FIELD OF THE INVENTION The present invention relates to refrigerant compositions comprising relatively polar, halogenated hydrocarbon refrigerant; relatively non-polar, conventional, compression refrigeration lubricant; and a compound that compatibilizes said polar halogenated hydrocarbon and non-polar lubricant. The compatibilizer decreases the viscosity of the lubricant in the coldest portions of a compression refrigeration apparatus by solubilizing halogenated hydrocarbon and lubricant, which results in efficient return of the lubricant from non-compressor zones to a compressor zone in a compression refrigeration system.

BACKGROUND Over the course of the last twenty (20) years it has been debated whether the release of chlofluorocarbons into the atmosphere has effected the stratospheric ozone layer. As a result of this debate and international treaties, the refrigeration and air-conditioning industries have been weaning themselves from the use and production of certain chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs). Presently, the industries are transitioning towards the use of hydrofluorocarbons (HFCs) having zero ozone depletion potential. Notably, this transition to HFCs necessitated the advent of a new class of lubricants because of the immiscibility of conventional lubricants, such as mineral oil, poly a-olefin and alkylbenzene with HFC refrigerants.

The new class of lubricants includes polyalkylene glycols (PAGs) and polyol esters (POEs) lubricants. While the PAG and POE lubricants have suitable lubricant properties, they are extremely hygroscopic and can absorb several thousand ppm (parts per million) of water on exposure to moist air. This absorbed water leads to undesirable formation of acids that cause corrosion of the refrigeration system and formation of intractable sludges. In comparison, conventional refrigeration lubricants are considerably less hygroscopic and have

low solubility, less than 100 ppm for water. Further, PAGs and POEs are considerably more expensive than conventional refrigeration lubricants-- typically on the order of three to six times more. PAGs and POEs have also been found to have unfavorable electrical insulating properties.

Accordingly, there existed a need and an opportunity to resolve this solubility problem so that the refrigeration industry could utilize the conventional non-polar mineral oil and alkylbenzene lubricants with polar HFC-based refrigerants. Another need and opportunity also existed when the industry began transitioning towards the use of HCFC-based refrigerants as a replacement for pure CFC refrigerants. This need became apparent due to the diminished solubility of HCFCs in mineral oil, which forced the industry to incur an additional expense of changing the lubricant to an alkylbenzene to achieve adequate lubricating and cooling performance.

For the last ten years the refrigeration and air-conditioning industries have been struggling with these long-felt but unsolved needs, finally, the present invention satisfies the pressing needs of these industries. While numerous attempts have been made to use conventional non-polar lubricants with polar hydrofluorocarbon refrigerants, the lack of solubility of the polar refrigerant in the non-polar conventional lubricant generally results in a highly viscous lubricant in the non-compressor zones, which unfortunately results in insufficient lubricant return to the compressor. When the non-polar conventional lubricant and the polar refrigerant naturally escape the compressor and enter the non-compressor zones, phase separation/insolubility of the lubricant and the refrigerant occurs.

This phase separation contributes to the highly viscous lubricant remaining in the non-compressor zone, whilst the refrigerant continues its path throughout the refrigeration system. The insolubility and highly viscous nature of the lubricant leaves the lubricant stranded in the non-compressor zones, which leads to an undesirable accumulation of lubricant in the non-compressor zones. This accumulation of lubricant and the lack of return of the lubricant to the compressor zone eventually starves the compressor of lubricant and results in the compressor overheating and seizing. Such stranded lubricant may also decrease the efficiency of the refrigeration system by interfering with heat transfer, due to thick lubricant films deposited on interior surfaces of the heat exchangers (e. g. condenser and evaporator). Further, during cold compressor starts, insoluble refrigerant and lubricant may cause compressor seizure due to poor lubrication and foaming of the lubricant.

Considerable commercial interest in solving the aforementioned long- felt but unsolved needs is evident from numerous patents and/or patent applications, such as: US 5368765, US 5254280, US 5154846, US 6074573, US 5431835, US 4755316, JP 2930963 (1999), JP 02286780 (1990), EP 784090, EP 406433 and EP 645443, which disclose refrigeration lubricants comprising alkyl benzenes and/or mineral oils, and polyethers and/or glycols; JP 05202389 (1993), which discloses solubilizing perfluorocarbons with aliphatic hydrocarbons using glycols and ethers; EP 571091 and JP 10140175 (1998), which disclose polyester refrigeration lubricant including a nitrogen-containing heterocyclic additive; US 5023007, US 5194171, JP 2997908 (2000) and JP 104087 (2000), which disclose refrigeration compositions comprising fluorine-containing hydrocarbons and nitrogen-containing heterocyclic lubricants; US 5300245, which discloses a refrigeration working fluid comprising a refrigerating lubricant comprising a compound having one or more ketone groups in the molecular structure as a base lubricant and a hydrofluorocarbon ; US 5104560, US 4359394 and CA 973700, which disclose refrigeration lubricant compositions for use with chlorofluorocarbon-based refrigerants comprising refrigeration lubricant and halogenated paraffin additives; and US 4355960, which discloses a refrigeration lubricant comprising an lubricant and minor amounts of an alkyl polyhalophenyl ether.

For the foregoing reasons, there is a well-recognized need in the refrigeration and air-conditioning industries for a compatibilizer that compatibilizes a polar halogenated hydrocarbon and a non-polar conventional lubricant in a compression refrigeration system, and promotes efficient return of lubricant to the compressor.

SUMMARY The present invention is directed to lubricant and refrigerant compositions containing a compatibilizer that satisfies the refrigeration and air- conditioning industry's problem of insolubility between conventional non-polar compression refrigeration lubricants and polar hydrofluorocarbon and/or hydrochlorofluorocarbon refrigerants. The compatibilizers decrease the viscosity of the non-polar lubricant in the coldest portions of a compression refrigeration apparatus by solubilizing the polar halogenated hydrocarbon and lubricant in the non-compressor zones, which results in efficient return of lubricant from non- compressor zones to a compressor zone. The present invention is also directed to processes for returning lubricant from a non-compressor zone to a compressor

zone in a compression refrigeration system, methods of solubilizing a halogenated hydrocarbon refrigerant in a lubricant, as well as methods of lubricating a compressor in a compression refrigeration apparatus containing a halogenated hydrocarbon refrigerant.

The present invention comprises lubricant compositions for use in compression refrigeration and air conditioning apparatus comprising: (a) at least one lubricant selected from the group consisting of paraffins, napthenes, aromatics and poly-a-olefins, and (b) at least one compatibilizer. The present invention further comprises refrigerant compositions for use in compression refrigeration and air conditioning comprising: (a) at least one halogenated hydrocarbon selected from the group consisting of hydrofluorocarbons and hydrochlorofluorocarbons ; (b) at least one lubricant selected from the group consisting of paraffins, napthenes, aromatics and poly-a-olefins ; and (c) at least one compatibilizer. The present invention further comprises compositions for use in compression refrigeration and air conditioning apparatus containing paraffinic, napthenic, aromatic and/or poly-a-olefinic lubricant comprising: (a) at least one halogenated hydrocarbon selected from the group consisting of hydrofluorocarbons and hydrochlorofluorocarbons; and (b) at least one compatibilizer.

The present invention also provides processes for returning lubricant from a non-compressor zone to a compressor zone in a compression refrigeration system comprising : (a) contacting a lubricant selected from the group consisting of paraffins, naphthenes, aromatics, and polyalphaolefins, in said non-compressor zone with a halogenated hydrocarbon selected from the group consisting of hydrofluorocarbons and hydrochlorofluorocarbons, in the presence of a compatibilizer to form a solution comprising said lubricant, said halogenated hydrocarbon, and said compatibilizer; and (b) transferring said solution from said non-compressor zone to said compressor zone of said refrigeration system.

The present invention further provides methods of solubilizing a halogenated hydrocarbon refrigerant selected from the group consisting of hydrofluorocarbons and hydrochlorofluorocarbons, in a lubricant selected from the group consisting of paraffins, naphthenes, aromatics, and polyalphaolefins, which comprise the steps of contacting said lubricant with said halogenated hydrocarbon refrigerant in the presence of an effective amount of a compatibilizer and forming a solution of said lubricant and said halogenated hydrocarbon refrigerant.

The present invention further pertains to methods of lubricating a compressor in a compression refrigeration apparatus containing a halogenated hydrocarbon refrigerant selected from the group consisting of hydrofluorocarbons and hydrochlorofluorocarbons, comprising the step of adding to said compressor a composition comprising: (a) at least one lubricant selected from the group consisting of paraffins, naphthenes, aromatics, and polyalphaolefins; and (b) at least one compatibilizer. The present invention also pertains to a method for delivering a compatibilizer to a compression refrigeration apparatus.

The lubricants and/or refrigerant compositions, as well as the above described methods and/or processes can optionally include a fragrance.

Compatibilizers of the present invention include: (i) polyoxyalkylene glycol ethers represented by the formula Rl [(oR2) xoR3] y wherein: x is selected from integers from 1 to 3; y is selected from integers from 1 to 4; Rl is selected from hydrogen and aliphatic hydrocarbon radicals having 1 to 6 carbon atoms and y bonding sites; R2 is selected from aliphatic hydrocarbylene radicals having from 2 to 4 carbon atoms; R3 is selected from hydrogen, and aliphatic and alicyclic hydrocarbon radicals having from 1 to 6 carbon atoms; at least one of Rl and R3 is selected from said hydrocarbon radicals; and wherein said polyoxyalkylene glycol ethers have a molecular weight of from 100 to 300 atomic mass units and a carbon to oxygen ratio of from 2.3 to 5.0 ; (ii) amides represented by the formulae R1CONR2R3 and cyclo- [R4CON (R5)-], wherein Rl, R2, R3 and Rs are independently selected from aliphatic and alicyclic hydrocarbon radicals having from 1 to 12 carbon atoms ; R4 is selected from aliphatic hydrocarbylene radicals having from 3 to 12 carbon atoms; and wherein said amides have a molecular weight of from 120 to 300 atomic mass units and a carbon to oxygen ratio of from 7 to 20, (iii) ketones represented by the formula RICOR2, wherein Rl and R2 are independently selected from aliphatic, alicyclic and aryl hydrocarbon radicals having from 1 to 12 carbon atoms, and wherein said ketones have a molecular weight of from 70 to 300 atomic mass units and a carbon to oxygen ratio of from 4 to 13, (iv) nitriles represented by the formula R'CN, wherein Rl is selected from aliphatic, alicyclic or aryl hydrocarbon radicals having from 5 to 12 carbon

atoms, and wherein said nitriles have a molecular-weight of from 90 to 200 atomic mass units and a carbon to nitrogen ratio of from 6 to 12, (v) chlorocarbons represented by the formula RClX, wherein; x is selected from the integers 1 or 2; R is selected from aliphatic and alicyclic hydrocarbon radicals having from 1 to 12 carbon atoms; and wherein said chlorocarbons have a molecular weight of from 100 to 200 atomic mass units and carbon to chlorine ratio from 2 to 10, (vi) aryl ethers represented by the formula RIO2, wherein: Rl is selected from aryl hydrocarbon radicals having from 6 to 12 carbon atoms; R is selected from aliphatic hydrocarbon radicals having from 1 to 4 carbon atoms; and wherein said aryl ethers have a molecular weight of from 100 to 150 atomic mass units and a carbon to oxygen ratio of from 4 to 20, (vii) 1, 1, 1-trifluoroalkanes represented by the formula CF3RI, wherein Rl is selected from aliphatic and alicyclic hydrocarbon radicals having from 5 to 15 carbon atoms; and (viii) fluoroethers represented by the formula R'OCF2CF2H, wherein Rl is selected from aliphatic and alicyclic hydrocarbon radicals having from 5 to 15 carbon atoms.

In the compositions of the present invention, the weight ratio of said lubricant to said compatibilizer is from 99: 1 to 1: 1.

BRIEF DESCRIPTION OF THE FIGURES The present invention is better understood with reference to the following figures, where: FIG. 1 is a graph of phase separation temperature ("PST") (°C) versus carbon to oxygen ratio for various polyoxyalkylene glycol ether compatibilizers (25 wt%), HFC-134a refrigerant (50 wt%) and Zerol 150 (alkyl benzene lubricant from Shrieve Chemicals) (25 wt%).

FIG. 2 is a graph of phase separation temperature (°C) versus carbon to oxygen ratio for various polyoxyalkylene glycol ether compatibilizers (10 wt%), R401A refrigerant (50 wt%) and Suniso 3GS (mineral oil lubricant from Crompton Co. ) (40 wt%).

FIG. 3 is a graph of phase separation temperature (°C) versus carbon to oxygen ratio for various ketone compatibilizers (25 wt%), HFC-134a refrigerant (50 wt%) and Zerol 150 (25 wt%).

FIG. 4 is a graph of phase separation temperature (°C) versus carbon to nitrogen ratio for various nitrile compatibilizers (25 wt%), HFC-134a refrigerant (50 wt%) and Zerol (g) 150 (25 wt%).

FIG. 5 is a graph of phase separation temperature (°C) versus carbon to chlorine ratio for various chlorocarbon compatibilizers (25 wt%), HFC-134a refrigerant (50 wt%) and Zerol@ 150 (25 wt%).

FIG. 6 is a graph of phase separation temperature (°C) versus carbon to chlorine ratio for various chlorocarbon compatibilizers (10 wt%), R401A refrigerant (50 wt%) and Suniso 3GS (40 wt%).

FIG. 7 is a graph of phase separation temperature (°C) versus carbon to oxygen ratio for various amide compatibilizers (25 wt%), HFC-134a refrigerant (50 wt%) and Zerol 150 (25 wt%).

FIG. 8 is a graph of phase separation temperature (°C) versus carbon to oxygen ratio for various amide compatibilizers (10 wt%), R401A refrigerant (50 wt%) and Suniso 3GS (40 wt%).

FIG. 9 shows graphs of phase separation temperature (°C) versus carbon to oxygen ratio for various polyoxyalkylene glycol ether compatibilizers (25 wt%), Zerol 150 (25 wt%) and refrigerant HFC-32, HFC-125 or R410A (50 wt%).

FIG. 10 is a graph of dynamic viscosity versus temperature for POE22 (Mobil Oil product Arctic EAL22, a polyol ester lubricant having a kinematic viscosity of 22 cs at 40°C), Zerol@ 150 and the composition: 10 wt% Propylene glycol n-butyl ether (PnB), 5 wt% Dipropylene glycol n-butyl ether (DPnB) and 85wt% Zerol 150.

These and other features, aspects, and advantages of the present invention will become better understood with reference to the following description and the appended claims.

