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United States Patent Office Patented Nov 3,770,640 United States Patent Office Patented Nov. 6, 1973 2 bility to heat and decompose under conditions of normal 3,770,640 use. Additionally, some azo dyes do not have the requisite REFRGERANTS COLORED FOR LEAK solubility, e.g., in refrigeration oil-dichlorodifluoro ENDICATION Philip Lee Bartlett, Wilmington, Del, assignor to E. I. du methane. Pont de Nemours and Company, Wilmington, Del. 5 In addition to these problems, some of the dyes utilized Filed Nov. 22, 1971, Ser. No. 201,120 in the art severely stain acrylic finishes such as those nor nt. C. CO9k 3/02 mally used in automobiles thus making it impractical to U.S. C. 252-68 15 Claims use refrigerants containing such dyes in automobile air conditioners. O Alburger in U.S. 3,489,898 discloses solutions and dis ABSTRACT OF THE DISCLOSURE persions of various fluorescent whitening agents in mix Refrigerants, refrigeration oils and refrigerant-refrigera tures of non-volatile fluorotelomers and volatile trichloro tion oil mixtures containing anthraquinone dyes having the fluoromethane of 1,1,2-trichloro-1,2,2-trifluoroethane and Structure fluoromethane of 1,1,2-trifluoroethane and NORO,)(tlo 5 the application of the solutions to the surfaces of contain ers intended for the storage of liquid oxygen. Surface de fects in the containers are made visible by evaporating the R R8 surface solution leaving some solution entrapped in the sur face cracks. Alburger also discloses, for this use, the dye 20 1,4-bis(4-methylanilino)anthraquinone. The same dye is disclosed as suitable in the process of U.S. 3,399,025 wherein the dye is tranfered from suspended trichloroflu oromethane to polymer granules in an aqueous slurry. The process is carried out under pressure and at temperatures 25 up to about 275 F. for times up to one hour. It has now been discovered that by incorporating antha wherein R, R2, R3 and R4 are each H or an anilino group, quinone dyes, having a designated structure, into fluoro substituted by from 1 to 3 saturated alkyl groups having carbon refrigerants, refrigeration oils and mixtures thereof, a total of from 4 to 24 carbon atoms, and wherein at least the resultant compositions provide positive indication of 30 leaks anywhere in a vapor compression heat transfer sys 2 and no more than 3 of R, R2, R3 and R are H. tem; possess adequate stability to the highest temperatures normally encountered in refrigeration systems in the pres BACKGROUND OF THE INVENTION ence of fluorinated refrigerants, refrigeration oils and materials of construction; do not interfere with the normal (1) Field of the invention 35 operation of such a heat transfer system and are easily The invention relates to refrigerants, refrigeration oils removed from painted surfaces, as for example, automo and refrigerant-refrigeration oils colored with anthraqui bile finishes, or refrigerator cabinets. none dyes for leak detection. They are particularly useful in the field of vapor compression heat transfer processes SUMMARY OF THE INVENTION wherein fluorocarbon refrigerants, at least in part in the 40 liquid phase, are subjected to elevated temperature, e.g., A composition which comprises in conventional home refrigeration, in freezing, air con (A) a refrigeration liquid selected from the group ditioning, heat pumping, and in heat engines employing consisting of power turbines. (a) a fluorocarbon refrigerant selected from the 45 group consisting of (2) Description of the prior art trichlorofluoromethane, Various dyes have been employed to indicate the pres dichlorodifluoromethane, ence and location of leaks in vapor compression heat chlorodifluoromethane, transfer systems such as refrigeration systems employing 1,1,2-trichloro-1,2,2-trifluoroethane, fluorocarbon refrigerants and refrigeration oils. Escaping 50 1,2-dichloro-1,1,2,2-tetrafluoroethane, refrigerant and/or oil containing dissolved dye are 1,1-difluoroethane/dichlorodifluoromethane intended to deposit easily visible dye indications on the aZeotrope, outside of the device, thus facilitating recognition and chloropentafluoroethane/chlorodifluoro location of a leak. None of the dyes of the art employed 55 methane azeotrope, for this purpose satisfy all of the stringent requirements chlorotrifluoromethane, of the refrigeration field. chlorotrifluoromethane/trifluoromethane U.S. 1,915,965 discloses the use of basic dyes such as azeotrope, methyl violet base, crystal violet, Auramine B, Rhodamine bromotrifluoromethane, B, etc., as leak indicators in refrigeration systems. The 60 basic dyes as a class are generally too unstable for use at trifluoromethane, the temperatures often encountered in modern refrigera chloropentafluoroethane tion, i.e., temperatures as high as 300' F. and even about difluoromethane/chloropentafluoroethane 