EP0421765A1 - Polyoxyalkylenäther als Schmiermittel für Haloalkangefriermittel - Google Patents

Polyoxyalkylenäther als Schmiermittel für Haloalkangefriermittel Download PDF

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Publication number
EP0421765A1
EP0421765A1 EP90310832A EP90310832A EP0421765A1 EP 0421765 A1 EP0421765 A1 EP 0421765A1 EP 90310832 A EP90310832 A EP 90310832A EP 90310832 A EP90310832 A EP 90310832A EP 0421765 A1 EP0421765 A1 EP 0421765A1
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EP
European Patent Office
Prior art keywords
oil
specimen
refrigerant
lubricant
molecular weight
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.)
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Application number
EP90310832A
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English (en)
French (fr)
Inventor
Masaaki C/O Tonen Corp. Corp. Res. And Fukuda
Saburo C/O Tonen Corp. Corp. Res. And Tsunoda
Mitsuo C/O Tonen Corp. Corp. Res. And Ohta
Hideki C/O Tonen Corp. Corp. Res. And Osaka
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Tonen General Sekiyu KK
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Tonen Corp
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Publication date
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Publication of EP0421765A1 publication Critical patent/EP0421765A1/de
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
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    • C10M145/18—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/24—Polyethers
    • C10M145/26—Polyoxyalkylenes
    • C10M145/34—Polyoxyalkylenes of two or more specified different types
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    • C10M145/18—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties

