EP0557796A1 - Schmiermittel für Kältemaschinen,die Tetrafluoroethane als Kühlmittel verwenden - Google Patents

Schmiermittel für Kältemaschinen,die Tetrafluoroethane als Kühlmittel verwenden Download PDF

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Publication number
EP0557796A1
EP0557796A1 EP93102037A EP93102037A EP0557796A1 EP 0557796 A1 EP0557796 A1 EP 0557796A1 EP 93102037 A EP93102037 A EP 93102037A EP 93102037 A EP93102037 A EP 93102037A EP 0557796 A1 EP0557796 A1 EP 0557796A1
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EP
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Prior art keywords
group
carbon atoms
lubricant
compound
olefin
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EP93102037A
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English (en)
French (fr)
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EP0557796B1 (de
Inventor
Tadashi c/o Idemitsu Kosan Co. Ltd. Katafuchi
Akira c/o Idemitsu Kosan Co. Ltd. Nakamura
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
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    • C10N2020/01—Physico-chemical properties

Definitions

  • the present invention relates to a lubricant for refrigerating machines employing a refrigerant comprising tetrafluoroethane. More particularly, it relates to a lubricant for refrigerating machines which is used along with a refrigerant comprising a substitute fluorohydrocarbon (hereinafter sometimes referred to as "flon compound”) such as 1,1,1,2-tetrafluoroethane (R-134a).
  • fluorohydrocarbon hereinafter sometimes referred to as "flon compound”
  • R-134a 1,1,1,2-tetrafluoroethane
  • the lubricant is excellent in the performance such as wear resistance, electrical insulating properties, hydrolytic stability, nonhygroscopicity and the like and further has excellent returnability of the lubricant in a compression-type refrigerating cycle (the characteristics that the lubricant is inclined to return to a compressor after it is circulated in the refrigerating cycle).
  • a flon compound including a fluorinated hydrocarbon such as dichlorodifluoromethane (R-12) and chlorodifluoromethane (R-22) has been used as the refrigerant.
  • a flon compound including a fluorinated hydrocarbon such as dichlorodifluoromethane (R-12) and chlorodifluoromethane (R-22) has been used as the refrigerant.
  • a flon compound including a fluorinated hydrocarbon such as dichlorodifluoromethane (R-12) and chlorodifluoromethane (R-22) has been used as the refrigerant.
  • R-12 dichlorodifluoromethane
  • R-22 chlorodifluoromethane
  • polyalkylene glycol compounds and ester compounds thereof both known as compatible with R-134a, have been found to have insufficient wear resistance, along with faulty electrical insulating properties. It has also been found that the polyalkylene glycol compounds are highly hygroscopic and the ester compounds thereof are hydrolytically unstable. Thus the demand for a solution in these problems has been raised in relevant industrial segments.
  • the present invention has been completed on the basis of a concept quite contrary to ordinary common knowledge as set forth above, in an effort to find a solution in the problems.
  • all these aspects of the performance can be unified by using a substance excellent in wear resistance, insulation resistance and the like as the lubricant, compounding therewith a fluidity improver to improve the fluidity of the lubricant in the presence of a refrigerant (R-134a and the like) and thus providing good returnability of the lubricant in a compression-type refrigerating cycle.
  • a lubricant combined even with a new refrigerant has all the required performance including excellent wear resistance, electrical insulating properties, hydrolytic stability and the like and further ensuring excellent returnability of the lubricant.
  • the present invention has been accomplished based on this finding.
