`
`(19) Japanese Patent Office
`(JP)
`(A)
`(12) Laid Open Patent Publication
`(11) Laid Open Patent Publication No. Hei 5-85970
`
`(43) Date of publication: April 6, 1993
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`(51) Int. Cl.5
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`Identification No.
`
`C07 C 21/18
`C09 K 5/04
`
`Internal Patent
`Classification
`9280-4H
`8930-4H
`
`FI
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`Request for examination: not yet filed,
`
`Requested Number of Claims: 1
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`(total 3 pages)
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`(21) Application No.:
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`Hei 3-245934
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`(22) Filing Date:
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`September 25, 1991
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`(71) Patent Applicant:
`
`(72) Inventor:
`
`(72) Inventor:
`
`000002853
`Daikin Industries, Ltd.
`Umeda Center Building, 4-12,
`Nakazaki nishi 2-chome,
`Kita-ku,Osaka-shi,
`Osaka-fu(JP) ,
`Yukio Omure
`Yodogawa-seisakusyo
`1-1 Nishihitotsuya Settsu-shi,
`Osaka-fu (JP)
`Masahiro Noguchi
`Yodogawa-seisakusyo
`1-1 Nishihitotsuya Settsu-shi,
`Osaka-fu (JP)
`
`(74) Representative: Yuji Kakehi (four others) , Patent Attorney
`
`To be continued to the last page
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`(54) Title of the invention:
`Refrigerant
`
`(57) Abstract
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`[Object]
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`A main purpose is to provide a refrigerant of which ODP
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`Page 1 of 9
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`Arkema Exhibit 1034
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`
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`is zero and which is excellent in various performances.
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`[Constitution]
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`A refrigerant made of
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`2-trifl uoromethyl -3,3,3-trifluoropropene
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`• 2 .
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`Page 2 of 9
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`
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`[SCOPE OF CLAIMS)
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`[Claim l] A refrigerant made of
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`2-trifluoromethyl-3,3,3-trifluoropropene.
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`[DETAILED DESCRIPTION OF THE INVENTION)
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`[0001]
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`[FIELD OF INDUSTRIAL APPLICATION]
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`The present invention relates to a novel refrigerant.
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`[0002)
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`[Prior art and problems thereof)
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`Heretofore, as a working fluid or a refrigerant, a
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`chlorofluoroalkane, an azeotropic composition thereof or a
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`composition having an analogue composition thereof, has been
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`known. Among them, at present, as a working fluid for a
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`refrigerator, CFCll (trichlorofluoromethane ) , CFC12
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`(dichloro-difluoromethane), CFC114
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`(1,2-dichloro-1,1,2,2-tetrafluoroethane), HCFC22
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`(chlorodifluoromethane) or the like, is mainly used. However,
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`in recent years, it is pointed out that, it takes a long t ime
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`to decompose such a chlorofluoroalkane when it is discharged
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`into the atmosphere , therefore it goes up to the stratosphere ,
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`chlorine radicals produced by the decomposition in the
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`stratosphere tend to destroy the ozone layer, and as a result
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`the ecosystem in the earth, including human beings, are
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`adversely affected. Accordingly, Use or Production of these
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`chlorofluoroalkanes which is highly likely to destroy the ozone
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`layer, is restricted according to the international agreement.
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`As a chlorofluoroalkane which is currently subj ect to restraint,
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`. 3.
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`Page 3 of 9
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`
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`the above Rll, Rl2 or Rl4 may, for example, be mentioned.
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`[0003]
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`Among the above chlorofluoroalkanes, HCFC22 is not subjected
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`to restraint since its ozone depleting potential (hereinafter,
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`referred to as "ODP") is qui te low as compared with the above
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`compound as an obj ect of restraint ( e . g . about 1/20 of CFCll),
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`but it is desirable that ODJ? is replaced by a compound of which
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`ODP is zero.
