JPH0347895A - 潤滑油 - Google Patents

潤滑油

Info

Publication number
JPH0347895A
JPH0347895A JP2045702A JP4570290A JPH0347895A JP H0347895 A JPH0347895 A JP H0347895A JP 2045702 A JP2045702 A JP 2045702A JP 4570290 A JP4570290 A JP 4570290A JP H0347895 A JPH0347895 A JP H0347895A
Authority
JP
Japan
Prior art keywords
group
oil
salt
acid
maleic acid
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
JP2045702A
Other languages
English (en)
Other versions
JP2844804B2 (ja
Inventor
Shinichi Akimoto
秋本　新一
Toru Yasukochi
徹 安河内
Kazuo Furuse
古瀬　和夫
Shinya Okumura
晋也 奥村
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.)
NOF Corp
Original Assignee
Nippon Oil and Fats 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 Nippon Oil and Fats Co Ltd filed Critical Nippon Oil and Fats Co Ltd
Priority to JP2045702A priority Critical patent/JP2844804B2/ja
Priority to BR909001925A priority patent/BR9001925A/pt
Priority to KR1019900005866A priority patent/KR0150003B1/ko
Priority to DE9090107994T priority patent/DE69000787T2/de
Priority to ES90107994T priority patent/ES2045624T3/es
Priority to EP90107994A priority patent/EP0399239B1/en
Publication of JPH0347895A publication Critical patent/JPH0347895A/ja
Priority to US07/801,633 priority patent/US5250205A/en
Application granted granted Critical
Publication of JP2844804B2 publication Critical patent/JP2844804B2/ja
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C10M173/00—Lubricating compositions containing more than 10% water
    • C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
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    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は潤滑油に関する。
〔従来の技術〕
ポリアルキ１７ングリコール誘導体１１潤滑油としてい
るい７）な用途に使用されている。たとえば、水溶性の
ポリアルキレングリコール誘導体）１作動油、切削油、
研削油、ギアー油等に、ポリオキシアルキレングリコー
ル（メタ）アクリ１／・−トの重合物は水系潤滑油（特
