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WO1992017563A1 - Glycols de polyoxyalkylene stabilises - Google Patents

Glycols de polyoxyalkylene stabilises Download PDF

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Publication number
WO1992017563A1
WO1992017563A1 PCT/US1992/002148 US9202148W WO9217563A1 WO 1992017563 A1 WO1992017563 A1 WO 1992017563A1 US 9202148 W US9202148 W US 9202148W WO 9217563 A1 WO9217563 A1 WO 9217563A1
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Prior art keywords
tert
ether
group
composition
butylphenol
Prior art date
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Ceased
Application number
PCT/US1992/002148
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English (en)
Inventor
Raymond Hilton Percival Thomas
Ruth Hsiu-Hua Chen
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.)
Honeywell International Inc
Original Assignee
AlliedSignal Inc
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Filing date
Publication date
Application filed by AlliedSignal Inc filed Critical AlliedSignal Inc
Publication of WO1992017563A1 publication Critical patent/WO1992017563A1/fr
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    • C10M2223/10—Phosphatides, e.g. lecithin, cephalin

Definitions

  • the present invention relates to stabilized polyoxyalkylene glycols. More particularly, the present invention relates to relates to stabilized refrigeration compositions comprising tetrafluoroethane and polyoxyalkylene glycols.
  • the tetrafluoroethane is 1,1,1,2-tetrafluoroethane (known in the art as R134a) .
  • R134a is a refrigerant which may replace dichlorodifluoromethane (known in the art as R12) in many applications because environmental concerns over the use of R12 exist.
  • R12 is used in closed loop refrigeration systems; many of these systems are automotive air-conditioning systems.
  • R12 refrigeration systems generally use mineral oils to lubricate the compressor.
  • Mineral oil is typically paraffin oil or naphthenic oil.
  • R134a has been mentioned as a possible replacement for R12 because concern over potential depletion of the ozone layer exists.
  • R134a has properties similar to those of R12 so that it is possible to substitute R134a for R12 with minimal changes in equipment being required.
  • the symmetrical isomer of R134a is R134 (1,1,2,2-tetrafluoroethane) ; the isomer is also similar in properties and may also be used. Consequently, it should be understood that in the following discussion, "tetrafluoroethane" will refer to both R134 and R134a.
  • chlorodifluorome hane (known in the art as R22) and chlorodifluoromethane/1-chloro-1,1,2,2,2- pentafluoroethane (known in the art as R502) are not completely miscible in common refrigeration oils. See Downing, FLUOROCARBONS REFRIGERANT HANDBOOK, Page 13.
  • R22 chlorodifluorome hane
  • R502 chlorodifluoromethane/1-chloro-1,1,2,2,2- pentafluoroethane
  • R502 chlorodifluoromethane/1-chloro-1,1,2,2,2- pentafluoroethane
  • R134a is not miscible with mineral oils; consequently, different lubricants will be required for use with R134a.
  • no major changes to equipment should be necessary when the refrigerant substitution is made. If the lubricant separates from the refrigerant, it is expected that serious operating problems could result. For example, the compressor could be inadequately lubricated if refrigerant replaces the lubricant. Significant problems in other equipment also could result if a lubricant phase separates from the refrigerant during condensation, expansion, or evaporation. These problems are expected to be most serious in automotive air-conditioning systems because the compressors are not separately lubricated and a mixture of refrigerant and lubricant circulates throughout the entire system.
  • Small amounts of lubricants may be soluble in R134a over a wide range of temperatures, but as the concentration of the lubricant increases, the temperature range over which complete miscibility occurs, i.e., only one liquid phase is present, narrows substantially.
  • two consolute temperatures i.e., a lower and a higher temperature, may exist. That is, a relatively low temperature below which two distinct liquid phases are present and above which the two phases become miscible and a higher temperature at which the single phase disappears and two phases appear again may exist.
  • a diagram of such a system for R502 refrigerant is shown as Figure 2 in the Kruse et al. paper mentioned above.
  • Kokai Patent Publication 179,699 published October 12, 1984; and Kokai Patent Publication 281,199 published December 11, 1988 teach additives such as epoxides for refrigeration lubricants.
  • U.S. Patents 4,248,726; 4,267,064; and 4,431,557 teach the addition of epoxides to compositions of refrigerants and lubricants.
  • the references also teach that known additives such as phenol or amine type antioxidants; sulphur or phosphorus type oiliness improvers; silicone type antifoam agents; metal deactivators such as benzotriazole, amines, and acid esters; and load carrying additives such as phosphoric acid esters, phosphorous acid esters, thiophosphoric acid esters, organic sulfur compounds, and organic halogen compounds can be used.
  • additives such as phenol or amine type antioxidants; sulphur or phosphorus type oiliness improvers; silicone type antifoam agents; metal deactivators such as benzotriazole, amines, and acid esters; and load carrying additives such as phosphoric acid esters, phosphorous acid esters, thiophosphoric acid esters, organic sulfur compounds, and organic
