WO1998050499A2 - Polyalkylene glycols comme lubrifiant de machines frigorifiques au co¿2? - Google Patents

Polyalkylene glycols comme lubrifiant de machines frigorifiques au co¿2? Download PDF

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Publication number
WO1998050499A2
WO1998050499A2 PCT/DE1998/001196 DE9801196W WO9850499A2 WO 1998050499 A2 WO1998050499 A2 WO 1998050499A2 DE 9801196 W DE9801196 W DE 9801196W WO 9850499 A2 WO9850499 A2 WO 9850499A2
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WIPO (PCT)
Prior art keywords
polyalkylene glycols
composition according
mixtures
operating fluid
fluid composition
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PCT/DE1998/001196
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German (de)
English (en)
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WO1998050499A3 (fr
Inventor
Jörg Fahl
David F. Pipe
Reiner Knickmeyer
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RWE-DEA Aktiengesellschaft für Mineraloel und Chemie
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Priority claimed from DE19719132A external-priority patent/DE19719132A1/de
Priority claimed from DE19719430A external-priority patent/DE19719430C1/de
Application filed by RWE-DEA Aktiengesellschaft für Mineraloel und Chemie filed Critical RWE-DEA Aktiengesellschaft für Mineraloel und Chemie
Priority to DE59808991T priority Critical patent/DE59808991D1/de
Priority to AU82089/98A priority patent/AU8208998A/en
Priority to EP98932037A priority patent/EP0980416B2/fr
Priority to DE19880588T priority patent/DE19880588D2/de
Priority to DK98932037T priority patent/DK0980416T4/da
Publication of WO1998050499A2 publication Critical patent/WO1998050499A2/fr
Publication of WO1998050499A3 publication Critical patent/WO1998050499A3/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
    • 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
    • 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
    • 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
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/008—Lubricant compositions compatible with refrigerants
    • 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
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic 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
    • C10M2207/282—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
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    • 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
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2207/286—Esters of polymerised unsaturated 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
    • 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
    • C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2209/1045—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only 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
    • 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
    • C10M2209/1055—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only 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
    • 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
    • C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
    • C10M2209/1065—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only 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
    • 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
    • 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
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
    • C10M2209/1085—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified 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
    • 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
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • 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
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • C10M2209/1095—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified used as base material
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/32—Wires, ropes or cables lubricants
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/34—Lubricating-sealants
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/36—Release agents or mold release agents
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/38—Conveyors or chain belts
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/40—Generators or electric motors in oil or gas winning field
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/42—Flashing oils or marking oils
    • C—CHEMISTRY; METALLURGY
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/44—Super vacuum or supercritical use
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Definitions

