EP0997519A1 - Kältemaschinenöl - Google Patents

Kältemaschinenöl Download PDF

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Publication number
EP0997519A1
EP0997519A1 EP99850142A EP99850142A EP0997519A1 EP 0997519 A1 EP0997519 A1 EP 0997519A1 EP 99850142 A EP99850142 A EP 99850142A EP 99850142 A EP99850142 A EP 99850142A EP 0997519 A1 EP0997519 A1 EP 0997519A1
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EP
European Patent Office
Prior art keywords
carbon atoms
group
acid
ester
refrigerating machine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99850142A
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English (en)
French (fr)
Inventor
Hiroyuki Nippon Mitsubishi Oil Corp. Hirano
Yuji c/o Nippon Mitsubishi Oil Corp. Shimomura
Satoshi c/o Nippon Mitsubishi Oil Corp. Suda
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eneos Corp
Original Assignee
Nippon Mitsubishi Oil Corp
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Publication date
Application filed by Nippon Mitsubishi Oil Corp filed Critical Nippon Mitsubishi Oil Corp
Publication of EP0997519A1 publication Critical patent/EP0997519A1/de
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    • 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
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    • 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
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    • C10M107/22—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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    • 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
    • C10M2209/1095—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • 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
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates

Definitions

  • This invention relates to refrigerating machine oils, and more particularly to refrigerating machine oils useful for refrigerating machines using a refrigerant containing dimethyl ether (DME).
  • DME dimethyl ether
  • an object of the present invention is to provide a refrigerating machine oil which can be used with a DME refrigerant and is superior in lubricity, miscibility with a refrigerant and safety.
  • a refrigerating machine oil for use with a dimethyl ether (DME) refrigerant, which oil comprises an oxygen-containing synthetic oil.
  • DME dimethyl ether
  • the refrigerating machine oil according to the present invention comprises an oxygen-containing synthetic oil.
  • Eligible oxygen-containing synthetic oils for the present invention are an ester, an polyoxyalkylene glycol, a polyvinyl ether, a ketone, a polyphenyl ether, silicone, a polysiloxane and a perfluoro ether, among which an ester, a polyoxyalkylene glycol, a polyvinyl ether and a mixture thereof are preferred.
  • Eligible esters are an aromatic ester, a dibasic ester, a polyol ester, a complex ester, a polyol carbonate and a mixture thereof.
  • the aromatic ester may be an ester of an aromatic carboxylic acid having 1 to 6, preferably 1 to 4, more preferably 1 to 3 valences and an aliphatic alcohol having 1 to 18, preferably 1 to 12 carbon atoms.
  • aromatic carboxylic acid having 1 to 6 valences are benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, pyromellitic acid and a mixture thereof.
  • the aliphatic alcohol having 1 to 18 carbon atoms may be straight-chain or branched.
  • aliphatic alcohols are methanol, ethanol, straight or branched propanol, straight or branched butanol, straight or branched pentanol, straight or branched hexanol, straight or branched heptanol, straight or branched octanol, straight or branched nonanol, straight or branched decanol, straight or branched undecanol, straight or branched dodecanol, straight or branched tridecanol, straight or branched tetradecanol, straight or branched pentadecanol, straight or branched hexadecanol, straight or branched heptadecanol, straight or branched octadecanol and a mixture thereof.
  • aromatic ester examples include dibutyl phthalate, di(2-ethylhexyl)phathalate, dinonyl phthalate, didecyl phthalate, didodecyl phthalate, ditridecyl phthalate, tributyl trimellitate, tri(2-ethylhexyl) trimellitate, trinonyl trimellitate, tridecyl trimellitate, tridodecyl trimellitate and tritridecyl trimellitate.
  • an aromatic carboxylic acid having at least two valences when used, it may be a simple ester made from one kind of an aliphatic alcohol or a complex ester made from at least two kinds of aliphatic alcohols.
  • the dibasic ester may be an ester obtained by reacting a dibasic acid having 5 to 10 carbon atoms such as glutamic acid, adipic acid, pimelic acid, suberic acid, azealic acid or sebacic acid with a monohydric alcohol having 1 to 15 carbon atoms and a straight or branched alkyl group, such as methanol, ethanol, propanol, butanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol or pentadecanol, or a mixture of these esters.
  • a dibasic acid having 5 to 10 carbon atoms such as glutamic acid, adipic acid, pimelic acid, suberic acid, azealic acid or sebacic acid
  • ester examples include ditridecyl glutarate, di2-ethylhexyl adipate, diisodecyl adipate, ditridecyl adipate, di2-ethylhexyl sebacate and a mixture thereof.
  • the polyol esters may be an ester of a diol or a polyol having 3 to 20 hydroxyl groups and a fatty acid having 6 to 20 carbon atoms.
  • the diol are ethylene glycol, 1,3-propanediol, propylene glycol, 1,4-butane diol, 1,2-butane diol, 2-methyl-1,3-propane diol, 1,5-pentane diol, neopentyl glycol, 1,6-hexane diol, 2-methyl-2-methyl-1,3-propane diol, 1,7-heptane diol, 2-methylol-2-propyl-1,3-propane diol, 2,2-diethyl-1,3-propane diol, 1,8-octane diol, 1,9-nonane diol, 1,10-decane diol, 1,11-undecane diol and 1,12-dodecane
  • polyol examples include polyalcohols such as trimethylol ethane, trimethylol propane, trimethylol butane, di-(trimethylol propane), tri-(trimethylol propane), pentaerythritol, di-(pentaerythritol), tri-(penthaerythritol), glycerin, polyglycerin (glycerin dimers to icosomer), 1,3,5-penthaerythritol, sorbitol, sorbitan, sorbitol-glycerin condensate, adonitol, arabitol, xylitol and mannitol; saccharides such as xylose, arabinose, ribose, rhamnose, glucose, fructose, galactose, mannose, sorbose, cellobiose, maltose, isomaltose, trehalose, sucrose,
  • preferred polyol esters are ester of hindered alcohols such as neopentyl glycol, trimethylol ethane, trimethylol propane, trimethylol butane, di-(trimethylol propane), tri-(trimethylol propane), penthaerythritol, di-(pentaerythritol) and tri-(penthaerythritol).
  • hindered alcohols such as neopentyl glycol, trimethylol ethane, trimethylol propane, trimethylol butane, di-(trimethylol propane), tri-(trimethylol propane), penthaerythritol, di-(pentaerythritol) and tri-(penthaerythritol).
  • a fatty acid having 1 to 24 carbon atoms is usually used.
  • fatty acids preferred are those having more than 3 carbon atoms, more preferred are those having more than 4 carbon atoms, further more preferred are those having more than 5 carbon atoms, and the most preferred are those having more than 10 carbon atoms in view of lubricity.
  • preferred fatty acids are those having fewer than 18 carbon atoms, more preferred are those having fewer than 12 carbon atoms, further more preferred are those having fewer than 9 carbon atoms.
  • the fatty acids may be of straight-chain or branched type. In view of lubricity, preferred are straight fatty acids, while in view of hydrolysis stability, preferred are branched fatty acids.
  • the fatty acids may be saturated or unsaturated ones.
  • fatty acid examples include pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, icosanoic acid and oleic acid, all of which may be straight or branched; or a neo acid where ⁇ carbon atom thereof is quarternary.
  • fatty acid More specific examples of the fatty acid are valeric acid (n-pentanoic acid), caproic acid (n-hexanoic acid), enathic acid (n-heptanoic acid), caprylic acid (n-octanoic acid), pelargonic acid (n-nonanoic acid), oleic acid (cis-9-octadecenoic acid), isopentanoic acid (3-methylbutanoic acid), 2-methylhexanoic acid, 2-ethylpentanoic acid, 2-ethylhexanoic acid and 3,5,5-trimethylhexanoic acid.
  • the polyol ester may be a partial ester having the hydroxyl groups of the polyol remaining unesterified, a full ester having the hydroxyl groups, all of which are esterified or a mixture of the partial ester and the full ester. Preferred are full esters.
  • a complex ester used herein denotes an ester obtained by reacting a fatty acid and a dibasic acid with a monohydric alcohol and a polyol.