DETAILED DESCRIPTION The present inventors discovered that using an effective amount of the present compatibilizers in conventional compression refrigeration lubricants results in efficient return of lubricant from non-compressor zones to a compressor zone in a compression refrigeration system. The compatibilizers travel throughout a compression refrigeration system mixed with refrigerant and with lubricant that escapes the compressor. Use of compatibilizers results in the decrease of the viscosity of lubricant in the coldest portions of compression

refrigeration systems, such as an evaporator, thereby enabling return of the lubricant from the evaporator to the compressor. The inventors discovered that the viscosity of lubricant in the coldest sections of compression refrigeration systems is reduced upon use of the present compatibilizers. This reduction in lubricant viscosity is due to an increase in solubility of halogenated hydrocarbon refrigerants in lubricant containing the compatibilizers. Through control of the ratio of carbon to polar groups (e. g. ether, carbonyl, nitrile, halogen) in the compatibilizer, the inventors discovered that the polar group-containing compatibilizer could surprisingly be caused to remain miscible with the essentially non-polar lubricants in the coldest sections of compression refrigeration apparatus and simultaneously increase the solubility of halogenated hydrocarbon refrigerant in the lubricant. Without wishing to be bound by theory, the polar functional groups in the present compatibilizers are attracted to the relatively polar halogenated hydrocarbon refrigerant while the hydrocarbon portion of the compatibilizer is miscible with the relatively low polarity lubricant.

The result upon use of the present compatibilizers in the present conventional lubricants is an increase in the solubility of halogenated hydrocarbon refrigerants in lubricant containing an effective amount of compatibilizer. This increased solubility of the relatively nonviscous halogenated hydrocarbon refrigerant in conventional lubricants leads to lowering of the viscosity of the lubricant, and results in efficient return of lubricant from non-compressor zones to a compressor zone in a compression refrigeration system. Reducing the amount of lubricant in the evaporator zone also improves heat transfer of the refrigerant and thus improves refrigerating capacity and efficiency of a system. Thus, the present compatibilizers allow for the use of relatively polar halogenated hydrocarbon refrigerants, such as hydrofluorocarbons and hydrochlorofluorocarbons, with relatively non-polar conventional lubricants; mixtures which are normally immiscible and previously thought to be not useful together as refrigerant compositions in compression refrigeration systems.

The result of increased solubility of halogenated hydrocarbon refrigerants in conventional lubricants further allows liquid refrigerant to dissolve and carry stranded lubricant out of the condenser, improving both lubricant return and heat transfer in the condenser and resulting in improved capacity and efficiency of the refrigeration system.

The present compatibilizers improve the energy efficiency and capacity of a compression refrigeration system by increasing the enthalpy change

upon desorption of halogenated hydrocarbon refrigerant from lubricant and compatibilizer composition in the evaporator, as well as absorption of refrigerant into the lubricant and compatibilizer composition in the condenser. Without wishing to be bound by theory, it is believed that forming and breaking attractions between the refrigerant and the polar functional group-containing compatibilizer results in the increase in enthalpy change.

In most instances, the volume resistivity (ohmxcm) of polyol ester and polyalkylene glycol lubricants presently used with hydrofluorocarbon-based refrigerants is unacceptably low. The present compositions comprising compatibilizer and conventional lubricant have increased volume resistivity versus polyol ester and polyalkylene glycol lubricants.

The present compatibilizers may beneficially increase the viscosity index of conventional lubricants. This gives the desirable result of lower viscosity at low temperature without significantly lowering viscosity at high temperature, a viscosity profile similar to that of many polyol esters. Such a viscosity index ensures lubricant return from the evaporator while maintaining acceptable viscosity for compressor operation.

In the present compositions comprising lubricant and compatibilizer, from 1 to 50 weight percent, preferably from 6 to 45 weight percent, and most preferably from 10 to 40 weight percent of the combined lubricant and compatibilizer composition is compatibilizer. In terms of weight ratios, in the present compositions comprising lubricant and compatibilizer, the weight ratio of lubricant to compatibilizer is from 99: 1 to 1: 1, preferably from 15.7 : 1 to 1. 2 : 1, and most preferably from 9: 1 to 1.5 : 1. Compatibilizer may be charged to a compression refrigeration system as a composition of compatibilizer and halogenated hydrocarbon refrigerant. When charging a compression refrigeration system with the present compatibilizer and halogenated hydrocarbon refrigerant compositions, to deliver an amount of compatibilizer such that the aforementioned relative amounts of compatibilizer and lubricant are satisfied, the compatibilizer and halogenated hydrocarbon refrigerant composition will typically contain from 0.1 to 40 weight percent, preferably from 0.2 to 20 weight percent, and most preferably from 0.3 to 10 weight percent compatibilizer in the combined compatibilizer and halogenated hydrocarbon refrigerant composition. In compression refrigeration systems containing the present compositions comprising halogenated hydrocarbon refrigerant, lubricant and compatibilizer, from 1 to 70 weight percent, preferably from 10 to 60 weight percent of the

halogenated hydrocarbon refrigerant, lubricant and compatibilizer composition is lubricant and compatibilizer. Compatibilizer concentrations greater than 50 weight percent of the combined lubricant and compatibilizer composition are typically not needed to obtain acceptable lubricant return from non-compressor zones to a compressor zone. Compatibilizer concentrations greater than 50 weight percent of the combined lubricant and compatibilizer composition can negatively influence the viscosity of the lubricant, which can lead to inadequate lubrication and stress on, or mechanical failure of, the compressor. Further, compatibilizer concentrations higher than 50 weight percent of the combined lubricant and compatibilizer composition can negatively influence the refrigeration capacity and performance of a refrigerant composition in a compression refrigeration system. An effective amount of compatibilizer in the present compositions leads to halogenated hydrocarbon and lubricant becoming solubilized to the extent that adequate return of lubricant in a compression refrigeration system from non-compressor zones (e. g. evaporator or condenser) to the compressor zone is obtained.

Halogenated hydrocarbon refrigerants of the present invention contain at least one carbon atom and one fluorine atom. Of particular utility are halogenated hydrocarbons having 1-6 carbon atoms containing at least one fluorine atom, optionally containing chlorine and oxygen atoms, and having a normal boiling point of from-90°C to 80°C. These halogenated hydrocarbons may be represented by the general formula CWF2w+2-x-yHxClyOz, wherein w is 1-6, x is 1-9, y is 0-3, and z is 0-2. Preferred of the halogenated hydrocarbons are those in which w is 1-6, x is 1-5, y is 0-1, and z is 0-1. The present invention is particularly useful with hydrofluorocarbon and hydrochlorofluorocarbon-based refrigerants. Halogenated hydrocarbon refrigerants are commercial products available from a number of sources such as E. I. du Pont de Nemours & Co., Fluoroproducts, Wilmington, DE, 19898, USA, or are available from custom chemical synthesis companies such as PCR Inc. , P. O. Box 1466, Gainesville, Florida, 32602, USA, and additionally by synthetic processes disclosed in art such as The Journal of Fluorine Chemistry, or Chemistry of Organic Fluorine Compounds, edited by Milos Hudlicky, published by The MacMillan Company, New York, N. Y. , 1962. Representative halogenated hydrocarbons include: CHC1F2 (HCFC-22), CHF3 (HFC-23), CH2F2 (HFC-32), CH3F (HFC-41), CF3CF3 (FC-116), CHClFCF3 (HCFC-124), CHF2CF3 (HFC-125), CH2C1CF3 (HCFC- 133a), CHF2CHF2 (HFC-134), CH2FCF3 (HFC-134a), CClF2CH3 (HCFC-142b),

CHF2CH2F (HFC-143), CF3CH3 (HFC-143a), CHF2CH3 (HFC-152a), CHF2CF2CF3 (HFC-227ca), CF3CFHCF3 (HFC-227ea), (HFC-236ca), CH2FCF2CF3 (HFC-236cb), CHF2CHFCF3 (HFC-236ea), CF3CH2CF3 (HFC- 236fa), CH2FCF2CHF2 (HFC-245ca), CH3CF2CF3 (HFC-245cb), CHF2CHFCHF2 (HFC-245ea), CH2FCHFCF3 (HFC-245eb), CHF2CH2CF3 (HFC-245fa), CH2FCF2CH2F (HFC-254ca), CH2CF2CHF2 (HFC-254cb), CH2FCHFCHF2 (HFC-254ea), CH3CHFCF3 (HFC-254eb), CHF2CH2CHF2 (HFC-254fa), CH2FCH2CF3 (HFC-254fb), CH3CF2CH3 (HFC-272ca), CH3CHFCH2F (HFC- 272ea), CH2FCH2CH2F (HFC-272fa), CH3CH2CF2H (HFC-272fb), CH3CHFCH3 (HFC-281ea), CH3CH2CH2F (HFC-281fa), CHF2CF2CF2CF2H (HFC-338pcc), CF3CHFCHFCF2CF3 (HFC-43-lOmee), C4F90CH3, and C4F90C2Hs.

The present invention is particularly useful with the hydrofluorocarbon and hydrochlorofluorocarbon-based refrigerants, such as, CHC1F2 (HCFC-22), CHF3 (HFC-23), CH2F2 (HFC-32), CHC1FCF3 (HCFC-124), CHF2CF3 (HFC-125), CHF2CHF2 (HFC-134), CH2FCF3 (HFC-134a), CF3CH3 (HFC-143a), CHF2CH3 (HFC-152a), CHF2CF2CF3 (HFC-227ca), CF3CFHCF3 (HFC-227ea), CF3CH2CF3 (HFC-236fa), CHF2CH2CF3 (HFC-245fa), CHF2CF2CF2CF2H (HFC-338pcc), CF3CHFCHFCF2CF3 (HFC-43-lOmee) ; and the azeotropic and azeotrope-like halogenated hydrocarbon refrigerant compositions, such as, HCFC-22/HFC-152a/HCFC-124 (known by the ASHRAE designations, R-401A, R-401B, and R-401C), HFC-125/HFC-143a/HFC-134a (known by the ASHRAE designation, R-404A), HFC-32/HFC-125/HFC-134a (known by ASHRAE designations, R-407A, R-407B, and R-407C), HCFC- 22/HFC-143a/HFC-125 (known by the ASHRAE designation, R-408A), HCFC- 22/HCFC-124/HCFC-142b (known by the ASHRAE designation: R-409A), HFC- 32/HFC-125 (R-410A), and HFC-125/HFC-143a (known by the ASHRAE designation : R-507).

The halogenated hydrocarbons of the present invention may optionally further comprise up to 10 weight percent of dimethyl ether, or at least one C3 to Cs hydrocarbon, e. g. , propane, propylene, cyclopropane, n-butane, i- butane, and n-pentane. Examples of halogenated hydrocarbons containing such C3 to Cs hydrocarbons are azeotrope-like compositions of HCFC-22/HFC- 125/propane (known by the ASHRAE designation, R-402A and R-402B) and HCFC-22/octafluoropropane/propane (known by the ASHRAE designation, R- 403A and R-403B).

Lubricants of the present invention are those conventionally used in compression refrigeration apparatus utilizing chlorofluorocarbon refrigerants.

Such lubricants and their properties are discussed in the 1990 ASHRAE Handbook, Refrigeration Systems and Applications, chapter 8, titled"Lubricants in Refrigeration Systems", pages 8.1 through 8. 21, herein incorporated by reference. Lubricants of the present invention are selected by considering a given compressor's requirements and the environment to which the lubricant will be exposed. Lubricants of the present invention preferably have a kinematic viscosity of at least 15 cs (centistokes) at 40°C. Lubricants of the present invention comprise those commonly known as"mineral oils"in the field of compression refrigeration lubrication. Mineral oils comprise paraffins (i. e. straight-chain and branched-carbon-chain, saturated hydrocarbons), naphthenes (i. e. cyclic paraffins) and aromatics (i. e. unsaturated, cyclic hydrocarbons containing one or more rings characterized by alternating double bonds).

Lubricants of the present invention further comprise those commonly known as "synthetic oils"in the field of compression refrigeration lubrication. Synthetic oils comprise alkylaryls (i. e. linear and branched alkyl alkylbenzenes), synthetic paraffins and napthenes, and poly (alphaolefins). Representative conventional lubricants of the present invention are the commercially available BVM 100 N (paraffinic mineral oil sold by BVA Oils), Suniso@ 3GS (napthenic mineral oil sold by Crompton Co.), Sontex (D 372LT (napthenic mineral oil sold by Pennzoil), Calumet@ RO-30 (napthenic mineral oil sold by Calument Lubricants), Zerol@ 75 and Zerol@ 150 (linear alkylbenzenes sold by Shrieve Chemicals) and HAB 22 (branched alkylbenzene sold by Nippon Oil).

Compatibilizers of the present invention comprise polyoxyalkylene glycol ethers represented by the formula Rl [ (OR), OW] y, wherein: x is selected from integers from 1-3; y is selected from integers from 1-4 ; Rl is selected from hydrogen and aliphatic hydrocarbon radicals having 1 to 6 carbon atoms and y bonding sites, R2 is selected from aliphatic hydrocarbylene radicals having from 2 to 4 carbon atoms ; R3 is selected from hydrogen and aliphatic and alicyclic hydrocarbon radicals having from 1 to 6 carbon atoms; at least one of Rl and R3 is said hydrocarbon radical ; and wherein said polyoxyalkylene glycol ethers have a molecular weight of from 100 to 300 atomic mass units and a carbon to oxygen ratio of from 2.3 to 5.0. In the present polyoxyalkylene glycol ether compatibilizers represented by R1 [(oR2) xoR3] y: x is preferably 1-2 ; y is preferably 1, R1 and R3 are preferably independently selected from hydrogen and

aliphatic hydrocarbon radicals having 1 to 4 carbon atoms; R2 is preferably selected from aliphatic hydrocarbylene radicals having from 2 or 3 carbon atoms, most preferably 3 carbon atoms; the polyoxyalkylene glycol ether molecular weight is preferably from 100 to 250 atomic mass units, most preferably from 125 to 250 atomic mass units; and the polyoxyalkylene glycol ether carbon to oxygen ratio is preferably from 2.5 to 4.0 when hydrofluorocarbons are used as halogenated hydrocarbon refrigerant, most preferably from 2.7 to 3.5 when hydrofluorocarbons are used as halogenated hydrocarbon refrigerant, and preferably from 3.5 to 5.0 when hydrochlorofluorocarbon-containing refrigerants are used as halogenated hydrocarbon refrigerant, most preferably from 4.0 to 4.5 when hydrochlorofluorocarbon-containing refrigerants are used as halogenated hydrocarbon refrigerant. The R1 and R3 hydrocarbon radicals having 1 to 6 carbon atoms may be linear, branched or cyclic. Representative R1 and R3 hydrocarbon radicals include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec- butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, and cyclohexyl. Where free hydroxyl radicals on the present polyoxyalkylene glycol ether compatibilizers may be incompatible with certain compression refrigeration apparatus materials of construction (e. g. Mylar (g)), Rl and R3 are preferably aliphatic hydrocarbon radicals having 1 to 4 carbon atoms, most preferably 1 carbon atom. The R2 aliphatic hydrocarbylene radicals having from 2 to 4 carbon atoms form repeating oxyalkylene radicals- (OR2) x-that include oxyethylene radicals, oxypropylene radicals, and oxybutylene radicals. The oxyalkylene radical comprising R2 in one polyoxyalkylene glycol ether compatibilizer molecule may be the same, or one molecule may contain different R2 oxyalkylene groups. The present polyoxyalkylene glycol ether compatibilizers preferably comprise at least one oxypropylene radical. Where Rl is an aliphatic or alicyclic hydrocarbon radical having 1 to 6 carbon atoms and y bonding sites, the radical may be linear, branched or cyclic. Representative Rl aliphatic hydrocarbon radicals having two bonding sites include, for example, an ethylene radical, a propylene radical, a butylene radical, a pentylene radical, a hexylen radical, a cyclopentylene radical and a cyclohexylene radical. Representative Rl aliphatic hydrocarbon radicals having three or four bonding sites include residues derived from polyalcohols, such as trimethylolpropane, glycerin, pentaerythritol, 1,2, 3- trihydroxycyclohexane and 1,3, 5-trihydroxycyclohexane, by removing their hydroxyl radicals. Representative polyoxyalkylene glycol ether compatibilizers include: CH30CH2CH (CH3) 0 (H or CH3) (propylene glycol methyl (or dimethyl)