  • the invention relates to equipment compositions containing lubricants based on polyalkylene glycols, which are suitable for the lubrication of refrigeration machines,
  • Heat pumps and related systems such as air conditioning systems that use carbon dioxide as a refrigerant, are suitable.
  • CFCs chlorofluorocarbons
  • Polyalkylene glycols have already been proposed as lubricants for both procedures (see e.g. Lubricants for Carbon Dioxide; U. Hesse, H.O.Spauschus in Ref ⁇ geration Science and Technology, Proceedings, Aarhus Denmark 3-6 Sept. 1996, ISSN 0 151 163).
  • CO 2 behaves very differently with regard to the solubility properties.
  • Subcritical CO 2 is polar, while CO 2 is non-polar in the supercritical range.
  • the polyalkylene glycols according to the invention are soluble in CO 2 for higher mass fractions of lubricants over the entire temperature range from the critical temperature T k to below -55 ° C. With smaller proportions of lubricants, the polyalkylene glycols are no longer or only partially soluble in carbon dioxide.
  • the invention is based on the problem of finding a selection of possible polyalkylene glycols which meet the following requirements for lubricants for CO 2 cooling machines:
  • chillers for the transcritical area are designed to be smaller and smaller often have small diameters in the pipe systems. This requires sufficient mobility of the lubricant in the corresponding temperature range.
  • equipment compositions for refrigeration machines, heat pumps and related systems such as air conditioning systems, containing carbon dioxide as the refrigerant, the refrigerant preferably consisting essentially exclusively of carbon dioxide, and polyalkylene glycols or their mixtures consisting of, in each case based on the polymer chain: (a) at least 40%, preferably 60%, of the monomer units from monomer units of the type - (- CH (CH 3 ) -CH 2 -O -) - and / or - (- CH 2 -CH (CH 3 ) -O -) - and (b) to the remainder essentially from monomer units of the type - (- RO -) -, where R is a linear or branched, saturated alkylene group with 2 to 6 carbon atoms, optionally 1 to Can carry 2 further oxy groups (-O-) and can be different for each monomer unit.
  • the polyalkylene glycols have hydrogen, alkyl, aryl, alkylaryl, aryloxy, alkoxy, alkylaryloxy and / or hydroxyl end groups (c).
  • the end groups of the alkyl or aryl type preferably have 1 to 8, particularly preferably 1 to 4
  • Carbon atoms In the latter case, these are alkyl and / or alkoxy end groups.
  • polyalkylene glycols according to the invention particularly good results are achieved with regard to high density and good lubricating properties on the one hand and the properties listed above on the other hand if the polyalkylene glycol as the main component, namely at least 60%, contains propylene oxide units (monomer units of type (a)).
  • the polyalkylene glycols according to the invention are thus either homopolymers, namely polypropylene glycol (or polypropylene oxide), or copolymers, terpolymers etc., furthermore containing monomer units of type (b).
  • the monomer units can have a statistical distribution or a block structure.
  • the monomer units of type (b) are at least 5% contained in the polymer chain.
  • Monomer units of type (b) are preferably ethylene oxide and / or butylene oxide units.
  • the polyalkylene glycols according to the invention can be prepared by reacting alcohols, including the polyalcohols, as starter compounds with alkylene oxides such as ethylene oxide, propylene oxide and / or butylene oxide. After the reaction, these only have a free hydroxyl group as the end group.
  • Polyalkylene glycols with only one hydroxyl group are preferred over those with two free hydroxyl groups.
  • hygroscopicity and compatibility are polyalkylene glycols, which e.g. after a further etherification step no longer have any free hydroxyl groups.
  • polyalkylene glycols which have average molecular weights from 400 to 3000 g / mol, particularly preferably from 1000 to 2000 g / mol.
  • the polyalkylene glycols according to the invention are distinguished by densities of more than 940 kg / m 3 , and preferably even more than 1000 kg / m 3 , and moreover surprisingly also have the properties listed above which are suitable for use as refrigerating machine oils in combination with carbon dioxide Refrigerants are required.
  • Polyalkylene glycols with a density of over 940 kg / m 3 are particularly suitable under these conditions. Practical tests have shown, however, that those with higher densities, above about 1000 kg / m 3, worked even better. This can be explained by a faster settling of the polyalkylene glycols according to the invention when complete solubility in the carbon dioxide refrigerant is no longer ensured.
  • additives customary in the equipment compositions such as wear improvers, anti-foaming agents, antioxidants such as alkylated phenolic antioxidants such as e.g. in particular Irganox® L101, viscosity index improvers, anti-corrosion agents or high-pressure additives, such as, in particular, phosphate esters.
  • polyalkylene glycols according to the invention can be used together with neopentyl polyol esters as lubricants.
  • neopentyl polyol esters are identified, for example, in German patent application DE 197 19 132 of RWE-DEA Aktiengesellschaft für Mineralöl und Chemie, filed on May 7, 1997.
  • This ester or the ester mixture preferably consists of neopentyl polyol esters of the following type:
  • the polyhydroxy alcohol as the alcohol component may further contain 0 to 4, preferably 0, 1 or 2, ether bridges.
  • the alcohol component is particularly preferred: pentaerythritol and / or dipentaerythritol and / or tripentaerythritol.
  • the operating agent composition contains an ester or an ester mixture, the alcohol component of which, based on the total alcohol group concentration (the ester), consists of at least 50 mol% dipentaerythritol and / or tripentaerythritol. Esters with these alcohol groups have proven particularly useful for refrigeration machines that are operated in the transcritical range.
  • esters or ester mixtures are also preferred, independently of one another, whose acid component according to (l) (a), based on the total carboxylic acid group concentration, consists of at least 60 mol% of n-pentanoic acid; whose acid component according to (l) (b) consists predominantly of branched monocarboxylic acids, particularly preferably of 5 to 40 mol% of branched monocarboxylic acids, based on the total carboxylic acid group concentration.
  • the acid components remaining for the complete esterification of all hydroxyl groups consist of linear C5 to C10 monocarboxylic acids.
  • all the hydroxyl groups of the alcohol component are completely esterified in the ester or the ester mixture.
  • the neopentyl glycol esters according to the invention preferably have densities above 940 kg / m 3 , generally even above 1000 kg / m 3 .
  • the polyalkylene glycols according to the invention can be used together with neopentyl polyol esters as lubricants, which predominantly, i.e. greater than 90%, preferably about 100%, have branched C5 to C10 acid groups, particularly preferably branched C8 to C10 acid groups.
  • neopentyl polyol esters having branched C5 to C10 acid groups, particularly preferably branched C8 to C10 acid groups.
  • the proportion of the polyalkylene glycols according to the invention is preferably at least 20% by weight, particularly preferably at least 40% by weight, based on the proportion of lubricant (i.e. the lubricants without refrigerants and additives) in the operating agent composition.
  • lubricant i.e. the lubricants without refrigerants and additives
  • lubricant is preferably 20 to 60% by weight, particularly preferably 40 to 60% by weight, in each case based on the lubricant content in the operating agent composition.
  • FIG. 1 shows the viscosity / vapor pressure / temperature behavior of a mixture of carbon dioxide and the polyalkylene glycol Triton GL-220 from DEA Mineraloel AG (butanol-started polypropylene oxide).