開昭５６−４７４１１号公ｖａ）Ｋ、ｈ−マシ油のポリ
オキシアルキレン付加物をさらにエステル化した化合物
は金属！ノＵ工油（特開昭５７−２０７６９９号公報）
に使用され、油溶性のポリアルキレングリコール誘導体
は鉱物油の粘度指数向」−剤（特公昭５３−・１４１９
６号公報）、冷凍機油（特開昭５７−５１７９５号公報
）等に使用きれている。
〔発明が解決しようとす−る課題〕
と二ろが、ポリオキシアルキレングリコールメタ）アク
リレートの重合物や、ヒマシ油の誘導体は長期にわたっ
て水溶液として使用すると性能が変ってしまい、また油
溶性のポリアルキレングリコールは鉱油にはよく溶ける
が水には全く溶けず、鉱油等を水に乳化することもでき
ず、使用できる範囲が限定されるという問題があった。
本発明は水溶液、油溶液、水−油乳化液のいずれの系に
も用いることのできる潤滑油な目的とする。
〔課題を解決するための手段〕
本発明は、一般式（１）で示されるフルヶニルエーテル
と無水マレイン酸、マレイン酸、マレイン酸塩またはマ
レイン酸エステルとを単量体の必須成分とする共重合体
からなる潤滑油である。
（０（ＡＯ）ａＲ）ｔ ／ （０（ＡＯ）。Ｈ）ｎ （ただし、２は２〜８個の水酸基をもつ化合物の残基，
ＡＯは炭素数２〜１８のオキシアルキレン基の１橿また
は２種以上で、２種以上のときはズロック状に付加して
いても、ランダム状に付加していてもよく、Ｒは炭素数
２〜５のフルケニル基、Ｒ１は炭素数１〜２４の炭化水
素基またはアシル基、ａ≧Ｏ，ｂ≧０，ｃ≧０、ｔは正
の整数，ｍとｎはＯまたは正の整数、ｔ　十ｍ　＋　ｎ
　＝　２　〜８、ｎ／（ｔ＋ｍ）≦ｌ／２、ａｔ＋　ｂ
ｍ＋　ａｎ　＝　１　−　１０００である。） 一般式（１１の２を残基とする２〜８個の水酸基をもつ
化合物としては、カテコール、レゾルシン、ヒドロキノ
ン、）ｐログルシン等の多価フェノール；エチレングリ
コール、プロピレングリコール、ブチレングリコール、
ドデシレングリコール、オクタデシレンゲリコール、ネ
オペンチルグリコール、スチレングリコール、グリセリ
ン、ジグリセリン、ポリグリセリン、トリメチルールエ
タン、トリメチロールプロパン、１，３．５−ペンタン
トリオール、エリスリトール、ペンタエリスリトール、
ジベンタヱリスリトール、ソルビトール、ソルビタン、
ソルバイト、ソルビトール−グリセリン縮合物、７ドニ
トール、アラビトール、キシリトール、マンニトールナ
トの多価アルコール；キシロース、７ラビノース、リポ
ース、ラムノース、グルコース、フルクトース、ガラク
トース、マンノース、シルポース、セミビオース、マル
トース。
イソマルトース、トレハロース、シュークロース、ラフ
ィノース、ゲンチアノース、メレジトースなどの糖類；
さらにそれらの部分エーテル化物や部分エステル化物等
がある。
ＡＯで示される炭素数２〜１８のオキシアルキレン基と
しては，オキシエチレン基、オキシプロピレン基，オキ
シブチレン基、オキシテトラメチレン基．オキシスチレ
ン基、オキシアルキレン基、オキシテトラメチレン基、
オキシヘキサデシレン基．オキシオクタデシレン基など
があるが、とくに炭素数２〜４のオキシアルキレン基が
好ましい。
Ｒで示される炭素数２〜５のフルケニル基としては，ビ
ニル基、アリル基、メタリル基、３−ブテニル基、４−
ペンテニル基、３−メチル−３−ブテニル基等がある。
５− Ｒ１で示される炭素数１〜２４の炭化水素基としてはメ
チル基、エチル基、プロピル基、イソプロピル基、ブチ
ル基、イソブチル基、第三ブチル基、ペンチル基、イン
ペンチル基、ヘキシル基、ヘプチル基、２−エチルヘキ
シル基、オクチル基、ノニル基、デシル基、ウンデシル
基、ドデシル基、イントリデシル基，テトラデシル基、
ヘキサデシル基、イソヘキサデシル基、オクタデシル基
、インオクタデシル基、オレイル基、オクチルドデシル
基、トコシル基、デシルテトラデシル基、ベンジ、ル基
、クレジル基、ブチルフェニル基、ジブチルフェニル基
、オクチルフェニル基、ノニルフェニル基、ドデシルフ
ェニル基、ジオクチルフェニル基、ジノニルフェニル基
、ナフチル基、スチレン化フェニル基などがあり、アシ
ル基としては、酢酸、プロピオン酸、酪酸、イソ醋酸、