  • Specific examples of eligible fatty acids, dibasic acids, monohydric alcohols and polyols for the complex ester are the same as those exemplified above with respect to the dibasic esters and the polyol esters.
  • a carbonic ester used herein denotes those having the following carbonic ester structure in its molecules;
  • the carbonic ester may contain one or more of the above structures per molecule.
  • Eligible alcohols for the carbonate ester are the above-exemplified aliphatic alcohols or polyols or may be polyglycol and products which can be obtained by the addition reaction of polyglycol with polyol.
  • esters used herein may be those made from one kind of an ester of single structure or a mixture made from at least two kinds of esters having different structures.
  • esters preferred are polyol esters and carbonic esters.
  • esters of hindered alcohols such as neopentyl glycol, trimethylolethane, trimethylolpropane, trimethylolbutane, di-(trimethylolpropane), tri-(trimethylolpropane), pentaerythritol, di-(pentaerythritol) and tri-(pentaerythritol) and more preferred are esters of neopentyl glycol, trimethylolethane, trimethylolpropane, trimethylolbutane or penthaerythritol, in view of superior hydrolytic stability. Most preferred is an ester of penthaerythritol in view of particular superiority in miscibility with a refrigerant and hydrolytic stability.
  • preferred polyol esters are diesters of neopentyl glycol and at least one member selected from valeric acid, caproic acid, enathic acid, caprylic acid, pelargonic acid, capric acid, oleic acid, isopentanoic acid, 2-methylhexanoic acid, 2-ethylpentanoic acid, 2-ethylhexanoic acid and 3,5,5-trimethylhexanoic acid; triesters of trimethylolethane and at least one member selected from valeric acid, caproic acid, enathic acid, caprylic acid, pelargonic acid, capric acid, oleic acid, isopentanoic acid, 2-methylhexanoic acid, 2-ethylpentanoic acid, 2-ethylhexanoic acid and 3,5,5-trimethylhexanoic acid; triesters of trimethylolpropane and at least one member selected from valeric acid, caproic
  • the esters comprising more than two kinds of fatty acids may be a mixture of more than two kinds of esters of one kind of fatty acid and polyol, or an ester of mixed fatty acids of more than two kinds and polyols.
  • the esters of polyol and more than two kinds of fatty acids, particularly mixed fatty acids are superior in characteristics in low temperatures and miscibility with a refrigerant.
  • X 1 is a hydrogen atom, an alkyl group, a cycloalkyl group or a group represented by Formula (2).
  • the alkyl group has generally 1 to 24, preferably 1 to 18, more preferably 1 to 12 carbon atoms.
  • the alkyl group may be straight-chain or branched.
  • alkyl group examples are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, straight or branched pentyl, straight or branched hexyl, straight or branched heptyl, straight or branched octyl, straight or branched nonyl, straight or branched decyl, straight or branched undecyl, straight or branched dodecyl, straight or branched tridecyl, straight or branched tetradecyl, straight or branched pentadecyl, straight or branched hexadecyl, straight or branched heptadecyl, straight or branched octadecyl, straight or branched nonadecyl, straight or branched icosyl, straight or branched heneicosyl, straight
  • cycloalkyl groups are cyclopentyl, cyclohexyl and cycloheptyl groups.
  • a 3 is an alkylene group having 2 to 24 carbon atoms.
  • Specific examples of the alkylene group are ethylene, propylene, trimethylene, butylene, tetramethylene, 1-methyltrimethylene, 2-methyltrimethylene, 1,1-dimethylethylene and 1,2-dimethylethylene group.
  • Y 2 is a hydrogen atom, an alkyl group or a cycloalkyl group.
  • the alkyl group has generally 1 to 24, preferably 1 to 18, more preferably 1 to 12 carbon atoms.
  • the alkyl group may be straight-chain or branched. Specific examples of such alkyl groups are those exemplified with respect to X 1 .
  • cycloalkyl groups are cyclopentyl, cyclohexyl and cycloheptyl groups.
  • Y 2 is preferably a hydrogen atom or an alkyl group having 1 to 12 carbon atoms and is more preferably a hydrogen atom or methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl, n-hexyl, iso-hexyl, n-heptyl, iso-heptyl, n-octyl, iso-octyl, n-nonyl, iso-nonyl, n-decyl, iso-dceyl, n-undecyl, iso-undecyl, n-dodecyl or iso-dodecyl group.
  • e is an integer of 1 to 50.
  • X 1 is preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or a group represented by Formula (2).
  • Preferred examples of X 1 are hydrogen atom, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl, n-hexyl, iso-hexyl, n-heptyl, iso-heptyl, n-octyl, iso-octyl, n-nonyl, iso-nonyl, n-decyl, iso-dceyl, n-undecyl, iso-undecyl, n-dodecyl or iso-dodecyl group and a group represented by Formula (2).
  • the compounds having 3 to 20 hydroxyl groups and providing a residue for B are the above-exemplified polyols.
  • a 1 and A 2 may be the same or different and are each independently a alkylene group having 2 to 4 carbon atoms.
  • Specific examples of the alkylene group are ethylene, propylene, trimethylene, butylene, tetramethylene, 1-methyltrimethylene, 2-methyltrimethylene, 1,1-dimethylethylene and 1,2-dimethylethylene.
  • Y 1 is a hydrogen atom, an alkyl group or a cycloalkyl group.
  • the alkyl group has generally 1 to 24, preferably 1 to 18, more preferably 1 to 12 carbon atoms.
  • the alkyl group may be of straight or branched chain type. Specific examples of such alkyl groups are those exemplified with respect to X 1 .
  • cycloalkyl group examples include cyclopentyl, cyclohexyl and cycloheptyl groups.
  • Y 1 is preferably a hydrogen atom or an alkyl group having 1 to 12 carbon atoms and is more preferably a hydrogen atom or methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl, n-hexyl, iso-hexyl, n-heptyl, iso-heptyl, n-octyl, iso-octyl, n-nonyl, iso-nonyl, n-decyl, iso-dceyl, n-undecyl, iso-undecyl, n-dodecyl or iso-dodecyl group.
  • c, d and e indicate the degree of polymerization at the polyoxyalkylene sites. These polyoxyalkylene sites may be the same or different. In the case where a plurality of different polyoxyalkylene group are contained, there is no restriction imposed on the polymerization form of oxyalkylene groups and thus it may be random polymerization or block polymerization.
  • the carbonate esters for use in the present invention may be obtained by reacting polyalkylene glycol polyolether produced by the addition reaction between a polyol compound and alkyleneoxide, with chloroformate in the presence of an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide, an alkali metal alkoxide such as sodium methoxide and sodium ethoxide or an alkali such as metal sodium at a temperature of 0 to 30 °C.
  • an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide
  • an alkali metal alkoxide such as sodium methoxide and sodium ethoxide
  • an alkali such as metal sodium at a temperature of 0 to 30 °C.
  • the carbonic ester may be obtained by reacting polyalkylene glycol polyol ester in the presence of the source of carbonic acid such as carbonic acid diester and phosgen, an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide, an alkali metal alkoxide such as sodium methoxide and sodium ethoxide or an alkali such as metal sodium at a temperature of 80 to 150 °C. After this, free hydroxyl groups are etherified as required.
  • the source of carbonic acid such as carbonic acid diester and phosgen
  • an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide
  • an alkali metal alkoxide such as sodium methoxide and sodium ethoxide or an alkali such as metal sodium
  • the product derived from the materials mentioned above may be subjected to refining treatment for removing the by-products and unreacted substances if any.
  • refining treatment for removing the by-products and unreacted substances if any.
  • small amounts of such by-products and unreacted substances may be present as long as they do not hinder the excellent characteristics of the inventive lubricating oil.
  • carbonic ester may be used singlely or in the form of a mixture.
  • molecular weight of the carbonate esters used in the present invention there is no particular restriction on the molecular weight of the carbonate esters used in the present invention.
  • the carbonic ester used in the present invention has a kinematic viscosity at 100 °C of preferably 2 to 150 mm 2 /s, more preferably 4 to 100 mm 2 /s.
