Anti-bit balling drilling fluids and methods of making and using drilling fluids are provided. The anti-bit balling drilling fluid contains water, a clay-based component, and at least one of a surfactant having the formula: R(OC.sub.2H.sub.4).sub.xOH, where R is a hydrocarbyl group having from 10 to 20 carbon atoms and x is an integer from 1 and 10, or a polyethylene glycol having the formula: H(OCH.sub.2CH.sub.2).sub.nOH, where n is an integer from 1 to 50. Methods of making and using these drilling fluids are also provided.

A compound of the formula (2) ##STR00001##
wherein R.sup.3 is a hydrocarbon group having 12 or 14 carbon atoms which is mainly composed of any one of 1-methylundecyl, 1-ethyldecyl, 1-dodecyl, 1-methyltridecyl, 1-ethyldodecyl and 1-tetradecyl, and 30 to 40 mole % of the total benzylic carbons of R.sup.3 being quaternary, R.sup.4 is a branched hydrocarbon group having 16 to 20 carbon atoms, 42 to 100 mole % of the total benzylic carbons of each R.sup.3 and R.sup.4 being quaternary, m and n are each a real number of 1.0m2.0, 1.0n2.0 and 2.0m+n3.0.

A compound of the formula (2) ##STR00001##
wherein R.sup.3 is a hydrocarbon group having 12 or 14 carbon atoms which is mainly composed of any one of 1-methylundecyl, 1-ethyldecyl, 1-dodecyl, 1-methyltridecyl, 1-ethyldodecyl and 1-tetradecyl, and 30 to 40 mole % of the total benzylic carbons of R.sup.3 being quaternary, R.sup.4 is a branched hydrocarbon group having 16 to 20 carbon atoms, 42 to 100 mole % of the total benzylic carbons of each R.sup.3 and R.sup.4 being quaternary, m and n are each a real number of 1.0m2.0, 1.0n2.0 and 2.0m+n3.0.

A wellbore servicing fluid comprises an aqueous base fluid, one or more alkali metal or alkali earth metal salts, at least one visocisifier, and a filtration control package. The filtration control package may comprise a carboxylic acid and an ethoxylated alcohol compound. Alternatively, the filtration control package may comprise a polyethylene glycol. The carboxylic acid may have from 8 to 20 carbon atoms. The ethoxylated alcohol compound may have a general formula R(OCH.sub.2CH.sub.2).sub.xOH, where R is a hydrocarbon having from 10 to 16 atoms and x is an integer from 6 to 9. The ethoxylated alcohol compound may have a hydrophilic-lipophilic balance of from 8.0 to 16.0. The polyethylene glycol may have a mass average molar mass (M.sub.w) of less than or equal to 1500 daltons.

A wellbore servicing fluid comprises an aqueous base fluid, one or more alkali metal or alkali earth metal salts, at least one visocisifier, and a filtration control package. The filtration control package may comprise a carboxylic acid and an ethoxylated alcohol compound. Alternatively, the filtration control package may comprise a polyethylene glycol. The carboxylic acid may have from 8 to 20 carbon atoms. The ethoxylated alcohol compound may have a general formula R(OCH.sub.2CH.sub.2).sub.xOH, where R is a hydrocarbon having from 10 to 16 atoms and x is an integer from 6 to 9. The ethoxylated alcohol compound may have a hydrophilic-lipophilic balance of from 8.0 to 16.0. The polyethylene glycol may have a mass average molar mass (M.sub.w) of less than or equal to 1500 daltons.

One aspect of the present invention relates to a naphthyl phenyl ether compound represented by formula (1):

##STR00001##

in the formula (1), R.sup.1 and R.sup.2 are the same or different and each represent a linear or branched hydrocarbon group having 6 to 28 carbon atoms; m and n are each a real number of 0 or more and satisfy 1.0?m+n?3.0.

One aspect of the present invention relates to a naphthyl phenyl ether compound represented by formula (1):

##STR00001##

in the formula (1), R.sup.1 and R.sup.2 are the same or different and each represent a linear or branched hydrocarbon group having 6 to 28 carbon atoms; m and n are each a real number of 0 or more and satisfy 1.0?m+n?3.0.

The lubricating oil composition for a refrigerator according to the present invention is a lubricating oil composition for a refrigerator containing a base oil containing a low-viscosity base oil component having added thereto a polyoxyalkylene glycol compound having a kinetic viscosity at 100 C. that is higher than the low-viscosity base oil component, and the base oil has a kinetic viscosity at 100 C. of 2.4 to 25 mm.sup.2/s and a ratio (Mw/Mn) of a weight average molecular weight (Mw) and a number average molecular weight (Mn) of 1.3 to 13.

Anti-bit balling drilling fluids and methods of making and using drilling fluids are provided. The anti-bit balling drilling fluid contains water, a clay-based component, and at least one of a surfactant having the formula: R(OC.sub.2H.sub.4).sub.xOH, where R is a hydrocarbyl group having from 10 to 20 carbon atoms and x is an integer from 1 and 10, or a polyethylene glycol having the formula: H(OCH.sub.2CH.sub.2).sub.nOH, where n is an integer from 1 to 50. Methods of making and using these drilling fluids are also provided.

Anti-bit balling drilling fluids and methods of making and using drilling fluids are provided. The anti-bit balling drilling fluid contains water, a clay-based component, and at least one of a surfactant having the formula: R(OC.sub.2H.sub.4).sub.xOH, where R is a hydrocarbyl group having from 10 to 20 carbon atoms and x is an integer from 1 and 10, or a polyethylene glycol having the formula: H(OCH.sub.2CH.sub.2).sub.nOH, where n is an integer from 1 to 50. Methods of making and using these drilling fluids are also provided.