カプリル酸、ペラルゴン酸、２−エチルヘキサン酸、ノ
ナン酸、カプリン酸、ウンデシル基酸、ラウリン酸、ミ
リスチン酸、パルミチン酸、マーガリン酸、ステアリン
酸、アラキン酸、ベヘン酸、パルミトレ６− イン酸、オレイン酸、リノール酸、リルン酸。
エルカ酸、イソパルミチン酸、イソステアリン醗、安息
香酸、ヒドロキシ安息香酸、桂皮酸、没食子酸等に由来
するアシル基がある。
マレイン酸頃としては、リチウム塩、ナトリウム塩、カ
リウム虐、マグネシウム塩、カルシウム塩等のアルカリ
金属喋、アルカリ土類金属塩のはｂｌ、アンモニウム塩
や有機アミン塩がある。
有機７ミン塩としては、メチルアミン塩、エチルアミン
塩、プロピルアミン壇、メチルアミン塩、ペンチルアミ
ン塩、ヘキシルアミン塩、オクチルアミン塩、２−エチ
ルヘキシルアミン塩、デシル７ミン塩、ドデシルアミン
塩、イントリデシルアミン塩、テトラデシルアミン塩、
ヘキサデシルアミン塩、インヘキサデシルアミン塩、オ
クタデシルアミン＠、インオクタデシルアミン塩、オク
チルドデシルアミン塩、トコジルアミン塩、デシルテト
ラデシルアミン塩、オレイルアミン壇、リノールアミン
塩、ジメチルアミン塩、トリメチルアミン塩、アニリン
塩等の脂肪族や芳香族のモノアミン頃、エチレンジアミ
ン塩、テトラメチレンジアミン塩、ドデシル−プロピレ
ンジアミン塩、テトラデシル−プロピレンジアミン塩、
ヘキサデシル−プロピレンジアミン塩、オクタデシル−
７’ｌ＝ピレンジアミン塩、オレイル−プロピレンジア
ミン塩、ジエチレントリアミン塩、トリエチレンテトラ
ミン塩、テトラエチレンペンタミン塩、ペンタエ、チレ
ンヘキサミン塩等のポリアミン塩、モノエタノールアミ
ン埴、ジェタノールアミン塩、トリエタノールアミン塩
、モノイソプロパツールアミン塩、ジイソプロパツール
アミン塩、トリイソプロパツールアミン塩、これらのフ
ルキレンオキシド付加物の塩、第一または第二アミンの
フルキレンオキシド付加物の塩等のアルカノールアミン
塩、リジン塩、アルギニン塩等のアミノ酸塩がある。こ
れらの５ち、とくにアルカリ金属塩、アンモニウム、塩
およびアルカノールアミン塩が好まし〜１゜ マレイン酸エステルとしては、メタノール、エタノール
、アリルアルコール、メタリルアルコール、プロパツー
ル、インプロパツール、ブタノール、イソブタノール、
第三ブタノール、ペンタノール、インペンタノール、ヘ
キサノール、ヘプタツール、２−エチルヘキサノール、
オクタツール、ノナノール、デカノール、ウンデカノー
ル、ドデカノール、インドリデカノール、テトラデカノ
ール、ヘキサデカノール、イソセチルアルコール、オク
タデカノール、インステアリルアルコール、オレイルア
ルコール、オクチルドデカノール、ドコサノール、デシ
ルテトラデカノール等のアルコールやこれらのフルキレ
ンオキシド付加物；フェノール、クレゾール、グチルフ
ェノール、オクチルフエ／−ル、ノニルフェノール、ド
デシルフェノール、カテコール、レゾルシン、ヒＦＲキ
ノン、フルルグルシン等のフェノール類のフルキレンオ
キシド付加物のマレイン酸エステルがある。さらにエチ
レングリコール、プロピレングリコール、ブチレングリ
コール、ドデシルフェノ−ル、オクタデシレンゲリコー
ル、ネオペンチルグリコール、スチレングリコール、グ
リセリン、ジグリセ＝９− リン、ポリグリセリン、トリメチロールエタン、トリメ
チロールプルパン、１，３．５−ヘンタントリオール、
エリスリトール、ペンタエリスリトール、ジペンタエリ
スリトール、ソルビトール、ソルビタン、ソルバイト、
ソルビトール−グリセリン縮金物、アドニトール、アラ
ビトール、キシリトール、マンニトールなどの多価アル
コール；キシロース、アラビノース、リボース、ラムノ
ーズ、グルコース、フルクトース、ガラクトース、マン
ノース、ソルボース、セルビオース、マルトース、イソ
マルトース、トレハロース、シュークロース、ラフィノ
ース、ゲンチ７ノース、メレジトースなどの糖類；さら
にそれらの部分エーテル化物や部分エステル化物、ある
いはそれらのフルキレンオキシド付加物；メチルアミン
、エチルアミン、プロピルアミン、ブチルアミン、アミ
