JPH01198694A - Lubricating oil for alkane refrigerant containing fluorine - Google Patents

Lubricating oil for alkane refrigerant containing fluorine

Info

Publication number
JPH01198694A
JPH01198694A JP63270835A JP27083588A JPH01198694A JP H01198694 A JPH01198694 A JP H01198694A JP 63270835 A JP63270835 A JP 63270835A JP 27083588 A JP27083588 A JP 27083588A JP H01198694 A JPH01198694 A JP H01198694A
Authority
JP
Japan
Prior art keywords
lubricating oil
polyglycol
freon
water content
fluorine
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.)
Granted
Application number
JP63270835A
Other languages
Japanese (ja)
Other versions
JPH06102792B2 (en
Inventor
Masato Kaneko
正人 金子
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Idemitsu Kosan Co Ltd
Original Assignee
Idemitsu Kosan Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Idemitsu Kosan Co Ltd filed Critical Idemitsu Kosan Co Ltd
Priority to JP63270835A priority Critical patent/JPH06102792B2/en
Publication of JPH01198694A publication Critical patent/JPH01198694A/en
Publication of JPH06102792B2 publication Critical patent/JPH06102792B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Abstract

PURPOSE:To obtain the title lubricating oil having excellent stability in fluorocarbon refrigerant, without the possibility of trouble such as copper plating phenomena and excellent miscibility, containing a polyglycol-based compound having specific properties and low water content as a main component. CONSTITUTION:A polyglycol-based compound having >=5cst kinetic viscosity at 40 deg.C, >=70 viscosity index and <=200ppm water content [preferable example, compound expressed by the formula (R<1> and R<3> is H, 1-20C hydrocarbon or acyl, R<2> is 2-4C alkylene; n>=5)] is used as a main component to afford the aimed lubricating oil.

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明はフッ素含有アルカン冷媒用潤滑油に関し、詳し
くは低水分含量のポリグリコール系化合物を主成分とし
、フッ素含有アルカンを冷媒とする冷凍機等の潤滑剤と
して好適な潤滑油に関する。
[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a lubricating oil for a fluorine-containing alkane refrigerant, and more specifically, a lubricating oil for a fluorine-containing alkane refrigerant, and more specifically, a lubricating oil for a refrigeration machine containing a polyglycol compound with a low water content as a main component and using a fluorine-containing alkane as a refrigerant. The present invention relates to a lubricating oil suitable as a lubricant such as the like.

〔従来の技術及び発明が解決しようとする課題〕従来か
ら、ポリグリコール系化合物は冷凍機等の潤滑油などと
として利用されているが、冷媒、特に難燃性冷媒との相
溶性が不充分である。また、このポリグリコール系化合
物を冷凍機油等として用いた場合に、冷凍機内の鉄表面
に銅メツキ現象(銅配管から溶出した銅が鉄表面を覆う
現象)が発生するため、ベーンや軸受等における作動不
良を引き起こすおそれがある。
[Prior art and problems to be solved by the invention] Polyglycol compounds have traditionally been used as lubricating oils for refrigerators, etc., but their compatibility with refrigerants, especially flame-retardant refrigerants, is insufficient. It is. In addition, when this polyglycol compound is used as refrigerating machine oil, copper plating phenomenon (a phenomenon in which copper eluted from copper piping covers the iron surface) occurs on the iron surface inside the refrigerating machine. It may cause malfunction.

そこで、本発明者は上記従来のポリグリコール系化合物
の欠点を解消し、冷凍機油等として好適な性状を有する
ポリグリコール系化合物を開発すべ(鋭意研究を重ねた
Therefore, the inventors of the present invention have conducted intensive research to overcome the drawbacks of the conventional polyglycol compounds and to develop a polyglycol compound having properties suitable for refrigerating machine oil and the like.

