AU670173B2 - Polyol ester lubricants for refrigerator compressors operating at high temperatures - Google Patents
Polyol ester lubricants for refrigerator compressors operating at high temperatures Download PDFInfo
- Publication number
- AU670173B2 AU670173B2 AU57645/94A AU5764594A AU670173B2 AU 670173 B2 AU670173 B2 AU 670173B2 AU 57645/94 A AU57645/94 A AU 57645/94A AU 5764594 A AU5764594 A AU 5764594A AU 670173 B2 AU670173 B2 AU 670173B2
- Authority
- AU
- Australia
- Prior art keywords
- acyl groups
- mixture
- carbon atoms
- contain
- consisting essentially
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/34—Esters of monocarboxylic acids
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
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- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
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- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/008—Lubricant compositions compatible with refrigerants
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- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/16—Naphthenic acids
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- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
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- C10M2211/06—Perfluorinated compounds
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/50—Medical uses
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Description
fii b. 1I~l-Yi /UU/U1 1 28s/91 Regulation 3.2(2)
AUSTRALIA
Patents Act 1990
ORIGINAL
COMPLETE SPECIFICATION STANDARD PATENT a b 0 0 0 0o 00.
Application Number: Lodged: 44l 4,' Invention Title: POLYOL ESTER LUBRICANTS FOR REFRIGERATOR COMPRESSORS OPERATING AT HIGH TEMPERATURES The following statement is a full description of this invention, including the best method of performing it known to us IL I L i _r .n
PATENT
Docket M 5303 EM POLYOL ESTER LUBRICANTS FOR REFRIGERATOR COMPRESSORS OPERATING AT HIGH TEMPERATURES BACKGROUND OF THE INVENTION Field of the Invention This invention relates to lubricant base stocks, which can also serve as complete lubricants in some cases; compounded lubricants, which include at least one additive for such purposes as improving high pressure resistance, corrosion inhibition, and the like along with the lubri- S 15 cant base stocks which contribute the primary lubricity to the compounded lubricants; refrigerant working fluids including lubricants according to the invention along with primary heat tre sfer fluids, and methods for using these 20 materials. The lubricants and lubricant base stocks are S 20 generally suitable for use with most or all halocarbon refrigerants and are particularly suitable for use with substantially chlorine-free, fluoro-group-containing organic refrigerating heat transfer fluids such as pentafluoroethane, 1,1-difluoroethane, 1,1,1-trifluroethane, and tetrafluoroethanes, most particularly 1,1,1,2-tetrafluoroethane. The lubricants and base stocks, in combination with these heat transfer fluids, are particularly suitable for lubricating compressors that operate at temperatures substantially higher than those at which humans can be comfortable; such compressors are generally used, for example, in vehicle air conditioning.
Statement of Related Art 1 r r 11LYL_-IL
P
Chlorine-free heat transfer fluids are desirable for use in refrigerant systems, because their escape into the atmosphere causes less damage to the environment than the currently most commonly used chlorofluorocarbon heat transfer fluids such as trichlorofluoromethane and dichlorodifluoromethane. The widespread commercial use of chlorinefree refrigerant heat transfer fluids has been hindered, however, by the lack of commercially adequate lubricants.
This is particularly true for one of the most desirable working fluids, 1,1,1,2-tetrafluoroethane, commonly known in the art as "Refrigerant 134a" or simply "R134a". Other fluoro-substituted ethanes are also desirable working fluids.
Esters of hindered polyols, which are defined for is this purpose as organic molecules containing a. least five carbon atoms, at least 2 -OH groups, and no hydrogen atoms on any carbon atom directly attached to a carbon atom bearing an -OH group, have already been recognized in the art as high quality lubricant basestocks for almost any type of refrigeration machinery employing a fluorocarbon refrigerant, particularly one free from chlorine. The following patents and published patent applications also teach many general classes and specific examples of polyol esters useful as refrigerant lubricants with chlorine-free fluoro group containing heat transfer fluids: US 4,851, 144; UK 2 216 541; US 5,021,179; US 5,096,606; WO 90/12849 (Lubrizol); EP 0 406 479 (Kyodo Oil); EP 0 430 657 (Asahi Denka KK); EP 0 435 253 (Nippon Oil); EP 0 445 610 and 0 445 611 (Hoechst AG); EP 0449 406; EP 0 458 584 (Unichema Chemie BV); and EP 0 485 979 (Hitachi).
DESCRIPTION OF THE INVENTION Except in the claims and the operating examples, or where otherwise expressly indicated, all numerical quantities in this description indicating amounts of material or conditions of reaction and/or use are to be understood as modified by the term "about" in defining the broadest scope of the invention. Practice of the invention within 2 the boundaries corresponding to the exact quantities stated is usually preferable, however.
More specifically, esters according to this invention should have a viscosity of not more than 157, or with increasing preference in the order given, not more than 145, 134, 123, 115, or 110, centistokes at 400 C. Independently, esters according to this invention should have a viscosity of at least 45, or with increasing preference in the order given, at least 51, 64, 76, 85, or 90, centistokes at 400 C.
It has now bren found that selected polyol esters provide high quality lubrication for this kind of service.