ルアミ／、ヘキシルアミン、オクチルアミン、２−エチ
ルヘキシルアミン、デシルアミン、ドデシルアミン、イ
ントリデシルアミン、テトラデシルアミン、ヘキサデシ
ルアミン、インヘキサデシルアミン、オク１０− タデジルアミン、インオクタデシルアミン、オクチルド
デシルアミン、トコジルアミン、デシルテトラデシルア
ミン、オレイルアミン、リノールアミン、ジメチルアミ
ン、トリメチルアミン、アニリン等の脂肪族や芳香族の
モノアミンのアルキレンオキシド付加物；エチレンジア
ミン、テトラメチレンジアミン、ドデシル−プロピレン
ジアミン、テトラデシル−プロピレンジアミン、ヘキサ
デシル−プロピレンジアミン、オクタデジループ−ピレ
ンジアミン、オレイル−プロピレンジアミン、ジエチン
ントリアミン、トリエチレンテトラミン、テトラエチレ
ンペンタミン、ペンタエチレンへキサミン等のポリアミ
ンのフルキレンオキシド付加物；モノエタノールアミン
、ジェタノールアミン、トリエタノールアミン、モノイ
ソプロパツールアミン、ジイソプロパツールアミン、ト
リイソプロパツールアミン等のアルカノールアミンやそ
れらのフルキレンオキシド付加物のマレイン酸エステル
がある。
本発明で用いる共重合体は一般式（１）の化合物と無水
マレイン酸、マレイン酸、マレイン酸塩またはマレイン
酸エステルとをラジカル触媒を用いて共重合させること
によって得る二とができるが、マレイン酸、その塩また
はそのエステルの共重合体は、無水マレイン酸共重合体
のエステル化、加水分解、それにつぐ中和反応等によっ
て得る方が便利である。
一般式（１）で示される化合物と無水マレイン酸、マレ
イン酸、マレイン酸塩またはマレイン酸エステルとを共
重合させるとぎの比は、重合性の二重結合な基準にした
当量比で３ニア〜７：３．とく知約１＝１が好ましい。
共重合の際、さらに他の単量体を加えて共重合させても
よいが、他の単量体の量は全単量体中の３０モルチ以下
である。
他の単量体としては、アクリル酸、メタクリル酸、イタ
コン酸、クロトン酸、これらの−価または二価の金側Ｌ
アンモニウム塩、有機アミン壇、炭素数１〜２４のアル
コールとのエステル、多価アルコールとのエステル、ポ
リオキシアルキレングリコールとのエステル、そのほか
エチレン、メチルスチレンなどの芳香族ビニル化合物、
塩化ビニル、塩化ビニリデンなどのハロゲン化ビニル化
合物、インブチレン、ジイソブチレンなどのオレフィン
、酢酸ビニル、アクリロニトリル、アクリルアミドなど
がある。
共重合体の重量平均分子量は１０００〜２００万、好ま
しくは３０００〜５０万である。
Ｒの炭素数は重合性と関係があり、長すぎると重合性が
乏しくなるので、炭素数２〜５が適当である。
ｔで示されるＲの数は１であると直線的な共重合体がで
き、２以上であると架橋した共重合体を形成する。
ル ｔ、ｍ、ｎの関係であるが、前はＯ〜２の範囲であれば
良いが、あまり多いと共重合反応中に酸とのエステルが
生成しやすい。エステルが生成すると、共重合体の分子
量が大きくなって高粘度になりすぎたり、水や油に溶解
しにくくなるので好ましくなく、少ない方が良い。従っ
て、ｔ、ｍ。
１３ ｎの関係はｎ／（１＋ｍ　）≦１／２が好ましい。
また、ａ、ｂおよびＣはａ≧ｏ、ｂ≧０、Ｃ≧０で、ａ
ｔ＋　ｂｍ＋　ａｎ　＝　１〜１０００であるが、好ま
しくは１〜３００、とくに好ましくは１〜１００である
。
一般式（１）のフルケニルエーテルにおけるＡＯの炭素
数、付加モル数、Ｒ１との組合せ、さらに無水マレイン
酸、マレイン酸、マレイン酸塩、マレイン酸エステルと
の組合せで本発明で用いる共重合体は親水性にも親油性
にもすることができる。
〔作用〕
本発明の潤滑油に使用する共重合体は水に溶けるが油に
は溶けないもの、油に溶けるが水圧は溶けないもの、油
と水の両者に溶解し、両者を乳化するもの等、種々の性
質を示すものがあるので多くの用途に使用することがで
きる。
本発明で用いる共重合体は単独で潤滑油として使用でき
るが、鉱物油、動植物油脂、水、エチレングリコール、
プロピレングリコール等と併用しても良い。この場合、
０．０２重量％のような低濃＝１４− 度でも効果を示す。また冷凍機油用に使用する場合は、
