Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M173/00—Lubricating compositions containing more than 10% water
  • C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
• • 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
  • C10M105/38—Esters of polyhydroxy compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
  • C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
  • C08G65/2645—Metals or compounds thereof, e.g. salts
  • C08G65/2663—Metal cyanide catalysts, i.e. DMC's
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
  • C08L71/02—Polyalkylene oxides
• • 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
  • C10M105/18—Ethers, e.g. epoxides
• • 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
  • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
  • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
  • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
  • C10M107/34—Polyoxyalkylenes
• • 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
  • C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
  • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
  • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
  • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
  • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
  • C10M2209/1075—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106 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
  • C10N2020/04—Molecular weight; Molecular weight distribution
• • 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
• • 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
  • C10N2030/64—Environmental friendly compositions
• • 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
  • C10N2040/20—Metal working
• • 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
  • C10N2040/20—Metal working
  • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling

Definitions

• the present invention relates, in general to functional fluids, and more specifically to synthetic, water-miscible metalworking fluids (MWFs) which provide effective cooling and lubrication of metal surfaces at high speeds of operation in the grinding, cutting, boring, drilling, and/or turning of metal parts, while also reducing aerosol inhalation toxicity.
• MVFs water-miscible metalworking fluids
• metalworking fluids results from the nature of the metalworking operations, i.e., a work piece rotates at a relatively high speed and both the work piece and a metalworking tool are lubricated by a metalworking fluid. Under such conditions, the metalworking fluid is frequently thrown from the surface of the metal in the form of droplets. Oftentimes, these droplets are small enough to be classified as a mist which may pose a potential inhalation risk to the metal worker.
• water-miscible polyether polyols useful in metalworking fluids have been prepared by semi-batch processes involving the base-catalyzed anionic polymerization of alkylene oxides.
• a basic catalyst such as sodium or potassium hydroxide
• the mixture is dehydrated, and an alkylene oxide or mixture of alkylene oxides is added to produce the polyether.
• DMC double metal cyanide
• DMC catalyst utilization for the preparation of random copolymers of ethylene and propylene oxide can be found in EP 0,992,523 B1, issued to Miller et al., which describes a process for the activation or initiation of the catalyst with 100% propylene oxide prior to feeding a mixture of ethylene oxide and propylene oxide to make a monofunctional polyether for use in silicone surfactant production.
• Miller et al. are silent as to any risks associated with aerosol or mist exposure to their polyethers.
• Polyether polyols useful as foam suppressants can be made using DMC catalysts as described in U.S. Pat. No. 7,001,634, issued to Browne. However, those random copolymers are marginally water soluble at slightly elevated temperatures with cloud points for 1% aqueous solutions being less than 30° C. Browne is also silent regarding potential risks associated with aerosol or mist exposure to his foam suppressants in metalworking applications.
• the present invention provides such a process for producing a water-miscible metalworking.
• fluid involving combining about 90 wt. % to about 5 wt. %, based on the weight of the fluid, of water and one or more additives chosen from plasticizers, chelating agents, biocides, surfactants, dispersants, dyes, odorants, extreme pressure agents, anti-oxidants and corrosion inhibitors with about 10 wt. % to about 95 wt.
• % based on the weight of the fluid, of a polyether polyol produced by mixing an active hydrogen compound with a double metal cyanide (DMC) catalyst in a reactor vessel, charging to the reactor vessel a mixture containing two or more alkylene oxides to activate the catalyst, and continuously feeding one-or more alkylene oxides-to produce the polyether polyol, wherein a 1% solution in water of the polyether polyol has a cloud point of from greater than about 32° C. to less than about 53° C., the polyether polyol has a number average equivalent weight of from greater than about 1,600 Da to about 10,000 Da, and a four-hour aerosol inhalation exposure to the polyether polyol has a LC 50 of greater than about 5 mg/L.
• DMC double metal cyanide
• the present invention provides a process for producing a water-miscible metalworking fluid involving combining 90 wt. % to 5 wt. %, based on the weight of the fluid, of water and one or more additives chosen from plasticizers, chelating agents, biocides, surfactants, dispersants, dyes, odorants, extreme pressure agents, anti-oxidants and corrosion inhibitors with 10 wt. % to 95 wt.
• the present invention further provides a process for producing a water-miscible metalworking fluid involving combining 90 wt. % to 5 wt. %, based on the weight of the fluid, of water and one or more additives chosen from plasticizers, chelating agents, biocides, surfactants, dispersants, dyes, odorants, extreme pressure agents, anti-oxidants and corrosion inhibitors with 10 wt. % to 95 wt.
• % based on the weight of the fluid, of a polyether polyol produced by mixing with a double metal cyanide (DMC) catalyst in a reactor vessel an initiator chosen from one or more of a polyol from a prior preparation (heel) having an equivalent weight greater than 300 Da, a lower molecular weight active hydrogen compound that does not deactivate the DMC catalyst and an inert solvent, charging to the reactor vessel a mixture containing two or more alkylene oxides to activate the catalyst, and continuously feeding one or more alkylene oxides and one or more starters to produce the polyether polyol, wherein a 1% solution in water of the polyether polyol has a cloud point of from greater than 32° C.