〔課題を解決するための手段〕[Means to solve the problem]

その研究過程において、上述した銅メツキ現象は、ポリ
グリコール系化合物中の水分に起因することを見出した
。本発明者はこの知見に基いてさらに研究を続けたとこ
ろ、水分含量が少ないポリグリコール系化合物は、上述
した如き銅メツキ現象を引き起こすおそれがないと同時
に、冷凍機等の冷媒として用いられる各種の冷媒、特に
フッ素含有アルカン(以下、フロン化合物とも言う。)
に対して相溶性が良好であることを見出した。本発明は
このような研究の結果として完成したものである。
In the course of the research, it was discovered that the copper plating phenomenon described above is caused by moisture in the polyglycol compound. Based on this knowledge, the inventor continued research and found that polyglycol compounds with low water content do not cause the copper plating phenomenon described above, and are suitable for various types of refrigerants used as refrigerants in refrigerators, etc. Refrigerants, especially fluorine-containing alkanes (hereinafter also referred to as fluorocarbon compounds)
It was found that the compatibility was good. The present invention was completed as a result of such research.

すなわち、本発明は40℃における動粘度が5CSt以
上であるとともに、粘度指数が70以上であり、かつ水
分含有量が200 ppm以下であるポリグリコール系
化合物を主成分とするフッ素含有アルカン冷媒用潤滑油
を提供するものである。
That is, the present invention provides a lubricant for a fluorine-containing alkane refrigerant that is mainly composed of a polyglycol compound that has a kinematic viscosity at 40° C. of 5 CSt or more, a viscosity index of 70 or more, and a water content of 200 ppm or less. It provides oil.

本発明の潤滑油は、ポリグリコール系化合物を主成分と
するものであるが、このポリグリコール系化合物は、動
粘度が5cSt以上、好ましくは5〜800cSt、さ
らに好ましくは6〜200cSt、最も好ましくは8〜
150cStのものである。ここで動粘度が5cSt未
溝のものでは、蒸発による油消費量が多く、あるいは油
循環量が多く、さらにシール性が悪いという問題がある
。また、このポリグリコール系化合物の粘度指数は70
以上であり、好ましくは80以上、特に好ましくは10
0以上のものである。粘度指数が100未満のものでは
、高温での潤滑性が低下するという問題が生ずる。
The lubricating oil of the present invention is mainly composed of a polyglycol compound, and the polyglycol compound has a kinematic viscosity of 5 cSt or more, preferably 5 to 800 cSt, more preferably 6 to 200 cSt, and most preferably 8~
It is of 150 cSt. If the kinematic viscosity is 5 cSt and there are no grooves, there are problems in that the amount of oil consumed due to evaporation is large, or the amount of oil circulated is large, and furthermore, the sealing performance is poor. In addition, the viscosity index of this polyglycol compound is 70
or more, preferably 80 or more, particularly preferably 10
It is 0 or more. If the viscosity index is less than 100, a problem arises in that the lubricity at high temperatures decreases.

このような性状を有するポリグリコール系化合物として
は、様々なものがあるが、好ましくは一般式 %式%(1) で表わされるポリグリコール、ポリグリコールエーテル
あるいはポリグリコールエステルである。
There are various polyglycol compounds having such properties, but polyglycols, polyglycol ethers, and polyglycol esters represented by the general formula % (1) are preferred.

式中、R1およびR3はそれぞれ水素、炭素数1〜20
(好ましくは1〜10)の炭化水素基(好ましくはアル
キル基)またはアシル基を示し、R2は炭素数2〜4の
直鎖アルキレン基または分岐アルキレン基を示す。また
、nは5以上、好ましくは5〜60、さらに好ましくは
5〜30、最も好ましくは5〜25の数を示す。なお、
n個のRzはそれぞれ同一でも異なってもよい。
In the formula, R1 and R3 are each hydrogen and have 1 to 20 carbon atoms.
(preferably 1 to 10) hydrocarbon group (preferably an alkyl group) or acyl group, and R2 represents a straight chain alkylene group or branched alkylene group having 2 to 4 carbon atoms. Further, n represents a number of 5 or more, preferably 5 to 60, more preferably 5 to 30, and most preferably 5 to 25. In addition,
The n Rz may be the same or different.