  • Eligible polyoxyalkylene glycols for the refrigerating machine oil of the present invention are a compound represented by the formula R 1 -[(OR 2 ) f ⁇ OR 3 ] g wherein R 1 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an acyl group having 2 to 10 carbon atoms or a residue of a compound having 2 to 8 hydroxyl groups, R 2 is an alkylene group having 2 to 4 carbon atoms, R 3 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an acyl group having 2 to 10 carbon atoms, f is an integer of 1 to 80 and g is an integer of 1 to 8.
  • the alkyl group for R 1 and R 3 in Formula (3) may be of straight-chain type, branched type or cyclic type. Specific examples of such alkyl groups are methyl, ethyl, n-propyl, straight or branched butyl, straight or branched pentyl, straight or branched hexyl, straight or branched heptyl, straight or branched octyl, straight or branched nonyl, straight or branched decyl, cyclopentyl and cyclohexyl groups. Alkyl groups having more than 10 carbon atoms are not preferred because of their poor miscibility with a refrigerant, leading to phase separation. Therefore, preferred alkyl groups are those having 1 to 6 carbon atoms.
  • the alkyl group of the acyl group for R 1 and R 3 may be of straight-chain type, branched type or cyclic type. Specific examples of such alkyl groups are the above exemplified alkyl groups having 1 to 9 carbon atoms. Acyl groups having more than 10 carbon atoms are not preferred because of its poor miscibility with a refrigerant, leading to the phase separation thereof. Therefore, preferred acyl groups are those having 2 to 6 carbon atoms.
  • R 1 and R 3 may be the same or different from each other. Furthermore, R 1 and R 3 may be the same or different in the same molecule when g is 2 or greater.
  • R 1 is a residue of a compound having 2 to 8 carbon atoms
  • the compound may be chain or cyclic ones.
  • Specific examples of the compound having 2 hydroxyl groups are ethylene glycol, 1,3-propanediol, propylene glycol, 1,4-butanediol, 1,2-butanediol, 2-methyl-1,3-propanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 2-ethyl-2-methyl-1,3-propanediol, 1,7-heptanediol, 2-methyl-2-propyl-1,3-propanediol,2,2-diethyl-1,3-propanediol, 1,8-ocatnediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol and 1,12-
  • the compound having 3 to 8 hydroxyl groups are polyhydric alcohols such as trimethylolethane, trimethylolpropane, trimethylolbutane, di-(timethylolpropane), tri-(trimethylolethane), pentaerythritol, di-(pentaerythritol), tri-(pentaerythritol), glycerin, polyglycerin (dimer to icosamer consisting of 2 to 20 glycerin monomers), 1,3,5-pentanetriol, sorbitol, sorbitan, sorbitol-glycerin condensate, adonitol, arabitol, xylitol and mannitol; saccharides such as xylose, arabinose, ribose, rhamnose, glucose, fructose, galactose, mannose, sorbose, cellobiose, maltose
  • a residue of a compound having hydroxyl groups denotes a residue other than the hydroxyl groups.
  • R 1 or R 3 is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms, particularly preferably methyl group in view of viscosity characteristics. Furthermore, for the same reason, both R 1 and R 3 are preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms, particularly preferably methyl group.
  • R 2 in Formula (3) is an alkylene group having 2 to 4 carbon atoms, such as ethylene, propylene and butylene groups.
  • the oxyalkylene group which is a repeating unit represented by (OR 2 ) may be oxyethylene, oxypropylene and oxybutylene groups.
  • the same oxyalkylene groups or more than two different kinds oxyalkylene groups may be present in the same molecule.
  • the polyoxyalkylene glycol is preferably a copolymer containing an oxyethylene group (EO) and an oxypropylene group (PO).
  • EO oxyethylene group
  • PO oxypropylene group
  • the value of EO / (PO + EO) is within the range of preferably 0.1 to 0.8, more preferably 0.3 to 0.6 in view of seizure load and viscosity characteristics.
  • the value of EO / (PO + EO) is within the range of preferably 0 to 0.5, more preferably 0 to 0.2, most preferably 0, in other words, a homopolymer of oxypropylene .
  • f is an integer of 1 to 80 and g is an integer of 1 to 8. If R 1 is an alkyl group or an acyl group, g is 1. If R 1 is a residue of a compound having 2 to 8 hydroxyl groups, g indicates the number of the hydroxyl groups.
  • the average value of f x g is preferably to be 6 to 80 so as to fulfill the above described requirements as a refrigerating machine oil.
  • the polyoxyalkylene glycol of Formula (3) encompasses those having in its terminal ends hydroxyl groups.
  • Such polyoxyalkylene glycols may be used for the inventive lubricating oil if the hydroxyl groups are contained in such an amount that the ratio thereof to all of the end groups is less than 50 mol percent.
  • the hydroxyl group content exceeding 50 mol percent is not preferable because the resulting oil is increased in hygroscopicity and reduced in viscosity index.
  • the polyoxyalkylene glycol used for the present invention is preferably a polyoxypropylene glycol dimethyl ether represented by the formula CH 3 O ⁇ (C 3 H 6 O) h -CH 3 wherein h is an integer of 6 to 8; or a polyoxyethylene polyoxypropylene glycol dimethyl ether represented by the formula CH 3 O ⁇ (C 3 H 6 O) i ⁇ (C 2 H 4 O) j ⁇ CH 3 wherein i and j are each an integer of greater than 1 but are such an integer that the total of i and j is within the range of 6 to 80, in view of being economical and effective; and is preferably a polyoxypropyleneglycol monobutyl ether represented by the formula C 4 H 9 O ⁇ (C 3 H 6 O) k -H wherein k is an integer of 6 to 80; and a poloxypropylene glycol diacetate, in view of being economical.
  • the polyoxyalkylene glycol may be a polyoxyalkylene glycol derivative having at least one constituting unit represented by the formula wherein R 4 through R 7 are each independently a hydrogen atom, a monovalent hydrocarbon group having 1 to 10 carbon atoms or a group represented by the formula wherein R 8 and R 9 are each independently a hydrogen atom, a monovalent hydrocarbon group having 1 to 10 carbon atoms or an alkoxyalkyl group having 2 to 20 carbon atoms, R 10 is an alkylene group having 2 to 5 carbon atoms, an alkyl-substituted alkylene group having 2 to 5 carbon atoms in total or an alkoxyalkyl-substituted alkylene group having 4 to 10 carbon atoms in total, p is an integer of 0 to 20 and R 11 is a monovalent hydrocarbon group having 1 to 10 carbon atoms; and at least one of R 4 through R 7 is a group represented by Formula (8).
  • R 4 through R 7 are each independently a hydrogen atom, a monovalent hydrocarbon group having 1 to 10 carbon atoms or a group represented by Formula (8).
  • monovalent hydrocarbon groups are a straight or branched alkyl group having 1 to 10 carbon atoms, a straight or branched alkenyl group having 2 to 10 carbon atoms, a cycloalkyl or alkylcycloalkyl group having 5 to 10 carbon atoms, an aryl or alkylaryl group having 6 to 10 carbon atoms and an arylalkyl group having 7 to 10 carbon atoms.
  • preferred are monovalent hydrocarbon groups having fewer than 6 carbon atoms and most preferred are those having fewer than 3 carbon atoms, such as methyl, ethyl, n-propyl and isopropyl.
  • R 8 and R 9 are each independently a hydrogen atom, a monovalent hydrocarbon group having 1 to 10 carbon atoms or an alkoxyalkyl group having 2 to 20 carbon atoms, among which an alkyl group having fewer than 3 carbon atoms and an alkoxyalkylene group having fewer than 6 carbon atoms are preferred.
  • alkyl groups are methyl, ethyl, n-propyl and isopropyl groups.