• DMC double metal cyanide
• the polyether polyol has a number average equivalent weight of greater than 1,600 Da to 10,000 Da, and a four-hour aerosol inhalation exposure to the polyether polyol has a LC 50 of greater than 5 mg/L.
• DMC double metal cyanide
• the inventors herein have unexpectedly discovered that double metal cyanide (DMC) catalysts can be used to prepare random copolymers of ethylene and propylene oxide that exhibit reduced toxicity to animals as measured by acute aerosol inhalation toxicity testing. More specifically, the inventors have discovered a process for the activation of DMC catalysts with a mixture of alkylene oxides in which the polymerization product has a number average equivalent weight of from greater than 1,600 Da to 10,000 Da, more preferably 1,600 to 6,000, is water-miscible with a cloud point of from greater than 32° C. to less than 53° C., and has a LC 50 greater than 5 mg/L for a four-hour aerosol exposure.
• DMC double metal cyanide
• water-miscible metalworking fluid means a liquid containing water, additives that help “wet” the part and other additives to improve performance and a polyether polyol.
• the polyether polyol makes up from 10 to 95 wt. %, more preferably from 40 to 90 wt. % of the water-miscible metalworking fluid produced by the inventive process.
• Water makes up from 90 to 5 wt. % more preferably from 60 to 10 wt. %, with the remainder of the water-miscible metalworking fluid being one or more additives.
• Suitable additives include, but are not limited to, plasticizers, chelating agents, surfactants, biocides, dispersants, dyes, and odorants, extreme pressure agents, anti-oxidants, and corrosion inhibitors to improve performance and increase fluid life.
• Particularly preferred for use in the present invention are those zinc hexacyanocobaltate catalysts prepared by the methods described in U.S. Pat. No. 5,482,908, the entire contents of which are incorporated herein by reference thereto.
• the DMC catalyst may also be bound to a support as described in U.S. Pat. No. 6,362,126.
• Polyfunctional initiators include, but are not limited to, water, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, propanediol, glycerine, trimethylolpropane, butanediol isomers, pentaerythritol, polypropylene glycols, polyethylene glycols, polybutylene glycols, and polyoxyalkylene glycol copolymers.
• Butanol is particularly preferred as the active hydrogen compound.
• alkylene oxides useful in the present invention include, but are not limited to, ethylene oxide, propylene oxide, 1,2- and 2,3-butylene oxide, isobutylene oxide, epichlorohydrin, cyclohexene oxide, styrene oxide, and the higher alkylene oxides such as the C 5 -C 30 ⁇ -alkylene oxides.
• Other polymerizable monomers may be used as well, e.g. anhydrides and other monomers as disclosed in U.S. Pat. Nos. 3,404,109, 3,538,043 and 5,145,883, the contents of which are herein incorporated in their entireties by reference thereto.
• a mixture of ethylene oxide and propylene oxide is particularly preferred wherein the amount of ethylene oxide is preferably less than 50% of the mixture.
• the process of the present invention may be semi-batch or continuous as described in U.S. Pat. No. 5,777,177, the entire contents of which are incorporated herein by reference thereto.
• the starter or initiator is preferably a monofunctional or polyfunctional active hydrogen compound with an average equivalent weight less than 300 Da, while the material charged initially to the reaction vessel may be one or more of a polyol from a prior preparation (heel) with an equivalent weight greater than 300 Da, a lower molecular weight active hydrogen compound that does not deactivate the DMC catalyst, and an inert solvent.
• the water-miscible metalworking fluids prepared by the process of the present invention may preferably be used to cool and/or lubricate metal surfaces during the grinding, cutting, boring, drilling and/or turning of metal parts.
• This example employed a product-to-product process together with continuous addition of starter (CAOS), in which a heel of product (prepared from butanol and propylene oxide/ethylene oxide to a hydroxyl number of about 35 mg KOH/g via a CAOS process) was added to the reactor at the beginning of the batch, a mixture of ethylene oxide and propylene oxide was added to activate the catalyst, and an initiator or starter was fed continuously to the reactor simultaneously with the alkylene oxide or oxides after activation.
• Double metal cyanide (DMC) catalyst prepared according to U.S. Pat. No. 5,482,908 was used in all examples. A heel of 2,500 g of product was added to a 20 kg reactor along with DMC catalyst (0.87 g).
• This product had an number average equivalent weight of 1,716 g/mol, a viscosity of 810 SUS at 37.8° C., a cloud point (1% in water) of 52° C., and an LC 50 concentration of >5.83 mg/L for a four-hour aerosol exposure.
• Example 2 The procedure described above in Example 1 was repeated, except the ethylene oxide/propylene oxide ratio was 35/65, and the amount of n-butanol fed was reduced to produce a polyether with a hydroxyl number of about 17 mg KOH/g.
• the resulting product had a number average equivalent weight of 3,187 g/mol, a viscosity of 2,060 SUS at 37.8° C., a cloud point (1% in water) of 40° C., and an LC 50 concentration of >5.38 mg/L for a four-hour aerosol exposure.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Emergency Medicine (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Toxicology (AREA)
• Polyethers (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Preventing Corrosion Or Incrustation Of Metals (AREA)
• Lubricants (AREA)

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• 2006
  • 2006-05-24 US US11/439,576 patent/US20070167336A1/en not_active Abandoned
• 2007
  • 2007-01-09 EP EP07000299A patent/EP1808475A3/en not_active Withdrawn
  • 2007-01-10 CA CA002573578A patent/CA2573578A1/en not_active Abandoned
  • 2007-01-11 MX MX2007000440A patent/MX2007000440A/es not_active Application Discontinuation
  • 2007-01-12 BR BRPI0700972-0A patent/BRPI0700972A/pt not_active IP Right Cessation
  • 2007-01-12 KR KR1020070003619A patent/KR20070076456A/ko not_active Application Discontinuation
  • 2007-01-12 JP JP2007004532A patent/JP2007186701A/ja not_active Withdrawn

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