  • Patent 4,948,525 teaches that known refrigerator oil additives such as phenol-type antioxidants such as di-tert-butyl-p-cresol; amine-type antioxidants such as phenyl- ⁇ -naphthylamine and N,N'- di(2-naphthyl) -p-phenylenediamine; load resistant additives such as zinc dithiophosphate, chlorinated paraffin, fatty acids, and sulfur type load resistant compounds; silicone-type antifoaming agents; metal inactivators such as benzotriazole; and hydrogen chloride captors such as glycidyl ethacrylate and phosphite esters may be used in refrigeration compositions.
  • phenol-type antioxidants such as di-tert-butyl-p-cresol
  • amine-type antioxidants such as phenyl- ⁇ -naphthylamine and N,N'- di(2-naphthyl) -p-phenylenediamine
  • the present invention provides stabilized polyoxyalkylene glycols.
  • the stabilized polyoxyalkylene glycols comprises: (a) polyoxyalkylene glycol and (b) a composition comprising: (i) at least one component selected from the group consisting of phenol and trivalent phosphorus compound and (ii) at least one epoxide selected from the group consisting of aromatic epoxide and fluorinated alkyl epoxide wherein the composition (b) substantially reduces the decomposition of the polyoxyalkylene glycol (a) .
  • the present invention provides a stabilized refrigeration composition
  • a stabilized refrigeration composition comprising: (a) a fluorine-containing refrigerant selected from the group consisting of fluorocarbon refrigerant and hydrofluorocarbon refrigerant; (b) polyoxyalkylene glycol; and (c) a composition comprising: (i) at least one component selected from the group consisting of phenol and trivalent phosphorus compound and (ii) at least one epoxide selected from the group consisting of aromatic epoxide and fluorinated alkyl epoxide wherein the composition (c) substantially reduces the decomposition of the polyoxyalkylene glycols (b) .
  • fluorocarbon as used herein means a compound having fluorine and carbon atoms.
  • hydrofluorocarbon as used herein means a compound having hydrogen, fluorine, and carbon atoms.
  • the present invention also provides a method of substantially reducing the decomposition of polyoxyalkylene glycol.
  • the method comprises the step of: employing a composition comprising: (i) at least one component selected from the group consisting of phenol and trivalent phosphorus compound and (ii) at least one epoxide selected from the group consisting of aromatic epoxide and fluorinated alkyl epoxide wherein the composition substantially reduces the decomposition of polyoxyalkylene glycol.
  • the stabilized polyoxyalkylene glycols of the present invention comprises: (a) polyoxyalkylene glycol and (b) a composition comprising: (i) at least one component selected from the group consisting of phenol and trivalent phosphorus compound and (ii) at least one epoxide selected from the group consisting of aromatic epoxide and fluorinated alkyl epoxide.
  • the present stabilized polyoxyalkylene glycols are useful in compression refrigeration and air-conditioning systems.
  • Any combination of at least phenol and/or at least one trivalent phosphorus compound and at least one aromatic epoxide and/or at least one fluorinated alkyl epoxide which substantially reduces the decomposition of polyoxyalkylene glycols can be used in the present invention.
  • the phenol is phenol selected from the group consisting of:
  • the most preferred phenols are hydroquinone and 2,6-di-tert-4-methylphenol.
  • the foregoing phenols are commercially available.
  • mixtures of phenols may be used in addition to the use of a single phenol in the present invention.
  • phenol as used herein includes sterically hindered phenols.
  • the trivalent phosphorus compound is trivalent phosphorus compound selected from the group consisting of tris(4-nonylphenyl)phosphite; tris(2,4-di-tert-butylphenyl)phosphite; 3,9-dioctadecyloxy-2,4,8,10-tetraoxa-3,9-diphospha-
  • the preferred trivalent phosphorus compound is tris(2,4-di-tert-butylphenyl)phosphite.
  • the foregoing phosphorus compounds are commercially available. As mentioned earlier, mixtures of phosphorus compounds may be used in addition to the use of a single phosphorus in the present invention.
  • Preferred aromatic epoxides are of the formula [Ri] n - - tiy a wherein R 2 is OCH 2 CHCH 2 -0; R t is hydrogen, alkyl having 1 to 20 carbon atoms, fluoroalkyl having 1 to 20 carbon atoms, aryl having 6 to 28 carbon atoms, or fluoroaryl having 1 to 28 carbon atoms; M is aryl selected from the group consisting of phenyl, naphthyl, anthracyl, and phenanthrenyl, or alkylaryl; and each n and m is from 1 to 10.
  • the aromatic epoxide is aromatic epoxide selected from the group consisting of butylphenylglycidyl ether; pentylphenylglycidyl ether; hexylphenylglycidyl ether; heptylphenylglycidyl ether; octylphenylglycidyl ether; nonylphenylglycidyl ether; glycidyl methyl phenyl ether; decylphenylglycidyl ether; 1,4-diglycidyl phenyl ether and derivatives thereof; 1,4-diglycidyl naphthyl ether and derivatives thereof; 2,2' [[[5- heptadecafluorooctyl] 1,3phenylene]bis [[2,2,2trifluorome thyl]ethylidene]oxymethylene]bisoxirane and derivatives thereof; naphthyl
  • aromatic epoxide is naphthyl glycidyl ether.
  • aromatic epoxides are commercially available.