更に、本発明のポリグリコール系化合物は、水分含有量
が200ppm以下でなければならず、好ましくは11
00pp以下である。ここで、水分含有量が200 p
pmを超えるものでは、上述した如き銅メツキ現象を引
き起こすおそれがある。このような、低水分含量のポリ
グリコール系化合物を得るにあたっては、上述した如き
一般式(1)のポリグリコール系化合物を、真空加熱処
理やシリカゲル、活性アルミナ、ゼオライト等と接触処
理するとよい。特に好ましくは、粒径0.1〜10鰭、
好ましくは0.2〜5III11のゼオライト(天然ゼ
オライトあるいはモレキュラーシープス3A。
Furthermore, the polyglycol compound of the present invention must have a moisture content of 200 ppm or less, preferably 11 ppm or less.
00pp or less. Here, the water content is 200 p
If it exceeds pm, there is a risk of causing the above-mentioned copper plating phenomenon. In order to obtain such a polyglycol compound with a low water content, the polyglycol compound of general formula (1) as described above is preferably subjected to a vacuum heat treatment or a contact treatment with silica gel, activated alumina, zeolite, etc. Particularly preferably, particle size 0.1 to 10 fins,
Preferably 0.2 to 5III11 zeolite (natural zeolite or Molecular Sheeps 3A).

4A、5A、13X等の合成ゼオライト)と接触処理す
ればよい。この際の接触条件は特に制限はなく、各種状
況に応じて定めればよい。また、必要に応じて接触処理
に際して10〜50KHzの超音波を照射するとさらに
脱水効率が向上する。
Synthetic zeolites such as 4A, 5A, 13X, etc.) may be contacted with the zeolite. The contact conditions at this time are not particularly limited and may be determined depending on various situations. Further, if necessary, irradiation with ultrasonic waves of 10 to 50 KHz during the contact treatment further improves the dehydration efficiency.

このようにして得た低水分含量のポリグリコール系化合
物は、吸水性を有するため、なるべく水分を遮断した条
件下に保管しておくことが好ましい。ここで、簡便かつ
有効な保管方法としては、ゼオライトをそのままあるい
は酸化マグネシウム等のバインダーで固めて成形したも
のを内蔵した密封容器に収納して保管する方法をあげる
ことができる。
Since the polyglycol compound with a low water content obtained in this way has water absorbing properties, it is preferable to store it under conditions where moisture is blocked as much as possible. Here, a simple and effective storage method is to store zeolite as it is or after solidifying it with a binder such as magnesium oxide and molding it in a sealed container.

本発明の潤滑油は、このようにして得られた低水分含量
のポリグリコール系化合物を主成分とするものであるが
、さらに必要に応じて摩耗防止剤。
The lubricating oil of the present invention is mainly composed of the thus obtained polyglycol compound with a low water content, and further contains an anti-wear agent as required.

塩素捕捉剤、酸化防止剤、金属不活性化剤、消泡剤等を
適量配合すことも有効である。ここで、塩素捕捉剤とし
ては各種のものがあるが、トリフェニルホスファイト 
トリクレジルホスファイト等の亜リン酸エステル系化合
物を好適なものとしてあげることができ、これを0.0
01〜0.5重量%の割合で添加すればよい。
It is also effective to incorporate appropriate amounts of chlorine scavengers, antioxidants, metal deactivators, antifoaming agents, and the like. There are various types of chlorine scavengers, but triphenyl phosphite
Preferred examples include phosphite ester compounds such as tricresyl phosphite;
It may be added in a proportion of 0.01 to 0.5% by weight.