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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

La présente invention porte sur des composés de carburant comprenant du lubrifiant à base de polyalkylène glycols, qui conviennent pour lubrifier des machines frigorifiques, des pompes à chaleur et des installations apparentées, pour lesquelles le carburant requis est du dioxyde de carbone.
PCT/DE1998/001196 1997-05-07 1998-04-29 Polyalkylene glycols comme lubrifiant de machines frigorifiques au co¿2? WO1998050499A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DE59808991T DE59808991D1 (de) 1997-05-07 1998-04-29 Polyalkylenglykole als schmiermittel für co 2-kältemaschinen
AU82089/98A AU8208998A (en) 1997-05-07 1998-04-29 Polyalkylene glycols as lubricants for co2-based refrigerating machines
EP98932037A EP0980416B2 (fr) 1997-05-07 1998-04-29 Polyalkylene glycols comme lubrifiant de machines frigorifiques au co 2
DE19880588T DE19880588D2 (de) 1997-05-07 1998-04-29 Polyalkylenglykole als Schmiermittel für CO¶2¶-Kältemaschinen
DK98932037T DK0980416T4 (da) 1997-05-07 1998-04-29 Polyalkylenglycoler som smöremidler til CO2-kuldemaskiner

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19719132A DE19719132A1 (de) 1997-05-07 1997-05-07 Polyol-Ester als Schmiermittel für CO¶2¶-Kältemaschinen
DE19719132.0 1997-05-07
DE19719430A DE19719430C1 (de) 1997-05-12 1997-05-12 Polyalkylenglykole als Schmiermittel für CO¶2¶-Kältemaschinen
DE19719430.3 1997-05-12

Publications (2)

Publication Number Publication Date
WO1998050499A2 true WO1998050499A2 (fr) 1998-11-12
WO1998050499A3 WO1998050499A3 (fr) 1999-02-04

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PCT/DE1998/001196 WO1998050499A2 (fr) 1997-05-07 1998-04-29 Polyalkylene glycols comme lubrifiant de machines frigorifiques au co¿2?