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`[0004)
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`In acc ordan ce with the prevalence of air
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`conditioning/re frigeration facilities, the restriction on
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`use/production of these refrigerant of w hich demands are
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`increased every year, greatly affe cts the present social
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`organization in gen eral, and therefore there are urgent needs
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`to develop a novel refriger ant which is n o or extremely low
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`danger of ozone-destroying problem.
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`[0005]
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`As the above promising compound (hereinafter, referred to as
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`an alternative candidate compound) which can be replaced by a
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`chlorofluoroalkane, a chl or of lu or oalkane or a fluoroalkane
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`containing hydrogen atom(s), such as HCFC21
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`{dichloromonofluorornethane) , HFC23 (trifluor om et hane ) , HFC32
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`(di fluor orn ethan e) , HCFC124
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`(monochlorotetrafluoromethane) ,
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`HFC125 (pentafluoroethane), HCFC133a
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`(monochlorotrifluoroethane), HFC134a (tetrafluoroethane),
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`HCFC142b (monochlorodifluoroethane) , HFC143a
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`{trifluoroethane) may, for example, be mentioned.
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`Page 4 of 9
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`[0006]
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`However, such an alternative candidate compound alone cannot
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`satisfy all of performances such as ODP, non-flammability, and
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`other performances required for a refrigerant. Therefore it
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`is considered that two or more of them are used as a mixture.
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`However, if a mixture is used as a refrigerant, the composition
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`of the mixture tends to change during phase change such as
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`evaporation or condensation in a heat exchanger, in a mere mixed
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`state, and therefore it is difficult to keep reliability in
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`operation of an apparatus.
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`[0007]
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`Further, as an azeotropic mixed composition, one having
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`CFC12/HFC152a=78.3/26.2 wt% (RSOO), HCFC22/CFCll5=48.8/51.2
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`wt%
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`(R502), CFC13/HFC23•59.9/40.l wt%
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`(R503) or
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`HFC32/CFC115-48.2/51.8 wt%
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`(RS04) has been known, but such
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`refrigerants contain chlorine atoms, and therefore their use
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`is expect ed to be restricted in future.
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`[0008]
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`[OBJECT TO BE ACCOMPLISHED BY THE INVENTION)
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`It is a main object of the present invention to provide a
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`refrigerant of which ODP is zero, which is excellent in
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`performances as a refrigerant, and which is not substantially
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`accompanied by compositional change during phase change in
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`operation of an apparatus.
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`(0009]
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`[MEANS TO ACCOMPLISH THE OBJECT ]
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`The present inventors have conducted extensive studies to
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`Page 5 of 9
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`
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`achieve the above objects. And as a result, they have
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`discovered that 2-trifluoromethyl-3,3,3-trifluoropropene
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`satisfies a requirement to accomplish its purpose.
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`[0010]
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`That is, the object of the present invention is to provide a
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`refrigerant made of
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`2-trifluoromethyl-3,3,3-trifluoropropene.
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`[0011]
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`The main properties of
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`2-trifluoromethyl-3,3,3-trifluoropropene to be used in the
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`present invention are shown in the following Table 1.
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`Table 1
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`Molecular weight
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`Boiling point(°C)
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`Critical temperature(°C}
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`Critical pressure(kg/cm2·a)
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`140
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`13
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`152
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`31.9
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`Latent heat of vaporization(kcal/kg:0°C)
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`36.9
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`Ozone resolution
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`0
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`[0012]
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`It is possible to use a stabilizer in combination with the
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`refrigerant of the present invention, as the case requires.
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`That is, in a case where high stability is required under severe
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`working conditions, it is possible to add an epoxide such as
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`propylene oxide, 1,2-butylene oxide or glycidol; a phosphite
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`such as dimethyl phosphite, diisopropyl phosphate or diphenyl
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`phosphite; a thiophosphite such as trilauryl trithiophosphite;
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`a phosphine sulfide such as triphenoxy phosphine sulfide or
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`. 6.