フロンＲ−１１（）リクロｐモノフルオｐメタン）、フ
ロンＲ−１２（ジクＲＧ７ジフルオロメタン）、フロン
Ｒ−２２（モノクロロジフルオロメタン）、フロンＲ−
１３４＆　（１，１，１，２−テトラフルオルエタン）
、フロンＲ−１５２８（１゜１−ジフルオロエタン）等
の冷媒に溶解する必要があるので、冷媒に溶解する平均
分子量１０００以下のポリオキシプロピレングリコール
、そのモノ−またはジ−アルキルエーテル、ポリオキシ
プロピレング′リセリルエーテル、ポリオキシエチレン
ポリオキシプロピレングリコール（オキシエチレン基が
５０モルチ以下）、その七ノーまたはジ−アルキルエー
テル、ポリオキシエチレンポリオキシプロピレングリセ
リルエーテルなどのポリアルキレングリコール誘導体を
併用することが好ましい。なお、ポリアルキレングリコ
ール誘導体が２種以上のフルキレンオキシドの付加物で
ある場合は、ブロック状付加物でもランダム状付加物で
もよい。
〔発明の効果〕
本発明は一般式（１）のフルケニルエーテルと無水マレ
イン酸、マレイン酸、マレイン酸塩またはマレイン酸エ
ステルとを単量体の必須成分とする共重合体からなる潤
滑油であり、水溶液、乳化液、油溶液のいずれの系に用
いても優れた潤滑効果を示す。
また、本発明の潤滑油は、作動油、ギアー油、切削油、
研削油、プレス油、圧延油、引抜油、摺動面油なと、潤
滑性を要求される種々の用途に利用することができる。
【実施例〕
以下に実施例な記載する。
表１に以下の実施例に使用した共重合体な構成する単量
体組成と共重合体の重量平均分子量を示す。
実施例　１゜ 水系の潤滑油の基剤として表１０扁１〜５に示した共重
合体を用い、下記の配合処方の潤滑油について性能を評
価した。比較として、共重合体の代りに既存のポリオキ
シアルキレングリコールを基剤として用いた潤滑油につ
いても性能試験を実施した。
配合処方 基剤　　　　　　　　　　　　ｉ　ｓ、　ｏ　ｏ重量％
プルピレングリコール　　　　３７．００＃イオン交換
水　　　　　　　　４０．０Ｏ＃オレイン酸　　　　　
　　　　　　３．４５＃モルホリン　　　　　　　　　
　０．６０１ベンゾトリアゾール　　　　　　０．１０
＃水酸化カリウム　　　　　　　　０．８５７ジメチル
シロキサン（粘度　上記合計量に対して３５０　ｃｓｔ
　）　　　　１００　ｐｐｍ性能試験の結果を表２に示
すが、本発明の共重合体を基剤とする潤滑油が優れた潤
滑剤であることがわかる。
１８ 実施例　λ 表１の／Ｉ６３、Ａ４．Ａ６、烹７、ム８および屋９の
共重合体を用いて、以下に示す配合処方で切削油を調製
し、下記の条件で切削加工試験（ＪＩＳＢ−４０１２）
を行なった。その結果を表３に示す。
配合処方 マシーン油　　　　　　　　　　８０．０重量％共重合
体　　　　　　　　　　　２０．Ｏ＃切削加工試験の条
件 切削される材料　快削ステンレス鋼（ＳＡＥ５１−４１
６Ｆ） ４０ｇＸ３００（ｍ） 切削工具　　　　５ＫＨ−４８（ＪＩＳ　Ｇ−４４０３
）切削速度　　　　７０　ｍ／　ｍｉｎ 加工速度　　　　８μ／ｍｉｎ 切削油流量　　　１ｔ／ｍｉｎ 比較のため共重合体の代りに、ポリエチレングリコール
（７モル）モノオレエートを使用して試験した。評価は
、１本のバイトで切削できた材料の数で評価した。結果
を表４に示すが、本発明の共重合体を用いた切削油は効
果が大ぎいことがわかる。
表３ 実施例　３゜ 実施例２に使用した配合処方の切削油２重量％とイオン
交換水９８重量％からなる乳化液を調製し、実施例２と
同じ条件で切削試験を行なった。
その結果を表４に示すが、乳化系切削油においても本発
明の潤滑油が優れていることがわかる。
表　　　　　４ 溶解性にすぐれ、潤滑性能にも優れていることがわかる
。
実施例　３゜ 表５に示す組成物について、７０ンＲ−１２およびＲ−
１３４ａへの溶解性試験とチムケン式油性試験を行った
。その結果を表６に示す。
なお、溶解性試験は表５の組成物とフロンとな耐圧ガラ
ス溶器にとり、−５〜６０Ｃの範囲で白濁が生ずるかど
うかを目視により観察し、白濁な生じる場合な溶解しな
いと判断した。
表６より本発明の潤滑油が冷媒である゛フロンの２２ ３ 表 ６ ２５−