Specifically effective are esters or mixtures of esters made by reacting a mixture of alcohol molecules selected from the group consisting of 2,2-dimethylol-l-butanol (also known as "trimethylolpropane" and often abbreviated hereinafter as di-trimethylolpropane (often abbreviated hereinafter as "DTMP"), a molecule with four hydroxyl groups and one ether linkage, formally derived from two molecules of TMP by removing one hydroxyl group from one of the TMP molecules and one hydrogen atom from a hydroxyl group of the other TMP molecule to form water and join the two remainders of the original TMP molecules with an ether bond; 2,2-dimethylol-l,3-propanediol (also known as "pentaerythritol" and often abbreviated hereinafter as and di-pentaerythritol (often abbreviated hereinafter as a molecule with six hydroxyl groups and one ether bond, formally derived from two PE molecules by the same elimination of the elements of water as described above for DTMP, tri-pentaerythritol (often abbreviated S.hereinafter as a molecule with eight hydroxyl A, groups and two ether bonds, formally derived from three PE molecules by an analogous elimination of the elements of two molecules of water as described above (for elimination of a single water molecule) for DTMP and DPE; and tritrimethylolpropane (hereinafter often abbreviated as "TTMP"), a molecule with five hydroxyl groups and two 3 r II 1. Y-"UrL LY_- -CI_ ether bonds, formally derived from three TMP molecules by the same elimination of the elements of two molecules of water as described above for TPE with (ii) a mixture of acid molecules selected from the group consisting of all the straight and branched chain monobasic and dibasic carboxylic acids with from four to twelve carbon atoms i each, with the alcohol moieties and acyl groups in the mixture of esters selected subject to the constraints that a total of at least 5 or, with increasing preference in the order given, at least 7, 10, 13, 16, 19, 23, or 26 of the acyl groups in the mixture are 2-methylbutanoyl or 3-methylbutanoyl groups, which are jointly abbreviated hereinafter as "acyl groups from [or of] i-C acid"; the ratio of the of acyl groups in the mixture that contain 8 or more carbon atoms and are unbranched to the of acyl groups in the mixture that are both branched and contain not more than six, preferably j not more than five, carbon atoms is not greater than 1.56, more preferably not greater than 1.21, or still more prefi 20 erably not greater than 1.00; the of acyl groups in 4 the ester mixture that contain at least nine carbon atoms, whether branched or not, is not greater than 81, or in- Screasingly more preferably, not greater than 67 or 49; and not more than 2, more preferably not more than 1, or still more preferably not more than 0.4, of the acyl groups in the ester mixture are from acid molecules with more than two carboxyl groups each; and either a .1 total of at least 20, or, with increasing preference in the order given, at least 29, 35, or 41 of the acyl 30 groups in the mixture are from one of the trimethylhexanoic acids, most preferably from 3,5,5-trimethylhexanoic acid; and not more than 7.5, or, with increasing preference in the order given, not more than 6.0, 4.5, 3.0, 1.7, or 0.4 of the acyl groups in the acid mixture are from dibasic acids; or at least 5.5, or with increasing preference in the order given, at least 6.6, 10.0, 10.8, or 11.5, but not more than 13.5 4 li 1 Pi preferably not more than 13.0 or still more preferably not more than 12.0 of the acyl groups in the ester mixture are dibasic; and a total of at least 82, or with increasing preference in the order given, at least 85, 89, 93, 96, or 99 of the monobasic acyl groups in the acid mixture have either five or six, or more preferably exactly five, carbon atoms each. In all these percentages, acyl groups are counted as a single group, irrespective of the number of valences they have. For example, each molecule of adipic acid yields a single, dibasic, acyl group when completely esterified.
(Of course, for all the types of esters described herein as part of the invention, it is possible to obtain the same esters or mixture of esters by reacting acid derivatives such as acid anhydrides, acyl chlorides, and esters of the acids with lower molecular weight alcohols than those desired in the ester products according to this invention, instead of reacting the acids themselves. The I acids are generally preferred for economy and are normally specified herein, but it is to be understood that the esters defined herein by reaction with acids can be equally well obtained by reaction of alcohols with the corresponding acid derivatives, or even by other reactions. The only critical feature is the mixture of acyl groups and alcohol moieties in the final mixture of esters formed.) Preferably, with increasing preference in the order given, at least 60, 75, 85, 90, 95, or 98 of the hydroxyl groups in the mixture of alcohols reacted to make esters according to this invention are moieties of PE mole- S 30 cules. Independently, in the mixtures reacted to make the i esters according to this invention, with increasing pref- S"erence in the order given, at least 60, 75, 85, 90, 95, or 98 of the monobasic acid molecules in the acid mixture consist of molecules having no more than ten carbon atoms each and, with increasing preference in the order given, at least 60, 75, 85, 90, 95, or 98 of the dibasic acid molecules in the acid mixture consist of molecules having I Vt no more than ten carbon atoms each, or more preferably from five to seven carbon atoms each. Most preferably, with increasing preference in the order given, at least 75, 85, 90, 95, or 98 of the monobasic acid molecules in the acid mixture consist of molecules having either five or nine carbon atoms each.
These preferences for the acyl groups and alcohol moieties in esters according to this invention are based on empirically determined generalizations. In order to achieve the desired range of viscosity, corresponding approximately to ISO grades 50 115, it is advantageous to have a substantial fraction of alcohols with at least four hydroxyl groups. Among the commercially available hindered alcohols that satisfy this criterion, PE is less expensive than DTMP and is free from the ether linkage in DTMP, which increases the hygroscopicity of the esters formed and thereby may promote undesirable corrosion of the metal surfaces lubricated. Alcohols with more than four hydroxyl groups produce esters with higher than optimum viscosities, but some such esters can be tolerated, and mixtures including them may be cheaper. Commercial grade PE often contains a substantial amount of DPE, and costs at least a little less than more purified PE. When cost factors are not severely constraining, removing most or all of the DPE from a predominantly PE mixture of alcohols used to make the esters is preferable, in order to minimize the chance of insolubility of part of the ester mixture at low temperatures.