Definitions

  • the present invention relates to a lubricant for the re­frigerant 1,1,1,2-tetrafluorethane, and in particular to such lubricant which has excellent compatibility in a refrigerator and low hygroscopic property and high viscosity.
  • R11 (CCl3F) is used as a refrigerant for refrigeration or air-conditioning systems in buildings
  • R12 Cl2F2
  • the destruction of ozone layer in stratosphere is now a serious environmental problem and there is an important need to develop an alternative refrigerant.
  • R123 (CF3CHCl2) has been considered as an alternative to R11, but it has some problems such as high costs and unproven results in toxicity tests.
  • R22 CHClF2
  • R22 CHClF2
  • the operating pressure at normal temperature is high because of its low boiling point, and this requires high pressure-proofness of the equipment used.
  • R134a 1,1,1,2-tetrafluorethane
  • the synthetic oil lubricant according to this invention is represented by the general formula: where R1 and R2 each represents an alkyl group having 1 to 4 carbon atoms which may be identical to or different from each other, and average molecular weight of 500 - 1800; these polyoxypropylene glycol alkylethers are herein­after referred to as "diether oil".
  • the invention also includes a blend of said refrigerant and lubricant and optionally other additives.
  • the lubricant also includes as additives, to improve the mixture, a polyoxyalkylene glycol (referred to as a "diol oil”) or polyoxyalkylene glycol monoalkyl­ether (referred to as a "monool oil”), of average molecular weight of 500 - 1800 and represented by the general formula: wherein R 3 and R 4 each represent a hydrogen atom or are a hydrocarbon group represented by C n H 2n+1 , where n is 1 - 18; R3 and R4 may be the same or different from each other, but they should not be a hydrocarbon group, and x and y are numbers not equal to zero.
  • a polyoxyalkylene glycol referred to as a "diol oil”
  • polyoxyalkylene glycol monoalkyl­ether referred to as a "monool oil”
  • a polyether synthetic oil with high viscosity has been used as lubricant.
  • the operating temp­erature of a refrigerator lubricant oil is normally from -30 to 100°C.
  • a polyether synthetic oil as lubricant is mixed with a refrigerant, they are (due to unknown causes) separated from each other at high temperature.
  • a refrigerator lubricant oil has high compatibility with refrigerant, i.e. it does not separate therefrom at high or low temperature and it does not react with the refrigerant. If this compatibility is low, overheated equipment components may be burned out.
  • the diether oil of the invention has very high compatibility with said refrigerant, and the refrigerant used has a low hygroscopic property and is thermally and chemically stable compared with R12 (CCl 2F2) as conventionally used.
  • R12 Cl 2F2
  • R1 and R2 may be a methyl group, ethyl group, propyl group or butyl group, and may be the same or differ­ent from each other.
  • R1 and R2 are both methyl groups, or one is a methyl group and the other is an ethyl or butyl group.
  • the average molecular weight is 500 - 1800, or more preferively, 800 - 1600. If it is less than 500, the compatibility with the refrigerant is high at high temperature, but its viscosity is decreased and thermal stability is lowered. If it exceeds 1800, its viscosity is high, but its com­patibility with the refrigerant is decreased.
  • the mixture When a small quantity of a diether oil having average mole­cular weight of more than 1800 is mixed with this diether oil, the mixture has a viscosity suitable as a refrigerant liquid while it maintains compatibility with the refrigerant and the low hygroscopic property in the diether oil. It is preferable that the proportion of high molecular weight oil is 10 wt % or less; if the blending quantity is high, the compatibility with the refrigerant is decreased.
  • the same effect can be obtained by adding said diol oil or monool oil to the diether oil, and the characteristics of the diether oil can be thus improved.
  • These blending substances are added as necessary to improve the viscosity, compatibility, etc., of the diether oil. There is no need to add any if the property of the diether oil itself is suitable for the refrigerator.
  • a diol oil or monool oil additive contains ethylene oxide and propylene oxide as monomer units. If the ethylene oxide is too high, the hygroscopic property of the lubricant is increased, and so its content is preferably 0.5 (weight ratio) or less of the total of such units.
  • the terminal alkyl group of a monool oil is preferably an alkyl group having 1 - 18 carbon atoms, more preferably, a methyl, ethyl, propyl or butyl group.
  • a diol oil or monool oil to be blended with the diether oil has a higher viscosity than a diether oil of similar molecular weight because of the presence of a terminal hydroxyl group, and the viscosity of the mixture can be increased when it is blended with diether oil. If too much is blended, the compatibility with refrigerant and low water absorption property are impaired.
  • an added diol oil or monool oil has high compatibility and low viscosity, but its viscosity is decreased and hygroscopic property is also worsened. If its molecular weight exceeds 1800, the viscosity can be increased, while the com­patibility with refrigerant is decreased. When the molecular weight reaches 2000, separation from the refrigerant occurs already at room temperature, and this is not desirable. Therefore, the average molecular weight of diol oil and monool oil is 500 - 1800.
  • Suitable antioxidants are metal deactivators (metal trappers) such as benzotriazole, a benzotriazole derivative, thiadiazole, a thiadiazole derivative, triazole, a triazole derivative or dithiocarbamate, amine type antioxidants such as dioctyl-diphenylamine, phenyl- ⁇ -naphthylamine, alkyldiphenylamine or N-nitrosophenylamine, phenol type antioxidants such as 2,6-di- t -butyl para cresol, 4,4′-methyl­ene- bis (2,6-di- t -butylphenol) or 2,6-di- t -butylphenol, or phosphorus type antioxidants such as tris (2,4-di- t -­butylphenyl)phosphite, tris -nonylphenylphosphite or triphenyl phosphite. It is prefer
