The invention provides a lubricating composition containing (a) an oil of lubricating viscosity, (b) a phosphite having at least one hydrocarbyl group that has 4 or more carbon atoms, and (c) a compound derived from a hydroxy-carboxylic acid. The invention further relates to the use of the lubricating composition in an internal combustion engine.

Drilling fluid compositions and methods for using drilling fluid compositions are provided with enhanced anti-bit balling properties that include an aqueous-based fluid, one or more drilling fluid additives, and an anti-bit balling additive. The anti-bit balling additive may be an epoxidized α-olefin and the drilling fluid may include the anti-bit balling additive in an amount ranging from about 0.5 ppb to about 20 ppb. Methods for using the drilling fluid compositions may further include mixing an aqueous base fluid with one or more drilling fluid additives and an anti-bit balling additive, wherein the anti-bit balling additive includes epoxidized α-olefin and the drilling fluid may include the anti-bit balling additive in an amount ranging from about 0.5 ppb to about 20 ppb, and introducing the drilling fluid to a subterranean formation.

The present invention provides a refrigerating machine oil comprising, as a base oil, a polymer having a structural unit represented by the following formula (1):

##STR00001##

wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same as or different from each other, represent a hydrogen atom or a hydrocarbon group; and R.sup.4 represents a hydrocarbon group or an organic group containing an oxygen atom, and having a number average molecular weight Mn of 300 or more and 3000 or less and a ratio of a weight-average molecular weight Mw to a number average molecular weight Mn (Mw/Mn) of 1.10 or more and 2.00 or less, and the refrigerating machine oil being used with a refrigerant selected from the group consisting of difluoromethane, a mixture of difluoromethane and pentafluoroethane, a mixture of difluoromethane, pentafluoroethane and 1,1,1,2-tetrafluoroethane, a mixture of pentafluoroethane, 1,1,1,2-tetrafluoroethane and 1,1,1-trifluoroethane, unsaturated hydrofluorocarbons, hydrocarbons and carbon dioxide.

A method for operating a refrigerant circulation system comprising a compressor, a condenser, an expansion mechanism, and an evaporator connected in this order with piping, wherein a refrigerant comprising trifluoroiodomethane is used as a refrigerant; a refrigerating machine oil comprising, as a base oil, a polyolester synthesized from a polyhydric alcohol and fatty acids, with a proportion of a fatty acid having 9 carbon atoms in the fatty acids being 65 mol % or less is used as a refrigerating machine oil; and a temperature of an entire area of the refrigerant circulation system is kept at 160° C. or lower.

The present invention provides a refrigerating machine oil containing a lubricating base oil, a dialkyl hydrogen phosphite having two alkyl groups having 1 to 12 carbon atoms in the molecule, and an epoxy compound.

A phenol derivative of the present invention has a structure as represented by the formula (I):

##STR00001##

The functional groups are defined in the description. The phenol derivative can be used as the antioxidant in lubricating oil, lubricating grease, plastic, rubber, or can be used as the base oil of the lubricating oil and the lubricating grease and the antiwear additive of the lubricating oil and the lubricating grease.

Drilling fluid compositions and methods for using drilling fluid compositions are provided with enhanced anti-bit balling properties that include an aqueous-based fluid, one or more drilling fluid additives, and an anti-bit balling additive. The anti-bit balling additive may be an epoxidized α-olefin and the drilling fluid may include the anti-bit balling additive in an amount ranging from about 0.5 ppb to about 20 ppb. Methods for using the drilling fluid compositions may further include mixing an aqueous base fluid with one or more drilling fluid additives and an anti-bit balling additive, wherein the anti-bit balling additive includes epoxidized α-olefin and the drilling fluid may include the anti-bit balling additive in an amount ranging from about 0.5 ppb to about 20 ppb, and introducing the drilling fluid to a subterranean formation.

The invention addresses a problem of providing a lubricating oil composition for refrigerators excellent in thermal stability for a refrigerant that contains difluoromethane (R32), trifluoroiodomethane (CF.sub.3I) and at least one compound (α) selected from saturated fluorinated hydrocarbon compounds (HFC) except difluoromethane (R32). The lubricating oil composition for refrigerators is used for a refrigerant containing difluoromethane (R32), trifluoroiodomethane (CF.sub.3I) and at least one compound (α) selected from saturated fluorinated hydrocarbon compounds (HFC) except difluoromethane (R32), and contains at least one kind of base oil selected from polyoxyalkylene glycols, polyvinyl ethers, copolymers of a poly(oxy)alkylene glycol or a monoether thereof and a polyvinyl ether and polyol esters, in which the hydroxyl value of the base oil is 15 mgKOH/g or less.

A lubricant composition comprises a lubricant and a stabilizer. The stabilizer comprises a first epoxide group and a second functional group selected from the group consisting of (i) a second epoxide group; (ii) an aliphatic carbon-carbon multiple bond conjugated with a second carbon-carbon multiple bond; (iii) an aliphatic carbon-carbon multiple bond conjugated with an electron withdrawing group; and (iv) an aliphatic carbon-carbon multiple bond conjugated with an aromatic group. A heat transfer composition comprises a lubricant composition as described above and a haloalkane, such as an iodoalkane (e.g., trifluoroiodomethane).

Aspects described herein generally relate to methods of making a phosphono paraffin comprising forming a reaction mixture by mixing a haloparaffin, a phosphite, and sodium iodide. Methods comprise heating the reaction mixture to form the phosphono paraffin. Aspects described herein further relate to a phosphono paraffin represented by formula (I):

##STR00001##

wherein each instance of R.sup.1 is independently —H or

##STR00002##

wherein each instance of R.sup.2 and R.sup.3 is independently linear or branched C.sub.1-20 alkyl, C.sub.1-20 cycloalkyl, or aryl; the number of instances where R.sup.1 is

##STR00003##

of formula (I) is between about 2 and about 8; and n is an integer between 4 and 22.