ether), CH30 [CH2CH (CH3) O] 2 (H or CH3) (dipropylene glycol methyl (or dimethyl) ether), CH30 [CH2CH (CH3) ou3 (H or CH3) (tripropylene glycol methyl (or dimethyl) ether), C2H50CH2CH (CH3) 0 (H or C2H5) (propylene glycol ethyl (or diethyl) ether), C2H50 [CH2CH (CH3) O] 2 (H or C2H5) (dipropylene glycol ethyl (or diethyl) ether), C2H5O [CH2CH (CH3) O] 3 (H or C2Hs) (tripropylene glycol ethyl (or diethyl) ether), C3H70CH2CH (CH3) 0 (H or C3H7) (propylene glycol n-propyl (or di-n-propyl) ether), C3H70 [CH2CH (CH3) O] 2 (H or C3H7) (dipropylene glycol n-propyl (or di-n-propyl) ether), C3H70 [CH2CH (CH3)O]3 (H or C3H7) (tripropylene glycol n-propyl (or di-n-propyl) ether), C4H90CH2CH (CH3) OH (propylene glycol n-butyl ether), C4H9O[CH2CH (CH3) 0] 2 (H or C4H9) (dipropylene glycol n-butyl (or di-n-butyl) ether), C4H9O [CH2CH (CH3) O] 3 (H or C4H9) (tripropylene glycol n-butyl (or di-n-butyl) ether), (CH3) 3COCH2CH (CH3) OH (propylene glycol t-butyl ether), (CH3) 3CO [CH2CH (CH3) O] 2 (H or (CH3) 3) (dipropylene glycol t-butyl (or di-t- butyl) ether), (CH3) 3CO [CH2CH (CH3) 0] 3 (H or (CH3) 3) (tripropylene glycol t- butyl (or di-t-butyl) ether), CsH110CH2CH (CH3) OH (propylene glycol n-pentyl ether), C4H90CH2CH (C2H5) OH (butylene glycol n-butyl ether), C4H9O [CH2CH (C2H5) O] 2H (dibutylene glycol n-butyl ether), trimethylolpropane tri-n-butyl ether (C2H5C (CH20 (CH2) 3CH3) 3) and trimethylolpropane di-n-butyl ether (C2H5C (CH20C (CH2) 3CH3) 2CH20H).

Compatibilizers of the present invention further comprise amides represented by the formulae R1CONR2R3 and cyclo-[R4CON (R5)-], wherein R, R2, R3 and Rs are independently selected from aliphatic and alicyclic hydrocarbon radicals having from 1 to 12 carbon atoms; R4 is selected from aliphatic hydrocarbylene radicals having from 3 to 12 carbon atoms; and wherein said amides have a molecular weight of from 120 to 300 atomic mass units and a carbon to oxygen ratio of from 7 to 20. The molecular weight of said amides is preferably from 160 to 250 atomic mass units. The carbon to oxygen ratio in said amides is preferably from 7 to 16, and most preferably from 10 to 14. Ru, R2, R3 and Rs may optionally include substituted hydrocarbon radicals, that is, radicals containing non-hydrocarbon substituents selected from halogens (e. g. , fluorine, chlorine) and alkoxides (e. g. methoxy). Ru, R2, R3 and Rs may optionally include heteroatom-substituted hydrocarbon radicals, that is, radicals which contain the atoms nitrogen (aza-), oxygen (oxa-) or sulfur (thia-) in a radical chain otherwise composed of carbon atoms. In general, no more than three non-hydrocarbon substituents and heteroatoms, and preferably no more than one, will be present for

each 10 carbon atoms in Rl-3, and the presence of any such non-hydrocarbon substituents and heteroatoms must be considered in applying the aforementioned ratio of carbon to oxygen and molecular weight limitations. Preferred amide compatibilizers consist of carbon, hydrogen, nitrogen and oxygen. Representative R1, R2, R3 and R'aliphatic and alicyclic hydrocarbon radicals include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and their configurational isomers. A preferred embodiment of amide compatibilizers are those wherein R4 in the aforementioned formula cyclo- [R4CON (R5)-] may be represented by the hydrocarbylene radical (CR6R7) n, in other words, the formula: cyclo-[(CR6R7) nCON (R5)-] wherein: the previously- stated values for (a) ratio of carbon to oxygen and (b) molecular weight apply; n is an integer from 3 to 5; Rs is a saturated hydrocarbon radical containing 1 to 12 carbon atoms ; R6 and R7 are indepedently selected (for each n) by the rules previously offered defining R1-3. In the lactams represented by the formula: cyclo-[(CR6R7) nCON (R5)-], all R6 and R7 are preferably hydrogen, or contain a single saturated hydrocarbon radical among the n methylene units, and R 5 is a saturated hydrocarbon radical containing 3 to 12 carbon atoms. For example, 1- (saturated hydrocarbon radical) -5-methylpyrrolidin-2-ones. Representative amide compatibilizers include: 1-octylpyrrolidin-2-one, 1-decylpyrrolidin-2-one, 1- octyl-5-methylpyrrolidin-2-one, 1-butylcaprolactam, 1-cyclohexylpyrrolidin-2- one, 1-butyl-5-methylpiperid-2-one, 1-pentyl-5-methylpiperid-2-one, 1- hexylcaprolactam, 1-hexyl-5-methylpyrrolidin-2-one, 5-methyl-1-pentylpiperid-2- one, 1, 3-dimethylpiperid-2-one, 1-methylcaprolactam, 1-butyl-pyrrolidin-2-one, 1,5-dimethylpiperid-2-one, 1-decyl-5-methylpyrrolidin-2-one, 1-dodecylpyrrolid- 2-one, N, N-dibutylformamide and N, N-diisopropylacetamide.

Compatibilizers of the present invention further comprise ketones represented by the formula R1COR2, wherein R1 and R2 are independently selected from aliphatic, alicyclic and aryl hydrocarbon radicals having from 1 to 12 carbon atoms, and wherein said ketones have a molecular weight of from 70 to 300 atomic mass units and a carbon to oxygen ratio of from 4 to 13. R1 and R2 in said ketones are preferably independently selected from aliphatic and alicyclic hydrocarbon radicals having 1 to 9 carbon atoms. The molecular weight of said ketones is preferably from 100 to 200 atomic mass units. The carbon to oxygen ratio in said ketones is preferably from 7 to 10. R1 and R2 may together form a hydrocarbylene radical connected and forming a five, six, or seven-membered

ring cyclic ketone, for example, cyclopentanone, cyclohexanone, and cycloheptanone. R1 and R2 may optionally include substituted hydrocarbon radicals, that is, radicals containing non-hydrocarbon substituents selected from halogens (e. g. , fluorine, chlorine) and alkoxides (e. g. methoxy). R1 and R2 may optionally include heteroatom-substituted hydrocarbon radicals, that is, radicals which contain the atoms nitrogen (aza-), oxygen (keto-, oxa-) or sulfur (thia-) in a radical chain otherwise composed of carbon atoms. In general, no more than three non-hydrocarbon substituents and heteroatoms, and preferably no more than one, will be present for each 10 carbon atoms in R'and W, and the presence of any such non-hydrocarbon substituents and heteroatoms must be considered in applying the aforementioned ratio of carbon to oxygen and molecular weight limitations. Representative R1 and R2 aliphatic, alicyclic and aryl hydrocarbon radicals in the general formula R1COR2 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and their configurational isomers, as well as phenyl, benzyl, cumenyl, mesityl, tolyl, xylyl and phenethyl. Representative ketone compatibilizers include: 2-butanone, 2- pentanone, acetophenone, butyrophenone, hexanophenone, cyclohexanone, cycloheptanone, 2-heptanone, 3-heptanone, 5-methyl-2-hexanone, 2-octanone, 3- octanone, diisobutyl ketone, 4-ethylcyclohexanone, 2-nonanone, 5-nonanone, 2- decanone, 4-decanone, 2-decalone, 2-tridecanone, dihexyl ketone and dicyclohexyl ketone.

Compatibilizers of the present invention further comprise nitriles represented by the formula R1CN, wherein Ru ils selected from aliphatic, alicyclic or aryl hydrocarbon radicals having from 5 to 12 carbon atoms, and wherein said nitriles have a molecular weight of from 90 to 200 atomic mass units and a carbon to nitrogen ratio of from 6 to 12. R1 in said nitrile compatibilizers is preferably selected from aliphatic and alicyclic hydrocarbon radicals having 8 to 10 carbon atoms. The molecular weight of said nitrile compatibilizers is preferably from 120 to 140 atomic mass units. The carbon to nitrogen ratio in said nitrile compatibilizers is preferably from 8 to 9. R1 may optionally include substituted hydrocarbon radicals, that is, radicals containing non-hydrocarbon substituents selected from halogens (e. g. , fluorine, chlorine) and alkoxides (e. g. methoxy). may optionally include heteroatom-substituted hydrocarbon radicals, that is, radicals which contain the atoms nitrogen (aza-), oxygen (keto-, oxa-) or sulfur (thia-) in a radical chain otherwise composed of carbon atoms. In general, no

more than three non-hydrocarbon substituents and heteroatoms, and preferably no more than one, will be present for each 10 carbon atoms in R', and the presence of any such non-hydrocarbon substituents and heteroatoms must be considered in applying the aforementioned ratio of carbon to nitrogen and molecular weight limitations. Representative R'aliphatic, alicyclic and aryl hydrocarbon radicals in the general formula R1CN include include pentyl, isopentyl, neopentyl, tert- pentyl, cyclopentyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and their configurational isomers, as well as phenyl, benzyl, cumenyl, mesityl, tolyl, xylyl and phenethyl. Representative nitrile compatibilizers include: 1- cyanopentane, 2,2-dimethyl-4-cyanopentane, 1-cyanohexane, 1-cyanoheptane, 1- cyanooctane, 2-cyanooctane, 1-cyanononane, 1-cyanodecane, 2-cyanodecane, 1- cyanoundecane and 1-cyanododecane. Nitrile compatibilizers are especially useful in compatibilizing HFC refrigerants with aromatic and alkylaryl lubricants.

Compatibilizers of the present invention further comprise chlorocarbons represented by the formula RClx, wherein; x is selected from the integers 1 or 2; R is selected from aliphatic and alicyclic hydrocarbon radicals having 1 to 12 carbon atoms; and wherein said chlorocarbons have a molecular weight of from 100 to 200 atomic mass units and carbon to chlorine ratio from 2 to 10. The molecular weight of said chlorocarbon compatibilizers is preferably from 120 to 150 atomic mass units. The carbon to chlorine ratio in said chlorocarbon compatibilizers is preferably from 6 to 7. Representative R aliphatic and alicyclic hydrocarbon radicals in the general formula RClx include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and their configurational isomers. Representative chlorocarbon compatibilizers include: 3- (chloromethyl) pentane, 3-chloro-3-methylpentane, 1- chlorohexane, 1,6-dichlorohexane, 1-chloroheptane, 1-chlorooctane, 1- chlorononane, 1-chlorodecane, and 1, 1, 1-trichlorodecane.

Compatibilizers of the present invention further comprise aryl ethers represented by the formula R1OR2, wherein: R1 is selected from aryl hydrocarbon radicals having from 6 to 12 carbon atoms; R2 is selected from aliphatic hydrocarbon radicals having from 1 to 4 carbon atoms; and wherein said aryl ethers have a molecular weight of from 100 to 150 atomic mass units and a carbon to oxygen ratio of from 4 to 20. The carbon to oxygen ratio in said aryl ether compatibilizers is preferably from 7 to 10. Representative R1 aryl radicals in the general formula R1OR2 include phenyl, biphenyl, cumenyl, mesityl, tolyl, xylyl,

naphthyl and pyridyl. Representative R2 aliphatic hydrocarbon radicals in the general formula R1OR2 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl. Representative aromatic ether compatibilizers include: methyl phenyl ether (anisole), 1,3-dimethyoxybenzene, ethyl phenyl ether and butyl phenyl ether.

Compatibilizers of the present invention further comprise 1, 1, 1- trifluoroalkanes represented by the general formula CF3R1, wherein R1 is selected from aliphatic and alicyclic hydrocarbon radicals having from 5 to 15 carbon atoms, preferably primary, linear, saturated, alkyl radicals. Representative 1, 1, 1- trifluoroalkane compatibilizers include: 1, 1, 1-trifluorohexane and 1,1, 1- trifluorododecane.

Compatibilizers of the present invention further comprise fluoroethers represented by the general formula R1OCF2CF2H, wherein Ru ils selected from aliphatic and alicyclic hydrocarbon radicals having from 5 to 15 carbon atoms, preferably primary, linear, saturated, alkyl radicals. Representative fluoroether compatibilizers include: CgHI7OCF2CF2H and C6H130CF2CF2H.

Compatibilizers of the present invention may comprise a single compatibilizer species or multiple compatibilizer species together in any proportion. For example, a compatibilizer may comprise a mixture of compounds from within a single compatibilizer species (e. g. a mixture of polyoxyalkylene glycol ethers) or a mixture of compounds chosen from different compatibilizer species (e. g. a mixture of a polyoxyalkylene glycol ether with a ketone).

Compatibilizer of the present invention may optionally further comprise from 1 to 50 weight percent, preferably from 1 to 10 weight percent based on total amount of compatibilizer, of an ester containing the functional group-C02-and having a carbon to ester functional group carbonyl oxygen ratio of from 2 to 6. The optional esters may be represented by the general formula RC02R, wherein R1 and R2 are independently selected from linear and cyclic, saturated and unsaturated, alkyl and aryl radicals. R1 and R2 are optionally connected forming a ring, such as a lactone. Preferred optional esters consist essentially of the elements C, H and O having a molecular weight of from 80 to 550 atomic mass units. Representative optional esters include: (CH3) 2CHCH20OC (CH2) 2-40COCH2CH (CH3) 2 (diisobutyl dibasic ester), ethyl hexanoate, ethyl heptanoate, n-butyl proprionate, n-propyl proprionate, ethyl benzoate, di-n-propyl phthalate, benzoic acid ethoxyethyl ester, dipropyl

carbonate,"Exxate 700" (a commercial C7 alkyl acetate), "Exxate 800" (a commercial C8 alkyl acetate), dibutyl phthalate, and t-butyl acetate.

Compatibilizer of the present invention may optionally further comprise at least one polyvinyl ether polymer, including polyvinyl ether homopolymers, polyvinyl ether copolymers, and copolymers of vinyl ethers with hydrocarbon alkenes (e. g. ethylene and propylene), and/or functionalized hydrocarbon alkenes (e. g. , vinyl acetate and styrene). A representative polyvinyl ether is PVE 32, sold by Idemitsu Kosan and having a kinematic viscosity of 32 cs at 40°C.