本発明の潤滑油は、フロン化合物を冷媒とじて用いる冷
凍機、クーラー、ヒートポンプ等の潤滑剤として有効で
あるが、ここで冷媒であるフロン化合物としては、トリ
クロロモノフルオロメタン(フロン−11)、ジクロロ
ジフルオロメタン(フロン−12)をはじめとして、各
種のものがある。本発明の潤滑油は、これらフロン−1
1゜フロン−12以外に、通常の潤滑油では難溶性とさ
れる水素含有フロンやパーフルオロアルカンに対しても
良好な相溶性を示す。ここで、水素含有フロンとしては
、1.1−ジクロロ−2,2,2−トリフルオロエタン
(フロン−123)il。
The lubricating oil of the present invention is effective as a lubricant for refrigerators, coolers, heat pumps, etc. that use fluorocarbon compounds as refrigerants, but the fluorocarbon compounds used as refrigerants include trichloromonofluoromethane (Freon-11), There are various types including dichlorodifluoromethane (Freon-12). The lubricating oil of the present invention has these Freon-1
In addition to 1° Freon-12, it also shows good compatibility with hydrogen-containing Freon and perfluoroalkane, which are poorly soluble in ordinary lubricating oils. Here, the hydrogen-containing fluorocarbon is 1,1-dichloro-2,2,2-trifluoroethane (fluorocarbon-123)il.

1.1.2−テトラフルオロエタン(フロン−134a
);1−クロロ−1,1−ジフルオロエタン(フロン−
142b);1.1−ジフルオロエタン(フロン−15
2a);)リフルオロメタン(フロン−23)あるいは
モノクロロジフルオロメタン(フロン−22)があげら
れる。また、パーフルオロアルカンとしては、1,1,
1,2゜2.2−へキサフルオロエタン(フロン−11
6);テトラフルオロメタン(フロン−14)等があげ
られる。
1.1.2-Tetrafluoroethane (Freon-134a
); 1-chloro-1,1-difluoroethane (fluorocarbon-
142b); 1,1-difluoroethane (Freon-15
2a);) Lifluoromethane (Freon-23) or monochlorodifluoromethane (Freon-22) can be mentioned. In addition, perfluoroalkanes include 1,1,
1,2゜2.2-hexafluoroethane (Freon-11
6); Examples include tetrafluoromethane (Freon-14).

〔実施例] 次に、本発明を実施例、比較例および参考例により更に
詳しく説明する。
[Examples] Next, the present invention will be explained in more detail with reference to Examples, Comparative Examples, and Reference Examples.

実施例1〜4.比較例1〜3および参考例1〜4第4表
に示す鉱油、アルキルベンゼンあるいはポリグリコール
を試料として下記の方法にしたがってその性能評価を行
った。結果を第2表に示す。
Examples 1-4. Comparative Examples 1 to 3 and Reference Examples 1 to 4 The mineral oils, alkylbenzenes, or polyglycols shown in Table 4 were used as samples to evaluate their performance according to the following method. The results are shown in Table 2.

フロン−22との二層分離温度 試料とフロン−22を2二8(重量)で混合し、二層に
分離する温度を測定した。
Two-layer separation temperature with Freon-22 The sample and Freon-22 were mixed at 228 (by weight), and the temperature at which they separated into two layers was measured.

フロン−134aとの二層分離温度 試料とフロン−134aを2二8(重量)で混合し、二
層に分離する温度を低温側と高温側で測定した。
Two-layer separation temperature with Freon-134a The sample and Freon-134a were mixed at 228 (by weight), and the temperature at which they separated into two layers was measured on the low-temperature side and the high-temperature side.

ファレックス焼付試験 ASTM D  3233に準拠し、焼付荷重(ポンド
)で評価した。
Falex Seizure Test Based on ASTM D 3233, the evaluation was based on the seizing load (pounds).

シールドチューブ試験 試料とフロン−22との2:1(重量)混合物を鉄、銅
、アルミニウムの触媒とともに、ガラス管に封入し、1
75℃において720時間加熱後、その外観ならびに析
出物の有無を測定した。
A 2:1 (by weight) mixture of shielded tube test sample and Freon-22 was sealed in a glass tube along with iron, copper, and aluminum catalysts.
After heating at 75° C. for 720 hours, the appearance and presence or absence of precipitates were measured.

蒸発性試験 JIS−C−2320に準拠して、試料20gをビーカ
ーに採取し、140℃124時間加熱後、その蒸発減量
(重量%)を測定した。
Evaporability test In accordance with JIS-C-2320, 20 g of a sample was collected in a beaker, heated at 140° C. for 124 hours, and then its evaporation loss (weight %) was measured.