  • an object of the present invention is to provide a lubricant for refrigerating machines employing a refrigerant comprising tetrafluoroethane, which is excellent in the performance such as wear resistance, electrical insulating properties, hydrolytic stability, nonhygroscopicity and the like and further has excellent returnability of the lubricant.
  • the lubricant can be used along with a substitute flon refrigerant in a compression-type refrigerating cycle without a hitch.
  • Another object of the present invention is to provide a lubricant for refrigerating machines employing a refrigerant comprising tetrafluoroethane, which is especially effective when used in automobile or household air conditioners and refrigerators and the like, having high industrial usefulness.
  • the present invention provides a lubricant for refrigerating machines employing a refrigerant comprising 1,1,1,2-tetrafluoroethane or 1,1,2,2-tetrafluoroethane which comprises as an essential component a base oil comprising (A) 40 to 95% by weight of a synthetic oil formed of a poly- ⁇ -olefin or a mixture of a poly- ⁇ -olefin and an alkylbenzene and (B) 5 to 60% by weight of a fluidity improver comprising at least one compound selected from the group consisting of a polyoxyalkylene glycol compound, a polysiloxane compound and a fluoride of polysiloxane compound.
  • a base oil comprising (A) 40 to 95% by weight of a synthetic oil formed of a poly- ⁇ -olefin or a mixture of a poly- ⁇ -olefin and an alkylbenzene and (B) 5 to 60% by weight of a fluidity improver comprising at
  • the lubricant of the present invention can be suitably used in various refrigerating machines and ordinarily in a compression-type refrigerating cycle comprising a compressor, a condenser, an expansion valve and an evaporator.
  • the lubricant of the present invention comprises the components (A) and (B) as the essential components, and the synthetic oil constituting the component (A) is a poly- ⁇ -olefin or a mixture of a poly- ⁇ -olefin and an alkylbenzene.
  • poly- ⁇ -olefins can be used and ordinarily are each a polymer of ⁇ -olefin having 8 to 14 carbon atoms and a kinematic viscosity of 10 to 350cSt at 40°C.
  • Preferred among them is a polymer of 1-dodecene, a polymer of 1-decene or a polymer of 1-octene, each having a kinematic viscosity of 10 to 350cSt at 40°C.
  • a lubricant containing a synthetic oil comprising such a poly- ⁇ -olefin has a lower viscosity at low temperatures in the presence of a tetrafluoroethane refrigerant, and thus returnability of the lubricant is all the more improved.
  • alkylbenzenes can be used as well and ordinarily are each an alkylbenzene having a kinematic viscosity of 5 to 500cSt, preferably 10 to 350cSt at 40°C. Meanwhile, either soft or hard alkylbenzene can be used provided that it meets this condition.
  • the alkylbenzene is not used singly but in the form of a mixture thereof with said poly- ⁇ -olefin as the synthetic oil as the component (A) in the present invention.
  • the mixing ratio of the poly- ⁇ -olefin to the alkylbenzene may be appropriately selected according to circumstances and is not particularly limited.
  • the mixture has a poly- ⁇ -olefin content of 5% or more by weight, more preferably 5 to 90% by weight, most preferably, when using high viscosity poly- ⁇ -olefin having a kinematic viscosity of about 50cSt or more at 40°C, 5 to 50 % by weight of the mixture.
  • the mixing stability of the poly- ⁇ -olefin and the fluidity improver as the component (B) is improved. This effect is especially remarkable with the use of a polyoxyalkylene glycol compound as the fluidity improver.
  • the fluidity improver acts to improve the fluidity of a hydrocarbonic compound at low temperatures (those of the evaporator) in the presence of a small amount of substitute flon refrigerant such as R-134a, so as to provide good returnability of the lubricant in the refrigerating cycle.
