EP0479338B1 - Utilisation d'un lubrifiant pour des compresseurs utilisant un réfrigérant hydrofluorocarboné ne contenant pas de chlore. - Google Patents

Utilisation d'un lubrifiant pour des compresseurs utilisant un réfrigérant hydrofluorocarboné ne contenant pas de chlore. Download PDF

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Publication number
EP0479338B1
EP0479338B1 EP91121101A EP91121101A EP0479338B1 EP 0479338 B1 EP0479338 B1 EP 0479338B1 EP 91121101 A EP91121101 A EP 91121101A EP 91121101 A EP91121101 A EP 91121101A EP 0479338 B1 EP0479338 B1 EP 0479338B1
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EP
European Patent Office
Prior art keywords
lubricant
acid
weight
chlorine
trimethylol
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.)
Expired - Lifetime
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EP91121101A
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German (de)
English (en)
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EP0479338A3 (en
EP0479338A2 (fr
Inventor
Takashi c/o Kyodo Oil Technical Research Kaimai
Hisashi c/o Kyodo Oil Technical Research Yano
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Eneos Corp
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Japan Energy Corp
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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
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    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/34—Lubricating-sealants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/36—Release agents or mold release agents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/38—Conveyors or chain belts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/42—Flashing oils or marking oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/44—Super vacuum or supercritical use
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Definitions