  • alkoxyalkylene groups are methoxymethyl, ethoxymethyl, n-propoxymetyhyl, isopropoxymethyl, n-butoxymethyl, isobutoxymethyl, sec-butoxymethyl, tert-butoxymethyl, pentoxymethyl (including all isomers), methoxyethyl (including all isomers), ethoxyethyl (including all isomers), propoxyethyl (including all isomers), butoxyethyl (including all isomers), methoxypropyl (including all isomers), ethoxypropyl (including all isomers), propoxypropyl (including all isomers), methoxybutyl (including all isomers), ethoxybutyl (including all isomers) and methoxypentyl groups (including all isomers).
  • R 10 is an alkylene group having 2 to 5 carbon atoms, an alkyl-substituted alkylene group having 2 to 5 carbon atoms in total or an alkoxyalkyl-substituted alkylene group having 4 to 10 carbon atoms in total, preferably an alkylene group having 2 to 4 carbon atoms or a substituted ethylene group having fewer than 6 carbon atoms.
  • Specific examples of such an alkylene group are ethylene, propylene and butylenes groups.
  • Such a substituted ethylene group are 1-(methoxymethyl)ethylene, 2-(methoxymethyl)ethylene, 1-(methoxyethyl)ethylene, 2-(methoxyethyl)ethylene, 1-(ethoxymethyl)ethylene, 2-(ethoxymethyl)ethylene, 1-methoxymethyl-2-methylethylene, 1,1-bis(methoxymethyl)ethylene, 2,2-bis(methoxymethyl)ethylene, 1,2-bis(methoxymethyl)ethylene, 1-methyl-2-methoxymethylethylene, 1-methoxymethyl-2-methylethylene, 1-ethyl-2-methoxymethylethylene, 1-methoxymethyl-2-ethylethylene, 1-methyl-2-ethoxymethylethylene, 1-ethoxymethyl-2-methylethylene, 1-methyl-2-methoxyethylethylene and 1-methoxyethyl-2-methylethylene groups.
  • R 11 is a monovalent hydrocarbon group having 1 to 10 carbon atoms.
  • a hydrocarbon group are a straight or branched alkyl group having 1 to 10 carbon atoms, a straight or branched alkenyl group having 2 to 10 carbon atoms, a cycloalkyl or alkylcycloalkyl group having 5 to 10 carbon atoms, an aryl or alkylaryl group having 6 to 10 carbon groups and an arylalkyl group having 7 to 10 carbon atoms.
  • preferred are monovalent hydrocarbon groups having fewer than 6 carbon atoms and particularly preferred are alkyl groups having fewer than 3 carbon atoms, such as methyl, ethyl and n-propyl groups.
  • R 4 through R 7 is a group represented by the Formula (8).
  • R 4 or R 6 is a group represented by Formula (8), and the other and R 5 and R 7 are each a hydrogen atom or a monovalent hydrocarbon having 1 to 10 carbon atoms.
  • the above-described polyoxyalkylene glycol derivative contains at least one constituting unit represented by Formula (7). More specifically, the polyoxyalkylene glycol derivative may be largely classified into three types: (i) a homopolymer comprising the constituting unit represented by Formula (7), (ii) a copolymer comprising two or more different constituting units represented by Formula (7) and (iii) a copolymer comprising the constituting unit represented by Formula (7) and another constituting unit such as those represented by the formula wherein R 12 through R 15 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • the homopolymer are those having 1 to 200 of constituting units (A) of Formula (7) and the terminal ends each comprising a hydroxyl group, an acyloxy group having 1 to 10 carbon atoms or an alkoxy or allyloxy group having 1 to 10 carbon atoms.
  • the copolymers are those having 1 to 200 of each of the two different constituting units A and B of Formula (7) or having 1 to 200 of constituting units A of Formula (7) and 1 to 200 constituting unit C of Formula (8) and the terminal ends each comprising a hydroxyl group, an acyloxy group having 1 to 10 carbon atoms or an alkoxy or allyloxy group having 1 to 10 carbon atoms.
  • copolymers may be of any variety, including alternating copolymers, random copolymers and block copolymers each containing the constituting units A and B or C and graft copolymers in which the constituting unit B is graft bonded onto the main chain of the constituting unit A.
  • Eligible polyvinyl ethers for the present invention are polyvinyl ether compounds which contain a constituting unit represented by the formula wherein R 16 , R 17 and R 18 are each independently a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms and may be the same or different and, R 19 is a divalent hydrocarbon group having 1 to 10 carbon atoms or a divalent ether bonded oxygen-containing hydrocarbon group having 2 to 20 carbon atoms, R 20 is a hydrocarbon group having 1 to 20 carbon atoms and q is the value of which average value is 0 to 10; and R 16 through R 20 may be the same or different from each other in every constituting unit and in the case where a plurality of R 19 O are present, they may be the same or different.
  • a polyvinyl ether compounds comprising block or random copolymers having the constituting unit of Formula (10) and a constituting unit represented by the formula wherein R 21 through R 24 are each independently a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms and may be the same or different, and R 21 through R 24 may be the same or different from each other in every constituting unit.
  • R 16 , R 17 and R 18 are each independently a hydrogen atom or a hydrocarbon group having 1 to 8, preferably 1 to 4 carbon atoms and may be the same or different.
  • hydrocarbon groups are an alkyl groups such as methyl, ethyl, n-propyl, isobutyl, sec-butyl, tert-butyl, various types of pentyl, various types of hexyl, various types of heptyl and various types of octyl groups; a cycloalkyl group such as cyclopentyl, cyclohexyl, various types of methylcyclohexyl, various types of ethylcyclohexyl and various types of dimethylcyclohexyl groups; an aryl group such as phenyl, various types of methylphenyl, various types of ethylphenyl and various types of dimethylphenyl groups; and an arylalkyl group such as phenyl
  • R 19 is a divalent hydrocarbon group having 1 to 10, preferably 2 to 10 carbon atoms or a divalent ether bonded oxygen-containing hydrocarbon group having 1 to 10 carbon atoms.
  • a divalent hydrocarbon group having 1 to 10 are a divalent aliphatic group such as methylene, ethylene, phenylethylene, 1,2-propylene, 2-phenyl-1,2-propylene, 1,3-propylene, various types of butylene, various types of pentylene, various types of hexylene, various types of heptylene, various types of octylene, various types of nonylene and various types of decylene groups; an alicyclic group with two bonding sites on the alicyclic hydrocarbon, such as cyclohexane, methylcyclohexane, ethylcyclohexane, dimethylcyclohexane and propylcyclohexane groups; a divalent aromatic hydrocarbon group such as
  • divalent ether bonded oxygen-containing hydrocarbon group having 1 to 10 carbon atoms are methoxymethylene, methoxyethylene, methoxymethylethylene, 1,1-bismethoxymethylethylene, 1,2-bismethoxymethylethylene, ethoxymethylethylene, (2-methoxyethoxy)methylethylene, (1-methyl-2-methoxy)methylethylene groups.
  • q in Formula (10) represents the number of repeating of R 19 O and the average value thereof is within the range of 0 to 10, preferably 0 to 5. In the case where a plurality of R 19 O are present, they may be the same or different from each other.
  • R 20 in Formula (10) is a hydrocarbon group having 1 to 20, preferably 1 to 10 carbon atoms.
  • a hydrocarbon group are an alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, various types of pentyl, various types of hexyl, various types of heptyl, various types of octyl, various types of nonyl and various types decyl groups; a cycloalkyl group such as cyclopentyl, cyclohexyl, various types of methylcyclohexyl, various types of ethylcyclohexyl, various types of propylcyclohexyl and various types of dimethylcyclohexyl groups; an aryl group such as phenyl, various types of methylphenyl, various types of ethylphenyl,
  • the molar ratio of carbon to oxygen in the polyvinyl ether compound (A) represented by Formula (10) is preferably within the range of 4.2 to 7.0.
  • the molar ratio less than 4.2 results in a compound increased in high hygroscopicity, while the molar ratio exceeding 7.0 results in a compound reduced in miscibility with a refrigerant.
  • R 21 through R 24 in Formula (11) are each independently a hydrogen or a hydrocarbon group having 1 to 20 carbon atoms and may be the same or different from each other. Specific examples of such a hydrocarbon group are the same as those exemplified above with respect to R 20 . R 21 through R 24 may be the same or different from each other in every constituting unit.