(以下余白) 〔発明の効果] 以上の如く、本発明の潤滑油は、フロン(即ちフッ素含
有アルカン)冷媒下での安定性が良好であって、銅メツ
キ現象等のトラブルを起こすおそれがなく、しかもフロ
ン−11,フロン−12のみならず、水素含有フロン化
合物やパーフルオロアルカンなどの難溶性冷媒に対して
も二層分離温度が低く、相溶性が良好である。特に、フ
ロン−134aのような極難溶性冷媒に対する低温側の
二層分離温度が低く、高温側の二層分離温度が高いので
、この種の冷媒に有用である。また耐焼付性が高く、蒸
発による油消費量も少なく、油循環量も少なくすること
ができる。
(The following is a blank space) [Effects of the Invention] As described above, the lubricating oil of the present invention has good stability under a fluorocarbon (i.e., fluorine-containing alkane) refrigerant, and there is no risk of causing problems such as copper plating. Moreover, the two-layer separation temperature is low and the compatibility is good not only with Freon-11 and Freon-12 but also with poorly soluble refrigerants such as hydrogen-containing Freon compounds and perfluoroalkanes. In particular, since the two-layer separation temperature on the low-temperature side is low and the two-layer separation temperature on the high-temperature side is high for extremely poorly soluble refrigerants such as Freon-134a, it is useful for this type of refrigerant. It also has high seizure resistance, reduces oil consumption due to evaporation, and reduces oil circulation.

したがって、本発明の潤滑油は、これら各種のフロン化
合物を冷媒として用いる冷凍機、クーラー(特にカーエ
アコン)、ヒートポンプ等の潤滑剤として有効に利用さ
れる。
Therefore, the lubricating oil of the present invention can be effectively used as a lubricant for refrigerators, coolers (especially car air conditioners), heat pumps, etc. that use these various fluorocarbon compounds as refrigerants.

Claims (2)

【特許請求の範囲】[Claims] (1)40℃における動粘度が5cSt以上であるとと
もに、粘度指数が70以上であり、かつ水分含有量が2
00ppm以下であるポリグリコール系化合物を主成分
とするフッ素含有アルカン冷媒用潤滑油。
(1) The kinematic viscosity at 40°C is 5 cSt or more, the viscosity index is 70 or more, and the water content is 2
A lubricating oil for fluorine-containing alkane refrigerants whose main component is a polyglycol compound having a content of 00 ppm or less.
(2)ポリグリコール系化合物が、 一般式 ▲数式、化学式、表等があります▼ 〔式中、R^1およびR^3はそれぞれ水素、炭素数1
〜20の炭化水素基またはアシル基を 示し、R^2は炭素数2〜4の直鎖アルキレン基または
分岐アルキレン基を示す。また、nは5以上の数を示す
。〕 で表わされるものである請求項1記載のフッ素含有アル
カン冷媒用潤滑油。
(2) Polyglycol compounds have the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 and R^3 are each hydrogen and the number of carbon atoms is 1
~20 hydrocarbon group or acyl group, and R^2 represents a straight chain alkylene group or branched alkylene group having 2 to 4 carbon atoms. Further, n represents a number of 5 or more. ] The lubricating oil for a fluorine-containing alkane refrigerant according to claim 1, which is represented by the following.
JP63270835A 1987-10-30 1988-10-28 Lubricating oil for fluorine-containing alkane refrigerant Expired - Lifetime JPH06102792B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP63270835A JPH06102792B2 (en) 1987-10-30 1988-10-28 Lubricating oil for fluorine-containing alkane refrigerant

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP62-273418 1987-10-30
JP27341887 1987-10-30
JP63270835A JPH06102792B2 (en) 1987-10-30 1988-10-28 Lubricating oil for fluorine-containing alkane refrigerant

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP4345705A Division JPH07103388B2 (en) 1987-10-30 1992-12-25 Lubricating oil for 1,1,1,2-tetrafluoroethane refrigerant

Publications (2)

Publication Number Publication Date
JPH01198694A true JPH01198694A (en) 1989-08-10
JPH06102792B2 JPH06102792B2 (en) 1994-12-14

