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United States Patent (19) 11 Patent Number: 6,096,692 Hagihara Et Al

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United States Patent (19) 11 Patent Number: 6,096,692 Hagihara Et Al US006096692A United States Patent (19) 11 Patent Number: 6,096,692 Hagihara et al. (45) Date of Patent: Aug. 1, 2000 54 SYNTHETIC LUBRICATING OIL 4,851,144 7/1989 McGraw et al.. 5,395,544 3/1995 Hagihara et al. ......................... 252/68 75 Inventors: Toshiya Hagihara, Izumisano; Shoji 5,523,010 6/1996 Sorensen et al. ....................... 508/307 Nakagawa, Wakayama; Yuichiro 5,575,944 11/1996 Sawada et al.. Kobayashi, Wakayama; Hiroyasu 5,720,895 2/1998 Nakagawa et al. ....................... 252/68 Togashi, Wakayama; Koji Taira, FOREIGN PATENT DOCUMENTS Wakayama; Akimitsu Sakai, Wakayama, all of Japan 0696564. 2/1996 European Pat. Off.. 2003067 8/1970 Germany. 73 Assignee: Kao Corporation, Tokyo, Japan 59-25892 2/1984 Japan. 4320498 11/1992 Japan. 21 Appl. No.: 08/776,751 657243 3/1994 Japan. 22 PCT Filed: Feb. 27, 1995 OTHER PUBLICATIONS 86 PCT No.: PCT/JP95/00304 Chemical Abstracts, vol. 77, No. 9, Abstract No. 61237u (XP-002097541), Jun. 29, 1990. S371 Date: Feb. 13, 1996 Primary Examiner Jacqueline V. Howard S 102(e) Date: Feb. 13, 1996 Attorney, Agent, or Firm-Birch, Stewart, Kolasch & Birch, LLP 87 PCT Pub. No.: WO96/06839 57 ABSTRACT PCT Pub. Date: Mar. 7, 1996 The present invention relates to a Synthetic lubricating oil 30 Foreign Application Priority Data comprising cyclic ketals or cyclic acetals obtained by a Aug. 29, 1994 JP Japan .................................... 6-228616 reaction between one or more polyhydric alcohols having an Oct. 31, 1994 JP Japan .................................... 6-292431 even number of hydroxyl groups of not less than 4 and not more than 10 and one or more Specific carbonyl compounds, 51) Int. Cl." ...................... C10M 105/18; CO7D 317/18 or one or more ketals or acetals which are reactive deriva 52 U.S. Cl. .................. ... 508/307; 549/372; 252/68 tives of Said carbonyl compounds, a working fluid compo 58 Field of Search ............................... 508/307; 252/67, Sition for a refrigerating machine comprising a hydrofluo 252/68; 549/372 rocarbon and a refrigeration oil containing the cyclic ketals or cyclic acetals; and novel compounds of the above cyclic 56) References Cited acetals and a production method thereof. The present inven U.S. PATENT DOCUMENTS tion provides a Synthetic lubricating oil which shows a good thermal Stability, a good oxidation resistance, no carboxylic 1,934,309 11/1933 Hoover .................................... 549/372 acid formation due to hydrolysis and a low hygroscopicity 3,714.202 1/1973 Nakaguchi et al. ... 549/372 and is inexpensive as well. Also, a working fluid composi 3,725,438 4/1973 Barone et al. ....... ... 549/372 tion for a refrigerating machine which shows a good insu 3,741,986 6/1973 Hartmann ......... ... 549/372 3,900,411 8/1975 Andress, Jr. ..... ... 508/307 lating property, favorable hygroscopicity, and no carboxylic 3,910,845 10/1975 Coon ............ ... 508/307 acid formation due to hydrolysis as well as being inexpen 4,076,727 2/1978 Zey et al. .................................. 252/68 Sive can be provided. 4,659,809 4/1987 Matsumura. 4,755,316 7/1988 Magid et al.. 7 Claims, No Drawings 6,096,692 1 2 SYNTHETIC LUBRICATING OL romethane (HFC32), and pentafluoroethane (HFC125), have been developed as substitutes for CFC12 or HCFC22. This application is a 371 of PCT/JP95/00304 filed Feb. However, since the polarity of hydrofluorocarbons is 27, 1995. higher than that of CFC12 or HCFC22, the use of conven tional lubricating oils, Such as naphthene mineral oils, TECHNICAL FIELD poly-C-olefins and alkylbenzenes, causes two-phase Separa The present invention relates to a Synthetic lubricating oil tion of the working fluid at low temperatures. This is due to using, as a base oil, cyclic ketals or cyclic acetals having a poor compatibility between the conventional lubricating oils particular structure, and also to a working fluid composition and the hydrofluorocarbons. Two-phase Separation hampers for a refrigerating machine which uses the Synthetic lubri oil return, which in turn interferes with heat transfer due to cating oil. deposition of a thick oil film around the condenser and evaporator used as heat eXchangers. It can also cause Sig The present invention further relates to cyclic acetals nificant failures, Such as poor lubrication and foaming upon which are useful as polar oils, organic Solvents, lubricants, Starting operation. Therefore, the conventional refrigeration Synthetic lubricating oils, or refrigeration oils, or as inter 15 oils cannot be used as refrigeration oils under these new mediates in the production of Surfactants, organic Solvents, refrigerant atmospheres. With this being the