  • This invention relates to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine such as hydrofluorocarbon (HFC), preferably HFC-134a (1,1,1,2-tetrafluoroethane).
  • HFC hydrofluorocarbon
  • HFC-134a 1,1,1,2-tetrafluoroethane
  • Japanese Patent laid open No. 61-281199 describes a mixture of polyglycol represented by a general formula of R 1 [O-(R 2 O) m -R 3 ] n , an alkylbenzene and the like
  • Japanese Patent laid open No. 57-63395 describes an oil obtained by mixing a polyether such as high molecular weight polyoxypropylene monobutyl ether with an epoxycycloalkyl compound
  • Japanese Patent laid open No. 59-117590 describes a high viscosity mixed oil of a polyether compound and a paraffinic or naphthanic mineral oil.
  • the conventional synthetic lubricants as mentioned above cannot be a refrigeration lubricant using HFC-134a as a refrigerant from a viewpoint of compatibility, for instance.
  • polyoxyalkylene glycol (hereinafter abbreviated as PAG) having hydroxyl groups (-OH) at both terminals is reported as a refrigeration lubricant using HFC-134a. Further, it is described that PAG is dissolved in HFC-134a within a wide temperature range as compared with general PAG containing hydroxyl group and alkyl group at its terminals, whereby the recycle of the lubricant into a compressor is improved in the refrigeration system and the seizuring in the actuation of the compressor at high temperature is prevented. Moreover, the temperature range compatible with HFC-134a is described to be between -40°C and +50°C.
  • HFC-134a is a replacing refrigerant of R-12 and is mainly expected for use in a car air conditioner or a refrigerator, for instance.
  • the refrigerator it is required to have a good compatibility between lubricant and refrigerant, and further the lubricant itself is necessary to have an electric insulating property because the motor is substantially existent in the refrigeration system.
  • the conventional compounds examined as a lubricant for HFC-134a refrigerant inclusive of PAG disclosed in US Patent No. 4,755,316 are remarkably poor in the electric insulating property as compared with the conventional refrigeration mineral oil and high in the hygroscopicity.
  • EP-A-0 378 176 discloses a fluid composition for use in compression refrigeration comprising
  • Said document is a document in the sense of Art. 54 (3) EPC.
  • WO-A-90 12 849 which also forms state of the art in the sense of Art. 54 (3) EPC only, describes a liquid composition comprising a major amount (more than 50% by weight) of a fluorine containing hydrocarbon refrigerant and a minor amount of (less than 50% by weight) of a lubricant comprising the carboxylic ester of a polyhydroxy compound.
  • esters At the present, a part of commercially available esters is used in systems using refrigerants such as R-12, R-22, but is incompatible with HFC-134a as a new refrigerant or is very narrow in the compatible range therewith.
  • the inventors have aimed at the fact that the ester has a high electric insulating property, a low hygroscopicity, a good lubricity and a high stability as compared with PAG and made various studies with respect to the molecule design of the ester showing a wide range of compatibility with HFC-134a, and found that only esters having a considerably restricted structure can be used in the HFC-134a refrigeration system, and as a result, the invention has been accomplished.
  • the present invention refers to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine, wherein said lubricant comprises an ester obtainable by reacting
  • the present invention refers to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine, wherein said lubricant comprises as a main component one or more esters obtainable by reacting
  • the present invention refers to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine, wherein said lubricant comprises as a main component one or more esters obtainable by reacting
  • the present invention refers to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine, wherein said lubricant comprises as a main component one or more esters obtainable by reacting
  • the present invention refers to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine, wherein said lubricant comprises as a main component one or more esters obtainable by reacting
  • the hydrofluorocarbon refrigerant is 1,1,1,2-tetrafluoroethane (HFC-134a).
  • trimethylol ethane, trimethylol propane and trimethylol butane which are represented by the following general formula (II): (in which R is an alkyl group having a carbon number of not more than 3) are used.
  • straight or branched-chain monovalent fatty acids having a carbon number of 3-10 or 4-10, resp., are used.
  • the monovalent fatty acid mention may be made of propionic acid, butanoic acid, isobutanoic acid, pentanoic acid, isopentanoic acid, hexanoic acid, heptanoic acid, isoheptanoic acid, octanoic acid, 2-ethyl hexanoic acid, nonanoic acid, isononanoic acid 3,5,5-trimethyl hexanoic acid and decanoic acid.
  • the polybasic acid having a carbon number of not more than 3 is a special product and is difficult to be cheaply available and is poor in the stability of the ester after the synthesis.
  • the carbon number of the polybasic acid is 4-10 for ensuring the compatibility with HFC-134a at a wide range.
  • the polybasic acid mention may be made of adipic acid, azelaic acid and sebacic acid.
  • the monovalent fatty acid is 2-ethylhexanoic acid
  • the polybasic acid is adipic acid.
  • the reason why the amount of the polybasic acid added in the invention is limited to not more than 25 mol% per the total fatty acid is due to the fact that when it exceeds 25 mol%, the gelation may be caused and it is difficult to obtain desirable physical properties.
  • the ester compounds used in the invention can be obtained by the esterification reaction through dehydration reaction between the specified polyvalent alcohol and the specified fatty acid as mentioned above, or the general esterification reaction through an acid anhydride, an acid chloride or the like as a derivative of the fatty acid.
  • ester does not contain carboxyl group.
  • the acid value exceeds 3
  • the metal soap is formed and precipitated by the reaction with a metal used inside the refrigerator
  • the acid value is preferably not more than 3.
  • the hydroxyl value exceeds 50
  • the esters used in the invention exhibit a good compatibility with the refrigerant HFC-134a and the like over a wide range of from low temperature to high temperature as a lubricant for use in a refrigerator using HFC-134a as a refrigerant, whereby the lubricity and thermal stability of the refrigeration lubricant can be considerably improved. Furthermore, they are high in the electric insulating property and small in the hygroscopicity as compared with PAG conventionally examined as a refrigeration lubricant for HFC-134a.
  • the refrigeration lubricants comprising the ester used in the invention as a main component the problems on the compatibility with HFC-134a and the hygroscopicity, which have never been solved in the conventional technique can be solved, and the electric insulating property, which comes into problem when HFC-134a is used in a compressor for a refrigerator, can be further enhanced.
  • additives usually used in the lubricant such as antioxidant, anti-wear agent and epoxy compound, for instance; may properly be added to the refrigeration lubricant used in the invention.
  • Seizuring load (Falex load-carrying capacity) was measured according to ASTM D-3233-73 under a controlled atmosphere of HFC-134a blown.
  • test lubricant Into a beaker of 100 ml there were charged 60 g of the test lubricant, which was left to stand at a temperature of 25°C and a humidity of 70% for 3 hours and then the water concentration was measured.
  • HFC-134a causing substantially no breakage of ozone layer is closed up instead of R-12 widely used as a refrigerant in order to cope with the breakage of ozone layer through chlorofluorocarbon and hydrochlorofluorocarbon being a greatest problem in world-wide scale, but is poor in the compatibility with the conventional refrigeration lubricant, which is a bar for the development of replacement system.
  • the refrigeration lubricants used in the invention have a sufficient compatibility with HFC-134a as a refrigerant and a high electric insulating property and also are excellent in the total performances, so that they have an effect that the conventional systems can be used as they are even when HFC-134a is used instead of the conventional R-12 and R-22 as a refrigerant.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (9)