Compatibilizers of the present invention may optionally further comprise from 0.5 to 50 weight percent (based on total amount of compatibilizer) of a linear or cyclic aliphatic or aromatic hydrocarbon containing from 5 to 15 carbon atoms. Representative hydrocarbons include pentane, hexane, octane, nonane, decane, Isopar H (a high purity C1l to C12 iso-paraffinic), Aromatic 150 (a Co to Cil aromatic), Aromatic 200 (a C9 to C15 aromatic) and Naptha 140. All of these hydrocarbons are sold by Exxon Chemical, USA.

Compatibilizers of the present invention may optionally further contain from 0.01 to 30 weight percent (based on total amount of compatibilizer) of an additive which reduces the surface energy of metallic copper, aluminum, steel, or other metals found in heat exchangers in a way that reduces the adhesion of lubricants to the metal. Examples of metal surface energy reducing additives include those disclosed in WIPO PCT publication WO 96/7721, such as Zonyl (t FSA, Zonyl (B) FSP and Zonyl FSj, all products of E. I. du Pont de Nemours and Co. In practice, by reducing the adhesive forces between the metal and the lubricant (i. e. substituting for a compound more tightly bound to the metal), the lubricant circulates more freely through the heat exchangers and connecting tubing in an air conditioning or refrigeration system, instead of remaining as a layer on the surface of the metal. This allows for the increase of heat transfer to the metal and allows efficient return of lubricant to the compressor.

Commonly used refrigeration system additives may optionally be added, as desired, to compositions of the present invention in order to enhance lubricity and system stability. These additives are generally known within the field of refrigeration compressor lubrication, and include anti wear agents, extreme pressure lubricants, corrosion and oxidation inhibitors, metal surface deactivators, free radical scavengers, foam control agents, and the like. In general, these additives are present only in small amounts relative to the overall

lubricant composition. They are typically used at concentrations of from less than 0.1 % to as much as 3 % of each additive. These additives are selected on the basis of the individual system requirements. Some typical examples of such additives may include, but are not limited to, lubrication enhancing additives, such as alkyl or aryl esters of phosphoric acid and of thiophosphates. These include members of the triaryl phosphate family of EP lubricity additives, such as butylated triphenyl phosphates (BTPP), or other alkylated triaryl phosphate esters, e. g. Syn-0-Ad 8478 from Akzo Chemicals, tricrecyl phosphates and related compounds. Additionally, the metal dialkyl dithiophosphates (e. g. zinc dialkyl dithiophosphate or ZDDP, Lubrizol 1375) and other members of this family of chemicals may be used in compositions of the present invention. Other antiwear additives include natural product oils and asymmetrical polyhydroxyl lubrication additives such as Synergol TMS (International Lubricants). Similarly, stabilizers such as anti oxidants, free radical scavengers, and water scavengers may be employed. Compounds in this category can include, but are not limited to, butylated hydroxy toluene (BHT) and epoxides.

Compatibilizers such as ketones may have an objectionable odor which can be masked by addition of an odor masking agent or fragrance. Typical examples of odor masking agents or fragrances may include Evergreen, Fresh Lemon, Cherry, Cinnamon, Peppermint, Floral or Orange Peel or sold by Intercontinental Fragrance, as well as d-limonene and pinene. Such odor masking agents may be used at concentrations of from 0. 001% to as much as 15% by weight based on the combined weight of odor masking agent and compatibilizer.

The present invention further comprises processes for producing refrigeration comprising evaporating the present halogenated hydrocarbon- containing refrigeration compositions in the vicinity of a body to be cooled, and processes for producing heat comprising condensing halogenated hydrocarbon refrigerant in the presence of lubricant and compatibilizer in the presence of a body to be heated.

The present invention further comprises processes for solubilizing a halogenated hydrocarbon refrigerant in a lubricant, comprising contacting the halogenated hydrocarbon refrigerant with the lubricant in the presence of an effective amount of compatibilizer, which forms a solution of the halogenated hydrocarbon refrigerant and the lubricant.

The present invention further relates to processes for returning lubricant from a non-compressor zone to a compressor zone in a compression refrigeration system comprising: (a) contacting the lubricant in the non-compressor zone with at least one halogenated hydrocarbon refrigerant in the presence of an effective amount of compatibilizer ; and (b) returning the lubricant from the noncompressor zone to the compressor zone of the refrigeration system.

The present invention further comprises processes for returning a lubricant from a low pressure zone to a compressor zone in a refrigeration system, comprising: (a) contacting the lubricant in the low pressure zone of the refrigeration system with at least one halogenated hydrocarbon refrigerant in the presence of an effective amount of compatibilizer ; and (b) returning the lubricant from the low pressure zone to the compressor zone of the refrigeration system.

EXAMPLES The following examples are provided to illustrate certain aspects of the present invention, and are not intended to limit the scope of the invention.

Herein, all percentages (%) are in weight percentages unless otherwise indicated.

Naptha 140 (paraffins and cycloparaffins with normal boiling point of 188-208°C), Aromatic 150 (aromatics with normal boiling point 184-204°C) and IsoparX H (isoparaffins with normal boiling point 161-203°C) are all products of Exxon Chemicals. Exxate 700 is a C7 alkyl acetate produced by Exxon."POE 22"is used herein as an abbreviation for Mobil Oil product Arctic EAL22, a polyol ester lubricant having a kinematic viscosity of 22 cs at 40°C."POE 32"is used herein as an abbreviation for Uniqema product Emkarate RL32, a polyol ester lubricant having a kinematic viscosity of 32 cs at 40°C. Zerol 75 is an alkylbenzene lubricant having a kinematic viscosity of 15 cs at 40°C, Zerol 150 is an alkylbenzene lubricant having a kinematic viscosity of 32 cs at 40°C, Zerol 200 TD is an alkylbenzene lubricant having a kinematic viscosity of 40 cs at 40°C, and Zerol 300 is an alkylbenzene lubricant having a kinematic viscosity of 57 cs at 40°C. The Zerol products are sold by the Shrieve Corporation. PVE 32 is a polyvinyl ether sold by Idemitsu Kosan having a kinematic viscosity of 32 cs

at 40°C. Ucon LB-65 is a polyoxyproplyene glycol lubricant sold by Union Carbide with an average molecular weight of about 340. Ucon 50-HB-100 is a lubricant containing equal amounts of oxyethylene and oxpropylene groups sold by Union Carbide with an average molecular weight of about 520. Ucon 488 is a polyalkylene glycol lubricant sold by Union Carbide having a kinematic viscosity of 130 cs at 40°C. Suniso 3GS (sometimes herein abbreviated as"3GS") is a napthenic mineral oil with a kinematic viscosity of 33 cs at 40°C, Suniso@ 4GS (sometimes herein abbreviated as"4GS") is a napthenic mineral oil with a kinematic viscosity of 62 cs at 40°C. The Suniso (g) products are sold by Crompton Corporation. HAB 22 is a branched alkylbenzene lubricant having a kinematic viscosity of 22 cs at 40°C and sold by Nippon Oil.

HCFC-22 is chlorodifluoromethane. HFC-134a is 1,1, 1,2- tetrafluoroethane. R401A is a refrigerant blend containing 53 wt% HCFC-22,13 wt% HFC-152a (1, 1-difluoroethane) and 34 wt% HCFC-124 (2-chloro-1, 1, 1, 2- tetrafluoroethane). R404A is a refrigerant blend containing 44 wt% HFC-125 (pentafluoroethane), 52 wt% HFC-143a (1, 1, 1-trifluoroethane) and 4 wt% HFC- 134a. R407C is a refrigerant blend containing 23 wt% HFC-32 (difluoromethane), 25 wt% HFC-125 and 52 wt% HFC-134a. R410A is a refrigerant blend containing 50 wt% HFC-32 and 50 wt% HFC-125.

Abbreviations used herein for a number of materials are shown in the table below with the corresponding material name, and if relevant, formula and molecular weight: Abbreviation Material Formula Molecular Weight BnB Butylene glycol n-butyl ether C4H90CH2CHOHCH2CH3 146 PnB Propylene glycol n-butyl ether C4H90CH2CHOHCH3 132 DPnB Dipropylene glycol n-butyl ether C4H90 [CH2CH (CH3) O] 2H 190 TPnB Tripropylene glycol n-butyl ether C4H90 [CH2CH (CH3) O] 3H 248 PnP Propylene glycol n-propyl ether C3H7OCH2CHOHCH3 118 DPnP Dipropylene glycol n-propyl ether C3H70 [CH2CH (CH3) O ZH 176 DPM Dipropylene glycol methyl ether CH3O [CH2CH (CH3) O] 2H 148 DMM Dipropylene glycol dimethyl ether CH30 [CH2CH (CH3) 0] 2CH3 162 PGH Propylene glycol hexyl ether C6H130CH2CHOHCH3 160 EGO Ethvlene zIvool octvl ether C8HI7OCH2CH2OH 174 w PTB Propylene glycol t-butyl ether C (CH3) 30CH (CH3) CH20H 132 1, 5-DMPD 1, 5-dimethyl piperidone C7HI3NO 127 DMPD Mixture of 70 wt% 1, 3-and 30 wt% C7HI3NO 127 I, 5-dimethyl piperid-2-one OP l-octyl pyrrolidin-2-one Cl2H23NO 197 DBE-IB Diisobutyl dibasic esters (e. g. diisobutyl (H3) 2CHCH20OC (CH2) 2- 242 avg. esters of succinic, glutaric and adipic 40COCH2CH (CH3) 2 acids)

EXAMPLE 1 Polyoxyalkylene glycol ether compatibilizers of the present invention were placed in a suitable container with refrigerant and lubricant and the temperature was lowered until two phases were observed to the naked eye (i. e., the phase separation temperature, also herein referred to as"PST"). The composition in the container was 50 wt% HFC-134a, 25 wt% Zerol 150 and 25 wt% of compatibilizer. Results are shown below, and in Figure 1.

Example 1 .., _,, Phasme-.,, , Separation B Compatibilizer Formula Séparation Temperature ratio Ethylene glycol butyl ether C6HI402 4 3. 0 Ethylene glycol diethyl ether C6H1402 5 3. 0 Ethylene glycol hexyl ether CloH22o2 26 4. 0 Dipropylene glycol methyl ether C7HI603 27 2. 33 Dipropylene glycol propyl ether CgH2003 5. 5 3. 0 Propylene glycol butyl ether C7HI602 6 3. 5 Propylene glycol propyl ether C6HI402 11 3. 0 Tripropylene glycol butyl ether Cl3H2g04 11 3. 25 Propylene glycol dimethyl ether C5Hs202 12 2. 5 Tripropylene glycol propyl ether C12H2604 12 3. 0 Dipropylene glycol dimethyl ether C8H, 803 13 2. 67 Dipropylene glycol butyl ether CloH2203 13 3. 33 Diethylene glycol butyl ether C8HI803 13 2. 7 Butylene glycol n-butyl ether C8HI802 16 4 Dibutylene glycol n-butyl ether CnOs 18 4 Propylene glycol t-butyl ether C7HI602 20 3. 5 Comparative Data mp Tetraethylene glycol dimethyl ether CloHzz0s 32 2. 0 Ucon LB-65 polyalkylene 28 3. 0 glycol Ucon 50-HB-100 polyalkylene 32 2. 5 glycol PVE 32 polyvinyl ether 62 5 Dipropylene glycol C6HI403 not miscible 2 with Zerol 150

The data show significantly lower phase separation temperatures versus 50 wt% HFC-134a/50 wt% Zerol 150 alkylbenzene lubricant which has a phase separation temperature of 137°C. The data show that a minimum phase separation temperature occurs at a specific carbon to oxygen ratio of the polyoxyalkylene glycol ether compatibilizer indicating maximum solubility improvement of hydrofluorocarbon refrigerant in alkylbenzene lubricant.

EXAMPLE 2 Polyoxyalkylene glycol ether compatibilizers of the present invention were placed in a suitable container with refrigerant and lubricant and the temperature lowered until two phases were observed. The composition in the container was 50 wt% R401A refrigerant, 40 wt% Suniso 3GS and 10 wt% of a polyoxyalkylene glycol ether compatibilizer. Results are shown below, and in Figure 2.

Example 2 Phasme--, c-- Carbon/ Compatibilizer Formula Separation Temperature Patio Propylene glycol hexyl ether C9H2002-26 4. 5 Butylene glycol butyl ether C8HI802-19 4. 0 Ethylene glycol octyl ether ClpH2202-18 5. 0 Propylene glycol butyl ether C7H1602-7 3. 5 Dipropylene glycol ClOH2203-11 3. 33 butyl ether Tripropylene glycol butyl ether C13H2804-7 3. 25 Comparative Data Tetraglyme ClOH2205 not miscible 2. 0 with 3GS The data show significantly lower phase separation temperature versus 50 wt% R401A refrigerant/50 wt% Suniso 3GS mineral oil, which has a phase separation temperature of 24°C. The data show that a minimum phase separation temperature occurs at a specific carbon to oxygen ratio of the polyoxyalkylene glycol ether compatibilizer, indicating maximum solubility improvement of hydrochlorofluorocarbon-containing refrigerant in mineral oil lubricant.

Butyl phenyl ether (CloHi40), an aryl ether compatibilizer, was also measured and showed a surprisingly low phase separation temperature of-32°C.

EXAMPLE 3

Ketone compatibilizers of the present invention were placed in a suitable container with refrigerant and lubricant and the temperature lowered until two phases were observed. The composition in the container was 50 wt% HFC- 134a, 25 wt% Zerol 150 and 25 wt% of a ketone compatibilizer. Results are shown below, and in Figure 3.

Example 3 Phasme,.,, Compatibilizer Formula separation Temperature Ratio OC Cycloheptanone C7HI20-24 7 2-Nonanone C9HI80-22 9 3-Octanone C8HI60-17 8 Cyclohexanone C6HIoO-16 6 2-Heptanone C7HI40-15 7 2-Decanone CloH200-15 10 4-Decanone CloHzoO-14 10 2-Octanone C8HI60-12 8 5-Nonanone C9H180-12 9 4-Ethylcyclohexanone CgH140-12 8 3-Heptanone C7H140-8 7 Diisobutyl ketone CgH180-4 9 2-Decalone CloHI60 10 Methyl propyl ketone C5HIoO 3 5 Acetophenone C8H80 4 8 Butyrophenone CIoHs20 8 10 2-tridecanone C13H260 8 13 Methyl ethyl ketone C4HSO 16 4 Dihexylketone C13H260 21 13 Hexanophenone C13HI80 28 13 Dicyclohexyl ketone C13H220 53 13 Comparative Data Acetone | C3H60 | 56 | 3

The data show significantly lower phase separation temperatures versus 50 wt% HFC-134a/50 wt% Zerol 150 alkylbenzene lubricant which has a phase separation temperature of 137°C. The data show that a minimum phase separation temperature occurs at a specific carbon to oxygen ratio of the ketone compatibilizer indicating maximum solubility improvement of hydrofluorocarbon refrigerant in alkylbenzene lubricant.

EXAMPLE 4

Nitrile compatibilizers of the present invention were placed in a suitable container with refrigerant and lubricant and the temperature lowered until two phases were observed. The composition in the container was 50 wt% HFC- 134a, 25 wt% Zerol 150 and 25 wt% of a nitrile compound. Results are shown below, and in Figure 4.