Situation, lubri polar oils, Synthetic lubricating oils, refrigeration oils, etc., cating oils with good compatibility with hydrofluorocarbons and to a method for producing the cyclic acetals. have been Sought. BACKGROUND ART As for lubricity, CFC12 and HCFC22 generate hydrogen chloride upon its partial decomposition. The hydrogen chlo With lengthened intervals of oil changes, need of energy ride thus formed reacts with the friction Surface to form a Saving, use of high performance machines, and down-sizing coating of chlorides, thereby improving the lubricity. On the of machines, demand for the performance of lubricating oils other hand, hydrofluorocarbons containing no chlorine has become Severe. In particular, lubricating oils with a high atoms are not expected to have Such an effect; therefore, the thermal Stability and a high oxidation resistivity have been 25 refrigeration oils used in combination with hydrofluorocar Strongly Sought. In the Situation where there has been bons are required to have a further excellent lubricity when increasing public concern about global environmental compared to the conventional refrigeration oils. pollution, Such as depletion of OZone layer caused by freon, In addition, the refrigeration oils used in combination the earth warming due to exceSS carbon dioxide and with hydrofluorocarbons have to have good thermal stability methane, destruction of forests by Sulfur dioxide and NO in in the presence of hydrofluorocarbons. exhaust fumes, and pollution of Soil and lakes due to Moreover, in the compression-type refrigerating chemical leakage, environmental protective measures have machines for electric refrigerators and air conditioners, Since been strongly sought also in the field of lubricating oils. organic materials are used for motor components Such as In order to meet the requirements for high thermal Sta insulators and enameled wires, the working fluid comprising bility and oxidation resistivity, ethers, Such as polyalkylene 35 a hydrofluorocarbon and a refrigeration oil is required to glycols, and esters, Such as aliphatic diesters and hindered have no adverse effects on the organic materials and also esters, have been developed and used for engine oils, have a good insulating property. hydraulic oils, grease base oils, gear oils, rolling oils, precision instrument oils, etc. AS refrigeration oils which can be used in combination 40 with hydrofluorocarbons Such as 1,1,1,2-tetrafluoroethane However, ethers, Such as polyalkylene glycols, have a (HFC134a), polyalkylene glycol compounds are disclosed in higher polarity than conventionally used mineral oils to U.S. Pat. No. 4,755,316 (Japanese Patent Unexamined cause the following drawbacks: (1) high hygroscopicity, and Application No. 2-502385), Japanese Patent Laid-Open No. (2) insolubility of additives which are conventionally used 3-14894 (European Patent No. 377122), and Japanese Patent for lubricating oils. An ether Synthesized from an alkyl 45 Laid-Open No. 2-182780 (WO90/05172). halide and a polyol, which has a lower polarity than poly Since polyalkylene glycol compounds have a higher alkylene glycols, is described in Japanese Patent Examined polarity than naphthene mineral oils, their compatibility Publication No. 1-29240. This ether also has a problem that with HFC 134a at low temperatures is certainly good. a trace of residual halogen in the ether product may impair However, polyalkylene glycol compounds have a problem to thermal stability and oxidation resistivity. 50 cause phase Separation as the temperature increases, as EsterS also are not free from drawbacks. That is, carboxy mentioned in U.S. Pat. No. 4,755,316. There are also several lic acid formed by hydrolysis of esters erodes metals, and other problems about polyalkylene glycol compounds. A esters tend to impair the effects of oilineSS improvers and poor insulating property is one of the problems. Due to this extreme pressure additives, though esters have a merit to Significant problem, polyalkylene glycol compounds cannot reduce friction because they are well adsorbed onto metals. 55 be used for refrigerating devices of electric refrigerators and Thus, Synthetic lubricating oils with adequately low air conditioners where a motor is incorporated in a com polarity, high thermal Stability, high oxidation resistivity, no preSSor. Therefore, applications of polyalkylene glycol com formation of carboxylic acids due to hydrolysis and low pounds are proposed for car air conditioners where their hygroscopicity are in high demand. poor insulating property does not cause any problems. High Recently, the use of dichlorodifluoromethane (CFC12) for 60 hygroscopicity is another significant problem of polyalky refrigerators and car air conditioners is restricted, and will be lene glycol compounds. Water absorbed by the compounds legally banned at the end of 1995 in
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