  1. Utilisation d'un lubrifiant pour des compresseurs utilisant un réfrigérant hydrofluorocarboné ne contenant pas de chlore, dans laquelle ledit lubrifiant comprend comme constituant principal un ester pouvant être obtenu en faisant réagir :
    a) le triméthylolpropane (TMP), avec
    b) l'acide 2-éthylhexanoïque.
  2. Utilisation d'un lubrifiant pour des compresseurs employant un réfrigérant hydrofluorocarboné ne contenant pas de chlore, dans laquelle ledit lubrifiant comprend comme constituant principal un ou plusieurs esters pouvant être obtenus en faisant réagir :
    a) le triméthylolpropane (TMP), avec
    b) l'acide 2-éthylhexanoïque,
    c) l'acide adipique
    où la quantité de l'acide adipique n'est pas supérieure à 25 % en moles par acide gras total.
  3. Utilisation d'un lubrifiant pour des compresseurs employant un réfrigérant hydrofluorocarboné ne contenant pas de chlore, dans laquelle ledit lubrifiant comprend comme constituant principal un ou plusieurs esters pouvant être obtenus en faisant réagir :
    a) un ou plusieurs alcools polyvalents choisis parmi
    le triméthyloléthane (TME),
    le triméthylolpropane (TMP), et
    le triméthylolbutane (TMB), avec
    b) un ou plusieurs acides gras monovalents à chaîne linéaire ayant un nombre d'atomes de carbone de 3 à 10, et/ou acides gras monovalents à chaîne ramifiée ayant un nombre d'atomes de carbone de 4 à 10.
    à condition que,
    i) ledit lubrifiant ne contienne pas un polyétherpolyol dans une quantité de 5 à 95 % en poids conformément à la formule générale :

            Z-[(CH2-CH(R1)-O-)n-(CH2-CH(CH3)-O-)m-R2]p

    dans laquelle :
    Z est le résidu d'un composé ayant 1 à 8 atomes d'hydrogène actifs,
    R1 est un atome d'hydrogène, un éthyle ou des mélanges de ceux-ci,
    n est O ou un nombre positif,
    m est un nombre positif,
    n+m est un nombre ayant une valeur qui donnera un polyétherpolyol avec un poids moléculaire moyen en nombre compris dans la gamme de environ 400 à environ 5000, R2 est un atome d'hydrogène ou un groupe alkyle ayant 1 à 6 atomes de carbone,
    p est un nombre entier ayant une valeur égale au nombre des atomes d'hydrogène actifs de Z,
    et
    ii) ledit lubrifiant ne soit pas utilisé dans une composition liquide comprenant une quantité principale (supérieure à 50 % en poids) d'un réfrigérant hydrocarboné contenant du fluor et une quantité mineure (inférieure à 50 % en poids) dudit lubrifiant.
  4. Utilisation d'un lubrifiant pour des compresseurs employant un réfrigérant hydrofluorocarboné ne contenant pas de chlore, dans laquelle ledit lubrifiant comprend comme constituant principal un ou plusieurs esters pouvant être obtenus en faisant réagir :
    a) un ou plusieurs alcools polyvalents choisis parmi
    le triméthyloléthane (TME),
    le triméthylolpropane (TMP), et
    le triméthylolbutane (TMB), avec
    b) un ou plusieurs acides gras monovalents à chaîne linéaire ayant un nombre d'atomes de carbone de 3 à 10, et/ou acides gras monovalents à chaîne ramifiée ayant un nombre d'atomes de carbone de 4 à 10, et
    c) un ou plusieurs acides polybasiques ayant un nombre d'atomes de carbone de 4 à 10,
    où la quantité du ou des acides polybasiques n'est pas supérieure à 25 % en moles par acide gras total,
    à condition que,
    i. ledit lubrifiant ne soit pas utilisé dans une composition liquide . comprenant une quantité principale (supérieure à 50 % en poids) d'un réfrigérant hydrocarboné contenant du fluor et une quantité mineure (inférieure à 50 % en poids) dudit lubrifiant.
  5. Utilisation d'un lubrifiant pour des compresseurs employant un réfrigérant hydrofluorocarboné ne contenant pas de chlore, dans laquelle ledit lubrifiant comprend comme constituant principal un ou plusieurs esters pouvant être obtenus en faisant réagir :
    a) un ou plusieurs alcools polyvalents choisis parmi
    le triméthyloléthane (TME),
    le triméthylolpropane (TMP), et
    le triméthylolbutane (TMB), avec
    b) un ou plusieurs acides gras monovalents à chaîne ramifiée ayant un nombre d'atomes de carbone de 4 à 10, et
    à condition que,
    i) ledit lubrifiant ne contienne pas un polyétherpolyol dans une quantité de 5 à 95 % en poids conformément à la formule générale :