  • the polyvinyl ether compound (B) composed of block or random copolymers having the constituting units of Formulae (10) and (11) is preferably within the range of 4.2 to 7.0 in a molar ratio of carbon to oxygen.
  • the molar ratio less than 4.2 results in a compound increased in hygroscopicity, while the molar ratio exceeding 7.0 would result in a compound reduced in miscibility with a refrigerant.
  • These compounds (A) and (B) may be produced by polymerization of the corresponding polyvinyl ether monomer or copolymerization of the corresponding hydrocarbon monomer having an olefinic double bond and the corresponding polyvinyl ether monomer.
  • the polyvinyl ether compound having one of the terminal ends represented by the formula wherein R 25 , R 26 and R 27 are each independently a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms and may be the same or different from each other, R 28 is a divalent hydrocarbon group having 1 to 10 carbon atoms or a divalent hydrocarbon containing ether-bonded oxygen having 2 to 20 carbon atoms, R 29 is a hydrocarbon group having 1 to 20 carbon atoms and r is the value of which average value is 0 to 10 and in the case where a plurality of R 28 O is present, they may be the same or different from each other; or represented by the formula wherein R 30 , R 31 , R 32 and R 33 are each independently a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms and may be the same or different from each other; and the other end represented by the formula wherein R 34 , R 35 and R 36 are each independently a hydrogen atom or a hydrocarbon group
  • polyvinyl ether compound having the terminal ends one of which is represented by Formula (14) or (15) and the other of which is represented by the formula wherein R 43 , R 44 and R 45 are each independently a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms and may be the same or different from each other.
  • R 43 , R 44 and R 45 are each independently a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms and may be the same or different from each other.
  • a polyvinyl ether compound composed of the constituting unit of Formula (10) and the terminal ends one of which is represented by Formula (12) and the other end of which is represented by the formula wherein R 46 , R 47 and R 48 are each independently a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms and may be the same or different from each other, R 49 and R 51 are each independently a divalent hydrocarbon group having 2 to 10 carbon atoms and may be the same or different from each other, t and u each represents the value of which average value is 0 to 10 and in the case where a plurality of R 49 O are present, they may be the same or different from each other and in the case where a plurality of R 51 O are present, they may be the same or different from each other.
  • the inventive refrigerating machine oil may comprises one or more than two members selected from the above-described oxygen-containing synthetic oil.
  • the content of the oxygen-containing synthetic oil in the inventive refrigerating machine oil is within the range of preferably more than 50 mass percent, more preferably more than 70 mass percent, further more preferably more than 80 mass percent, based on the total mass of the refrigerating machine oil in view of imparting the resulting oil with excellent lubricity, miscibility with a refrigerant, thermal and chemical stability and electric insulation.
  • oxygen-containing synthetic oil may be used in combination with hydrocarbon oils such as mineral oils, olefin polymers, naphthalene compounds and alkylbenzene oils.
  • the refrigerating machine oil according to the present invention contains the oxygen-containing synthetic oil and the hydrocarbon oil which is added as required, as a base oil.
  • inventive refrigerating machine oil can be put in use without being blended with any additives, it can be used in the form of a mixture with any of various additives.
  • the inventive refrigerating machine oil can be blended with at least one kind of a phosphorus compound selected from the group consisting of phosphoric esters, acidic phosphoric esters, amine salts of acidic phosphoric esters, chlorinated phosphoric esters and phosphorous esters in view of improving the refrigerating apparatus in wear resistance and load resistance by the use of the inventive refrigerating machine oil.
  • a phosphorus compound selected from the group consisting of phosphoric esters, acidic phosphoric esters, amine salts of acidic phosphoric esters, chlorinated phosphoric esters and phosphorous esters in view of improving the refrigerating apparatus in wear resistance and load resistance by the use of the inventive refrigerating machine oil.
  • phosphoric esters are tributyl phosphate, tripentyl phosphate, trihexyl phosphate, triheptyl phosphate, trioctyl phosphate, trinonyl phosphate, tridecyl phosphate, triundecyl phosphate, tridodecyl phosphate, tritridecyl phosphate, tritetradecyl phosphate, tripentradecyl phosphate, trihexadecyl phosphate, triheptadecyl phosphite, trioctadecyl phosphate, trioleyl phosphate, triphenyl phosphate, tricresyl phosphate, trixylyl phosphate, cresyldiphenyl phosphate and xylyldiphenyl phosphate.
  • acidic phosphoric esters are monobutyl acid phosphate, monopentyl acid phosphate, monohexyl acid phosphate, monoheptyl acid phosphate, monooctyl acid phosphate, monononyl acid phosphate, monodecyl acid phosphate, monoundecyl acid phosphate, monododecyl acid phosphate, monotridecyl acid phosphate, monotetradecyl acid phosphate, monopentadecyl acid phosphate, monohexadecyl acid phosphate, monoheptadecyl acid phosphate, monooctadecyl acid phospahte, monooleyl acid phosphate, dibutyl acid phosphate, dipentyl acid phospahte, dihexyl acid phospahte, diheptyl acid phospahte, dioctyl acid phosphate, dinonyl
  • amine salts of acidic phosphoric esters are methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, octylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, trimethylamine, triethylamine, tripropylamine, tributylamine, tripentylamine, trihexylamine, triheptylamine and trioctylamine of the acidic phosphoric ester.
  • chlorinated phosphoric esters are tris-dichloropropyl phosphate, tris-chloroethyl phosphate, tris-chlorophenyl phosphate and polyoxyalkylene bis[di(chloroalkyl)] phosphate.
  • phosphorous esters are dibutyl phosphite, dipentyl phosphite, dihexyl phosphite, diheptyl phosphite, dioctyl phosphite, dinonyl phosphite, didecyl phosphite, diundecyl phosphite, didodecyl phosphite, dioleyl phosphite, diphenyl phosphite, dicresyl phosphite, tributyl phosphite, tripentyl phosphite, trihexyl phosphite, triheptyl phosphite, trioctyl phophite, trinonyl phosphite, tridecyl phosphite, triundecyl phosphite, tridodecyl
  • these phosphorus compounds may be blended with the inventive refrigerating machine oil in any suitable ratio, their contents may be within the range of 0.01 to 5.0 mass percent, preferably 0.02 to 3.0 mass percent, based on the total mass of the refrigerating machine oil (based on the total mass of the base oil and the whole additives).
  • an epoxy compound selected from the group consisting of: (1) phenylglycidyl ether type epoxy compounds, (2) alkylglycidyl ether type compounds, (3) glycidyl ester type epoxy compounds, (4) aryl oxirane compounds, (5) alkyl oxirane compounds, (6) alicyclic epoxy compounds, (7) epoxidized fatty monoesters and (8) epoxidized vegetable oils.
  • phenylglycidyl ether type epoxy compounds (1) are phenylglycidyl ether and alkylphenylglycidyl ethers.
  • the alkylphenylglycidyl ether may be those having 1 to 3 alkyl groups each having 1 to 13 carbon atoms, preferably those having one alky group having 4 to 10 carbon atoms.
  • alkylphenylglycidyl ethers are n-butylphenylglycidyl ether, i-butylphenylglycidyl ether, sec-butylphenylglycidyl ether, tert-butylphenylglycidyl ether, pentylphenylglycidyl ehter, hexylphenylglycidyl ether, heptylphenylglycidyl ehter, octylphenylglycidyl ether, nonylphenylglycidyl ehter and decylphenylglycidyl ehter.
  • alkylglycidyl ether type compounds (2) are decylglycidyl ether, undecylglycidyl ether, dodecylglycidyl ether, tridecylglycidyl ether, tetradecylglycidyl ether, 2-ethylhexylglycidyl ether, neopentylglycoldiglycidyl ether, trimethylolpropane triglycidyl ehter, pentaerythritol tetraglycidyl ether, 1,6-hexanediol diglycidyl ether, sorbitol polyglycidyl ether, polyalkyleneglycol monoglycidyl ether and polyalkyleneglycol diglycidyl ether.