In order to obtain esters with adequate viscosity, a considerable fraction of the acid molecules reacted need to have eight or more carbon atoms or be dibasic. In general, using at least some dibasic acid is preferred for ester mixtures in this viscosity range, but the amount of dibasic acid must be carefully controlled to avoid the 35 undesired possibility of forming a substantial fraction of very high molecular weight polymeric or oligomeric esters, which would be inadequately soluble, 6 When substantially only monobasic acids are used to make the esters, in order to obtain adequate viscosity in the mixture, a substantial fraction of the acid molecules must have at least eight carbon atoms. With acids of such length, solubility in the fluorocarbon refrigerant fluids is less than for esters with shorter acids, and this reduced solubility is particularly marked for straight chain acids, so that a substantial fraction of the longer acids normally needs to be branched; alternatively, it has been found that these longer straight chain acids can be "balanced" for solubility with an equal or not too much less than equal fraction of branched acids with five or six carbon atoms. When the number of carbon atoms per molecule is nine or more, not even branching is sufficient to produce adequate solubility by itself, so that an upper limit on the fraction of such acids is independently required. In general, a minimum amount of the particularly advantageous i-C 5 acid is specified to aid in solubilizing the parts of the esters in the mixture that contain dibasic acids or those with eight or more carbon atoms.
For both performance and economic reasons, it has been found that five and nine carbon monobasic acids are the most preferred constituents, and they are very effective in balancing each other to achieve a mix of viscosity and solubility characteristics that is better suited than others to most applications. Trimethylhexanoic acids, with their three methyl branches, produce the most soluble o esters among the readily available nine carbon acids. (In general, methyl branches are the most effective in promot- 1al. 30 ing solubility without increasing viscosity excessively, because of the larger number of carbon atoms in other branching groups.) Branches on the carbon alpha to the carboxyl increase the difficulty of esterification and do e. S not appear to be any more effective in increasing solubility than more remotely located branches. The most economical commercially available mixture of branched nine carbon acids, which contains from 88 95 mole of 3,5,5trimethylhexanoic acid with all but at most 1 mole of the remainder being other branched C 9 monobasic acids, appears at least as effective as any other and is therefore preferred for economic reasons as the source of C 9 monobasic acids.
It is to be understood that only the desired alcohols and acids are explicitly specified, but some amount of the sort of impurities normally present in commercial or industrial grade products can be tolerated in most cases.
For example, commercial pentaerythritol normally contains only about 85 90 mole of pure pentaerythritol, along with 10 15 mole of di-pentaerythritol, and commercial pentaerythritol is satisfactory for use in making lubricant esters according to this invention in many cases. In general, however, it is preferred, with increasing preference in the order given, that not more than 25, 21, 17, 12, 8, 5, 3, 2, i, 0.5, or 0.2 of either the hydroxyl groups in the alcohol mixtures specified herein or of the carboxyl groups in the acid mixtures specified herein should be part of any molecules other than those explicitly specified for each type of lubricant base stock. Percentages of specific chemical molecules or moieties specified herein, such as the percentages of carboxyl and hydroxyl groups stated in the preceding sentence, are to be understood as number percentages, which will be mathematically identical to percentages by chemical equivalents, with Avogadro's number of each specified chemical moiety regarded as a single chemical equivalent.
The above descriptions for each of the acid and alcohol mixtures reacted to produce lubricant esters according to this invention refers only to the mixture of acids or alcohols that actually reacts to form esters and does not necessarily imply that the mixtures of acids or alcohols contacted with each other for the purpose of reaction will have the same composition as the mixture that actually reacts. In fact, it has been found that reaction between the alcohol(s) and the acid(s) used proceeds more 8 k i I 1 effectively if the quantity of acid charged to the reaction mixture initially is enough to provide an excess of 25 of equivalents of acid over the equivalents of alcohol reacted with the acid. (An equivalent of acid is defined for the purposes of this specification as the amount containing one gram equivalent weight of carboxyl groups, while an equivalent of alcohol is the amount containing one gram equivalent weight of hydroxyl groups.) The composition of the mixture of acids that actually reacted can be determined by analysis of the product ester mixture for its acyl group content.
In making most or all of the esters and mixtures of esters preferred according to this invention, the acid(s) reacted will be lower boiling than the alcohol(s) reacted and the product ester(s). When this condition obtains, it is preferred to remove the bulk of any excess acid remaining at the end of the esterification reaction by distillation, most preferably at a low pressure such as I torr.
2o After such vacuum distillation, the product is often ready for use as a lubricant or lubricant base stock according to this invention. If further refinement of the product is desired, the content of free acid in the product after the first vacuum distillation may be further reduced by treatment with epoxy esters as taught in U. S.
Patent 3,485,754 or by neutralization with any suitable K alkaline material such as lime, alkali metal hydroxide, or i 4 t alkali metal carbonates. If treatment with epoxy esters is used, excess epoxy ester may be removed by a second distillation under very low pressure, while the products of reaction between the epoxy ester and residual acid may be left behind in the product without harm. If neutralization with alkali is used as the refinement method, subsequent washing with water, to remove any unreacted excess alkali and the small amount of soap formed from the excess fatty acid neutralized by the alkali, is strongly preferred before using the product as a lubricant and/or base 9 stock according to this invention.