            Z-[(CH2-CH(R1)-O-)n-(CH2-CH(CH3)-O-)m-R2]p

    dans laquelle :
    Z est le résidu d'un composé ayant 1 à 8 atomes d'hydrogène actifs,
    R1 est un atome d'hydrogène, un éthyle ou des mélanges de ceux-ci,
    n est O ou un nombre positif,
    m est un nombre positif,
    n+m est un nombre ayant une valeur qui donnera un polyétherpolyol avec un poids moléculaire moyen en nombre compris dans la gamme de environ 400 à environ 5000, R2 est un atome d'hydrogène ou un groupe alkyle ayant 1 à 6 atomes de carbone,
    p est un nombre entier ayant une valeur égale au nombre des atomes d'hydrogène actifs de Z,
    et
    ii) ledit lubrifiant ne soit pas utilisé dans une composition liquide comprenant une quantité principale (supérieure à 50 % en poids) d'un réfrigérant hydrocarboné contenant du fluor et une quantité mineure (inférieure à 50 % en poids) dudit lubrifiant.
  6. Utilisation d'un lubrifiant selon l'une quelconque des revendications 3 à 4, dans laquelle l'acide gras monovalent à chaîne linéaire est choisi parmi :
    l'acide propionique, l'acide butanoïque, l'acide pentanoïque, l'acide hexanoïque, l'acide heptanoïque, l'acide octanoïque, l'acide nonanoïque et l'acide décanoïque.
  7. Utilisation d'un lubrifiant selon l'une quelconque des revendications 3 à 5, dans laquelle l'acide gras monovalent à chaîne ramifiée est choisi parmi:
    l'acide isopentanoïque, l'acide isoheptanoïque, l'acide 2-éthylhexanoïque, l'acide isononanoïque et l'acide 3,5,5-triméthylhexanoïque.
  8. Utilisation d'un lubrifiant selon la revendication 4, dans laquelle l'acide polybasique est choisi parmi
    l'acide adipique, l'acide azélaïque, et l'acide sébacique.
  9. Utilisation d'un lubrifiant selon l'une quelconque des revendications 1 à 8, dans laquelle le réfrigérant hydrofluorocarboné est le 1,1,1,2-tétrafluoroéthane.
EP91121101A 1989-07-05 1989-10-17 Utilisation d'un lubrifiant pour des compresseurs utilisant un réfrigérant hydrofluorocarboné ne contenant pas de chlore. Expired - Lifetime EP0479338B1 (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
JP17200089 1989-07-05
JP172002/89 1989-07-05
JP17200189 1989-07-05
JP17200289 1989-07-05
JP172000/89 1989-07-05
JP172001/89 1989-07-05
EP89119265A EP0406479B2 (fr) 1989-07-05 1989-10-17 Lubrifiants pour la réfrigération