Example 4 Phasme-,, separation Compatibilizer Formula nu Temperature Ratio cl) 1-cyanooctane C9HrN-26 9 2-çyanooctane CgHI7N-23 9 1-cyanoheptane C8Hz5N-18 8 1-cyanodecane ClIH2, N-13 11 2-cyanodecane CIlH2lN-12 11 1-cyanopentane C6HI lN-3 6 1-cyanoundecane C l2H23N 3 12 The data show significantly lower phase separation temperatures versus 50 wt% HFC-134a/50 wt% Zerol 150 alkylbenzene lubricant which has a phase separation temperature of 137°C. The data show that a minimum phase separation temperature occurs at a specific carbon to nitrogen ratio of the nitrile compatibilizer indicating solubility improvement of hydrofluorocarbon refrigerant in alkylbenzene lubricant.

EXAMPLE 5 Chlorocarbon compatibilizers of the present invention were placed in a suitable container with refrigerant and lubricant and the temperature lowered until two phases were observed. The composition in the container was 50 wt% HFC-134a, 25 wt% Zerol 150 and 25 wt% of a chlorocarbon compatibilizer.

Results are shown below, and in Figure 5.

Example 5 Phasme, separation Compatibilizer Formula Separatio Chlorine Ratio 1-chlorobutane C4H9Cl 16 4 3-(chlorometllyl) pentane C6Hz3Cl 34 6 1-chloroheptane C7HI5Cl 40 7 1, 6-dichlorohexane C6HI2Ci 47 3 1-chlorooctane C8HI7Cl 54 8

1-chlorohexane C6H13C1 3 6 3-chloro-3-methylpentane CgHCl 23 6 The data show significantly lower phase separation versus 50 wt% HFC-134a/50 wt% Zerol 150 alkylbenzene lubricant which has a phase separation temperature of 137°C. The data show that a minimum phase separation temperature occurs at a specific carbon to chlorine ratio of the chlorocarbon compatibilizer indicating maximum solubility improvement of hydrofluorocarbon refrigerant in alkylbenzene lubricant.

EXAMPLE 6 Chlorocarbon compatibilizers of the present invention were placed in a suitable container with refrigerant and lubricant and the temperature lowered until two phases were observed. The composition in the container was 50 wt% R401A refrigerant, 40 wt% Suniso 3GS and 10 wt% chlorocarbon compatibilizer.

Results are shown below and in Figure 6.

Example 6 Phasme,. Compatibilizer Formula Separation Corine Temperature Ratio oc 3- (chloromethyl) pentane C6H13Cl-25 6 1-chloroheptane C7HI5Cl-24 7 C6&C8 monochlorides,-17 6-8 1 : 2 weight ratio 1, 6-dichlorohexane C6Hz2C12-14 3 1-chlorooctane C8H17Cl-13 8 1-chlorohexane C6Hl3CI-10 6 3-chloro-3-methylpentane C6HI3Cl-10 6 1-chlorononane CgHIgCl-7 9 The data show significantly lower phase separation versus 50 wt% R401A refrigerant/50 wt% Suniso 3GS mineral oil which has a phase separation temperature of 24°C. The data show that a minimum phase separation temperature occurs at a specific carbon to chlorine ratio of the chlorocarbon compatibilizer indicating maximum solubility of hydrochlorofluorocarbon- containing refrigerant in mineral oil lubricant.

EXAMPLE 7

Amide compatibilizers of the present invention were placed in a suitable container with refrigerant and lubricant and the temperature lowered until two phases were observed. The composition in the container was either HFC- 134a or R401A refrigerants, Zerol 150 or Suniso 3GS lubricants, and an amide compatibilizer. Results are shown below and in Figures 7 and 8.

Example 7 PST (oc) PST C charbon 25% Zerol 150 40% 3GS to Compatibilizer Formula 25% 10% Ox Compatibilizer Compatibilizer Ratio 50% HFC-134a 50% R401A 1-octyl pyrrolidin-2-one C12H23NO-25-34 12 1-heptyl-5-methylpyrrolidin-2-one C12H23NO-18-12 1-octyl-5-methyl pyrrolidin-2-one Cl3H25NO-17-13 1-butylcaprolactam CloHlgNo-17-10 1-cyclohexylpyrrolidin-2-one CloHl7NO-15-27 10 1-butyl-5-methylpiperidone CloHl9No-13-20 10 1-pentyl-5-methyl piperidone C11Hz1N0-10-25 11 1-hexyl caprolactam C12H23NO-10-12 1-hexyl-5-methylpyrrolidin-2-one C1lH2lNO-10-1 1 1, 3-dimethyl piperidone C7Hl3NO-9-7 DMPD C7Hl3NO-6-7 1-decyl-2-pyrrolidin-2-one Cl4Hz7NO-4-14 1, 1-dibutylformamide CgHIoNO-2-16 1-methyl caprolactam C7Hl3NO-1-31 7 1-butyl pytTolidin-2-one C8Hl5NO-1-4 8 1-decyl-5-methylpyrrolidin-2-one C15H29NO 2-15 1, 5-dimethyl piperidone C7Hl3NO 2-15 7 1-dodecyl pyrrolidin-2-one C16H31NO 8-38 16 1, 1-diisopropyl acetamide CSHl7NO 13 4 8

The data show significantly lower phase separation temperatures for both hydrofluorocarbori and hydrochlorofluorocarbon-containing refrigerant/lubricant systems versus 50 wt% HFC-134a/50 wt% Zerol 150 which has a phase separation temperature of 137°C, and 50 wt% R401A refrigerant/50 wt% Suniso 3GS which has a phase separation temperature of 24°C. The minimum phase separation temperature for amide compatibilizers with HFC-134a and Zerol 150 occurs at a specific carbon to amide oxygen ratio indicating a maximum solubility improvement for hydrofluorocarbon refrigerants and alkylbenzene lubricant. The phase separation temperature for amide compatibilizers with R401A refrigerant and Suniso 3GS mineral oil lubricant decreases with increasing carbon to amide oxygen ratio.

EXAMPLE 8 Polyoxyalkylene glycol ether compatibilizers of the present invention were placed in a suitable container with refrigerant and lubricant and the temperature was lowered until two phases were observed. The composition in the container was 25 wt% Zerol 150,25 wt% of compatibilizer and 50% of either HFC-32, HFC-125 or R410A refrigerants. Results are shown below, and in Figure 9.

Example 8 PST with PST with PST with Carbon/ Compatibilizer Formula HFC-125 R410A Oxygen HFC-32 °C) o Ratio Ethylene glycol dimethyl ether C4Hto02 29 27 12 2. 0 Propylene glycol dimethyl ether C5HI202 23 7 6 2. 5 Ethylene glycol diethyl ether C6Hz402 16-1 3. 0 Propylene glycol butyl ether C7HI602 25 2 9 3. 5 Butylene glycol n-butyl ether CsHisOz-6-4 The data show an unexpected and generally lower phase separation temperature when HFC-32 and HFC-125 refrigerants are combined to form R410A refrigerant versus neat HFC-32 or HFC-125.

EXAMPLE 9 Aryl ether, 1,1, 1-trifluoroalkane and fluoroether compatibilizers of the present invention were placed in a suitable container with refrigerant and lubricant and the temperature lowered until two phases were observed. The composition in the container was 50 wt% HFC-134a refrigerant, 25 wt% Zerol 150 alkylbenzene lubricant and 25 wt% of compatibilizer.. Results are shown below.

Example 9 PST (°C) PST (°C) 25% Zerol 150 40% 3GS Compatibilizer Formula 25% 10% Compatibilizer Compatibilizer 50% HFC-134a 50% R401A methoxybenzene C7H80 13 1, 3-dimethoxybenzene C8HI002 15 ethoxybenzene C8HIoO 20 1, 1, 1-trifluorododecane Cl2H23F3 27-28 1, 1, 1-trifluorohexane C6HI IF3 32

CsHnOCFzCFzH C1oH18F40 21 -12 C6H13OCF2CF2H C8HI4F4O 27-11 The data show significantly lower phase separation temperatures for these compatibilizers with both hydrofluorocarbon and hydrochlorofluorocarbon- containing refrigerants versus 50 wt% HFC-134a/50wt% Zerol 150, which has a phase separation temperature of 137°C, and 50 wt% R401A refrigerant/50wt% Suniso 3GS, which has a phase separation temperature of 24°C.

EXAMPLES 10-28 A test tube was filled with 7.5 grams of HFC-43-lOmee (CF3CF2CHFCHFCF3), herein referred to as"4310", and 2.5 grams of selected lubricant. Compatibilizers of the present invention were added in 1 gram increments to the 4310/lubricant mixture and the contents of the tube were agitated at 25°C. Changes in phase levels were recorded and compositions of layers analyzed by gas chromatography. One gram increments of compatibilizer were added until the contents of the tube reached one homogeneous phase.

Results are shown below.

EXAMPLE 10 Grams of Total Bottom DPM added Composition in Heightß mm Laver wt% wt% to Tube Tube Heiht, mm Hei hg t 75. 0% 4310 20 35-- 25. 0% Zerol 150 9.1% DPM 5% DPM 11% DPM 1 68. 2% 4310 21 41 7% 4310 85% 4310 22.7% Zerol 150 88% Zerol 150 4% Zerol 150 16.7% DPM 9% DPM 21% DPM 2 62.5% 4310 20 49 9% 4310 73% 4310 20.8% Zerol 150 82% Zerol 150 6% Zerol 150 23. 1 % DPM 10% DPM 29% DPM 3 57. 7% 4310 18 59 7% 4310 63% 4310 19.2% Zerol 150 83% Zerol 150 8% Zerol 150 28.6% DPM 18% DPM 35% DPM 4 53.6% 4310 14 71 11% 4310 53% 4310 17. 8% Zerol 150 71% Zerol 150 12% Zerol 150 33.3% DPM 24% DPM 37% DPM 5 50.0% 4310 5 87 14% 4310 45% 4310 16.7% Zerol 150 62% Zerol 150 18% Zerol 150 37.5% DPM 6 46.9% 4310--one layer one layer 15. 6% Zerol 150 EXAMPLE 11 Grams of Total Bottom Top Laver Top Layer Bottoin La, yer PnB added Composition in--Layer 0 0 to added Tube'Height. mm 0 75. 0% 4310 21 34- 25. 0% Zerol 150 9. 1% D PnB 19% PnB 8% PnB 1 68. 2% 4310 23 40 15% 4310 89% 4310 22. 7% Zerol 150 66% Zerol 150 3% Zerol 150 16. 7% PnB 31% PnB 17% PnB 2 62. 5% 4310 25 47 25% 4310 79% 4310 20. 8% Zerol 150 44% Zerol 150 4% Zerol 150 23. 1% PnB 35% PnB 25% PnB 3 57. 7% 4310 23 57 35% 4310 69% 4310 19. 2% Zerol 150 30% Zerol 150 6% Zerol 150 28. 6% PnB 4 53. 6% 4310 one layer one layer 17. 8% Zerol 150 EXAMPLE 12 Grams of Total Bottom Top La er Ton Layer Bottom Laver DPnB added Composition in Layer o 0 to Tube Tube 0 75. 0% 4310 21 34 25. 0% Zerol 150 9.1% DPnB 14% DPnB 7% DPnB 1 68.2% 4310 23 40 13% 4310 88% 4310 22.7% Zerol 150 72% Zerol 150 5% Zerol 150 16.7% DPnB 25% DPnB 15% DPnB 2 62.5% 4310 26 45 18% 4310 79% 4310 20.8% Zerol 150 57% Zerol 150 6% Zerol 150 23.1% DPnB 35% DPnB 24% DPnB 3 57.7% 4310 27 51 29% 4310 68% 4310 19.2% Zerol 150 36% Zerol 150 8% Zeroll50 28. 6% DPnB 4 53.6% 4310--one layer one layer 17.8% Zerol 150 EXAMPLE 13 Grams of Total Bottom Top La, yer Top Layer Bottom Layer TPnB added Composition in--Laver o 0 to Tube Tube Height, 75. 0% 4310 21 34 25. 0% Zerol 150 9. 1% TPnB 29% TPnB 6% TPnB 1 68. 2% 4310 24 40 23% 4310 93% 4310 22. 7% Zerol 150 48% Zerol 150 1% Zerol 150 16. 7% TPnB 33% TPnB 14% TPnB 2 62. 5% 4310 27 44 25% 4310 84% 4310 20. 8% Zerol 150 42% Zerol 150 2% Zerol 150 23. 1% TPnB 32% TPnB 19% TPnB 3 57. 7% 4310 30 48 33% 4310 77% 4310 19. 2% Zerol 150 35% Zerol 150 4% Zeroll50 28. 6% TPnB 4 53. 6% 4310--one layer one layer 17. 8% Zerol 150 EXAMPLE 14 Grams of Total Bottom Top Layer Top Layer Bottom Layer PnP added to Composition * 1, LUer Tube Tube Heiht, mm- 75. 0% 4310 25. 0% Zerol 150 9. 1% PnP 17% PnP 9% PnP 1 68. 2% 4310 21 41 15% 4310 89% 4310 22. 7% Zerol 150 68% Zerol 150 2% Zerol 150 16. 7% PnP 27% PnP 18% PnP 2 62. 5% 4310 23 48 22% 4310 74% 4310 20. 8% Zerol 150 51% Zerol 150 8% Zerol 150 23. 1% PnP 29% PnP 26% PnP 3 57. 7% 4310 20 59 25% 4310 68% 4310 19. 2% Zerol 150 46% Zerol 150 6% Zerol 150 28. 6% PnP 4 53. 6% 4310--one layer one layer 17. 8% Zerol 150