  • phosphorus type anti-wear agents tricresyl phosphate, trioleyl phospite, dioleyl hydrogenphospite or zinc thiophosphate may be added. It is preferable to use the anti-wear agent in amount of 0 - 10 wt % of the base oil, more preferably, 0 - 1.0 wt %.
  • Suitable rust preventives are succinic acid and succinic acid ester, oleic acid beef tallow amide, barium sulfonate or calcium sulfonate. It is preferable to use a rust pre­ventive in amount of 0.01 - 10 wt %, more preferably 0.01 - 1.0 wt %.
  • a glass tube there was put the lubricant oil and re­frigerant (1,1,1,2-tetrafluorethane) to a total volume of 2 ml, with the specimen oil and refrigerant as 3 wt % and 10 wt % respectively. After mixing well, the glass tube was placed in a constant-temperature chamber furnished with heating and cooling units, and the temperature of separation into separate phases of the specimen oil and refrigerant was measured.
  • the specimen oil was placed in a dessicator containing water, and its hygroscopic property was measured over time at room temperature and humidity of 95%.
  • Table 1 shows the results of the performance evaluation as refrigerator lubricant oil when various types of diether oil were added to 1,1,1,2-tetrafluroethane, which is the refrigerant according to the present invention.
  • EO/PO refers to the ratio of ethylene oxide to propylene oxide units in the diether oil.
  • Table 1 Specimen oil 1 2 3 4 5 6 7 8 9 10
  • the present invention The present invention
  • the present invention The present invention
  • the present invention End alkyl group in polyalkylene glycol Methylmethyl Methylmethyl Methylmethyl Butylmethyl Butylmethyl Butylmethyl Butylmethyl Butylmethyl Butylmethyl Ethylmethyl Ethylmethyl Methylmethyl EO/PO ratio in polyalkylene glycol 0/100 0/100 25/75 0/100 0/100 25/75 50/50 0/100 25/75 0/100 Average molecular weight 1,000 2,000 1,000 900 1,000 1,000 1,000 1,000 1,000 1,000 1,000 700 Viscosity (cSt 100°C) 8.9 18.9 8.1 6.8 9.8 7.9 10.0 7.7 7.8 4.0 Compatibility with refrigerant High temperature 2-phase separation temperature ° Oil content 10 wt %
  • Table 2 summarizes the results of an evaluation similar to Table 1, using a diol oil and monool oil (butyl group as alkyl group) having the molecular weight similar to the above diether oil.
  • Table 2 Specimen oil 11 12 13 14 15 16 Type of polyalkylene glycol Diol Diol Diol Monool Monool EO/PO ratio in polyalkylene glycol 0/100 0/100 0/100 70/30 0/100 50/50 Average molecular weight 700 1,000 2,000 1,000 1,100 1,000 Viscosity (cSt 100°C) 7.5 11.0 22.6 13.3 11.5 11.6 Compatibility with refrigerant High temperature 2-phase separation temperature ° Oil content 10 wt % 83°C 64 Separated at room temperature 45 50 55 ° Oil content 3 wt % 90°C or higher 84 - - - - Low temperature 2-phase separation temperature ° Oil content 10 wt % -40°C or lower -40°C or lower - -40
  • Table 3 shows the results of the evaluation similar to Example 1 when diol oil or monool oil is added to the mixed oil of diether oil or diether oil to use as refrigerator oil.
  • Table 3 Specimen oil 17 18 19 20 21 22 23 24 25 The present invention The present invention The present invention The present invention The present invention The present invention The present invention The present invention The present invention The present invention The present invention Base oil Specimen oil 5 Specimen oil 5 Specimen oil 5 Specimen oil 1 Specimen oil 1 Specimen oil 1 Specimen oil 1 Specimen oil 1 Specimen oil 1 Specimen oil 1 Added oil Specimen oil 12 Specimen oil 7 Specimen oil 11 Specimen oil 2 Specimen oil 16 Specimen oil 15 Specimen oil 11 Specimen oil 12 Specimen oil 2 Blending ratio 1) 50/50 50/50 24/76 97/3 90/10 90/10 38/62 88/12 80/20 Viscosity (cSt 100°C) 10.3 9.
  • the mixed oil of this invention is a mixed oil, containing diether oil of the specimen oil 1 added to a diether having molecular weight of 2000 of specimen oil 2 in a weight ratio of 97/3.
  • the viscosity is apparently improved from the specimen oil 1 shown in Table 1.
  • Diether oil of specimen oil 5 has butyl group at the end group, and it has lower compatibility with refrigerant at low temperature as molecular weight increases, whereas, when specimen oil 12 is added (specimen oil 17), the compatibility at low temperature is improved, and it is suitable as a refrigerator oil.
  • speciment oil 11 is added instead of speciment 12 (specimen oil 19), hygroscopic property is increased although compatibility is improved, and it is apparently not suitable as a refrigerator oil.
  • a sealed tube test at high temperature was performed, using mixtures of various amounts (and controls without the additive) of the specimen oils 1 and 24 of this invention added to 1,1,1,2-tetrafluorethane refrigerant.
  • the testing method (sealed tube test) 1 g of the specimen oil, 1,1.1,2-tetrafluorethane and one each of iron, copper and aluminum test pieces (shape: 1.7 mm in diameter, 40 mm in length) were placed into a glass tube and the tube was sealed by welding. Then, the tube was heated at 175°C for 14 davs (336 hours). At the completion of the test, the discoloration degree of the specimen oil was measured, and the metal pieces were examined.
  • the hue may not be worsened after the test with the compatibility substance of 1,1,1,2-­tetrafluoroethane and refrigerator oil of this invention, and less sludge is generated after the test.
  • the external appearance of the test samples were also satisfactory and they were chemically and thermally stable.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
EP90310832A 1989-10-03 1990-10-03 Polyoxyalkylenäther als Schmiermittel für Haloalkangefriermittel Withdrawn EP0421765A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP1258079A JP2673587B2 (ja) 1989-10-03 1989-10-03 １．１．１．２―テトラフルオルエタン冷媒を使用する冷凍機用潤滑油
JP258079/89 1989-10-03