Under some conditions of use, the ester(s) as described herein will function satisfactorily as complete lubricants. It is generally preferable, however, for a complete lubricant to contain other materials generally denoted in the art as additives, such as oxidation resistance and thermal stability improvers, corrosion inhibitors, metal deactivators, lubricity additives, viscosity index improvers, pour and/or floc point depressants, detergents, dispersants, antifoaming agents, anti-wear agents, and extreme pressure resistant additives. Many additives are multifunctional. For example, certain additives may impart both anti-wear and extreme pressure resistance properties, or function both as a metal deactivator and a corrosion inhibitor. Cumulatively, all a additives preferably do not exceed 8 by weight, or more preferably do not exceed 5 by weight, of the total compounded lubricant formulation.
An effective amount of the foregoing additive types is generally in the range from 0.01 to 5 for the antioxidant component, 0.01 to 5 for the corrosion inhibitor component, from 0.001 to 0.5 for the metal deactivator component, from 0.5 to 5 for the lubricity additives, from 0.01 to 2 for each of the viscosity index improvers and pour and/or floc point depressants, from 0.1 to 5 for each of the detergents and dispersants, from 0.001 to 0.2 for anti-foam agents, and from 0.1 2 for each of the anti-wear and extreme pressure resistance components.
All these percentages are by weight and are based on the I 30 total lubricant composition. It is to be understood that i i more or less than the stated amounts of additives may be L more suitable to particular circumstances, and that a single molecular type or a mixture of types may be used for each type of additive component. Also, the examples listed below are intended to be merely illustrative and not limiting, except as described in the appended claims.
Examples of suitable oxidation resistance and thermal h6 L I, I 11 A -11h -L stability improvers are diphenyl-, dinaphthyl-, and phenylnaphthyl-amines, in which the phenyl and naphthyl groups can be substituted, N,N'-diphenyl phenylenediamine, p-octyldiphenylamine, p,p-dioctyldiphenylamine, N-phenyll-naphthyl amine, N-phenyl-2-naphthyl amine, N-(p-dodecyl)phenyl-2-naphthyl amine, di-1-naphthylamine, and di-2naphthylamine; phenothazines such as N-alkylphenothiazines; imino(bisbenzyl); and hindered phenols such as 6- (t-butyl) phenol, 2,6-di-(t-butyl) phenol, 4-methyl-2,6di-(t-butyl) phenol, 4,4'-methylenebis(-2,6-di-{t-butyl} phenol), and the like.
Examples of suitable cuprous metal deactivators are imidazole, benzamidazole, 2-mercaptobenzthiazole, 2,5-6±mercaptothiadiazole, salicylidine-propylenediamine, pyrazole, benzotriazole, tolutriazole, 2-methylbenzamidazole, pyrazole, and methylene bis-benzotriazole.
Benzotriazole derivatives are preferred. Other examples of more general metal deactiv itors and/or corrosion inhibitors include organic acids and their esters, metal salts, and anhydrides, N-oleyl-sarcosine, sorbitan monooleate, lead naphthenate, dodecenyl-succinic acid and its partial esters and amides, and 4-nonylphenoxy acetic acid; primary, secondary, and tertiary aliphatic and cycloaliphatic amines and amine salts of organic and inorganic acids, oil-soluble alkylammonium carboxylates; heterocyclic nitrogen containing compounds, thiadiazoles, substituted imidazolines, and oxazolines; quinolines, quinones, and anthraquinones; propyl gallate; barium dinonyl naphthalene sulfonate; ester and amide derivatives of alkenyl succinic anhydrides or acids, dithiocarbamates, dithiophosphates; amine salts of alkyl acid phosphates and Li" 1 their derivatives.
Examples of suitable lubricity additives include long chain derivatives of fatty acids and natural oils, such as
,I
esters, amines, amides, imidazolines, and borates.
Examples of suitable viscosity index improvers include polymethacrylates, copolymers of vinyl pyrrolidone 11 1 'Uand methacrylates, polybutenes, and styrene-acrylate copolymers.
Examples of suitable pour point and/or floc point depressants include polymethacrylates such as methacrylateethylene-vinyl acetate terpolymers; alkylated naphthalene derivatives; and products of Friedel-Crafts catalyzed condensation of urea with naphthalene or phenols.
Examples of suitable detergents and/or dispersants include polybutenylsuccinic acid amides; polybutenyl phosphonic acid derivatives; long chain alkyl substituted aromatic sulfonic acids and their salts; and metal salts of alkyl sulfides, of alkyl phenols, and of condensation products of alkyl phenols and aldehydes.
Examples of suitable anti-foam agents include silicone polymers and some acrylates.
Examples of suitable anti-wear and extreme pressure resistance agents include sulfurized fatty acids and fatty acid esters, such as sulfurized octyl tallate; sulfurized terpenes; sulfurized olefins; organopolysulfides; organo phosphorus derivatives including amine phosphates, alkyl acid phosphates, dialkyl phosphates, aminedithiophosphates, trialkyl and triaryl phosphorothionates, trialkyl and triaryl phosphines, and dialkylphosphites, amine salts of phosphoric acid monohexyl ester, amine salts of dinonylnaphthalena sulfonate, triphenyl phosphate, trinaphthyl phosphate, diphenyl cresyl and dicresyl phenyl phosphates, naphthyl diphenyl phosphate, triphenylphosphorothionate; dithiocarbamates, such as an antimony dialkyl dithiocarbamate; chlorinated and/or fluorinated hydrocarbons, and xanthates.