  • glycidyl ester type epoxy compounds (3) are phenylglycidyl ester, alkylglycidyl esters and alkenylglycidyl esters. Preferred are glycidyl-2,2-dimethyloctanoate, glycidyl benzoate, glycidyl acrylate and glycidyl methacrylate.
  • aryl oxirane compounds (4) are 1,2-epoxystyrene and alkyl-1,2-epoxystyrene.
  • alkyl oxirane compounds (5) are 1,2-epoxybutane, 1,2-epoxypentane, 1,2-epoxyhexane, 1,2-epoxyheptane, 1,2-epoxyoctane, 1,2-epoxynonane, 1,2-epoxydecane, 1,2-epoxyundecane, 1,2-epoxydodecane, 1,2-epoxytridecane, 1,2-epoxytetradecane, 1,2-epoxypentadecane, 1,2-epoxyhexadecane, 1,2-epoxyheptadecane, 1,2-epoxyoctadecane, 1,2-epoxynonadecane and 1,2-epoxyeicosane.
  • alicyclic epoxy compounds (6) are 1,2-epoxycyclohexane, 1,2-epoxycyclopentane, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, bis(3,4-epoxycyclohexylmetyl) adipate, exo-2,3-epoxynorbornane, bis(3,4-epoxy-6-methycyclohexylmetyl) adipate, 2-(7-oxabicyclo[4.1.0] hept-3-yl)-spiro(1,3-dioxane-5, 3'-[7]oxabicyclo[4.1.0]) heptane, 4-(1'-metylepoxyethyl)-1,2-epoxy-2-methylcyclohexane and 4-epoxyethyl-1,2-epoxycyclohexane.
  • epoxidized fatty monoesters (7) are an ester formed by reacting an epoxidized fatty acid having 12 to 20 carbon atoms with an alcohol having 1 to 8 carbon atoms, phenol or alkylphenol.
  • Particularly preferred are epoxystearates such as butyl, hexyl, benzyl, cyclohexyl, methoxyethyl, phenyl and butylphenyl esters of epoxystearic acid.
  • epoxidized vegetable oils (8) are epoxy compounds of vegetable oils such as soybean oil, linseed oil and cottonseed oil.
  • epoxy compounds preferred are phenylglycidyl ether type epoxy compounds, glycidyl ester type epoxy compounds, alicyclic epoxy compounds and epoxidized fatty monoesters. More preferred are phenylglycidyl ether type epoxy compounds and glycidyl ester type epoxy compounds. Particularly preferred are phenylglycidyl ether, butylphenylglycidyl ether, alkylglycidyl ester and mixtures thereof.
  • the inventive refrigerating machine oil may be blended with these epoxy compounds in any suitable blending ratio.
  • the epoxy compound is generally blended in an amount of 0.1 to 5.0 mass percent, preferably 0.2 to 2.0 mass percent, based on the total mass of the refrigerating machine oil (based on the total mass of the base oil and the whole additives).
  • each of the phosphorus compounds and the epoxy compounds may be used in combination.
  • the suitable additives may be anti-oxidants of a phenol type such as di-tert-butyl-p-cresol and bisphenol A or of an amide type such as phenyl- ⁇ -naphthyl amine and N,N-di(2-naphthyl)-p-phenylenediamine; anti-wear additives such as zinc dithiophosphate; extreme pressure agents such as chlorinated paraffin and sulfur compounds; oiliness improvers such as fatty acid; silicone-type antiforming agents; metal inactivators such as benzotriazole; viscosity index improvers; pour point depressants; and detergent-dispersants.
  • These additives may be added in an amount of less than 10 mass percent, preferably less than 5 mass percent, based on the total mass of the refrigerating machine oil (based on the total mass of the base oil and the whole additive
  • the kinematic viscosity of the refrigerating machine oil of the present invention preferably has a kinematic viscosity at 40 °C of preferably 3 to 100 mm 2 /s, more preferably 4 to 50 mm 2 /s, most preferably 5 to 40 mm 2 /s and a kinematic viscosity at 100 °C of preferably 1 to 20 mm 2 /s, more preferably 2 to 10 mm 2 /s.
  • the refrigerating machine oil of the present invention preferably has a volume resistivity of greater than 1.0 x 10 12 ⁇ • cm, preferably greater than 1.0 x 10 13 ⁇ • cm, more preferably greater than 1.0 x 10 14 ⁇ • cm.
  • volume resistivity used herein denotes a value measured at a temperature of 40 °C in accordance with JIS C 2101 "Testing methods of electrical insulating oils".
  • the water content of the refrigerating machine oil of the present invention is not particularly restricted, but may be present within the range of preferably less than 200 ppm, more preferably less than 100 ppm, most preferably less than 50 ppm.
  • refrigerating machine oils are used in a sealed type refrigerating machine, less water contents are preferred in view of the stability and electric insulation of the oils.
  • the total acid value of the refrigerating machine oil of the present invention is not particularly restricted, but may be preferably less than 0.1 mgKOH/g, more preferably 0.05 mgKOH/g in order to prevent the corrosion of metals used in a refrigerating machine or pipes thereof.
  • the total acid value used herein denotes a total acid value measured in accordance with JIS K 2501 "Petroleum products and lubricants-Determination of neutralization number".
  • the ash content of the refrigerating machine oil of the present invention is not particularly restricted, but may be preferably less than 100 ppm, more preferably 50 ppm.
  • the ash content used herein denotes a value of ash content measured in accordance with JIS K 2272 "Testing Methods for Ash and Sulfated Ash of Crude Oil and Petroleum Products".
  • the refrigerant used in a refrigerating machine together with the refrigerating machine oil is dimethyl ether (DME) or alternatively a mixture of DME and other refrigerants such as hydrofluorocarbon, hydrocarbon, carbon dioxide and ammonia.
  • DME dimethyl ether
  • other refrigerants such as hydrofluorocarbon, hydrocarbon, carbon dioxide and ammonia.
  • the hydrofluorocarbon refrigerants may be hydrofluorocarbon having 1 to 3 carbon atoms, preferably 1 to 2 carbon atoms.
  • Specific examples of the hydrofluorocarbon refrigerants are difluoromethane (HFC-32), trifluoromethane (HFC-23), pentafluoroethane (HFC-125), 1,1,2,2-tetrafluoroethane (HFC-134), 1,1,1,2-tetrafluoroethane (HFC-134a), 1,1,1-trifluoroethane (HFC-143a), 1,1-difluoroethane (HFC-152a) and a mixture of at least two kinds of thereof.
  • refrigerants are HFC-32 alone; HFC-23 alone; HFC-134a alone; HFC-125 alone; a mixture of HFC-134a / HFC-32 in a ratio of 60-80 mass % / 40-20 mass %; a mixture of HFC-32 / HFC-125 in a ratio of 40-70 mass % / 60-30 mass %; a mixture of HFC-125 / HFC-143a in a ratio of 40-60 mass % / 60-40 mass %; a mixture of HFC-134a / HFC-32 / HFC-125 in a ratio of 60 mass % / 30 mass % / 10 mass %; a mixture of HFC-134a / HFC-32 / HFC-125 in a ratio of 40-70 mass % / 15-35 mass % / 5-40 mass % and a mixture of HFC-125 / HFC
  • the HFC refrigerant mixtures include a mixture of HFC-134a / HFC-32 in a ratio of 70 mass % / 30 mass %; a mixture of HFC-32 / HFC-125 in a ratio of 60 mass % / 40 mass %; a mixture of HFC-32 / HFC-125 in a ratio of 50 mass % / 50 mass % (R410A); a mixture of HFC-32 / HFC-125 in a ratio of 45 mass % / 55 mass % (R410B) ; a mixture of HFC-125 / HFC-143a in a ratio of 50 mass % / 50 mass % (R507C); a mixture of HFC-32 / HFC-125 / HFC-134a in a ratio of 30 mass % / 10 mass % / 60 mass %; a mixture of HFC-32 / HFC-125 / HFC-134a in a ratio of 23 mass %/ 25
  • the hydrocarbon refrigerants may be those which are gaseous at 25 °C and one atmospheric pressure.