EXAMPLE 15 Grams of Total Bottom Grams of Total Top Layer Bottom DPM adds Composition in Laye_r o 0 to Tube Tubf-Height, mm 75. 0% 4310 21 34 25. 0% Zerol 150 9. 1% DPnP 8% DPnP 8% DPnP 1 68. 2% 4310 22 41 7% 4310 87% 4310 22. 7% Zerol 150 85% Zerol 150 5% Zerol 150 16. 7% DPnP 16% DPnP 17% DPnP 2 62. 5% 4310 23 47 12% 4310 76% 4310 20. 8% Zerol 150 72% Zerol 150 7% Zerol 150 23. 1% DPnP 27% DPnP 24% DPnP 3 57. 7% 4310 22 56 19% 4310 67% 4310 19. 2% Zero1150 54% Zerol 150 9% Zero1150 28. 6% DPnP 4 53. 6% 4310--one layer one layer 17. 8% Zerol 150 EXAMPLE 16 Grams of Total Bottom Top Laver To Laver Bottom Layer DMM added Composition in L o 0 to Tube Tube Heightmm 75. 0% 4310 21 34 25. 0% Zerol 150 9. 1% DMM 8% DMM 9% DMM 1 68.2% 4310 22 40 11% 4310 90% 4310 22.7% Zerol 150 81% Zerol 150 1% Zerol 150 16.7% DMM 16% DMM 16% DMM 2 62.5% 4310 23 47 14% 4310 82% 4310 20.8% Zerol 150 70% Zerol 150 2% Zerol 150 23. 1% DMM 24% DMM 21% DMM 3 57.7% 4310 22 55 21% 4310 72% 4310 19.2% Zerol 150 55% Zerol 150 7% Zerol 150 28.6% DMM 33% DMM 29% DMM 4 53.6% 4310 4 81 37% 4310 55% 4310 17.8% Zerol 150 30% Zerol 150 16% Zerol 150 33.3% DMM 5 50.0% 4310--one layer one layer 16.7% Zerol 150 EXAMPLE 17 In this example, DIP = equal parts by weight of PnB, DPnB and Isopar H. Grams of DIP Total Bottom Top Layer Top La, Bottom Layer added to Tube Composition in-Layer o 0 Tube Height, mm Height, mm wt% Wt% 75. 0% 4310 25. 0% Zerol 150 3. 0% PnB 6% PnB no/io/3% PnB 3. 0% 16% 1% Isopar (R) H 1 Isopar (R) H 26 37 Isopar (R) H 3% DPnB 3. 0% DPnB 6% DPNB 91% 4310 68. 2% 4310 17% 4310 2% Zerol 150 22. 7% Zerol 150 55% Zerol 150 5. 6% PnB 11% PnB 5% PnB 5. 6% 24% 2% Isopar (R) H T T 2% Isopar (R) H Isopar (R) H 30 41 Isopar (R) H 5% DPnB 5. 6% DPnB 11% DPnB g6oo 4310 62. 5% 4310 29% 4310 2% Zerol 150 20. 8% Zerol 150 25% Zerol 150 7. 7% PnB 11% PnB'7% PnB 7. 7% 19% 4% Isopar (R) H T T 4% Isopar (R) H 3 36 43 Isopar (R) H 8% DPnB 7. 7% DPnB 11% DPnB % 4310 57. 7% 4310 29% 4310 19. 2% Zerol 150 30% Zerol 150 4% Zerol 150 9. 5% PnB 10% PnB 9% PnB 9. 5% 1 % T TT T 7% Isopar (R) H Isopar (R) H Isopar (R) H % Isopar (R) H 9. 5% DPNB 11% DPNB 64% 4310 53. 6% 4310 30% 4310 64% 4310 17. 8% Zerol 150 35% Zerol 150 11. 1% PnB 11. 1% Isopar (R) H _ _ one layer one layer 11. 1/o DPnB 50. 0% 4310 16. 7% Zerol 150 EXAMPLE 18 In this example, 2-heptanone is referred to as"A". Grams of A Total Layer Bottom Top Layer Bottom Layer Composition in-La er o 0 added to Tube T Height mm Heightz mm wt% Wt% 75. 0% 4310 19 34 25. 0% 3GS 9. 1% A 3. 2% A 9. 8% A 1 68. 2% 4310 20 42 3. 2% 4310 86. 4% 4310 22. 7% 3GS 92. 9% 3GS 3. 8% 3GS 16. 7% A 7. 6% A 16. 9% A 2 62. 5% 4310 19 52 6. 7% 4310 77. 7% 4310 20. 8% 3GS 85. 7% 3GS 5. 4% 3GS 23. 1% A X0. 8% A 23. 2% A 3 57. 7% 4310 15 64 10. 6% 4310 63. 7% 4310 19. 2% 3GS 78. 6% 3GS 13. 1% 3GS 28. 6% A 4 53. 6% 4310 one layer one layer 17. 8% 3GS EXAMPLE 19

In this example, 5-methyl-2-hexanone is referred to as"A". Grams of A Composition-to Total Composition Heights of both Composition- Tube in Tube layer bottom layer Tubé 0 75% 4310 Top-19 mm 25% 3GS Bottom-34 mm 9. 1% A Top-21 mm, clear 3. 0% A 10. 3% A 1 68. 2% 4310 Bottom-42 mm, 3. 4% 4310 87. 9% 4310 22. 7% 3GS clear 93. 6% 3GS 1. 8%-3GS 16. 7% A Top-19 mm, clear 8. 9% A 18. 2% A 2 62. 5% 4310 Bottom-51 mm, 6. 9% 4310 78. 6% 4310 20. 8% 3GS clear 84. 2% 3GS 3. 2% 3GS 23. 1% A Top-16 mm, clear 10. 8% A 23. 7% A 3 57. 7% 4310 Bottom-62 mm, 7. 9% 4310 62. 9% 4310 19. 2% 3GS clear 81. 3% 3GS 13. 4% 3GS 28. 6% A Top-10 mm, clear 13. 6% A 25. 8% A 4 53. 6% 4310 Bottom-78 mm, 9. 9% 4310 59. 2% 4310 17. 8% 3GS clear 76. 5% 3GS 15. 0% 3GS 31. 0% A Top-3 mm, clear 27. 0% A 29. 8% A 4. 5 51. 7% 4310 Bottom-90 mm, 14. 1% 4310 50. 0% 4310 17. 3% 3GS clear 58. 9% 3GS 20. 2% 3GS 5 50. 0% 4310 Clear one layer- 5 50. 0/0 4310 97 mm-- 16. 7% 3GS EXAMPLE 20 Grams of Total Bottom Top Laver To Laver Bottom Layer Isopar H added Composition in Laver o 0 to Tube Tube Height, nim 75. 0% 4310 25. 0% 3GS 19 34 9. 1% 31. 4% 5. 4% 1 Isopar (R) H 29 34 Isopar (R) H Isopar (R) H 68. 2% 4310 0. 4% 4310 93. 9% 4310 22. 7% 3GS 68. 2% 3GS 0. 7% 3GS 16. 7% 45. 7% 8. 2% 2 Isopar (R) H 37 34 Isopar (R) H Isopar (R) H 62. 5% 4310 1. 0% 4310 90. 7% 4310 20. 8% 3GS 53. 3% 3GS 1. 0% 3GS 23. 1% 56. 8% 9. 5% 3 Isopar (R) H 46 34 Isopar (R) H Isopar (R) H 57. 7% 4310 1. 9% 4310 89. 6% 4310 19. 2% 3GS 41. 3% 3GS 0. 9% 3GS 28. 6% 62. 9% 10. 5% 4 Isopar (R) H 57 33 Isopar (R) H Isopar (R) H 53. 6% 4310 2. 9% 4310 88. 6% 4310 17. 8% 3GS 34. 2% 3GS 0. 9% 3GS 33. 3% 69. 0% 11. 6% 5 Isopar (R) H 66 33 Isopar (R) H Isopar (R) H 50. 0% 4310 3. 3% 4310 87. 7% 4310 16. 7% 3GS 27. 7% 3GS 0. 7% 3GS 10 Never Reached one phase EXAMPLE 21 In this example, PDD = equal parts by weight of PnB, DMM and DPnB. Grams of PDD Total Top Laper Bottom Top Layer Bottom Layer added to Tube Composition in Height, Layer Wt% Wt% Tube Height, 75. 0% 4310 0 25. 0% Zerol 150 21 34 3. 0% PnB 5% PnB 3% PnB 3. 0% DMM 4% DMM 3% DMM 1 3. 0% DPnB 23 39 5% DPnB 3% DPnB 68. 2% 4310 14% 4310 87% 4310 22. 7% Zerol 150 72% Zerol 150 4% Zerol 150 5. 6% PnB 6% PnB 6% PnB 5. 6% DMM 5% DMM 6% DMM 2 5. 6% DPnB 24 46 6% DPnB 6% DPnB 62. 5% 4310 15% 4310 76% 4310 20. 8% Zerol 150 68% Zerol 150 6% Zerol 150 7. 7% PnB ll% PnB 8% PnB 7. 7% DMM 10% DMM 9% DMM 3 7. 7% DPnB 23 55 11% DPnB 8% DPnB 57. 7% 4310 24% 4310 63% 4310 19. 2% Zerol 150 44% Zerol 150 12% Zerol 150 11. 1% PnB 11. 1% DMM 4 11. 1% DPnB. one layer one layer 50. 0% 4310 16. 7% Zerol 150 EXAMPLE 22 In this example, DDN = equal parts by weight of DPnB, DMM and Naptha 140 ("N140"). Grams of DDN Total Top Laver Bottom Top Layer Bottom Layer added to Tube--'-'---Height, mm .,.. wt% Wt% Tube Hgipht_mm 75. 0% 4310 0 25. 0% Zerol 150 21 34 3. 0% DPnB 3% DPnB 3% DPnB 3. 0% DMM 3% DMM 3% DMM 1 3. 0% N140 25 38 9% N140 <1% N140 68. 2% 4310 8% 4310 93% 4310 22. 7% Zerol 150 77% Zerol 150 1% Zerol 150 5. 6% DPnB 7% DPnB 5% DPnB 5. 6% DMM 6% DMM 5% DMM 2 5. 6% N140 29 42 16% N140 1% N140 62. 5% 4310 12% 4310 87% 4310 20. 8% Zerol 150 59% Zerol 150 2% Zerol 150 7. 7% DPnB 9% DPnB 7% DPnB 7. 7% DMM 8% DMM 8% DMM 3 7. 7% N140 34 45 19% N140 3% N140 57. 7% 4310 17% 4310 80% 4310 19. 2% Zerol 150 47% Zerol 150 2% Zerol 150 9.5% DPnB 10% DPnB 9% DPnB 9.5% DMM 9% DMM 10% DMM 4 9.5% N140 39 48 18% N140 5% N140 53.6% 4310 23% 4310 70% 4310 17.8% Zerol 150 40% Zerol 150 6% Zerol 150 11. 1% DPnB 11% DPnB 11% DPnB 11. 1% DMM 11% DMM 11% DMM 5 11.1% N140 43 52 15% N140 9% N140 50.0% 4310 39% 4310 58% 4310 16. 7% Zerol 150 24% Zerol 150 11% Zerol 150 12.5% DPnB 12.5% DMM 6 12.5% N140 One Layer One Layer 46.9% 4310 15.6% Zerol 150 EXAMPLE 23 In this example, DDA = equal parts by weight of DPnB, DMM and Aromatic 150 ("A150").

Grams of DDA Total Top Layer Bottom Top Layer Bottom Layer ,,,, , Composition m Tr-u'-Layer-'---,.,, n,'- added to Tube C°mTuben Hei h Hei h wt% Wt% Tube Height, mm 75. 0% 4310 0 25. 0% Zerol 150 21 34 3. 0% DPnB 5% DPnB 2% DPnB 3. 0% DMM 4% DMM 2% DMM 1 3. 0% A150 24 38 13% A150 1% A150 68. 2% 4310 18% 4310 93% 4310 22. 7% Zerol 150 60% Zerol 150 2% Zerol 150 5. 6% DPnB 6% DPnB 5% DPnB 5. 6% DMM 5% DMM 5% DMM 2 5. 6% A150 28 42 12% A150 2% A150 62. 5% 4310 17% 4310 86% 4310 20. 8% Zerol 150 60% Zerol 150 2% Zerol 150 7. 7% DPnB 11% DPnB 7% DPnB 7. 7% DMM 10% DMM 8% DMM 3 7. 7% A150 32 46 20% A150 4% A150 57. 7% 4310 36% 4310 77% 4310 19. 2% Zerol 150 23% Zerol 150 4% Zerol 150 9. 5% DPnB 12% DPnB 9% DPnB 9. 5% DMM 12% DMM 9% DMM 4 9. 5% A150 35 51 18% A150 7% A150 53. 6% 4310 40% 4310 68% 4310 17. 8% Zerol 150 18% Zerol 150 7% Zerol 150 11. 1% DPnB 11. 1% DMM 5 11. 1% A150 One Layer One Layer 50. 0% 4310 16. 7% Zerol 150 EXAMPLE 24 In this example, PD = 2 parts by wt PnB, 1 part DPnB. Grams of PD Total Top Layer Bottom Top Layer Bottom Layer added to Tube Composition in Height, mm Layer wt% Wt% Tube Height, mm 75. 0% 4310 0 25. 0% Zerol 150 21 34 9. 1% PD 8% PnB 5% PnB 9 1% PD 8% PnB 5% PnB 22. 7% Zerol 150 12% 4310 91% 4310 76% Zerot 150 2% Zerol 150 16. 7% PD 14% PnB 10% PnB 2 62. 5% 4310 25 44 % DPnB 5% DPnB 20. 8% Zerol 150 20% 4310 82% 4310 59% Zerol 150 3% Zerol 150 24% PnB 15% PnB 3 57. 7% 4310 26 52 11% DPNB 7% DPnB 19. 2% Zerol 150 43% 4310 70% 4310 22% Zerol 150 8% Zerol 150 28. 6% PD 4 50. 0% 4310--one layer one layer 16. 7% Zerol 150 EXAMPLE 25 In this example, PD = 2 parts by wt PnB, 1 part DPnB. r. T Total Bottom r,. r T. . Grams of PD Total Top Laver Bottom Top Laver Bottom Layer ,,,. , Composition m 'Layer-'/---.," added to Tube Comosition in geight, mm L wt% Wt% Tube He iS h tm m 75. 0% 4310 0 25. 0% 3GS 21 34 t 9. 1% PD 7% PnB 5% PnB 1 68. 2% 4310 21 41 '% DP'B 2% DPnB 10% 4310 91% 4310 79% 3GS 2% 3GS 16. 7% PD 16% PnB 11% PnB 2 62. 5% 4310 21 48 8% DPnB 5% DPnB 20. 8% 3GS 18% 4310 81% 4310 58°fo 3GS 3% 3GS 23. 1% PD 17% PnB 15% PnB 3 57. 7% 4310 20 57 9% DPnB 8% DPnB 19. 2% 3GS 18% 4310 71% 4310 56% 3GS 6% 3GS 28. 6% PD 18% PnB 17% PnB 4 50. 0% 4310 16 69 9% DPnB 9% DPnB 16. 7% 3GS 19% 4310 65% 4310 54% 3GS 9% 3GS 33. 3% PD 5 50. 0% 4310--one layer one layer 16. 7% 3GS EXAMPLE 26 In this example, PD = 2 parts by wt PnB, 1 part DPnB. Grams of PD Total Top Lgy Bottom Tgp L Bottom Layer added to Tube C°mposition in gei h L wt% Wt% Tube Height, 75. 0% 4310 25. 0% HAB22 9. 1% PD 7% PnB 5% PnB 1 68. 2% 4310 23 39 4% DPnB 2% DPnB 22. 7% HAB22 14% 4310 91% 4310 75% HAB22 2% HAB22 16. 7% PD 15% PnB 11% PnB 2 62 5% 4310 25 45 7% DPNB 5% DPNB 20. 8% HAB22 28% 4310 78% 4310 50% HAB22 6% HAB22 23. 1% PD 3 57. 7% 4310--One Layer One Layer 19. 2% HAB22

EXAMPLE 27 Grams of Total Bottom Top Layer Top Laver Bottom Layer DMPD added Composition in Height, Layer wto/o wto/o to Tube Tube Height, mm to TubeTube"'-Heisht. mm---- 75. 0% 4310 0 25. 0% Zerol 150 21 35 9. 1% 1, 5-DMPD 3% 1, 5-DMPD 9% 1, 5-DMPD 1 68. 2% 4310 20 42 13% 4310 89% 4310 22. 7% Zerol 150 84% Zerol 150 2% Zerol 150 16. 7% 1, 5-18%1, 5- '9% 1, 5 DMPD' '6210 ", J ?, n 77% 0 62. 18 52', % O 7% 4} 10 20. 8% Zero ! 1505% Zerol 150 23. 1% 1, 5- 14% 1, 5- 24% 1, 5- 3 DMPD 8 68 DMPD DMPD 57. 7% 4310 25% 4310 63% 4310 19. 2% Zerol 150 61% Zerol 150 13% Zerol 150 28. 6% 1, 5- DMPD 4 DMPD One Layer One Layer 50. 0% 4310 16. 7% Zerol 150 EXAMPLE 28 -,, ,-. Total Bottom r . r Grams of OP Total Top Layer Bottom Top Laver Bottom Layer added to Tube Composltion in Heights mm ayer wt% Wt% Tube-Height mm- 75. 0% 4310 0 25. 0% Zerol 21 34-- 150 9. 1% OP 7. 8% OP 6. 4% OP 68. 2% 4310 22 40 16. 3% 4310 91. 5% 4310 22. 7% Zerol 75. 9% Zerol 2. 1% Zerol 150 150 150 16. 7% OP 14. 7% OP 13 4% OP 62. 5°fo 4310 19 51 32. 6% 4310 79. 3% 4310 20. 8% Zerol 52. 7% Zeros 150 150 23. 1% OP 3 57. 7% 4310 One Layer One Layer 19. 2% Zerol 150

Results show compatibilizers of the present invention improve the solubility between hydrofluorocarbons and conventional lubricants by drawing significant amounts of refrigerant (4310) into the lubricant phase (top layer), and lubricant (3GS or Zerol 150) into the refrigerant phase (bottom layer). The compatibilizers improve solubility significantly better than Isopar H alone, which never reached one phase. The combination of PnB, DPnB and Isopar H surprisingly draws more 4310 into the lubricant phase (17%) than either PnB, DPnB or Isopar H alone

(15%, 13% and 0.4%) respectively after one gram is added. A most preferred compatibilizer by this method is 1-octyl pyrrolidin-2-one, which required only 3 grams to reach one layer with Zerol 150 alkylbenzene lubricant.