Family

ID=26549398

Family Applications (1)

Application Number Title Priority Date Filing Date
JP63270835A Expired - Lifetime JPH06102792B2 (en) 1987-10-30 1988-10-28 Lubricating oil for fluorine-containing alkane refrigerant

Country Status (1)

Country Link
JP (1) JPH06102792B2 (en)

Cited By (23)

* Cited by examiner, † Cited by third party
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JPH01256594A (en) * 1988-04-06 1989-10-13 Nippon Oil Co Ltd Refrigerating machine oil composition for refrigerating apparatus
JPH01259095A (en) * 1988-04-08 1989-10-16 Kiyouseki Seihin Gijutsu Kenkyusho:Kk Lubricating oil useful for fluorocarbon compressor
JPH01271491A (en) * 1988-04-22 1989-10-30 Nippon Oil Co Ltd Refrigerating machine oil composition for car air conditioner
JPH0237256A (en) * 1988-05-27 1990-02-07 Cpi Eng Services Inc Improved refrigerator and method of improving efficiency of refrigerator
JPH0243290A (en) * 1988-04-22 1990-02-13 Nippon Oil Co Ltd Refrigerant oil composition for automotive air conditioner
JPH0284491A (en) * 1988-04-06 1990-03-26 Nippon Oil Co Ltd Lubricating oil composition for freezing refrigerator
JPH02102296A (en) * 1988-10-07 1990-04-13 Tonen Corp Lubricating oil for refrigerator wherein 1,1,1,2-tetrafluoroethane refrigerant is used
JPH02182780A (en) * 1989-01-10 1990-07-17 Asahi Glass Co Ltd Tetrafluoroethane-base composition for refrigerator
JPH02305893A (en) * 1988-12-06 1990-12-19 Idemitsu Kosan Co Ltd Lubricating oil for compression refrigerating machine
JPH03115493A (en) * 1989-09-29 1991-05-16 Nishi Nippon Tsusho Kk Refrigerating machine oil
JPH03281688A (en) * 1990-03-30 1991-12-12 Hitachi Ltd Refrigerator
US5300245A (en) * 1991-07-01 1994-04-05 Kao Corporation Working fluid composition having ketone-containing compound for use in refrigeration system
EP0693546A1 (en) 1994-07-19 1996-01-24 NIPPON OIL Co. Ltd. Refrigerator oil and fluid composition for refrigerator
EP0699742A2 (en) 1994-08-03 1996-03-06 Nippon Oil Co. Ltd. Refrigerator oil composition and fluid composition for refrigerator
EP0711824A2 (en) 1994-11-07 1996-05-15 Nippon Oil Co. Ltd. Lubricating oil and composition for refrigerating machine, and refrigerating machine
EP0717098A2 (en) 1994-12-12 1996-06-19 Nippon Oil Co. Ltd. A refrigerating machine oil and a fluid composition for use in a refrigerating machine
JPH08239676A (en) * 1995-12-28 1996-09-17 Asahi Glass Co Ltd Tetrafluoroethane composition for refrigerator
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US7914697B2 (en) * 2006-03-10 2011-03-29 Idemitsu Kosan Co., Ltd. Refrigerating machine oil composition
JP2012513527A (en) * 2008-12-23 2012-06-14 シュリーブ ケミカル プロダクツ インコーポレーテッド Refrigerant lubricant composition
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JP2514090B2 (en) * 1988-04-06 1996-07-10 日本石油株式会社 Lubricating oil composition for freezers
JPH0284491A (en) * 1988-04-06 1990-03-26 Nippon Oil Co Ltd Lubricating oil composition for freezing refrigerator
JPH01256594A (en) * 1988-04-06 1989-10-13 Nippon Oil Co Ltd Refrigerating machine oil composition for refrigerating apparatus
JPH01259095A (en) * 1988-04-08 1989-10-16 Kiyouseki Seihin Gijutsu Kenkyusho:Kk Lubricating oil useful for fluorocarbon compressor