Under some conditions of operation, it is believed that the presence in lubricants of the types of polyether polyols that have been prominent constituents of most prior art lubricant base stocks taught as useful with fluoro- 35 carbon refrigerant working fluids are less than optimally stable and/or inadequately compatible with some of the most useful lubricant additives. Thus, in one embodiment 12
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I
j i j i i j/ of this invention, it is preferred that the lubricant base stocks and lubricants be substantially free of such polyether polyols. By "substantially free", it is meant that the compositions contain no more than about 10 by weight, preferably no more than about 2.6 by weight, and more preferably no more than about 1.2 by weight of the materials noted.
One major embodiment of the present invention is a refrigerant working fluid comprising both a suitable heat transfer fluid such as a fluorocarbon and a lubricant according to this invention. Preferably, the refrigerant working fluid and the lubricant should have chemical characteristics and be present in such a proportion to each other that the working fluid remains homogeneous, i.e., 15 free from visually detectable phase separations or turbidity, over the entire range of working temperatures to which the working fluid is exposed during operation of a refrigeration system in which the working fluid is used.
This working range may vary from -600 C to as much as +1750 C. It is often adequate if the working fluid remains single phase up to +300 C, although it is increasingly more preferable if the single phase behavior is maintained up to 40, 56, 71, 88, or 100 0 C. Similarly, it is often adequate if the working fluid compositions 25 remains a single phase when chilled to 00 C, although it is increasingly more preferable if the single phase behavior persists to -10, -20, -30, -40, or -55 0 C. Single phase mixtures with chlorine free hydrofluorocarbon refrigerant working fluids are usually obtained with the suitable and preferred types of esters described above.
Inasmuch as it is often difficult to predict exactly how much lubricant will be mixed with the heat transfer fluid to form a working fluid, it is most preferable if the lubricant composition forms a single phase in all proportions with the heat transfer fluid over the temperature ranges noted above. This however, is a very stringent requiremnent, and it is often sufficient if there is O0 00 0 oo O 0 0~ Fo 0t 0000 00r 0 00 S 4 C L 1 LL-I ~L single phase behavior over the entire temperature range for a working fluid mixture containing up to 1 by weight of lubricant according to this invention. Single phase behavior over a temperature range for mixtures containing up to 2, 4, 10, and 15 by weight of lubricant is successively more preferable.
In some cases, single phase behavior is not required.
The term "miscible" is used in the refrigeration lubrication art and hereinafter, except when part of the phrase "miscible in all proportions", when two phases are formed but are readily capable of being mixed into a uniform dispersion that remains stable as long as it is at least moderately agitated mechanically. Some refrigeration (and other) compressors are designed to operate satisfactorily with such miscible mixtures of refrigerant working fluid and lubricant. In contrast, mixtures that lead to coagui lation or significant thickening and form two or more ii phases are unacceptable commercially and are designated herein as "immiscible". Any such mixture described below is a comparative example and not an embodiment of the present invention.
Another major embodiment of the invention is the use of a lubricant according to the invention, either as total lubricant or lubricant base stock, in a process of operating refrigerating machinery in such a manner that the lubricant is in contact with the refrigerant working fluid.
The practice of the invention may be further understool and appreciated by consideration of the following examples and comparative examples.
General Ester Synthesis Procedure S* The alcohol(s) and acid(s) to be reacted, together with a suitable catalyst such as dibutyltin diacetate, tin oxalate, phosphoric acid, and/or tetrabutyl titanate, were charged into a round bottomed flask equipped with a stirrer, thermometer, nitrogen sparging means, condenser, and a recycle trap. Acid(s) were charged in about a 15 molar excess over the alcohol(s). The amount of catalyst was from 0.02 to 0.1% by weight of the weight of the total acid(s) and alcohol(s) reacted.
The reaction mixture was heated to a temperature between about 220 and 2300 C, and water from the resulting reaction was collected in the trap while refluxing acids were returned to the reaction mixture. Partial vacuum was maintained above the reaction mixture as necessary to achieve a reflux rate of between 8 and 12 cf the original reaction mixture volume per hour.
The reaction mixture was sampled occasionally for determination of hydroxyl number, and after the hydroxyl number had fallen below 5.0 mg of KOH per gram of mixture, the majority of the excess acid was removed by distillation after applying the highest vacuum obtainable with the apparatus used, corresponding to a residual pressure of about 0.05 torr, while maintaining the reaction temperature. The reaction mixture was then cooled, and any residual acidity was removed, if desired, by treatment with lime, sodium hydroxide, or epoxy esters. The resulting lubricant or lubricant base stock was dried and filtered before phase compatibility testing.
General Procedure for Phase Compatibility Testing One milliliter of the lubricant to be tested is placed into a thermal shock resistant, volumetrically graduated glass test tube 17 millimeters in diameter and 145 mm long. The test tube is then stoppe-ed and placed into a cooling bath regulated to -29 0.20 C. After the tube and contents have equilibrated in the cooling bath for 5 minutes sufficient refrigerant working fluid is added to give a total volume of 10 ml.
At least 15 min after the working fluid has been added, during which time the tube and contents have been equilibrating in the cooling bath and the contents may have been agitated if desired, the tube contents are visu- 4 35 ally examined for evidence of phase separation. If there is any such phase separation, the tube is shaken to determine whether the combination can be rated as miscible or is totally unacceptable.