Hexylene glycol was also tested as comparative data with HFC- 4310mee and Zerol 150 but the solution remained two layers even after 10 grams of hexylene glycol was added.

EXAMPLE 29 Lubricant return was tested in an lubricant-return apparatus as follows. Liquid refrigerant was fed from a pressurized cylinder through copper tubing to a heater where it was vaporized. The refrigerant vapor then passed through a pressure regulator and metering valve to control flow at a constant rate of 1,100 cc per minute and 101 kPa (1 atmosphere) pressure. The refrigerant vapor was fed to another copper tube 180 cm in length and 0.635 cm outer diameter formed into a U-shape and placed in a constant temperature bath. The U-shaped tube (U-tube) began with a straight vertical section 37 cm long then bent to a horizontal section 27 cm long at the bottom of the bath. The tube then rose vertically in a zigzag pattern with four 23 cm lengths, followed by another vertical straight section 23 cm long. The U-tube was filled with 10 grams of lubricant, optionally containing compatibilizer, which was added to the U-tube through the 37 cm vertical tube. Vapor refrigerant passed slowly through the lubricant in the U-tube. Refrigerant and lubricant exiting the U-tube was collected in a receiver and then the refrigerant allowed to evaporate from the lubricant. Lubricant was then weighed to determine how much lubricant was carried out of the U-tube by the refrigerant.

Refrigerant R407C was placed in the refrigerant cylinder. Suniso 3GS mineral oil, or Suniso 3GS oil and compatibilizers of the present invention were placed in the copper U-tube, wherein the combined lubricant and compatibilizer equaled 10 grams. The constant temperature bath was held at a temperature of-20°C. Refrigerant R407C vapor was fed through the U-tube at a flow rate of 1,100 cubic centimeters per minute and weight of lubricant in the receiver measured at 6,10, and 20 minute time intervals. Data are shown below.

Example 29 Wt% Lubricant Returned Lubricant Composition in U- 6 Min 10 Min 20 Min tube 6% 5-methyl-2-hexanone in 11. 3 18. 1 26. 2 3GS 6%2-Heptanone in 3GS 12.7 20.0 28.1 Comparative Data POE 22 9. 3 20. 0 29. 6 3GS 0 0 0 6% Isopar (R) H in 3GS 0 7. 9 17.0

Results show the addition of 2-heptanone and 5-methyl-2-hexanone ketone compatibilizers to 3GS mineral oil shows significant improvement in lubricant return versus neat 3GS or Isopar H in 3GS.

EXAMPLE 30 The apparatus and procedure of Example 29 was used to test refrigerant HFC-134a with Zerol 150 alkylbenzene lubricant, with and without compatibilizers. Results are shown below: Example 30 Wt% Lubricant Returned Lubricant Composition in U-6 Min 10 Min 20 Min tube 10% PnB/5% DPnB in Zerol 15 24 34 150 10% PnB/5% DPnB/2% Syn-17 25 36 0-Ad 8478*** in Zerol 150 10% PnB/5% DPnB/0. 5% 16 25 36 BHT in Zerol 150 10% PnB/5% DPnB/1.5% n-23 29 36 pentane in Zerol 150 10% PnB/5% DPnB/1. 5% n-21 30 39 octane in Zerol 150 10% PnB/5% DPnB/15% 15 27 38 PVE 32 in Zerol 150 Comparative Data POE 22 16 27 36 Zerol 150 0 0 3 15% Ucon LB-65* in Zerol 0 4 19 150 15% Ucon 50-HB-100** in 0 0 7 Zerol 150

* Ucon LB-65 is a polyoxyproplyene glycol lubricant sold by Union Carbide with an average molecular weight of about 340.

** Ucon 50-HB-100 is a lubricant containing equal amounts of oxyethylene and oxpropylene groups sold by Union Carbide with an average molecular weight of about 520

*** Syn-0-Ad 8478 is an alkylated triaryl phosphate ester produced by Akzo Chemicals Results show addition of polyoxyalkylene glycol ether compatibilizers, optionally with additional additives such as antiwear agents or hydrocarbons, significantly improve lubricant return of alkylbenzene lubricant and provide performance. equivalent to POE 22 polyol ester lubricant. The comparative data shows higher molecular weight polyoxypropylene lubricants do not provide acceptable lubricant return.

EXAMPLE 31 The apparatus and procedure of Example 29 was used to test refrigerant R404A with Zerol 150 alkyl benzene lubricant, with and without compatibilizers versus POE22 polyol ester lubricant. Results are shown below.

Example 31 o Wt% Wt% Lubricant wto/o Wt% Lubricant T i-j. --TTL Wt% Lubricant Lubricant-..--,. Lubricant Composition in U-tube Wt% Lubricant Lubricant Returned 20 Returned 6 Min Returned 10 Min Mit 35% l-octyl pyrrolidin-2-one in Zerol 150 26 36 45 12% DMM in Zerol 150 18 26 35 6% DMM/12% l-octyl pyrrolidin-2-one/2% 13 23 34 Synergol in Zerol 150 20% 1, l-dibutyl formamide in Zerol 150 10 18 29 20% l-methyl caprolactam in Zerol 150 12 24 36 17% 1, 3-dimethyoxybenzene in Zerol 150 17 24 35 Co arative Data mp POE 22 0 5 17 Zerol 150 0 0 <1 Results show addition of compatibilizers of the present invention to Zerol 150 provide significantly improved lubricant return versus polyol ester lubricant POE 22 polyol ester lubricant.

EXAMPLE 32 The apparatus and procedure of Example 29 was used to test refrigerant HFC-134a with Zerol 150 alkyl benzene lubricant, with and without compatibilizers versus POE 22 polyol ester lubricant. Results are shown below.

Example 32 Wt% Wt% Wt% Lubricant Lubricant Composition in U-tube Wt% Lubricant Lubricant Returned 20 Returned 6 Min Returned 10 Min Min 15% Cycloheptanone/1% Orange* in Zerol 27 35 42 150 15% 2-Nonanone/1% Orange* in Zerol 150 33 40 46 15% Diisobutyl ketone/l % Cinnamon* in 31 37 43 Zerol 150 20% DMPD in Zerol 150 32 38 44 20% Propylene glycol tert-butyl ether in 25 32 38 Zerol 150 15% cyanoheptane in Zerol 150 32 39 47 Comparative Data POE 22 19 29 3 Zerol 150 0 0 7

*"Orange"and"Cinnamon"are fragrances sold by Intercontinental Fragrance Results show addition of compatibilizers of the present invention to Zerol 150 provide lubricant return comparable to POE 22 polyol ester lubricant.

EXAMPLE 33 The apparatus and procedure of Example 29 was used to test refrigerant R401A with Suniso 3GS mineral oil lubricant, with and without compatibilizers versus neat Zerol 150. Results are shown below.

Example 33 Wt% WtoO Lubricant MT i.. T i-Wt% Lubricant ,., .... TTi Wt% Lubricant Lubricant-..--,- Lubricant Composition in U-tube Wt°So Lubricant Lubricant Returned 20 Returned 6 Min Returned 10 min Mit 10% Chlorooctane in 3GS 25 36 46 15% Chlorooctane in 3GS 35 43 50 Comparative Data Zerol 150 0 12 38 3GS005

Results show the addition of compatibilizers of the present invention to Suniso 3GS provide improved lubricant return versus Zerol 150.

EXAMPLE 34 The apparatus and procedure of Example 29 was used to test refrigerant R410A with Zerol 150 alkyl benzene lubricant, with and without compatibilizers versus POE 22 polyol ester lubricant. Results are shown below.

EXAMPLE 34 Ut% vtn/T - T 1--Wt% Lubricant T -t-t--nt Wt% Lubricant Lubricant-,.--.-,, Lubricant Composition in U-tube Wt% Lubricant Lubricant Returned 20 Returned 6 Min Returned 10 min Mit 15% PnB in Zerol 150 15 26 33 15% DPnB in Zerol 150 9 17 26 15% TPnB in Zerol 150 0 10 19 15% PnP in Zerol 150 15 22 32 5% PnB/5% DPnB/5% Isopar H in 12 19 29 Zerol 150 5% PnB/5% DPnB/5% Aromatic 150 in 15 23 33 Zerol 150 Comparative Data POE 22 0 11 22 Zerol 150 0 0 1 15% Propylene Glycol in Zerol 150 * * * 15% Dipropylene glycol in Zerol 150 * * * 15% Ucon 50-HB100** in Zerol 150 0 0 6

* Not soluble in Zerol 150 ** Polyalkylene glycol lubricant sold by Union Carbide with oxyethylene and oxypropylene groups with an average molecular weight of 520 Results show use of compatibilizers of the present invention in Zerol 150 provide comparable to improved lubricant return versus POE 22 polyol ester lubricant.

EXAMPLE 35-36 Tests were conducted to determine if refrigerant R41 OA could be used in an HCFC-22 Carrier heat pump (Model Tech 2000), using Zerol 150 alkylbenzene lubricant and compatibilizers of the present invention. The heat pump was outfitted with an R410A Copeland scroll compressor (ZP32K3E R- 410) equipped with a sight glass and level tube in the lubricant sump. The fan- coil unit was installed in the indoor room of an environmental chamber and the outdoor unit was installed in the outdoor room. The two units were connected by 1.59 cm (5/8-inch) outer diameter copper tubing in the suction line and by 1.27 cm (1/2-inch) outer diameter copper tubing in the liquid line. The system was charged with 3,180 grams of refrigerant and 1,110 grams of lubricant containing compatibilizer. Refrigerant R410A with polyol ester lubricant was used as a baseline for comparison. Tests were conducted at ASHRAE cooling and low temperature heating conditions. For cooling the indoor room was controlled at

26. 7°C (80°F) and 50% relative humidity, the outdoor room at 27. 8°C (82°F) and 40% relative humidity. For low temperature heating, the indoor room was controlled at 21. 1°C (70°F) and 57% relative humidity, the outdoor room at- 8. 3°C (17°F) and 60% relative humidity. Results from refrigerant side measurements are shown below.

EXAMPLE 35-Cooling Test Lubricant Composition Vol Capacity Lubricant kB. t. u. /hr EER Lost From (kW) Sump (cm) 15% PnB in Zerol 150 15% 2.91 (0.852) 11.29 20% PnB in Zerol 200TD 14% 2.90 (0.849) 11.30 20% DPnB in Zerol 150 20% 2.90 (0.849) 11.28 10% PnB/5% DPnB in Zerol 18% 2.93 (0.858) 11.61 150 10% PnB/5% DPnB in HAB22 18% 3.00 (0.878) 11.50 10% PnB/5% DPnB in 3GS 26% 2.92 (0.855) 11.08 18% PnB/10% DPnB in 4GS 23% 2.88 (0.843) 11.03 10% PnB/5% DPnB/15% z 26% 2.92 (0.855) 11.14 HAB22 in 3GS 5%PnB/5% DPnB/5% Isopar 18% 2.94 (0.861) 11.48 H in Zerol 150 3% PnB/8% DPnB/4% 23% 2.95 (0.864) 11.25 Aromatic 150 in Zerol 150 4% PnB/7% DPnB/4% DMM 20% 2.97 (0.870) 11.32 in Zerol 150 10% PnB/5% DPnB/1. 5% 20% 3.10 (0.908) 11.70 Pentane in Zerol 150 10% PnB/5% DPnB/15% PVE 22% 3.00 (0.878) 11.67 32 in Zerol 150 10% PnB/5% DPnB/15% PVE 20% 2.95 (0.864) 11.40 32 in 3GS 7% PnB/7% DPnB/7% TPnB 26% 2.92 (0.855) 11.18 in3GS 15% BnB in 3GS 33% 2.91 (0.852) 11. 17 20% PTB in 3GS 27% 2. 92 (0.855) 11.28 10% PnB/5% DPnB/2.5% 15% 2.96 (0.867) 11.41 BTPP in Zerol 150 Comparative Data POE 22 10% 2. 98 (0.873) 11.70 POE 32 12% 2.97 (0.870) 11.48 Zerol 150 30% 2.86 (0.838) 10.97 Suniso 3GS 40% 2.86 (0.838) 10.82 EXAMPLE 36-Low Temperature Heating Tests Lubricant Composition Sump Lubricant Capacity Level (cm) kB.t.u/hr (kW) EER 10% PnB/5% DPnB in 4.6 20.2 (5.92) 8.38 Zerol 150 3% PnB/8% DPnB/4% 4.4 20.4 (5.97) 8.45 Aromatic 150 in Zerol 150 10% PnB/5% DPnB in 4.9 20.4 (5.97) 8.42 HAB22 10% PnB/5% DPnB/2% 5.7 20.1 (5. 89) 8. 37 BTPP in Zerol 150 15% PVE32/10% 4.6 19.9 (5.83) 8.30 PnB/5% DPnB in 3GS 5% PnB/5% DPnB/5% 4.7 20.2 (5.92) 8.35 Isopar H in Zerol 150 Comparative Data POE22 5.5 20. 0 (5.86) 8. 35 Zerol 150 4. 3 19. 3 (5.65) 8. 00

Results show significant increases in lubricant return, energy efficiency and capacity when compatibilizers are added to Zerol 150, Suniso 3GS or 4GS and several cases with performance equivalent to or superior than polyol esters. There is also significant EER improvement during heating.

EXAMPLE 37 The apparatus and procedure of Example 32 was used to test R410A refrigerant with compatibilizers of the present invention. Results for cooling are in the table below.