  • the kinematic viscosity of the fluidity improver is not particularly limited but is ordinarily 2 to 100cSt, preferably 3 to 50cSt at 40°C.
  • a typical example thereof is a polyoxyalkylene glycol compound.
  • Various polyoxyalkylene glycol compounds can be used and an appropriate one may be selected from them according to the intended use.
  • Preferred among them is a polyoxyalkylene glycol compound represented by the general formula (I): wherein R1 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, an acyl group having 2 to 10 carbon atoms or an aliphatic hydrocarbon group having 2 to 6 bonding links;
  • R2 is an alkylene group having 2 to 6 carbon atoms;
  • R3 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group
  • the alkyl group having 1 to 10 carbon atoms may be straight chain, branched chain or cyclic.
  • Specific examples of the alkyl group include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, various butyl groups, various pentyl groups, various hexyl groups, various heptyl groups, various octyl groups, various nonyl groups, various decyl groups, a cyclopentyl group, a cyclohexyl group, a phenyl group, a tolyl group, a xylyl group, a benzyl group, a phenethyl group and the like.
  • alkyl group having more than 10 carbon atoms leads to the degradation of the effect on improving the fluidity of the lubricant.
  • the alkyl group has preferably 1 to 6 carbon atoms.
  • An alkyl moiety of said acyl group may be straight chain, branched chain or cyclic.
  • Specific examples of the alkyl moiety of the acyl group include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, various butyl groups, various pentyl groups, various hexyl groups, various heptyl groups, various octyl groups, various nonyl groups, a cyclopentyl group, a cyclohexyl group and the like.
  • An acyl group having more than 10 carbon atoms leads to the degradation of the effect on improving the fluidity of the lubricant.
  • the acyl group has preferably 2 to 6 carbon atoms.
  • Said R1 and R3 may be same or different one another.
  • a plurality of R3s in a molecule may be same or different when n is 2 or more.
  • R1 is an aliphatic hydrocarbon group having 1 to 10 carbon atoms and 2 to 6 bonding links
  • the aliphatic hydrocarbon group may be either chain or cyclic.
  • Examples of the aliphatic hydrocarbon group having 2 bonding links include an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a nonylene group, a decylene group, a cyclopentylene group, a cyclohexylene group, a vinyl group, an allyl group, a butenyl group, an ethynyl group, a propynyl group, and the like.
  • Examples of the aliphatic hydrocarbon group having 3 to 6 bonding links include a residue after a hydroxyl group is removed from a polyhydric alcohol such as trimethylolpropane, glycerin, pentaerythritol, d ipentaerythritol, sorbitol, 1,2,3-trihydroxycyclohexane and 1,3,5-trihydroxycyclohexane.
  • a polyhydric alcohol such as trimethylolpropane, glycerin, pentaerythritol, d ipentaerythritol, sorbitol, 1,2,3-trihydroxycyclohexane and 1,3,5-trihydroxycyclohexane.
  • An aliphatic hydrocarbon group having more than 10 carbon atoms leads to the degradation of the effect on improving the fluidity of the lubricant.
  • the aliphatic hydrocarbon has preferably 2 to 6 carbon atoms.
  • R2 of said general formula (I) is an alkylene group having 2 to 6 carbon atoms and examples of the oxyalkylene group as a repeating unit include an oxyethylene group, an oxypropylene group, an oxybutylene group, an oxypentylene group and an oxyhexylene group.
  • a molecule thereof may comprise either same oxyalkylene groups or two or more different kinds of oxyalkylene groups.
  • a molecule thereof comprises the alkylene groups each having at least 3 carbon atoms, more preferably 50% or more by mole of the alkylene groups each having at least 4 carbon atoms per oxyalkylene unit.
  • n of said general formula (I) is an integer of 1 to 6 and depends on the number of bonding links of R1.