  • mixtures of aromatic epoxides may be used in addition to the use of a single aromatic epoxide in the present invention.
  • Preferred fluorinated alkyl epoxides are of the formula wherein R f is fluor nated or perfluorinated alkyl group having 1 to 20 carbon atoms. More preferably, the fluorinated alkyl epoxide is fluorinated alkyl epoxide selected from the group consisting of glycidyl trifluoromethyl ether; glycidyl pentafluoroethyl ether; glycidyl heptafluoropropyl ether; and glycidyl monofluorobutyl ether.
  • the most preferred fluorinated alkyl epoxide is glycidyl pentafluoroethyl ether.
  • the foregoing fluorinated alkyl epoxides are commercially available. As mentioned earlier, mixtures of fluorinated alkyl epoxides may be used in addition to the use of a single fluorinated alkyl epoxide.
  • the ratio of phenol or phosphorus to epoxide in the stabilizing polyoxyalkylene glycols can be varied from 1:99 to 99:1.
  • the amount of phenol and aromatic or fluorinated alkyl epoxide used is about 0.01 to about 5 percent by weight based on the amount of the polyoxyalkylene glycols.
  • polyoxyalkylene glycols include the polyoxyalkylene glycols of commonly assigned U.S. Patent 4,755,316 which is incorporated herein by reference. Such polyoxyalkylene glycols have a molecular weight between about 300 and about 2000, a viscosity of about 25 to about 150 centistokes at 37°C, and a viscosity index of at least 20.
  • the polyoxyalkylene glycols preferably have at least 80 percent propylene oxide units; the remaining units may be ethylene oxide, butylene oxide, or other units such as esters and olefins which may be polymerized with propylene oxide.
  • the polyoxyalkylene glycols may also be capped with at least one hydrocarbon group such as alkyl, aryl, or ester.
  • a preferred example of such a capped polyoxyalkylene glycol is a copolymer of ethylene oxide and propylene oxide wherein one end is capped with a butyl group.
  • polyoxyalkylene glycols include the polyoxyalkylene glycols having a cap of a fluorinated alkyl group on at least one end thereof of commonly assigned U.S. Patent 4,975,212 which is incorporated herein by reference. These glycols have a molecular weight between about 300 and about 3,000, a viscosity of about 5 to about 150 centistokes at 37°C, and a viscosity index of at least 20.
  • the foregoing fluorinated lubricants comprise the formula (I)
  • the lubricant may be terminated by a hydrogen at one end and a fluorinated alkyl group at the other end, by an alkyl group at one end and a fluorinated alkyl group at the other end, or by a fluorinated alkyl group at both ends.
  • the fluorinated alkyl group may be branched or straight chain as long as fluorine atoms are attached thereto.
  • the foregoing fluorinated lubricants may be formed by fluorinating polyoxyalkylene glycols.
  • the polyoxyalkylene glycols used may have primary carbons at both ends, a primary carbon at one end and a secondary carbon at the other end, or secondary carbons at both ends.
  • the polyoxyalkylene glycols used have a primary carbon at one end and a secondary carbon at the other end or secondary carbons at both ends.
  • At least one of R, and R is a fluorinated alkyl group of the formula
  • x is 1 to 4 and y is 0 to 15. More preferably, x is 1 and y is 0 so that at least one of R. and R 4 is a fluorinated alkyl group of the formula -CH 2 CF 3 or x is 1 and y is 2 so that at least one of R ! and R 4 is a fluorinated alkyl group of the formula -CH 2 (CF 2 ) 2 CF 3 . Even more preferably, both R, and R, are fluorinated alkyl groups, m is 7 to 34, and n is 0.
  • the foregoing fluorinated lubricating compositions may be formed by capping a polyoxyalkylene glycol with at least one fluorinated alkyl group.
  • the lubricating compositions may be formed by copoly erizing ethylene and propylene oxides and terminating the resulting copolymer with at least one fluorinated alkyl group.
  • the foregoing fluorinated lubricants wherein one end has an alkyl group and the other end has a fluorinated alkyl group or both ends have fluorinated alkyl groups are formed as follows.
  • the polyoxyalkylene glycol is converted to the tosylate by treatment with p-toluenesulfonyl chloride in a suitable base such as pyridine and then the tosylated polyglycol is reacted with the sodium alkoxide of the appropriate fluorinated alcohol.
  • the foregoing fluorinated lubricants wherein one end has a h droxyl group and the other has a fluorinated alkyl group are formed as follows.
  • An alcohol initiator such as the sodium alkoxide of trifluoroethanol is used in the polymerization of polypropylene oxide.
  • the fluorinated lubricant is a fluorinated copolymer of butylene oxide and propylene oxide or is a mixture of fluorinated butylene oxide and fluorinated propylene oxide.
  • the stabilized polyoxyalkylene glycols are used with a fluorine- containing refrigerant to form a refrigeration composition.
  • the present refrigeration compositions are useful in compression refrigeration and air- conditioning systems.
  • the fluorocarbon or hydrofluorocarbon refrigerant is selected from those listed those listed in Table I below.
  • R134a is used. Until R134a becomes available in commercial quantities, it may be produced by any known method including reacting ethylene with carbon having elemental fluorine adsorbed therein as taught by commonly assigned U.S. Patent 4,937,398 which is incorporated herein by reference.