EXAMPLE 37 Sump Capacity Lubricant Composition Lubricant kB. t. u./hr EER Level cm) (kW) 10° o PnB/5% DPnB in Zerol 5. 00 3.01 (0.882) 11.71 150 10% PnB/5% DPnB/1. 5% 4.95 3. 04 (0. 890) 11.98 Pentane in Zerol 150 Comparative Data POE22 5. 72 3.09 (0.905) 12. 04 1. 5% Pentane in Zerol 150 4. 40 2.93 (0. 858) 11.23

The data show that using only pentane provides inadequate lubricant return, capacity and energy efficiency. PnB/DPnB as compatibilizer provides increased performance and a combination PnB/DPnB/pentane as compatibilizer

provides the best overall performance, including comparable EER with polyol ester lubricant POE22.

EXAMPLE 38 The apparatus and procedure of Example 32 was used to test R410A refrigerant with compatibilizers of the present invention. In this test, however, the HCFC-22 evaporator was replaced with and R410A evaporator. Results for cooling are below.

EXAMPLE 38 Lubricant Composition Sump Capacity Lubrica kB. t. u. /hr EER nt Level (kW) (cm) 10% 2-heptanone/1% orange* in 5.33 3.17 (0.928) 11.87 Zerol 150 15% 2-nonanone/1% cinnamon* in 5.60 3.15 (0.923) 11.89 Zerol 150 20% DMPD in Zerol 150 5. 70 3.15 (0.923) 11.92 10% PnB/10% DMPD in Zerol 5.50 3.16 (0.925) 11.94 150 20% 1, 5-DMPD in Zerol 150 5.90 3.14 (0.920) 11.97 Comparative Data POE 22 6. 80 3.35 (0. 981) 12. 55 Zerol 150 4. 27 3.07 (0. 899) 11.30 *"Orange"and"Cinnamon"are fragrances sold by Intercontinental Fragrance The data shows a significant improvement in capacity, energy efficiency and lubricant return using compatibilizers versus neat Zerol 150, even though the system had an HCFC-22 condenser and an R410A evaporator.

EXAMPLE 39 Tests were conducted to determine if R41 OA refrigerant could be used in an R410A heat pump using Zerol 150 alkylbenzene lubricant and compatibilizers. The heat pump was outfitted a sight glass and level tube in the lubricant sump. The fan-coil unit was installed in the indoor room of an environmental chamber and the outdoor unit was installed in the outdoor room.

The two units were connected by 1.59 cm (5/8-inch) outer diameter copper tubing in the suction line and by 1.27 cm (1/2-inch) outer diameter copper tubing in the liquid line. The system was charged with 3,860 grams of refrigerant and 1270 ml

of lubricant containing compatibilizers of the present invention. Refrigerant R410A with POE 22 polyol ester lubricant was used as a baseline for comparison.

Tests were conducted at ASHRAE cooling conditions. For cooling the indoor room was controlled at 26. 7°C (80°F) and 50% relative humidity, the outdoor room at 27. 8°C (82°F) and 40% relative humidity. Results from refrigerant side measurements are shown below.

EXAMPLE 39-Coolin Test Lubricant Composition Vol Capacity Lubricant kB. t. u./hr EER Lost From (kW) Sum cm 10% PnB/5% DPnB in Zerol 16% 3.04 (0.890) 12. 59 150 10% PnB/5% DPnB/in Zerol 17% 3.05 (0. 893) 12. 67 150 with R410A +0. 5% pentane 10% PnB/5% DPnB in Zerol 23% 3*03 (0.887) 13.06 150 with R410A + 0. 5% 1,1, 1,3, 3-pentafluoropropane 10% PnB/5% DPnB in Zerol 19% 3.04 () 13.11 150 with R410A + 0. 5% 1,1- dichloro-1, 1, 1-trifluoroethane 12% DMM in Zerol 150 20% 3.04 (0. 890) 12. 88 11% Diisobutyl ketone/1% 21% 3.02 (0.884) 12.99 orange** in Zerol 150 11% 2-Nonanonell% 20% 3.03 (0.887) 13.02 cinnamon** in Zerol 150 20% 1-octyl-pyrrolidin-2-one 18% 3.07 (0.899) 13. 35 in Zerol 150 45% 1-octyl-pyrrolidin-2-one 13% 3.09 (0. 905) 13.50 in Zerol 150 20% N-methylcaprolactam in 21% 3.11 (0.911) 13.56 Zerol 150 Comparative Data POE 22 10% 3.09 (0.905) 13. 54 Zerol 150* 38% 2.96 (0.867) 12. 43

* Zerol 150 test was stopped before completion-compressor sump lubricant level became too low **"Orange"and"Cinnamon"are fragrances sold by Intercontinental Fragrance Results show improved lubricant return, capacity and efficiency when compatibilizers of the present invention are added to Zerol 150. Use of 1-octyl pyrrolidin-2-one amide compatibilizer shows performance equivalent to the POE 22 polyol ester lubricant baseline.

EXAMPLE 40

Tests were conducted to determine if HFC-134a refrigerant could be used in a domestic refrigerator (Whirlpool 21 cubic foot) using conventional lubricants Zerol 150 or Suniso 3GS and compatibilizers of the present invention.

The refrigerator was outfitted with pressure and temperature measuring devices as well as power measurement to the hermetic reciprocating compressor and two fans. The compressor was also fitted with a sight glass to monitor lubricant level during operation. The refrigerator was tested in a room controlled at 27. 8°C and 40% relative humidity. The refrigerator was turned on and allowed to cool until the refrigerated compartment reached 3. 3°C. The energy efficiency (COP) and capacity were then calculated using a thermodynamic model based on temperature, pressure and power inputs. In all tests, lubricant level was adequate indicating no lubricant return problems.

EXAMPLE 40 Lubricant Capacity % Change in COP % Change in Composition (Watts) Capacity vs POE COP vs POE 10% PnB/5% DPnB 145 +1. 4% 1.31 +8. 3% in Zerol 150 12% DMM in 3GS 143 1. 33 +9.9% 12% DMM in Zerol 145 +1.4% 1.34 +10. 7% 150 6% DMM in Zerol 148 +3.5% 1.30 +7.4% 100 20% OP in Zerol 100 145 +1. 4% 1.30 +7.4% 45% OP in Zerol 300 146 +2.1% 1.32 +9. 1% Comparative Data POE 22 143 1. 21 Zerol 150 * * * * Zerol 75 146 +2. 1% 1.25 +3.3% * Evaporator was flooded and test could not be completed.

Results show a significant improvement in energy efficiency when compatibilizers of the present invention are used with conventional lubricants.

Improvement is also shown when compared with using a low viscosity alkyl benzene lubricant (Zerol 75) alone. Capacities also showed improvement versus POE 22 polyol ester lubricant.

EXAMPLE 41 Compatibilizers of the present invention were mixed with Zerol 150 and placed in shallow dishes in a 50% constant humidity chamber. Periodic samples of the compositions were taken and analyzed by Karl Fischer titration for water. Results are shown in ppm water versus polyol ester, polyvinyl ether and polyalkylene glycol lubricants.

EXAMPLE 41

Samples 0 2 3.5 5. 5 21 26 45 50 69 74 Hours 15% DIP in Zerol 15 124 154 318 351 402 392 401 375 10% PnB 5% DPnB in 209 242 506 533 538 661 756 708 Eros 150 Comparative Data VE32 185 398 505 785 1784 1917 2511 2451 2791 2630 erol 150 43 47 36 41 37 33 30 29 39 34 Ucon488 1175 1517 3123 4158 12114 12721 16741 18592 20133 19997 POE 22 153 165 173 181 693 733 1022 1096 1199 1165 Results show compatibilizer/lubricant compositions of the present invention absorb less water than polyol ester and significantly less water than polyvinyl ether and polyalkylene glycol lubricants. Since compatibilizer/lubricant compositions of the present invention do absorb some water, they also have lower risk of having free (immisicible) water available than Zerol 150. Free water can freeze in expansion devices and cause compressor failure.

EXAMPLE 42 Compositions of the present invention were tested for thermal stability. Stainless steel, aluminum and copper coupons were placed in sealed glass tubes containing R410A refrigerant, Zerol 150 lubricant and compatibilizers of the present invention. In four cases, 1,000 ppm water was added. Tubes were held for 14 days at 175°C. Results are shown in the table below.

EXAMPLE 42 After 14 R410A/Zerol R410A/Zerol 150 R407C/Zerol R410A/Zerol Comparative days at 150 + 15%PnB +5% DMM/5% 100 + 20% 1- 150+100% Data: 175°C DPnB/5% 140 octylpyrrolidin-PnB/5% DPnB R410A/POE Naptha + 1000 2-one +1000 + 1000 ppm 22 + 1000 ppm ppm H20 ppm H20 H20 H20 Copper No observable No observable No observable No observable Corrosion and Appearance changes changes changes changes discoloration observed Aluminum No observable No observable No observable No observable No observable Appearance changes changes changes changes changes Steel No observable No observable No observable No observable No observable Appearance changes changes changes Acidity as <1 <1 <1 29 577 HCl in ppm

R410A 99. 9 99. 9 99. 9 99. 9 99.8 zona Results show compositions of the present invention are thermally stable even in the presence of 1,000 ppm water, indicating no acid formation.

Polyol ester lubricant in the presence of water caused corrosion of copper due to hydrolysis and acid formation.

EXAMPLE 43 Volume resistivity was measured by ASTM D-1169 method using a Balsbaugh liquid test cell connected to a Keithley model 617 electrometer. A Keithley model 247 high voltage power supply was used as the excitation source.

Capacitance used for calculating both resistivity and dielectric constant was measured with a GenRad model 1189 capacitance bridge. Results are shown below.

EXAMPLE 43 Composition Volume Resistivity Dielectric Constant (Ohmxcm) Zerol 150/PnB/DPnB 9. 12x10 2. 73 (85/10/5 wt%) Zerol 150/PnB/DPnB/Isopar 1. 73x10'3 2. 62 H (85/5/5/5 wt%) Comparative Data POE 22 5.50x 1011 3.54 Results show compositions of the present invention have improved electrical properties versus POE 22 polyol ester lubricant. They show an increase in volume resistivity and a decrease in dielectric constant that improves electrical insulating properties and protects compressor electrical motor winding materials.

EXAMPLE 44 Solubility and viscosity measurements were made for compositions of the present invention in Zerol 150 with R410A refrigerant. The data were used to determine the amount of refrigerant dissolved in lubricant under evaporator conditions at 10°C, 1 MPa and subsequent viscosity reduction. Data were compared with R410A/POE 22 and R410A/Zerol 150. The viscosity and percent refrigerant dissolved in lubricant at compression conditions was also determined, 80°C, 2.5 MPa. Results are shown below.

EXAMPLE 44

Composition % Refrigerant Viscosity % Refrigerant Viscosity Dissolved in (cPoise) at Dissolved in (cPoise) at Lubricant at Evaporator at Lubricant at Compressor at Evaporator 10°C Compression 80°C Conditions Conditions R410A/10% PnB + 18 8 11 2.5 5% DPnB in Zerol 150 Comparative Data R410A/POE22 45 3 17 3. 1 R410A/Zeroll50 10 38 7 3. 2 Results show a significant increase in refrigerant solubility and subsequent viscosity reduction in the evaporator by a compatibilizer of the present invention when added to a conventional alkyl benzene lubricant. This viscosity reduction can result in improved lubricant return to the compressor. Because less refrigerant is dissolved in the lubricant than POE 22 at compression conditions, viscosity remains high enough to effectively lubricate the compressor.

EXAMPLE 45 Dynamic viscosity measurements were made using a ViscoPro2000 viscometer of POE 22, Zerol 150 and Zerol 150 containing 10 wt% PnB and 5 wt% DPnB. Results are shown in Figure 10. Results show 10% PnB and 5% DPnB increase the viscosity index of Zerol 150. This gives the desirable result of lower viscosity at low temperature without lowering viscosity at high temperature, a profile similar to POE 22. This enhances lubricant return from the evaporator while maintaining good viscosity in the compressor.

EXAMPLE 46 A four ball wear test using ASTM D4172B was conducted using steel balls was conducted to assess the lubricating properties for compositions of the present invention. The test was run for 60 minutes using different combinations of compatibilizer in alkyl benzene lubricant and compared to lubricant without compatibilizer. Wear scar and average coefficient of friction were measured.

Results are shown below.

Wear Scar (mm) Average Coefficient of Friction 6% DMM in Zerol 100 0. 85 0. 108 20% 1-octyl pyrrolidin-0. 61 0.093 2-one in Zerol 100 35% l-octyl pyrrolidin-0. 64 0.091 2-one in Zerol 150 12% DMM/2% 0.52 0.113 Synergol in Zerol 150 Comparative Data Zerol 150 0. 88 0. 110 Results show lubrication properties are similar or improved when compatibilizers of the present invention are added to conventional lubricants, as evidenced by reduced size of wear scar and similar lower coefficient of friction. Addition of antiwear additives such as Synergol further improves lubrication properties.

EXAMPLE 47 Compressor durability tests were conducted with compositions of the present invention. A flooded start test was performed on scroll and rotary compressors. A flooded start test is a severe condition where the compressor sump is flooded with refrigerant on shutdown. During startup, presence of refrigerant can reduce lubricant viscosity resulting in inadequate compressor lubrication. This is particularly difficult with immiscible refrigerant/lubricant systems where two layers can form in the compressor sump with the refrigerant layer on the bottom, the point at which lubricant is normally drawn into the compressor bearings. The compressors were tested at-12. 2°C suction temperature and 37. 8°C discharge temperature. The compressors were cycled for three minutes on and fifteen mutes off for 1,000 cycles. After the tests the compressors were disassembled and inspected for wear. No significant wear was observed.

EXAMPLE 47 Compressor Type Refrigerant Lubricant Significant Wear Rotary R407C 10% PnB/5% DPnB None in Zerol 150 Scroll R407C 10% PnB/5% DPnB None in Zerol 150 Comparative Data Rot HCFC-22 MineralOil None Scroll HCFC-22 Mineral Oil None

EXAMPLE 48 Compatibilizers of the present invention were tested for compatibility with polyester motor materials used in certain hermetic compressors. Strips of polyester film were placed in a sealed tube with HFC-134a refrigerant and different lubricant/compatibilizer combinations. The tubes were held at 150°C for two weeks. The polyester strips were removed and bent ten times through an arc of 180° to evaluate for embrittlement. Strips in both the liquid and vapor phases were evaluated. Results are shown in the table below.

EXAMPLE 48 Lubricant tested # of Bends Before # of Bends Before with HFC-134a Breaking Liquid Breaking Vapor Phase Phase 10% PnB/5% DPnB 1 1 in Zerol 150 12% DMM in Zerol >10 >10 150 20% 1-octyl >10 >10 pyrrolidin-2-one in Zerol 150 Comparative Data Zerol 150 7 9 POE 22 10 1

The data show DMM (CH3O [CH2CH (CH3) O] 2CH3) with no free hydroxyl groups has significantly improved polyester motor material compatibility versus PnB (C4H90CH2CH (CH3) OH) and DPnB (C4H90 (CH2CH (CH3) O) 2H), both with terminal hydroxyl groups. The data also show alkyl pyrrolidones such as 1-octyl- 2-pyrrolidone are compatible with polyester motor materials and preferred for use in certain hermetic compressors.