  • R1 is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or an acyl group
  • n is 1.
  • R1 is an aliphatic hydrocarbon group having 2, 3, 4, 5 or 6 bonding links
  • n is 2, 3, 4, 5 or 6, respectively.
  • m is a figure satisfying that the average value of mxn is 2 to 40, and when the average value of mxn is out of said range, the object of the present invention is not achieved to a full extent.
  • examples of the polyoxyalkylene glycol compound for use in the present invention include a polyoxyalkylene glycol compound containing at least one constitutional unit represented by the general formula (II): wherein R4 is a monovalent hydrocarbon group having 1 to 10 carbon atoms and R5 to R9 are each a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms.
  • polyoxyalkylene glycol compounds other than enumerated above can be used in the present invention as well, including those having a glycidyl group, those having a carbonyl bond in the molecule, those resulting from the substitution by a fluorine atom and the like.
  • a polyoxypropylene glycol compound, a polyoxybutylene glycol compound, a polyoxypentylene glycol compound and a polyoxyhexylene glycol compound are preferably used in the present invention because of their improvement in the mixing stability.
  • Most suitable is a fluidity improver containing 50% or more of at least one compound selected from the group consisting of the polyoxybutylene glycol compound, the polyoxypentylene glycol compound and the polyoxyhexylene glycol compound.
  • a polyoxyalkylene glycol compound should contain the oxybutylene, oxypentylene and oxyhexylene units to foot up to 50 or more among oxyalkylene units forming the compound.
  • a polysiloxane compound such as dimethylpolysiloxane and a fluoride thereof can be used as the fluidity improver in the present invention as well. It is also effective to use a mixture of 2 or more different fluidity improvers.
  • the synthetic oil (A) and the fluidity improver (B) are mixed at a ratio by weight of 40 to 95%, desirably 50 to 90%, particularly desirably 60 to 90% of (A) to 5 to 60%, desirably 10 to 50%, particularly desirably 10 to 40%, respectively of (B).
  • the fluidity of the lubricant is undesirably not improved and therefore the sufficient returnability of the lubricant is not achieved as well.
  • wear resistance and the like are undesirably degraded. This is accompanied by the degradation of the fundamental performance required for refrigerating machine lubricant, including the reduction of insulation resistance, worsening of hydrolytic stability, the increase in hygroscopicity and the like.
  • the lubricant of the present invention comprises as the essential component the base oil comprising the synthetic oil (A) and the fluidity improver (B) as set forth above and as the need arises various additives can be incorporated therein.
  • the additive include an anti-wear additive such as phosphoric acid ester and phosphorous acid ester, an antioxidant, a chlorine scavenger, a metal deactivator, a defoaming agent, a detergent-dispersant, a viscosity index improver, a rust preventive, a corrosion inhibitor and the like.
  • the lubricant for refrigerating machines employing the refrigerant comprising tetrafluoroethane as claimed herein is excellent in the performance such as wear resistance, electrical insulating properties, hydrolytic stability, nonhygroscopicity and the like and further has excellent returnability of the lubricant.
  • the lubricant of the present invention can be used along with a substitute flon refrigerant in a compression-type refrigerating cycle without a hitch.
  • the lubricant of the present invention is especially effective when used in automobile or household air conditioners, refrigerators and the like, having high industrial usefulness.
  • the lubricants were evaluated by determining each aspect of the performance thereof in accordance with the following test method:

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
EP93102037A 1992-02-18 1993-02-10 Schmiermittel für Kältemaschinen,die Tetrafluoroethane als Kühlmittel verwenden Expired - Lifetime EP0557796B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP30528/92 1992-02-18
JP3052892 1992-02-18

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EP0557796A1 true EP0557796A1 (de) 1993-09-01
EP0557796B1 EP0557796B1 (de) 1997-06-11

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EP (1) EP0557796B1 (de)
JP (1) JPH05295384A (de)
KR (1) KR0139612B1 (de)
AU (1) AU655345B2 (de)
DE (1) DE69311396T2 (de)
SG (1) SG72627A1 (de)
TW (1) TW224133B (de)

Cited By (9)

* Cited by examiner, † Cited by third party
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EP0699742A3 (de) * 1994-08-03 1996-05-15 Nippon Oil Co Ltd Kältemaschinenölzusammensetzung und Kältemittelzusammensetzung für Kältemaschine
US5547593A (en) * 1993-08-11 1996-08-20 Asahi Kasei Kogyo Kabushiki Kaisha Lubricant oil composition comprising a fluorine-containing aromatic compound and an alkyl- or alkyl derivative-substituted aromatic compound, and a refrigerant composition containing the same
US5648018A (en) * 1995-01-12 1997-07-15 Albemarle Corporation Ester/polyolefin refrigeration lubricant
EP0861883A2 (de) * 1997-02-27 1998-09-02 Idemitsu Kosan Co., Ltd. Ölzusammensetzung für Kältemaschine
WO1999036485A1 (en) * 1998-01-16 1999-07-22 E.I. Du Pont De Nemours And Company Halogenated hydrocarbon refrigerant compositions containing polymeric oil-return agents
EP1018538A1 (de) * 1997-06-17 2000-07-12 Nippon Mitsubishi Oil Corporation Kühlschrank öl zusammensetzung und kühlschrank fuid zusammensetzung
US6251300B1 (en) 1994-08-03 2001-06-26 Nippon Mitsubishi Oil Corporation Refrigerator oil compositions and fluid compositions for refrigerator
WO2010008640A1 (en) * 2008-07-16 2010-01-21 Dow Global Technologies Inc. Refrigerant compositions including silyl terminated polyalkylene glycols as lubricants and methods for making the same
CN107353973A (zh) * 2016-05-10 2017-11-17 特灵国际有限公司 减少制冷剂溶解度的润滑剂共混物

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* Cited by examiner, † Cited by third party
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KR100496780B1 (ko) * 1996-06-25 2005-09-09 이데미쓰 고산 가부시키가이샤 냉동기오일조성물
JP4079469B2 (ja) * 1996-06-25 2008-04-23 出光興産株式会社 冷凍機油組成物
JP4809607B2 (ja) * 2005-01-11 2011-11-09 Ｊｘ日鉱日石エネルギー株式会社 組付け油、並びに冷凍空調機器の構成部品の組付け方法

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US3733850A (en) * 1970-01-16 1973-05-22 Chevron Res Refrigeration heat pump,and heat engine apparatus
FR2299398A1 (fr) * 1975-01-29 1976-08-27 Mobil Oil Procede et composition pour lubrifier un systeme de refrigeration
EP0203494A2 (de) * 1985-05-20 1986-12-03 Nippon Mining Company Limited Schmieröl für Verwendung in einer Flon-Atmosphäre
WO1990005172A1 (en) * 1988-11-11 1990-05-17 Asahi Glass Company Ltd. Tetrafluoroethane composition for a regrigerator
EP0377122A1 (de) * 1988-12-06 1990-07-11 Idemitsu Kosan Company Limited Vervendung eines specifischen Polyalkylenglykol Derivats als Schmiermittel für Kompressorkühlanlagen, Verfahren zum Schmieren und dieses Derivat enthaltende Kompressorkühlanlage
US4946611A (en) * 1987-12-11 1990-08-07 Idemitsu Kosan Co., Ltd. Refrigerator oil containing fluorinated siloxane compounds
EP0461262B1 (de) * 1989-12-14 1995-05-03 Idemitsu Kosan Company Limited Anwendung von Schmierölzusammensetzung für Fluorkohlenwasserstoff-Kältemittel

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US3733850A (en) * 1970-01-16 1973-05-22 Chevron Res Refrigeration heat pump,and heat engine apparatus
FR2299398A1 (fr) * 1975-01-29 1976-08-27 Mobil Oil Procede et composition pour lubrifier un systeme de refrigeration
EP0203494A2 (de) * 1985-05-20 1986-12-03 Nippon Mining Company Limited Schmieröl für Verwendung in einer Flon-Atmosphäre
US4946611A (en) * 1987-12-11 1990-08-07 Idemitsu Kosan Co., Ltd. Refrigerator oil containing fluorinated siloxane compounds
WO1990005172A1 (en) * 1988-11-11 1990-05-17 Asahi Glass Company Ltd. Tetrafluoroethane composition for a regrigerator
EP0377122A1 (de) * 1988-12-06 1990-07-11 Idemitsu Kosan Company Limited Vervendung eines specifischen Polyalkylenglykol Derivats als Schmiermittel für Kompressorkühlanlagen, Verfahren zum Schmieren und dieses Derivat enthaltende Kompressorkühlanlage
EP0461262B1 (de) * 1989-12-14 1995-05-03 Idemitsu Kosan Company Limited Anwendung von Schmierölzusammensetzung für Fluorkohlenwasserstoff-Kältemittel