Publications (1)

Publication Number Publication Date
EP0421765A1 true EP0421765A1 (de) 1991-04-10

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EP (1) EP0421765A1 (de)
JP (1) JP2673587B2 (de)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992017563A1 (en) * 1991-04-08 1992-10-15 Allied-Signal Inc. Stabilized polyoxyalkylene glycols
EP0533165A1 (de) * 1991-09-19 1993-03-24 Japan Energy Corporation Schmieröle für Fluoroalkanverdichter, dafür geeignete Zusammensetzungen, die Mischungen von diesen Schmierölen und Fluoroalkane enthalten und Verfahren zur Schmierung von Fluoroalkanverdichter mit diesen Schmierölen
EP0536940A3 (en) * 1991-10-11 1993-11-03 Ici Plc Lubricants
US5543068A (en) * 1988-04-08 1996-08-06 Japan Energy Corporation Lubricating oils for flon compressors, compositions adapted for flon compressors and composed of mixtures of said lubricating oils and flon, and process for lubricating flon compressor by using said lubricating oils
EP0803564A3 (de) * 1996-04-26 1997-12-29 Idemitsu Kosan Company Limited Kältemaschinenölzusammensetzung
US5711896A (en) * 1993-11-05 1998-01-27 Japan Energy Corporation Polyoxyalkylene glycol lubricating oils, working fluid compositions and methods of lubricating
EP0861883A3 (de) * 1997-02-27 1998-12-09 Idemitsu Kosan Co., Ltd. Ölzusammensetzung für Kältemaschine
WO1998050499A3 (de) * 1997-05-07 1999-02-04 Rwe Dea Ag Polyalkylenglykole als schmiermittel für co2-kältemaschinen
EP2691498A1 (de) * 2011-03-29 2014-02-05 Dow Global Technologies LLC Schmiermittelzusammensetzungen mit polylkylenglycodiether mit niedriger noack-flüchtigkeit
CN108026467A (zh) * 2015-08-14 2018-05-11 范德比尔特化学品有限责任公司 改善的抗氧化剂组合物和含有所述抗氧化剂组合物的润滑组合物
WO2020161051A1 (fr) * 2019-02-05 2020-08-13 Total Marketing Services Composition lubrifiante pour compresseur

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DE2943446A1 (de) * 1978-10-25 1980-05-14 Matsushita Electric Ind Co Ltd Schmieroel fuer kaeltemaschinen
US4755316A (en) * 1987-10-23 1988-07-05 Allied-Signal Inc. Refrigeration lubricants
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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5543068A (en) * 1988-04-08 1996-08-06 Japan Energy Corporation Lubricating oils for flon compressors, compositions adapted for flon compressors and composed of mixtures of said lubricating oils and flon, and process for lubricating flon compressor by using said lubricating oils
WO1992017563A1 (en) * 1991-04-08 1992-10-15 Allied-Signal Inc. Stabilized polyoxyalkylene glycols
EP0533165A1 (de) * 1991-09-19 1993-03-24 Japan Energy Corporation Schmieröle für Fluoroalkanverdichter, dafür geeignete Zusammensetzungen, die Mischungen von diesen Schmierölen und Fluoroalkane enthalten und Verfahren zur Schmierung von Fluoroalkanverdichter mit diesen Schmierölen
EP0536940A3 (en) * 1991-10-11 1993-11-03 Ici Plc Lubricants
US5711896A (en) * 1993-11-05 1998-01-27 Japan Energy Corporation Polyoxyalkylene glycol lubricating oils, working fluid compositions and methods of lubricating
EP0803564A3 (de) * 1996-04-26 1997-12-29 Idemitsu Kosan Company Limited Kältemaschinenölzusammensetzung
US6193906B1 (en) 1997-02-27 2001-02-27 Idemitsu Kosan Co., Ltd. Refrigerating oil composition containing a polyether additive
EP0861883A3 (de) * 1997-02-27 1998-12-09 Idemitsu Kosan Co., Ltd. Ölzusammensetzung für Kältemaschine
US6322719B2 (en) 1997-02-27 2001-11-27 Idemitsu Kosan Co., Ltd. Refrigerating oil composition
WO1998050499A3 (de) * 1997-05-07 1999-02-04 Rwe Dea Ag Polyalkylenglykole als schmiermittel für co2-kältemaschinen
EP2691498A1 (de) * 2011-03-29 2014-02-05 Dow Global Technologies LLC Schmiermittelzusammensetzungen mit polylkylenglycodiether mit niedriger noack-flüchtigkeit
CN108026467A (zh) * 2015-08-14 2018-05-11 范德比尔特化学品有限责任公司 改善的抗氧化剂组合物和含有所述抗氧化剂组合物的润滑组合物
WO2020161051A1 (fr) * 2019-02-05 2020-08-13 Total Marketing Services Composition lubrifiante pour compresseur
FR3092585A1 (fr) * 2019-02-05 2020-08-14 Total Marketing Services Composition lubrifiante pour compresseur
CN113597465A (zh) * 2019-02-05 2021-11-02 道达尔销售服务公司 用于压缩机的润滑组合物
US11535809B2 (en) 2019-02-05 2022-12-27 Total Marketing Services Compressor lubricant composition
CN113597465B (zh) * 2019-02-05 2023-03-31 道达尔销售服务公司 用于压缩机的润滑组合物

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JP2673587B2 (ja) 1997-11-05
JPH03121195A (ja) 1991-05-23

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