Related Parent Applications (2)

Application Number Title Priority Date Filing Date
EP89119265A Division-Into EP0406479B2 (fr) 1989-07-05 1989-10-17 Lubrifiants pour la réfrigération
EP89119265.0 Division 1989-10-17

Publications (3)

Publication Number Publication Date
EP0479338A2 EP0479338A2 (fr) 1992-04-08
EP0479338A3 EP0479338A3 (en) 1992-05-27
EP0479338B1 true EP0479338B1 (fr) 1997-08-27

Family

ID=27323564

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Application Number Title Priority Date Filing Date
EP89119265A Expired - Lifetime EP0406479B2 (fr) 1989-07-05 1989-10-17 Lubrifiants pour la réfrigération
EP92121965A Expired - Lifetime EP0536814B1 (fr) 1989-07-05 1989-10-17 utilisation d'un lubrifiant pour compresseurs utilisant un réfrigérant hydrofluorocarboné ne contenant pas de chlore.
EP91121100A Expired - Lifetime EP0480479B2 (fr) 1989-07-05 1989-10-17 Utilisation d'un lubrifiant pour des compresseurs utilisant un réfrigérant hydrofluorocarboné ne contenant pas de chlore
EP91121101A Expired - Lifetime EP0479338B1 (fr) 1989-07-05 1989-10-17 Utilisation d'un lubrifiant pour des compresseurs utilisant un réfrigérant hydrofluorocarboné ne contenant pas de chlore.

Family Applications Before (3)

Application Number Title Priority Date Filing Date
EP89119265A Expired - Lifetime EP0406479B2 (fr) 1989-07-05 1989-10-17 Lubrifiants pour la réfrigération
EP92121965A Expired - Lifetime EP0536814B1 (fr) 1989-07-05 1989-10-17 utilisation d'un lubrifiant pour compresseurs utilisant un réfrigérant hydrofluorocarboné ne contenant pas de chlore.
EP91121100A Expired - Lifetime EP0480479B2 (fr) 1989-07-05 1989-10-17 Utilisation d'un lubrifiant pour des compresseurs utilisant un réfrigérant hydrofluorocarboné ne contenant pas de chlore

Country Status (5)

Country Link
EP (4) EP0406479B2 (fr)
KR (3) KR950005694B1 (fr)
DE (4) DE68927916T3 (fr)
ES (4) ES2051340T5 (fr)
SG (2) SG49157A1 (fr)

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DE68914448T3 (de) 2003-03-06
KR950005694B1 (ko) 1995-05-29
DE68927916T2 (de) 1997-08-21
EP0480479B1 (fr) 1997-03-26
ES2099120T5 (es) 2005-03-16
DE68914448T2 (de) 1994-08-25
EP0480479A3 (en) 1992-06-17
EP0536814A1 (fr) 1993-04-14
EP0406479B1 (fr) 1994-04-06
EP0536814B1 (fr) 1996-01-24
EP0406479A1 (fr) 1991-01-09
KR970078831A (ko) 1997-12-12
KR0131017B1 (ko) 1998-04-14
DE68925537D1 (de) 1996-03-07
EP0480479A2 (fr) 1992-04-15
ES2104650T3 (es) 1997-10-16
EP0406479B2 (fr) 2002-09-04
DE68928281D1 (de) 1997-10-02
DE68927916T3 (de) 2005-03-10
ES2082341T3 (es) 1996-03-16
EP0480479B2 (fr) 2004-09-01
DE68928281T2 (de) 1998-01-15
SG49165A1 (en) 1998-05-18
SG49157A1 (en) 1998-05-18
EP0479338A3 (en) 1992-05-27
KR910003077A (ko) 1991-02-26
EP0479338A2 (fr) 1992-04-08
ES2051340T5 (es) 2003-03-16
DE68914448D1 (de) 1994-05-11
ES2051340T3 (es) 1994-06-16
KR970078832A (ko) 1997-12-12
DE68927916D1 (de) 1997-04-30
KR0131016B1 (ko) 1998-04-14
DE68925537T2 (de) 1996-07-04
ES2099120T3 (es) 1997-05-16

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