Claims (1)

  1. 【特許請求の範囲】 １、一般式（１）で示されるアルケニルエーテルと無水
    マレイン酸、マレイン酸、マレイン酸塩またはマレイン
    酸エステルとを単量体の必須成分とする共重合体からな
    る潤滑油。▲数式、化学式、表等があります▼・・・・
    ・・・・・・・・（１） （ただし、ｚは２〜８個の水酸基をもつ化合物の残基、
    ＡＯは炭素数２〜１８のオキシアルキレン基の１種また
    は２種以上で、２種以上のときはブロック状に付加して
    いても、ランダム状に付加していてもよく、Ｒは炭素数
    ２〜５のアルケニル基、Ｒ＾１は炭素数１〜２４の炭化
    水素基またはアシル基、ａ≧０、ｂ≧０、ｃ≧０、ｌは
    正の整数、ｍとｎは０または正の整数、ｌ＋ｍ＋ｎ＝２
    〜８、ｎ／（ｌ＋ｍ）≦１／２、ａｌ＋ｂｍ＋ｃｎ＝１
    〜１０００である。）
JP2045702A 1989-04-26 1990-02-28 潤滑油 Expired - Fee Related JP2844804B2 (ja)

Priority Applications (7)

Application Number Priority Date Filing Date Title
JP2045702A JP2844804B2 (ja) 1989-04-26 1990-02-28 潤滑油
BR909001925A BR9001925A (pt) 1989-04-26 1990-04-25 Oleo lubrificante e composicao de oleo lubrificante
DE9090107994T DE69000787T2 (de) 1989-04-26 1990-04-26 Verwendung eines copolymers aus polyoxyalkylen-alkenyl-ether und maleinsaeureanhydrid, maleinsaeure, einem maleinsaeuresalz oder maleinsaeureester als schmiermittel.
ES90107994T ES2045624T3 (es) 1989-04-26 1990-04-26 El uso de un copolimero de monomeros.
KR1019900005866A KR0150003B1 (ko) 1989-04-26 1990-04-26 윤활유
EP90107994A EP0399239B1 (en) 1989-04-26 1990-04-26 The use of a copolymer of polyalkylene alkenyl ether and maleic anhydride, maleic acid, or a salt or ester of maleic acid as a lubricating agent.
US07/801,633 US5250205A (en) 1989-04-26 1991-12-04 Lubricating oil