If there is no evidence of phase separation at -290 C, the temperature of the cooling bath is usually lowered at a rate of 0.30 per min until phase separation is observed. The temperature of first observation of phase separation, if within the range of the cooling equipment used, is then noted as the insolubility onset temperature.
Composition of Specific Example A suitable ester mixture as described above was prepared by reacting a mixture of alcohol molecules in which 99,4 were PE molecules, with most of the remainder being DPE molecules, with a mixture of acid molecules that included 57.1 of pentanoic n-valeric) acid, 30.7 of 2-methylbutanoic acid, and 11.7 of adipic acid, with the is remainder predominantly 3-methylbutanoic acid. This ester mixture had an ISO grade of 100.
16 (1 1 i _i -3 L
Claims (16)
1. A composition of matter suitable for serving as a lub- ricant or lubricant base stock, said composition being a liquid with a viscosity between ahewt 45. and abat 157 centistokes at 400 C and consisting essentially of a mix- ture of polyol ester molecules in which at least about 92 of the alcohol moieties are selected from the group con- sisting of the alcohol moieties derived from TMP, DTMP, PE, DPE, TPE, and TTMP and at least about 92 of the acyl groups are selected from the group consisting of the acyl groups of all the straight and branched chain monobasic and dibasic carboxylic acids with from four to twelve carbon atoms each, said alcohol moieties and acyl groups being further selected subject to the constraints that (a) a total of at least about 5 of the acyl groups in the mixture are acyl groups of i-C 5 acid; the ratio of the of acyl groups in the mixture that contain 8 or more carbon atoms and are unbranched to the of acyl groups in the mixture that are both branched and contain not more than six carbon atoms is not greater than about 1.56; (c) the of acyl groups in the mixture that contain at least nine carbon atoms, whether branched or not, is not greater than about 81; and not more than about 2 of the acyl groups in the ester mixture are part of acid molecules with more than two carboxyl groups each; and either a total of at least about 20 of the acid molecules' in the mixture are one of the trimethylhexanoic acids; at least about 90 of the alcohol moieties in the esters are those of PE; and not more than about 7.5 of the acyl groups in the ester mixture are dibasic; or at least about 5.5 but not more than 13.5 of the acyl groups in the ester mixture are dibasic; and a total of at least about 82 of the monobasic acyl groups in the acid mixture have either five or six carbon atoms each. i f '417 l ^ro^ L L- 1_IC -L _L -C f C K
2. A composition according to claim 1, with a viscosity between at-et 51 and a~e4ht 145 centistokes at 400 C and consisting essentially of a mixture of polyol ester mole cules in which the alcohol moieties and acyl groups are selected subject to the constraints that a total of at least about 10 of the acyl groups in the mixture are acyl groups of i-C 5 acid; the ratio of the of acyl groups in the mixture that contain 8 or more carbon atoms and are unbranched to the of acyl groups in the mixture that are both branched and contain not more than six carbon atoms is not greater than about 1.56; the of acyl groups in the mixture that contain at least nine car- bon atoms, whether branched or not, is not greater than about 67; and either a total of at least about 29 of the acyl groups in the mixture are from one of the trimethylhexanoic acids and not more than about 6.0 of the acyl groups in the acid mixture are dibasic; or at least about 6.6 but not more than about 13.0 of the acyl groups in the ester mixture are dibasic and a total of at least about 85 of the monobasic acyl groups in the ester mixture have either five or six carbon atoms each. 18 I L~ L11 i i ~I
3. A composition according to claim 2 with a viscosity between a*ee 64 and atet 134 centistokes at 400 C and consisting essentially of a mixture of polyol ester mole- cules in which at least about 95 of the alcohol moieties are selected from the group consisting of the alcohol moi- eties derived from TMP, DTMP, TTMP, PE, DPE, and TPE and at least about 95 of the acyl groups are selected from the group consisting of the acyl groups of all the straight and branched chain monobasic and dibasic carbox- ylic acids with from four to twelve carbon atoms each, said alcohol moieties and acyl groups being further se- lected subject to the constraints that a total of at least about 13 of the acyl groups in the mixture are acyl groups of i-C s acid; the ratio of the of acyl groups in the mixture that contain 8 or more carbon atoms and are unbranched to the of acyl groups in the mixture that are both branched and contain not more than six car- bon atoms is not greater than about 1.21; the of acyl groups in the mixture that contain at least nine car- 20 bon atoms, whether branched or not, is not greater than about 67; and not more than 1 of the acyl groups in the esters contain more than two carboxyl groups each; and either a total of at least about 35 of the acid molecules in the mixture are one of the trimethylhexanoic acids and not more than about 3.0 of the acyl groups in the ester mixture are dibasic; or at least about of the acyl groups in the ester mixture are dibasic; and a total of at least about 93 of the monobasic acyl groups in the acid mixture have five carbon atoms each. 0 00 o o oao 0o4o 00 oa o 0 a I^ q 0B L L 1.1 r L u it I -11