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`Page 6 of 9
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`trimethylphosphine sulfide; a boron compound such as boron,
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`triethyl borate, triphenyl borate, phenylboronic acid or
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`diphenylboronic acid; a phenol such as
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`2,6-di-tert-butyl-p-cresol; a nitroalkane such as
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`nitromethane or nitroethane; an acrylate such as methyl
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`acrylate or ethyl acrylate; dioxane; tert butanol;
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`pentaerythritol; or p-isopropenyl toluene, in an amount of from
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`0.01 to 5% of the weight of a refrigerant.
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`[0013]
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`Further, it is possible to blend other compounds with the
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`refrigerant of the present invention, within a range not to
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`impair the purpose or the effect of the present invention. Such
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`other compounds may, for example, be an ether such as dimethyl
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`ether or pentafluorodimethyl ether; an amine such as
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`perfluoroethyl amine; or LPG.
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`[0014)
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`[EFFECT OF THE INVENTION]
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`2-trifluoromethyl-3,3,3-trifluoropropene to be used in the
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`present invention is easily decomposable and contains no
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`chlorine atoms which has an impact on ari ozone layer, therefore
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`it has zero ODP and no risk of disruption of the ozone layer.
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`The refrigerant of the present invention has high refrigerating
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`capacity and relatively good coefficient of performance. For
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`example, it shows comprehensively exceilent performances that
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`the refrigerating capacity is about 1.25 times and that the
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`coefficient of performance is the same, as compared with CFCll.
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`Accordingly, the refrigerant of the present invention can be
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`. 7.
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`Page 7 of 9
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`
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`replaced with CFCll currently used as a refrigerant for e.g.
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`turbo.
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`Since the refrigerant of the present invention is a
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`single compound, it is possible to advantageously carry out e.g.
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`control of fluid or recycling after recovery. The refrigerant
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`of the present invention may be used as it is, without changing
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`materials for existing refrigerators, since the solubility in
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`a polymer compound is low. The refrigerant of the present
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`invention is exc ellent in compatibility with e.g. PAG
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`(polyalkylene glycol) type oil or polyester type oil. The
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`refrigerant of the present invention is relatively excellent
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`in thermal stability.
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`[0015]
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`[EXAMPLE]
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`Now, Examples and Comparative Example will be shown below so
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`as to make more clear the feature of the present invention .
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`[0016] Example l
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`With respect to a refrigerator having a l horsepower and using
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`the refrig erant of the present invention, the evaporation
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`temperature of the refrigerant in a condenser was adjusted to
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`5°C, the condensation temperature was adjusted to 40°C, the
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`superheating temperature at an inlet of a compressor was
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`adj usted to 9°C, the supercooling degree at an outlet of the
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`condenser was adjusted to 5°C to carry out ope ra ti on. As
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`refrigeration oil, a polyalkylene glycol was used.
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`Coefficient of performance (COP) , refrigerating capacity
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`[kcal/m3] and a compressor gas discharge temperature
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`(°C) are
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`shown in Table 2. Further, in Table 2, results of CFCll are
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`. 8.
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`Page 8 of 9
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`
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`also shown for comparison.
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`Table 2
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`COP
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`refrigerating
`compressor gas
`capacity (kcal/m3) discharge
`temperature
`
`(°C)
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`The Present
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`7 . 1
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`157
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`Invention
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`(CFC11)
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`7.3
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`125
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`40
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`51
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`From the result shown in Table 2, it is clear that, as compared
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`with CFCl l, the refrigerant of the present invention is
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`excellent especially in refrigerating capacity, has the same
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`coefficient of performance, and has comprehensively
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`well-balanced characteristics.
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`Continued from front page
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`(72) Inventor:
`
`( 7 2) Inventor:
`
`Katsuki Fujiwara
`Yodogawa-seisakusyo
`1-l Nishihitotsuya Settsu - shi ,
`Osaka-fu (JP)
`Hiroshi Momota
`Yodogawa-seisakusyo
`1-1 Nishihitotsuya Settsu-shi,
`(JP)
`Osaka-fu
`
`. 9.
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`Page 9 of 9