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP10464689 1989-04-26
JP1-104646 1989-04-26
JP2045702A JP2844804B2 (ja) 1989-04-26 1990-02-28 潤滑油

Publications (2)

Publication Number Publication Date
JPH0347895A true JPH0347895A (ja) 1991-02-28
JP2844804B2 JP2844804B2 (ja) 1999-01-13

Family

ID=26385755

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2045702A Expired - Fee Related JP2844804B2 (ja) 1989-04-26 1990-02-28 潤滑油

Country Status (6)

Country Link
EP (1) EP0399239B1 (ja)
JP (1) JP2844804B2 (ja)
KR (1) KR0150003B1 (ja)
BR (1) BR9001925A (ja)
DE (1) DE69000787T2 (ja)
ES (1) ES2045624T3 (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
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JP2007509227A (ja) * 2003-10-21 2007-04-12 ユニオン・カーバイド・ケミカルズ・アンド・プラスティックス・テクノロジー・コーポレイション 冷媒組成物

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EP0586705B1 (en) * 1991-12-26 1999-08-25 Tonen Corporation Lubricating oil for refrigerator
AU2004237804B2 (en) * 1999-08-16 2006-08-24 Ecolab Inc. Conveyor lubricant, passivation of a thermoplastic container to stress cracking and thermoplastic stress crack inhibitor
ES2935302T3 (es) * 2011-05-06 2023-03-03 Chemetall Gmbh Fluido para labrado de metales
EP4063472A4 (en) * 2019-11-19 2023-01-11 ENEOS Corporation REFRIGERATOR OIL, REFRIGERATOR WORKING FLUID COMPOSITION, LUBRICATION METHOD AND PROCESS FOR REFRIGERATOR OIL MANUFACTURE
CN112899055A (zh) * 2021-02-24 2021-06-04 武汉百洁科技有限公司 一种共聚物改性纤维素纳米晶用于聚二甲基硅氧烷增稠的方法

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JPS5647411A (en) * 1979-09-28 1981-04-30 Nippon Oil & Fats Co Ltd Polymer of polyoxyalkylene glycol monoacrylate or monomethacrylate and lubricant, antistatic and cosmetic agent therefrom
EP0056627B1 (en) * 1981-01-16 1984-10-03 Nippon Shokubai Kagaku Kogyo Co., Ltd Copolymer and method for manufacture thereof
US4469611A (en) * 1982-11-01 1984-09-04 The Dow Chemical Company Water-based hydraulic fluids
JPH0644927B2 (ja) * 1987-03-14 1994-06-15 日本油脂株式会社 徐放性活性成分放出剤
FR2619573B1 (fr) * 1987-08-17 1989-11-17 Commissariat Energie Atomique Liquide de lubrification et d'environnement utilisable pour tester des protheses osseuses
JP2692202B2 (ja) * 1988-11-29 1997-12-17 日本油脂株式会社 無機粉末の油中分散安定剤
JP2676854B2 (ja) * 1988-12-16 1997-11-17 日本油脂株式会社 ポリオキシアルキレン不飽和エーテルーマレイン酸エステル共重合体およびその用途

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007509227A (ja) * 2003-10-21 2007-04-12 ユニオン・カーバイド・ケミカルズ・アンド・プラスティックス・テクノロジー・コーポレイション 冷媒組成物

Also Published As

Publication number Publication date
DE69000787T2 (de) 1993-07-01
EP0399239B1 (en) 1993-01-20
DE69000787D1 (de) 1993-03-04
JP2844804B2 (ja) 1999-01-13
BR9001925A (pt) 1991-07-30
KR900016439A (ko) 1990-11-13
KR0150003B1 (ko) 1998-10-01
ES2045624T3 (es) 1994-01-16
EP0399239A1 (en) 1990-11-28

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