  • Specific examples of the hydrocarbon refrigerants are alkanes, cycloalkanes and alkenes each having 1 to 5 carbon atoms, preferably 1 to 4 carbon atoms, such as methane, ethylene, ethane, propylene, propane, cyclopropane, butane, isobutane, cyclobutane, methylcyclopropane and a mixture of at least two kinds thereof.
  • the blending ratio of DME to hydrofluorocarbon and/or hydrocarbon refrigerants is not particularly restricted.
  • the total amount of hydrofluorocarbon and/or hydrocarbon may be within the range of preferably 1 to 200 parts by weight, more preferably 10 to 100 parts by weight per 100 parts by weight of DME.
  • the refrigerating machine oil according to the present invention is generally present in the form of a fluid composition admixed with DME alone or with other refrigerants in a refrigerating machine.
  • the mixing ratio of the inventive refrigerating machine oil to the refrigerants are not particularly restricted, but the refrigerating machine oil may be present in a ratio of 1 to 500 parts by weight, more preferably 2 to 400 parts by weight per 100 parts by weight of the refrigerant.
  • the refrigerating machine oil according to the present invention can be used as a lubricating oil for the refrigerant compressors of any types of refrigerating machine.
  • Refrigerating machines to which the inventive refrigerating machine oil is applicable are room air conditioners, packaged air conditioning systems, refrigerators, automobile air conditioners, dehumidifiers, freezers, refrigerating chambers, vending machines, show-cases and cooling systems for chemical plants.
  • the inventive refrigerating machine oil is preferably used in refrigerating machines having sealed compressors.
  • the inventive refrigerating machine oil is also eligible for use in a reciprocating, rotary, or centrifugal type compressor.
  • Sample oils of Examples 1 - 15 were prepared by blending polyol esters and additives shown in Table 1 in accordance with the formulations shown in Tables 2 - 4.
  • Tables 2 - 4 shows the properties (kinematic viscosity at 40 °C and 100 °C and total acid value) of each of the sample oils.
  • each of the sample oils was subjected to a friction test in which a test machine was run under a load of 250 lb for two hours after being warmed up at an oil temperature of 100 °C under a load of 150 lb for a period of one minute.
  • Each of the sample oils were evaluated by measuring the level of abrasion of the test journal (pin). The results are shown in Tables 2 - 4.
  • Example 1 Example 2 Example 3 Example 4 Example 5 Base oil Ester A Ester B Ester C Ester D Ester E (mass %) 100 100 100 100 100 100 100 Additive - - - - - (mass %) Kinematic 40°C(mm 2 /s) 24.2 7.3 48.9 20.2 52.0 Viscosity 100°C(mm 2 /s) 5.9 2.1 9.7 4.5 7.1 Total acid value (mgKOH/g) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 Miscibility Miscible Miscible Miscible Miscible Volume resistivity ( ⁇ cm) 2.8 ⁇ 10 13 1.9 ⁇ 10 14 8.9 ⁇ 10 13 4.5 ⁇ 10 13 6.9 ⁇ 10 13 Thermal Stability test Sample oil appearance Not Changed Not changed Not changed Not Changed Not Changed Catalyst appearance Not Changed Not changed Not changed Not Changed Not Changed Volume resistivity ( ⁇ cm) 1.1 ⁇ 10 13 9.2 ⁇ 10 13 4.6 ⁇
  • the sample oils of Examples 1 to 15 containing a polyether ester as the oxygen-containing synthetic oil specified by the present invention were found to have an excellent lubricity, miscibility with a refrigerant, thermal stability, electric insulation, hydrolytic stability and kinematic viscosity, all of which are well-balanced, when used together with a DME refrigerant.
  • Example 16 Carbonic ester having an average-molecular weight of 1,000 and represented by the formula wherein X represents the formula wherein (PO) m and (PO) n represent a polyoxypropylene group.
  • Example 17 Carbonic ester having an average-molecular weight of 2,000 and represented by the formula wherein X represents the formula wherein (PO) l - (EO) m is a random copolymer of a polyoxypropylene group and a polyoxyethylene group and indicates that the weight ratio therebetween is 90 : 10 and (PO)n is a polyoxypropylene group.
  • Example 18 Carbonic ester having an average-molecular weight of 2,000 and represented by the formula wherein X represents wherein (PO) l - (EO) m is a random copolymer of a polyoxypropylene group and a polyoxyethylene group and indicates that the weight ratio therebetween is 90 : 10 and (PO)n is a polyoxypropylene group.
  • Example 19 Carbonic ester having an average-molecular weight of 2,000 and represented by the formula wherein X represents wherein (PO) l - (EO) m is a random copolymer of a polyoxypropylene group and a polyoxyethylene group and indicates that the weight ratio therebetween is 90 : 10 and (PO)n is a polyoxypropylene group.
  • Example 20 Carbonic ester having an average-molecular weight of 1,000 and represented by the formula wherein X represents wherein (PO)m and (PO)n represent a polyoxypropylene group, respectively.
  • Example 21 Carbonic ester having an average-molecular weight of 2,000 and represented by the formula wherein X represents wherein (PO) l - (EO) m is a random copolymer of a polyoxypropylene group and a polyoxyethylene group and indicates that the weight ratio therebetween is 90 : 10 and (PO)n indicates a polyoxypropylene group.
  • Example 22 Carbonic ester having an average-molecular weight of 2,000 and represented by the formula wherein X represents wherein (PO) l - (EO) m is a random copolymer of a polyoxypropylene group and a polyoxyethylene group and indicates that the weight ratio therebetween is 90 : 10 and (PO)n represents a polyoxypropylene group.
  • Example 16 Example 17
  • Example 18 Example 19
  • Example 20 Example 21
  • Example 22 VIS@100°C 11.5 27.1 32.2 28.4 10.9 28.1 35.2 Volume resistivity 8.3E14 5.4E14 7.1 E14 1.2E13 6.9E14 2.4E14 8.9E13 Miscibility Miscible Miscible Miscible Miscible Miscible Miscible Autoclave test
  • Sample oil appearance Not changed Not changed Not changed Not changed Not changed Not changed Not changed Not changed
  • Catalyst appearance Not changed Not changed Not changed Not changed Not changed Not changed Not changed Not changed Not changed Not changed Not changed
  • Volume resistivity 4.8E14 5.1E14 2.9E14 3.2E13 3.8E14 7.9E13 1.5E13
  • Total acid value 0.01 0.02 0.01 0.03 0.01 0.02 0.02
  • the sample oils of Examples 16 to 22 containing a carbonic acid ester as the oxygen-containing synthetic oil specified by the present invention were found to have an excellent lubricity, miscibility with a refrigerant, thermal stability, electric insulation, hydrolytic stability and kinematic viscosity, all of which are well-balanced, when used together with a DME refrigerant.
  • Sample oils of Examples 23 to 35 were prepared by blending polyoxyalkylene glycol (PAG : base oil) or polyvinyl ether (PVE : base oil) shown in Table 6 and additives in accordance with the formulations shown in Tables 7 to 9. Tables 7 to 9 also show the properties (kinematic viscosity at 40 °C and 100 °C and total acid value) of each of the sample oils.
  • PAG polyoxyalkylene glycol
  • PVE polyvinyl ether
  • each of the sample oils was subjected to a friction test in which a test machine was run under a load of 250 lb for two hours after being warmed up at an oil temperature of 100 °C under a load of 150 lb for a period of one minute.
  • Each of the sample oils was evaluated by measuring the level of abrasion of the test journal (pin). The results are shown in Tables 7 to 9.