Country Status (6)

Country Link
EP (1) EP0980416B2 (fr)
AR (1) AR012666A1 (fr)
AU (1) AU8208998A (fr)
DE (2) DE19880588D2 (fr)
DK (1) DK0980416T4 (fr)
WO (1) WO1998050499A2 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1008643A3 (fr) * 1998-12-11 2000-12-06 Idemitsu Kosan Company Limited Composition d'huile pour machines frigorifiques et methode pour l'emploi de la composition pour lubrifier
EP1063279A1 (fr) * 1999-06-21 2000-12-27 Idemitsu Kosan Co., Ltd. Huile pour refrigerateur utilisant le dioxide de carbone comme refrigérant et procédé de son utilisation comme lubrifiant
EP1132457A2 (fr) * 2000-03-10 2001-09-12 Sanyo Electric Co. Ltd Machine frigorifique utilisant du dioxyde de carbone comme réfrigérant
EP1199348A1 (fr) * 2000-10-17 2002-04-24 Nippon Mitsubishi Oil Corporation Composition lubrifiante pour réfrigérant à base de CO2 utilisée dans une machine réfrigérante
EP1209357A1 (fr) * 1999-08-31 2002-05-29 Sanyo Electric Co., Ltd. Compresseur entraine par un moteur en enceinte fermee
EP1243639A1 (fr) * 1999-12-28 2002-09-25 Idemitsu Kosan Co., Ltd. Composition lubrifiante pour refrigerant a base de dioxyde de carbone utilisee dans une machine frigorifique
WO2003074641A1 (fr) * 2002-03-07 2003-09-12 Clariant Gmbh Polyalkyleneglycols thermiquement stables utilises comme lubrifiants pour machines frigorifiques
JP2014065923A (ja) * 2014-01-07 2014-04-17 Jx Nippon Oil & Energy Corp 二酸化炭素冷媒用冷凍機油及び冷凍機用流体組成物

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WO2006068664A2 (fr) 2004-07-13 2006-06-29 Tiax Llc Systeme et procede de refrigeration
US7811071B2 (en) 2007-10-24 2010-10-12 Emerson Climate Technologies, Inc. Scroll compressor for carbon dioxide refrigerant

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EP0017072A2 (fr) * 1979-04-02 1980-10-15 The Dow Chemical Company Lubrifiant résistant à l'eau pour compresseurs et moteurs marins
EP0421765A1 (fr) * 1989-10-03 1991-04-10 Tonen Corporation Polyoxyalkylène éthers comme lubrifiants pour réfrigerant à base d'alcane halogéné

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JP2588287B2 (ja) † 1989-02-22 1997-03-05 日本石油株式会社 冷凍機油組成物
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GB9516909D0 (en) † 1995-08-18 1995-10-18 Ici Plc Refrigerant compositions
JP4079469B2 (ja) * 1996-06-25 2008-04-23 出光興産株式会社 冷凍機油組成物
JP3271905B2 (ja) * 1996-08-06 2002-04-08 出光興産株式会社 冷凍機用潤滑油組成物
GB9618207D0 (en) * 1996-08-30 1996-10-09 Ici Plc Refrigerant compositions
AU730693B2 (en) * 1996-11-27 2001-03-15 Idemitsu Kosan Co. Ltd Lubricating oil composition for refrigerators and method for lubrication with the composition
TW385332B (en) * 1997-02-27 2000-03-21 Idemitsu Kosan Co Refrigerating oil composition

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EP0017072A2 (fr) * 1979-04-02 1980-10-15 The Dow Chemical Company Lubrifiant résistant à l'eau pour compresseurs et moteurs marins
EP0421765A1 (fr) * 1989-10-03 1991-04-10 Tonen Corporation Polyoxyalkylène éthers comme lubrifiants pour réfrigerant à base d'alcane halogéné

