PCT/IB2009/050254 2008-01-29 2009-01-22 Lubrifiant se composant de polyester d'oligosaccharide hautement estérifié pour machinerie WO2009095824A1 (fr)

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CA2709964A CA2709964A1 (fr) 2008-01-29 2009-01-22 Lubrifiant se composant de polyester d'oligosaccharide hautement esterifie pour machinerie
EP09704953A EP2240558A1 (fr) 2008-01-29 2009-01-22 Lubrifiant se composant de polyester d'oligosaccharide hautement estérifié pour machinerie

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US61/024,363 2008-01-29

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US20100041821A1 (en) * 2008-08-18 2010-02-18 Eslinger Delano R Resin and Paint Coating Compositions Comprising Highly Esterified Polyol Polyesters with One Pair of Conjugated Double Bonds
CN114317066A (zh) * 2021-12-29 2022-04-12 三合润一材料科技(广州)有限公司 一种低气味增溶润滑剂制备方法及其产品

Citations (7)

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US2700022A (en) * 1952-07-15 1955-01-18 California Research Corp Sugar ester-containing lubricant compositions
EP0879872A1 (fr) * 1997-05-20 1998-11-25 Igol Industrie Composition d'huile lubrifiante formée par un polyester de sucre biodégradable et non-toxique
JP2001192690A (ja) * 1999-10-25 2001-07-17 Nippon Mitsubishi Oil Corp 極微量油剤供給式切削・研削加工用油剤組成物
US6291409B1 (en) * 1998-07-02 2001-09-18 Cargill, Inc. Process for modifying unsaturated triacylglycerol oils; Resulting products and uses thereof
WO2002092733A2 (fr) * 2001-05-17 2002-11-21 Exxonmobil Chemical Patents, Inc. Lubrifiants synthetiques biodegradables
US20050245404A1 (en) * 2002-08-01 2005-11-03 Harri Repo Lubricating oil and its use
WO2005111054A2 (fr) * 2004-05-07 2005-11-24 The Procter & Gamble Company Synthèse de compositions des acides gras de polyester polyol modérément estérifié, purifié

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WO2001030945A1 (fr) * 1999-10-25 2001-05-03 Nippon Mitsubishi Oil Corporation Composition de fluide pour systeme de coupe ou de meulage utilisant une quantite de fluide a peine decelable

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2700022A (en) * 1952-07-15 1955-01-18 California Research Corp Sugar ester-containing lubricant compositions
EP0879872A1 (fr) * 1997-05-20 1998-11-25 Igol Industrie Composition d'huile lubrifiante formée par un polyester de sucre biodégradable et non-toxique
US6291409B1 (en) * 1998-07-02 2001-09-18 Cargill, Inc. Process for modifying unsaturated triacylglycerol oils; Resulting products and uses thereof
JP2001192690A (ja) * 1999-10-25 2001-07-17 Nippon Mitsubishi Oil Corp 極微量油剤供給式切削・研削加工用油剤組成物
WO2002092733A2 (fr) * 2001-05-17 2002-11-21 Exxonmobil Chemical Patents, Inc. Lubrifiants synthetiques biodegradables
US20050245404A1 (en) * 2002-08-01 2005-11-03 Harri Repo Lubricating oil and its use
WO2005111054A2 (fr) * 2004-05-07 2005-11-24 The Procter & Gamble Company Synthèse de compositions des acides gras de polyester polyol modérément estérifié, purifié

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AR074614A1 (es) 2011-02-02
PE20100017A1 (es) 2010-02-02
US20090192060A1 (en) 2009-07-30

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