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5547593A (en) * 1993-08-11 1996-08-20 Asahi Kasei Kogyo Kabushiki Kaisha Lubricant oil composition comprising a fluorine-containing aromatic compound and an alkyl- or alkyl derivative-substituted aromatic compound, and a refrigerant composition containing the same
EP0699742A3 (de) * 1994-08-03 1996-05-15 Nippon Oil Co Ltd Kältemaschinenölzusammensetzung und Kältemittelzusammensetzung für Kältemaschine
US6251300B1 (en) 1994-08-03 2001-06-26 Nippon Mitsubishi Oil Corporation Refrigerator oil compositions and fluid compositions for refrigerator
US5648018A (en) * 1995-01-12 1997-07-15 Albemarle Corporation Ester/polyolefin refrigeration lubricant
EP0861883A3 (de) * 1997-02-27 1998-12-09 Idemitsu Kosan Co., Ltd. Ölzusammensetzung für Kältemaschine
EP0861883A2 (de) * 1997-02-27 1998-09-02 Idemitsu Kosan Co., Ltd. Ölzusammensetzung für Kältemaschine
US6322719B2 (en) 1997-02-27 2001-11-27 Idemitsu Kosan Co., Ltd. Refrigerating oil composition
US6193906B1 (en) 1997-02-27 2001-02-27 Idemitsu Kosan Co., Ltd. Refrigerating oil composition containing a polyether additive
EP1018538A4 (de) * 1997-06-17 2002-01-30 Nippon Mitsubishi Oil Corp Kühlschrank öl zusammensetzung und kühlschrank fuid zusammensetzung
EP1018538A1 (de) * 1997-06-17 2000-07-12 Nippon Mitsubishi Oil Corporation Kühlschrank öl zusammensetzung und kühlschrank fuid zusammensetzung
US6299792B1 (en) * 1998-01-16 2001-10-09 E. I. Du Pont De Nemours And Company Halogenated hydrocarbon refrigerant compositions containing polymeric oil-return agents
WO1999036485A1 (en) * 1998-01-16 1999-07-22 E.I. Du Pont De Nemours And Company Halogenated hydrocarbon refrigerant compositions containing polymeric oil-return agents
AU761993B2 (en) * 1998-01-16 2003-06-12 E.I. Du Pont De Nemours And Company Halogenated hydrocarbon refrigerant compositions containing polymeric oil-return agents
WO2010008640A1 (en) * 2008-07-16 2010-01-21 Dow Global Technologies Inc. Refrigerant compositions including silyl terminated polyalkylene glycols as lubricants and methods for making the same
CN107353973A (zh) * 2016-05-10 2017-11-17 特灵国际有限公司 减少制冷剂溶解度的润滑剂共混物
EP3243893A3 (de) * 2016-05-10 2018-02-14 Trane International Inc. Schmiermittelmischungen zur reduzierung der löslichkeit von kältemittel
US10612825B2 (en) 2016-05-10 2020-04-07 Trane International Inc. Lubricant blends to reduce refrigerant solubility
US11085680B2 (en) 2016-05-10 2021-08-10 Trane International Inc. Lubricant blends to reduce refrigerant solubility
CN115651740A (zh) * 2016-05-10 2023-01-31 特灵国际有限公司 减少制冷剂溶解度的润滑剂共混物

Also Published As

Publication number Publication date
TW224133B (de) 1994-05-21
DE69311396T2 (de) 1997-10-16
SG72627A1 (en) 2000-05-23
DE69311396D1 (de) 1997-07-17
EP0557796B1 (de) 1997-06-11
JPH05295384A (ja) 1993-11-09
AU3207993A (en) 1993-08-19
AU655345B2 (en) 1994-12-15
KR0139612B1 (ko) 1998-06-15
KR930018012A (ko) 1993-09-21

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