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Title
"Lubricants for carbon dioxide"; U.Hesse, H.O.Spauschus in "Refrigeration Science and Technology", Proceedings, Aarhus (DK),3-6Sept.1996, ISSN 0151 1637. XP002081402 in der Anmeldung erwähnt *
PATENT ABSTRACTS OF JAPAN vol. 098, no. 006, 30. April 1998 & JP 10 046169 A (IDEMITSU KOSAN CO LTD), 17. Februar 1998 *
See also references of EP0980416A2 *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6263683B1 (en) 1998-12-11 2001-07-24 Idemitsu Kosan Co., Ltd. Refrigerator oil composition, and method of using the composition for lubrication
EP2325290A1 (fr) * 1998-12-11 2011-05-25 Idemitsu Kosan Co., Ltd. Composition d'huile pour machines frigorifiques et methode pour l'emploi de la composition pour lubrifier
EP1008643A3 (fr) * 1998-12-11 2000-12-06 Idemitsu Kosan Company Limited Composition d'huile pour machines frigorifiques et methode pour l'emploi de la composition pour lubrifier
US6354094B2 (en) 1998-12-11 2002-03-12 Idemitsu Kosan Co., Ltd. Refrigerator oil composition, and method of using the composition for lubrication
EP1063279A1 (fr) * 1999-06-21 2000-12-27 Idemitsu Kosan Co., Ltd. Huile pour refrigerateur utilisant le dioxide de carbone comme refrigérant et procédé de son utilisation comme lubrifiant
US6306803B1 (en) 1999-06-21 2001-10-23 Idemitsu Kosan Co., Ltd. Refrigerator oil for carbon dioxide refrigerant, and method of using it for lubrication
EP1491616A1 (fr) * 1999-06-21 2004-12-29 Idemitsu Kosan Co., Ltd. Huile pour réfrigérateur utilisant le dioxide de carbone comme réfrigérant et procédé de son utilisation comme lubrifiant
EP1209357A4 (fr) * 1999-08-31 2007-10-10 Sanyo Electric Co Compresseur entraine par un moteur en enceinte fermee
EP1209357A1 (fr) * 1999-08-31 2002-05-29 Sanyo Electric Co., Ltd. Compresseur entraine par un moteur en enceinte fermee
US6759373B2 (en) 1999-12-28 2004-07-06 Idemitsu Kosan Co., Ltd. Refrigerating machine oil composition for carbon dioxide refrigerant
EP1243639A1 (fr) * 1999-12-28 2002-09-25 Idemitsu Kosan Co., Ltd. Composition lubrifiante pour refrigerant a base de dioxyde de carbone utilisee dans une machine frigorifique
EP1243639A4 (fr) * 1999-12-28 2003-06-11 Idemitsu Kosan Co Composition lubrifiante pour refrigerant a base de dioxyde de carbone utilisee dans une machine frigorifique
EP1132457A3 (fr) * 2000-03-10 2001-12-19 Sanyo Electric Co. Ltd Machine frigorifique utilisant du dioxyde de carbone comme réfrigérant
EP1795570A2 (fr) 2000-03-10 2007-06-13 Sanyo Electric Co., Ltd. Machine frigorifique utilisant du dioxyde de carbone comme réfrigérant
EP1790712A3 (fr) * 2000-03-10 2007-10-17 Sanyo Electric Co., Ltd. Réfrigération utilisant du dioxyde de carbone comme réfrigérant
EP1795570A3 (fr) * 2000-03-10 2007-10-17 Sanyo Electric Co., Ltd. Machine frigorifique utilisant du dioxyde de carbone comme réfrigérant
EP1132457A2 (fr) * 2000-03-10 2001-09-12 Sanyo Electric Co. Ltd Machine frigorifique utilisant du dioxyde de carbone comme réfrigérant
US6936576B2 (en) 2000-10-17 2005-08-30 Nippon Mitsubishi Oil Corporation Refrigerating machine oil, and fluid composition for refrigerating machine
EP1199348A1 (fr) * 2000-10-17 2002-04-24 Nippon Mitsubishi Oil Corporation Composition lubrifiante pour réfrigérant à base de CO2 utilisée dans une machine réfrigérante
WO2003074641A1 (fr) * 2002-03-07 2003-09-12 Clariant Gmbh Polyalkyleneglycols thermiquement stables utilises comme lubrifiants pour machines frigorifiques
JP2014065923A (ja) * 2014-01-07 2014-04-17 Jx Nippon Oil & Energy Corp 二酸化炭素冷媒用冷凍機油及び冷凍機用流体組成物

Also Published As

Publication number Publication date
WO1998050499A3 (fr) 1999-02-04
DK0980416T4 (da) 2009-10-12
AR012666A1 (es) 2000-11-08
DE19880588D2 (de) 2000-04-13
EP0980416A2 (fr) 2000-02-23
EP0980416B1 (fr) 2003-07-09
AU8208998A (en) 1998-11-27
EP0980416B2 (fr) 2009-06-10
DK0980416T3 (da) 2003-10-20
DE59808991D1 (de) 2003-08-14

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