JPH01271491A (en) * 1988-04-22 1989-10-30 Nippon Oil Co Ltd Refrigerating machine oil composition for car air conditioner
JPH0243290A (en) * 1988-04-22 1990-02-13 Nippon Oil Co Ltd Refrigerant oil composition for automotive air conditioner
JPH0237256A (en) * 1988-05-27 1990-02-07 Cpi Eng Services Inc Improved refrigerator and method of improving efficiency of refrigerator
JPH02102296A (en) * 1988-10-07 1990-04-13 Tonen Corp Lubricating oil for refrigerator wherein 1,1,1,2-tetrafluoroethane refrigerant is used
JPH02305893A (en) * 1988-12-06 1990-12-19 Idemitsu Kosan Co Ltd Lubricating oil for compression refrigerating machine
JPH02182780A (en) * 1989-01-10 1990-07-17 Asahi Glass Co Ltd Tetrafluoroethane-base composition for refrigerator
JPH03115493A (en) * 1989-09-29 1991-05-16 Nishi Nippon Tsusho Kk Refrigerating machine oil
JPH03281688A (en) * 1990-03-30 1991-12-12 Hitachi Ltd Refrigerator
US5300245A (en) * 1991-07-01 1994-04-05 Kao Corporation Working fluid composition having ketone-containing compound for use in refrigeration system
US5401433A (en) * 1991-07-01 1995-03-28 Kao Corporation Working fluid composition having ketone-containing compound for use in refrigeration system
US6217791B1 (en) 1991-12-18 2001-04-17 Asahi Denka Kogyo K.K. Refrigerant incorporating a polyoxyalkylene glycol monomethylether
EP0693546A1 (en) 1994-07-19 1996-01-24 NIPPON OIL Co. Ltd. Refrigerator oil and fluid composition for refrigerator
EP0699742A2 (en) 1994-08-03 1996-03-06 Nippon Oil Co. Ltd. Refrigerator oil composition and fluid composition for refrigerator
EP0711824A2 (en) 1994-11-07 1996-05-15 Nippon Oil Co. Ltd. Lubricating oil and composition for refrigerating machine, and refrigerating machine
EP0717098A2 (en) 1994-12-12 1996-06-19 Nippon Oil Co. Ltd. A refrigerating machine oil and a fluid composition for use in a refrigerating machine
JPH08239676A (en) * 1995-12-28 1996-09-17 Asahi Glass Co Ltd Tetrafluoroethane composition for refrigerator
US7018961B2 (en) 1999-07-06 2006-03-28 Idemitsu Kosan Co., Ltd. Refrigerating machine oil composition for carbon dioxide refrigerant
WO2001002521A1 (en) * 1999-07-06 2001-01-11 Idemitsu Kosan Co., Ltd. Refrigerating machine oil composition for carbon dioxide refrigerant
EP1203807A4 (en) * 1999-07-06 2006-07-05 Idemitsu Kosan Co Refrigerating machine oil composition for carbon dioxide refrigerant
US8324140B2 (en) 1999-07-06 2012-12-04 Idemitsu Kosan Co., Ltd. Refrigerating machine oil composition for carbon dioxide refrigerant
WO2001090282A1 (en) * 2000-05-22 2001-11-29 Idemitsu Kosan Co., Ltd. Lubricating oil composition for refrigerating machine
US6894010B2 (en) 2000-05-22 2005-05-17 Idemitsu Kosan Co., Ltd. Lubricating oil composition for refrigerating machine
US7914697B2 (en) * 2006-03-10 2011-03-29 Idemitsu Kosan Co., Ltd. Refrigerating machine oil composition
JP2012513527A (en) * 2008-12-23 2012-06-14 シュリーブ ケミカル プロダクツ インコーポレーテッド Refrigerant lubricant composition
WO2013005647A1 (en) * 2011-07-01 2013-01-10 出光興産株式会社 Lubricant oil composition for compression refrigerator
JP2013014673A (en) * 2011-07-01 2013-01-24 Idemitsu Kosan Co Ltd Lubricant composition for compression type refrigerator
US9902917B2 (en) 2011-07-01 2018-02-27 Idemitsu Kosan Co., Ltd. Lubricant oil composition for compression refrigerator

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