  • Example 23 Example 24 Example 25 Example 26 Example 27 base oil PAG 1 PAG 2 PAG 3 PAG 4 PAG 5 (mass %) 100 100 100 100 100 100 additive - - - - - (mass %) Kinematic 40°C (mm 2 /s) 50.5 43.4 45.2 102 48.8 Viscosity 100°C (mm 2 /s) 9.9 9.6 9.3 20.4 10.4 Total acid value (mgKOH/g) 0.00 0.01 0.01 0.00 0.00 Miscibility Miscible Miscible Miscible Miscible Miscible Volume resistivity ( ⁇ cm) 1.3 ⁇ 10 11 7.8 ⁇ 10 11 8.9 ⁇ 10 10 1.0 ⁇ 10 11 1.0 ⁇ 10 11 Thermal stability test Sample oil Appearance Not changed Not changed Not changed Not changed Not changed Not changed Catalyst appearance Not changed Not changed Not changed Not changed Not changed Not changed Not changed Not changed Volume resistblity ( ⁇ cm) 4.6 ⁇ 10 10 8.5 ⁇ 10 10 1.8 ⁇ 10 10 1.2 ⁇
  • the sample oils of Examples 23 to 35 containing polyalkylene glycol or polyvinyl ether as the oxygen-containing synthetic oil specified by the present invention were found to have an excellent lubricity, miscibility with a refrigerant, thermal stability, electric insulation, hydrolytic stability and kinematic viscosity, all of which are well-balanced, when used together with a DME refrigerant.
  • the refrigerating machine oil according to the present invention can reach a high level of standard in performances required for a refrigerating machine oil, such as lubricity, miscibility with a refrigerant and thermal stability .
EP99850142A 1998-09-29 1999-09-27 Kältemaschinenöl Withdrawn EP0997519A1 (de)

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JP10275560A JP2000104085A (ja) 1998-09-29 1998-09-29 ジメチルエーテルを冷媒とする冷凍機用潤滑油
JP27556098 1998-09-29

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Cited By (11)

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EP0992572A3 (de) * 1998-09-29 2000-11-15 Nippon Mitsubishi Oil Corporation Verwendung von Kohlendioxid als Kältemittel in einer Ölzusammensetzung für Kältemaschinen
EP1167495A1 (de) * 1999-03-05 2002-01-02 Idemitsu Kosan Co., Ltd. Ölzusammensetzung für kühlmaschine
WO2002077135A1 (en) * 2001-03-26 2002-10-03 Imperial Chemical Industries Plc Compressor lubricant compositions
WO2002083607A2 (de) * 2001-03-29 2002-10-24 Cognis Deutschland Gmbh & Co. Kg Oxidationsstabiles hydrauliköl
EP1632555A1 (de) * 2000-02-09 2006-03-08 Citizen Watch Co., Ltd. Schmierölzusammensetzung und diese verwendende Uhr
CN101305084A (zh) * 2005-11-15 2008-11-12 出光兴产株式会社 冷冻机油组合物
WO2009134638A2 (en) * 2008-04-28 2009-11-05 Dow Global Technologies Inc. Polyoxyalkylene glycol diether lubricating composition preparation and use
US7683015B2 (en) 2005-10-25 2010-03-23 Chevron U.S.A. Inc. Method of improving rust inhibition of a lubricating oil
US20100247971A1 (en) * 2009-03-30 2010-09-30 Fujifilm Corporation Lubricant composition, magnetic recording medium, and novel polyether compound
CN103649040A (zh) * 2011-07-13 2014-03-19 Kh新化株式会社 季戊四醇的四酯
CN106103992A (zh) * 2014-03-14 2016-11-09 三菱电机株式会社 压缩机以及制冷循环装置

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JP2005344057A (ja) * 2004-06-04 2005-12-15 Japan Petroleum Exploration Co Ltd ジメチルエーテルと二酸化炭素の混合物冷媒
JP2006022305A (ja) * 2004-06-04 2006-01-26 Japan Petroleum Exploration Co Ltd ジメチルエーテルと二酸化炭素の混合物冷媒
JP5407052B2 (ja) * 2005-08-17 2014-02-05 昭和電工ガスプロダクツ株式会社 冷媒組成物
JP5407053B2 (ja) * 2005-09-27 2014-02-05 昭和電工ガスプロダクツ株式会社 冷媒組成物
JP2007145922A (ja) * 2005-11-25 2007-06-14 Japan Petroleum Exploration Co Ltd 冷媒組成物
JP2007155183A (ja) * 2005-12-02 2007-06-21 Showa Denko Kk 熱交換器
JP5216231B2 (ja) * 2007-03-29 2013-06-19 Ｊｘ日鉱日石エネルギー株式会社 冷凍機用作動流体組成物
JP5248800B2 (ja) * 2007-03-29 2013-07-31 Ｊｘ日鉱日石エネルギー株式会社 冷凍機用作動流体組成物

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DE4313584A1 (de) * 1993-04-26 1994-10-27 Leuna Werke Gmbh Kältemittelgemisch
EP0724003A2 (de) * 1995-01-25 1996-07-31 Oho, Suk Jae Kühlzusammensetzung
EP0844299A1 (de) * 1995-07-10 1998-05-27 Idemitsu Kosan Company Limited Kältemaschinenöl und methode zur schmierung damit
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Cited By (23)

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Publication number Priority date Publication date Assignee Title
EP0992572A3 (de) * 1998-09-29 2000-11-15 Nippon Mitsubishi Oil Corporation Verwendung von Kohlendioxid als Kältemittel in einer Ölzusammensetzung für Kältemaschinen
US6692654B2 (en) 1998-09-29 2004-02-17 Nippon Mitsubishi Oil Corporation Refrigerating machine oil
EP1167495A1 (de) * 1999-03-05 2002-01-02 Idemitsu Kosan Co., Ltd. Ölzusammensetzung für kühlmaschine
EP1167495A4 (de) * 1999-03-05 2004-03-10 Idemitsu Kosan Co Ölzusammensetzung für kühlmaschine
US6878677B1 (en) 1999-03-05 2005-04-12 Idemitsu Kosan Co., Ltd. Refrigerating machine oil compositions
EP1632555A1 (de) * 2000-02-09 2006-03-08 Citizen Watch Co., Ltd. Schmierölzusammensetzung und diese verwendende Uhr
WO2002077135A1 (en) * 2001-03-26 2002-10-03 Imperial Chemical Industries Plc Compressor lubricant compositions
WO2002083607A2 (de) * 2001-03-29 2002-10-24 Cognis Deutschland Gmbh & Co. Kg Oxidationsstabiles hydrauliköl
WO2002083607A3 (de) * 2001-03-29 2003-01-09 Cognis Deutschland Gmbh Oxidationsstabiles hydrauliköl
US7906466B2 (en) 2005-10-25 2011-03-15 Chevron U.S.A. Inc. Finished lubricant with improved rust inhibition
US7910528B2 (en) 2005-10-25 2011-03-22 Chevron U.S.A. Inc. Finished lubricant with improved rust inhibition made using fischer-tropsch base oil
US7947634B2 (en) 2005-10-25 2011-05-24 Chevron U.S.A. Inc. Process for making a lubricant having good rust inhibition
US7683015B2 (en) 2005-10-25 2010-03-23 Chevron U.S.A. Inc. Method of improving rust inhibition of a lubricating oil
US7732386B2 (en) 2005-10-25 2010-06-08 Chevron U.S.A. Inc. Rust inhibitor for highly paraffinic lubricating base oil
CN101305084A (zh) * 2005-11-15 2008-11-12 出光兴产株式会社 冷冻机油组合物
CN101305084B (zh) * 2005-11-15 2013-05-22 出光兴产株式会社 冷冻机油组合物
WO2009134638A2 (en) * 2008-04-28 2009-11-05 Dow Global Technologies Inc. Polyoxyalkylene glycol diether lubricating composition preparation and use
WO2009134638A3 (en) * 2008-04-28 2009-12-23 Dow Global Technologies Inc. Polyoxyalkylene glycol diether lubricating composition preparation and use
US20100247971A1 (en) * 2009-03-30 2010-09-30 Fujifilm Corporation Lubricant composition, magnetic recording medium, and novel polyether compound
US8604233B2 (en) * 2009-03-30 2013-12-10 Fujifilm Corporation Lubricant composition, magnetic recording medium, and novel polyether compound
CN103649040A (zh) * 2011-07-13 2014-03-19 Kh新化株式会社 季戊四醇的四酯
CN103649040B (zh) * 2011-07-13 2016-06-15 Kh新化株式会社 季戊四醇的四酯
CN106103992A (zh) * 2014-03-14 2016-11-09 三菱电机株式会社 压缩机以及制冷循环装置

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