4. A composition according to claim 3 with a viscosity between -eeet 85 and 'be 123 centistokes at 40° C and consisting essentially of a mixture of polyol ester mole- cules in which the alcohol moieties and acyl groups are selected subject to the constraints that a total of at least about 16 of the acyl groups in the mixture are acyl groups of i-C 5 acid; the ratio of the of acyl groups in the mixture that contain 8 or more carbon atoms and are unbranched to the of acyl groups in the mixture that are both branched and contain not more than six car- bon atoms is not greater than 1.00; the of acyl groups in the mixture that contain at least nine carbon atoms, whether branched or not, is not greater than about 49; and not more than 0.4 of the acyl groups in the ester mixture contain more than two carboxyl groups each; and either a total of at least about 35 of the acyl groups in the mixture are one of the trimethylhexa- noic acids and at least about 29 of the acyl groups in the mixture are 3,5,5-trimethylhexanoyl groups; at least about 95 of the alcohol moieties in the esters are those of PE; and not more than about 1.7 of the acyl groups in the ester mixture are dibasic; or at least about of the acyl groups in the ester mixture are dibasic and contain from five to seven carbon atoms each and a total of at least about 96 of the monobasic acyl groups in the acid mixture have five carbon atoms each. 9* 0 Bit, 6') Csri VT L ,3 L L- ~A I -LIL I -U -C 4 4 A composition according to claim 4 with a viscosity between a t 85 and Asett 115 centistokes at 40° C and consisting essentially of a mixture of polyol ester mole- cules in which at least about 95 of the acyl groups are selected from the group consisting of the acyl groups of all the straight and branched chain monobasic and dibasic carboxylic acids with from four to twelve carbon atoms each and the alcohol moieties and acyl groups are selected subject to the constraints that a total of at least 19 of the acyl groups in the ester mixture are acyl groups of i-Cg acid; the ratio of the of acyl groups in the mixture that contain 8 or more carbon atoms and are un- branched to the of acyl groups in the mixture that are both branched and contain not more than five carbon atoms is not greater than about 1.00; the of acyl groups in the mixture that contain at least nine carbon atoms, whether branched or not, is not greater than about 49; and at least about 95 of the alcohol moieties in the I" esters are those of PE, and either a total of at least about 41 of the acyl groups in the ester mixture are acyl groups of one of the trimethylhexanoic acids and at least about 29 of the acyl groups in the mixture are 3,5,5-trimethylhexanoyl groups or at least 10.0 of the acyl groups in the ester mixture are dibasic.
6. A compounded lubricant consisting essentially of at least about 95 by weight of a composition according to claim 5 and a balance of one or more additives selected from the group consisting of oxida ion resistance and thermal stability improvers, corrosion inhibitors, metal deactivators, lubricity additives, viscosity index im- Sprovers, pour and floc point depressants, detergents, dis- persants, antifoaming agents, anti-wear agents, and ex- treme pressure resistant additives. 21 21 CP.^ I'. i .Ir _1 U _,1 P i i ii ii I V
7. A compounded lubricant consisting essentially of at least about 92 by weight of a composition according to claim 3 and a balance of one or more additives selected from the group consisting of oxidation resistance and thermal stability improvers, corrosion inhibitors, metal deactivators, lubricity additives, viscosity index im- provers, pour and floc point depressants, detergents, dis- persants, antifoaming agents, anti-wear agents, and ex- treme pressure resistant additives.
8. A compounded lubricant consisting essentially of at least about 92 by weight of a composition according to claim 2 and a balance of one or more additives selected from the group consisting of oxidation resistance and thermal stability improvers, corrosion inhibitors, metal deactivators, lubricity additives, viscosity index im- provers, pour and floc point depressants, detergents, dis- persants, antifoaming agents, anti-wear agents, and ex- treme pressure resistant additives.
9. A compounded lubricant consisting essentially of at least about 92 by weight of a composition according to .slaim 1 and a balance of one or more additives selected from the group consisting of oxidation resistance and thermal stability improvers, corrosion inhibitors, metal deactivators, lubricity additives, viscosity index im- provers, pour and floc point depressants, detergents, dis- persants, antifoaming agents, anti-wear agents, and ex- treme pressure resistant additives. A refrigerant working fluid consisting essentially of wtm t 5 b*y- t .i a primary heat transfer fluid 30 selected from the group consisting of pentafluoroethane, 1, -difluoroethane, 1,1,1-trifluroethane, tetrafluoroeth- anes, and mixtures thereof and a balance of a lubricant according to claim 9. Ii )i v. S S .L l r~ 23
11. A refrigerant working fluid consisting essentially of a primary heat transfer fluid selected from the group consisting of pentafluoroethane, 1,1- difluoroethane, 1,1,1-trifluroethane, tetrafluoroethanes, and mixtures thereof and a balance oir lubricant according to claim 8.
12. A refrigerant working fluid consisting essentially of a primary heat transfer fluid selected from the group consisting of pentafluoroethane, 1,1- difluoroethane, 1,1,1-trifluroethane, tetrafluoroethanes, and mixtures thereof and a balance of a lubricant according to claim 7.
13. A refrigerant working fluid consisting essentially of 1,1,1,2- .tetrafluroethane and a balance of a lubricant according to claim 6.
14. A refrigerant working fluid consisting essentially of a primary heat transfer fluid selected from the group consisting of pentafluoroethane, 1,1- t difluctoethane, 1,1,1-trifluroethane, tetrafluoroethanes, and mixtures thereof and a balance of a composition according to claim A refrigerant working fluid consisting essentially of a primary heat transfer fluid selected from the group consisting of pentafluoroethane, 1,1- difluoroethane, 1,1,1-trifluroethane, tetrafluoroethanes, and mixtures thereof and a balance of a composition according to claim 4.