400 F. at the compressor outlet valve. The color is azeotrope, destroyed and the dye is converted to tars which may plug chloropentafluoroethane/1,1-difluoroethane the system. Further, such dyes generally possess inade 65 azeotrope, quate solubility in the refrigeration oils. For example, dichlorofluoromethane, methyl violet base dissolves to the extent of less than 1 wt. dichlorodifluoromethane/chlorofluoro percent in well known “Suniso' 3GS refrigeration oil. methane azeotrope, U.S. 3,370,013 discloses the use of oil soluble azo dyes 70 chlorofluoromethane/1,2-dichlorotetra as leak indicators in fluorocarbon refrigerants. Like the fluoroethane azeotrope, basic dyes, the azo dyes generally possess inadequate sta difluoromethane, 3,770,640 3 4. 1,2-dibromotetrafluoroethane, dichlorodifluoromethane/chlorofluoromethane azeo 1,1,1-trifluoroethane, trope (British Pat. 1,218,917), 1,1-difluoro-1-chloroethane, chlorofluoromethane/1,2-dichlorotetrafluoroethane azeo 1,1-difluoroethane, trope (U.S. Pat. 3,505,232), bromotrifluoromethane/difluoromethane difluoromethane, azeotrope, 1,2-dibromotetrafluoroethane, 1,2-dichlorotetrafluoroethane/dichloro 1,1,1-trifluoroethane, fluoromethane azeotrope, and 1,1-difluoro-1-chlorethane, hexafluoroethane/trifluoromethane 1,1-difluoroethane, azeotrope, O bromotrifluoromethane/difluoromethane azeotrope (b) a refrigeration oil and (U.S. Pat. 3,418,242), (c) a mixture of (a) and (b) and 1,2-dichlorotetrafluoroethane/dichlorofluoromethane (B) an anthraquinone dye or mixture of anthraqui azeotrope (U.S. Pat. 2,630,686), and none dyes having the structure hexafluoroethane/trifluoromethane azeotrope (Hadley et 5 al. Journ. Amer. Chem. Soc. 62 3302 (1940)). Trichlorofluoromethane, dichlorodifluoromethane, Ri O R3 chlorofluoromethane, 1,1,2-trichloro-1,2,2-trifluoroethane, /N 20 1,2-dichloro-1,1,2,2-tetrafluoroethane, 1,1-difluoroethane/dichlorodifluoromethane azeo trope, chloropentafluoroethane/chlorodifluoromethane azeo R2 s R4 trope 25 are preferred, dichlorodifluoromethane being most pre ferred. Useful refrigeration oils include any of the oils which wherein R, R2, R2 and R4 are each H or an anilino are well known in the art and are commonly used in group substituted by from 1 to 3 saturated alkyl heat transfer apparatus, e.g., naphthenic oils, paraffinic groups having a total of from 4 to 24 carbon atoms, 30 oils, alkylated benzene oils and polyalkyl silicate oils. and wherein at least 2 and no more than 3 of R Useful illustrative oils include for example R, R3 and R are hydrogen, and wherein the anthraquinone dye is soluble in the refriger ation liquid, the concentration of said dye being at least about 0.007 gram per 100 cc. of said refrigeration liquid. 35 The process aspect of this invention is a process for Trade name Oil type Manufacturer indicating leaks in a vapor compression heat transfer 'Suniso'3GS.-------------- Naphthenic----------- Sun Oil Co. "Suniso' 4GS------------------- do----------------- Do. system which comprises circulating through said system 'Sunis0'5GS- ----do--- - - - D0. 40 'Capella' D--- ----do--- - Texaco Oil Co. a composition of this invention as described above. 'Delco' 15-117------- Paraffinic Do. DESCRIPTION OF THE INVENTION "Zerice'CE (General S-41.------------- Electric) Alkylated---do---- benzene--- HygieDQ. g. Co. ace). The present invention is directed to a composition 'Fluicil' S-55K.---------- Polyisobutyl silicate.-- Farbenfabriken which is particularly useful in the detection of leaks oc Bayer A.G. curring in vapor compression heat transfer systems. The 45 "Sometimes called Alaska Bleu. composition comprises a refrigeration liquid containing at least about 0.007 gram of a dissolved anthraquinone dye per 100 cc. of refrigeration liquid at 77 F., from about 0.007 to about 1.3 grams of dye per 100 cc. of When the refrigeration liquid is a mixture of fluorocarbon refrigeration oil being preferred in most instances. By 50 refrigerant and refrigeration oil, the ratio of one to the the term "refrigeration liquid” as used herein is meant other is not critical; however, about a 1:1 weight ratio a fluorocarbon refrigerant, a refrigeration oil or a mix is preferred. ture of a fluorocarbon refrigerant and refrigeration oil. The dyes useful in this invention include an anthra Useful fluoocarbon refrigerants include quinone dye or mixture of anthraquinone dyes having the 55 trichlorofluoromethane, Structure dichlorodifluoromethane, chlorodifluoromethane, 1,1,2-trichloro-1,2,2-trifluoroethane, 1,2-dichloro-1,1,2,2-tetrafluoroethane, 60 1,1-difluoroethane/dichlorodifluoromethane azeo trope (U.S. Pat. 2,479,259, Re. 23,358), chloropentafluoroethane/chlorodifluoromethane azeo trope (U.S. Pat. 2,641,579), chlorotrifluoromethane, 65 chlorotrifluoromethane/trifluoromethane
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