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  • Lubricants (AREA)

Abstract

A des températures supérieures à 200 °C, des lubrifiants constitués de glycols de polyoxyalkylène se décomposent pour former de l'eau et d'autres produits. Ce phénomène est indésirable dans des systèmes de réfrigération et de conditionnement d'air, car l'eau présente entraîne la corrosion des parties métalliques du système, gène et bloque les soupapes de détente lors du refroidissement du réfrigérant, et réagit avec les films de poly(éthylène téréphtalate) qui isolent les parties du moteur électrique dans des systèmes hermétiques de sorte que lesdits films peuvent être détruits et que l'eau peut entrer en contact avec les parties du moteur électrique. La présente invention propose une composition stabilisée qui réduit nettement la décomposition des glycols de polyoxyalkylène. Les glycols de polyoxyalkylène stabilisés comprennent: (a) un glycol de polyoxyalkylène et (b) une composition comprenant: (i) au moins un composant choisi dans le groupe constitué de phénol et d'un composé de phosphore trivalent et (ii) au moins un époxyde sélectionné dans le groupe constitué d'un époxyde aromatique et d'un époxyde d'alkyle fluoré.
PCT/US1992/002148 1991-04-08 1992-03-18 Glycols de polyoxyalkylene stabilises Ceased WO1992017563A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US68183591A 1991-04-08 1991-04-08
US681,835 1991-04-08

Publications (1)

Publication Number Publication Date
WO1992017563A1 true WO1992017563A1 (fr) 1992-10-15

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PCT/US1992/002148 Ceased WO1992017563A1 (fr) 1991-04-08 1992-03-18 Glycols de polyoxyalkylene stabilises

Country Status (2)

Country Link
AU (1) AU1775492A (fr)
WO (1) WO1992017563A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009110584A1 (fr) * 2008-03-07 2009-09-11 出光興産株式会社 Composition lubrifiante pour machine frigorifique
US8568609B2 (en) 2007-11-22 2013-10-29 Idemitsu Kosan Co., Ltd. Lubricating oil composition for refrigerating machine
US8906250B2 (en) 2007-11-22 2014-12-09 Idemitsu Kosan Co., Ltd. Lubricant composition for refrigerating machine and compressor using the same
US9410105B2 (en) 2012-11-16 2016-08-09 Basf Se Lubricant compositions comprising epoxide compounds

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EP0460614A1 (fr) * 1990-06-08 1991-12-11 Nippon Oil Company, Limited Huiles lubrifiantes pour réfrigérateurs

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8568609B2 (en) 2007-11-22 2013-10-29 Idemitsu Kosan Co., Ltd. Lubricating oil composition for refrigerating machine
US8906250B2 (en) 2007-11-22 2014-12-09 Idemitsu Kosan Co., Ltd. Lubricant composition for refrigerating machine and compressor using the same
WO2009110584A1 (fr) * 2008-03-07 2009-09-11 出光興産株式会社 Composition lubrifiante pour machine frigorifique
JP2009235111A (ja) * 2008-03-07 2009-10-15 Idemitsu Kosan Co Ltd 冷凍機用潤滑油組成物
EP2251400A4 (fr) * 2008-03-07 2011-10-26 Idemitsu Kosan Co Composition lubrifiante pour machine frigorifique
US8673169B2 (en) 2008-03-07 2014-03-18 Idemitsu Kosan Co., Ltd. Lubricant composition for refrigerating machine
US9410105B2 (en) 2012-11-16 2016-08-09 Basf Se Lubricant compositions comprising epoxide compounds

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