16. A refrigerant working fluid consisting essentially of a primary heat transfer fluid selected from the group consisting of pentafluoroethane, 1,1- difluoroethane, 1,1,1-trifluroethane, tetrafluoroethanes, and mixtures thereof and a balance of a composition according to claim 3.
17. A refrigerant working fluid consisting essentially of a primary heat transfer fluid selected from the group consisting of pentafluoroethane, 1,1- difluoroethane, 1,1,1-trifluroethane, tetrafluoroethanes, and mixtures thereof and a balance of a composition ccording to claim 2. 7 ujj rogy *ii ~LL I I1-Lb"~
18. A refrigerant working fluid consisting essentially of a primary heat transfer fluid selected from the group consisting of pentafluoroethane, 1,1- difluoroethane, 1,1,1-trifluroethane, tetrafluoroethanes, and mixtures thereof and a balance of a composition according to claim 1.
19. A process for operating a refrigerator comprising cyclic compression, liquefaction, expansion, and evaporation of a heat transfer fluid, said heat transfer fluid consisting essentially of 1,1,1,2-tetrafluoroethane and a balance of ,o a lubricant according to claim 6. O* 20. A process for operating a refrigerator comprising cyclic compression, liquefaction, expansion, and evaporation of a heat transfer fluid, said heat transfer fluid consisting essentially of a primary heat transfer fluid selected from the group consisting of pentafluoroethane, 1,1-difluoroethane, 1,1,1- trifluroethane, tetrafluoroethanes, and mixtures thereof and a balance of a composition according to claim 1. DATED this 9th day of May, 1996. HENKEL CORPORATION WATERMARK PATENT TRADEMARK ATTORNEYS 4TH FLOOR, "DURACK CENTRE" 263 ADELAIDE TERRACE PERTH W.A. 6000 iAUSTRALIA Abstract of the Disclosure A high. quality lubricant for compressors operated during at least part of their compression cycle at temper- atures above normal human comfort temperatures, such as most automotive air conditioners, especially those using chlorine free hydrofluorocarbon refrigerant working flu- ids, is provided by mixed esters of hindered polyols, most desirably pentaerythritol, with a mixture of carboxylic I acids including at least some iso-pentanoic acid along with either or both of iso-nonanoic acid and dibasic acids such as adipic. i 2 2 I2 5 L n -d. t
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US1992/004438 WO1993024585A1 (en) | 1992-06-03 | 1992-06-03 | Polyol ester lubricants for refrigerant heat transfer fluids |
US2762993A | 1993-03-10 | 1993-03-10 | |
US027629 | 1993-03-10 |
Publications (2)
Publication Number | Publication Date |
---|---|
AU5764594A AU5764594A (en) | 1994-09-15 |
AU670173B2 true AU670173B2 (en) | 1996-07-04 |
Family
ID=26702721
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU57645/94A Expired AU670173B2 (en) | 1992-06-03 | 1994-03-09 | Polyol ester lubricants for refrigerator compressors operating at high temperatures |
Country Status (6)
Country | Link |
---|---|
KR (1) | KR100254623B1 (en) |
AT (2) | ATE301179T1 (en) |
AU (1) | AU670173B2 (en) |
BR (1) | BR9401111A (en) |
DE (2) | DE69333851T2 (en) |
HK (1) | HK1008682A1 (en) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5021179A (en) * | 1990-07-12 | 1991-06-04 | Henkel Corporation | Lubrication for refrigerant heat transfer fluids |
EP0448402A2 (en) * | 1990-03-23 | 1991-09-25 | Asahi Denka Kogyo Kabushiki Kaisha | Refrigerator oil composition |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2801703B2 (en) * | 1989-09-01 | 1998-09-21 | 花王株式会社 | Refrigerating machine oil |
-
1993
- 1993-05-27 DE DE69333851T patent/DE69333851T2/en not_active Expired - Lifetime
- 1993-05-27 AT AT99115560T patent/ATE301179T1/en not_active IP Right Cessation
- 1993-05-27 AT AT93911387T patent/ATE189902T1/en not_active IP Right Cessation
- 1993-05-27 KR KR1019940704424A patent/KR100254623B1/en not_active IP Right Cessation
- 1993-05-27 DE DE69327903T patent/DE69327903T2/en not_active Expired - Lifetime
-
1994
- 1994-03-09 AU AU57645/94A patent/AU670173B2/en not_active Expired
- 1994-03-10 BR BR9401111A patent/BR9401111A/en not_active IP Right Cessation
-
1998
- 1998-07-28 HK HK98109462A patent/HK1008682A1/en not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0448402A2 (en) * | 1990-03-23 | 1991-09-25 | Asahi Denka Kogyo Kabushiki Kaisha | Refrigerator oil composition |
US5021179A (en) * | 1990-07-12 | 1991-06-04 | Henkel Corporation | Lubrication for refrigerant heat transfer fluids |
Also Published As
Publication number | Publication date |
---|---|
DE69333851D1 (en) | 2005-09-08 |
HK1008682A1 (en) | 1999-05-14 |
KR950701965A (en) | 1995-05-17 |
DE69333851T2 (en) | 2006-01-12 |
KR100254623B1 (en) | 2000-05-01 |
DE69327903D1 (en) | 2000-03-30 |
AU5764594A (en) | 1994-09-15 |
BR9401111A (en) | 1994-10-18 |
ATE189902T1 (en) | 2000-03-15 |
DE69327903T2 (en) | 2000-10-05 |
ATE301179T1 (en) | 2005-08-15 |
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