JP2844804B2 - 潤滑油 - Google Patents

潤滑油

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Publication number
JP2844804B2
JP2844804B2 JP2045702A JP4570290A JP2844804B2 JP 2844804 B2 JP2844804 B2 JP 2844804B2 JP 2045702 A JP2045702 A JP 2045702A JP 4570290 A JP4570290 A JP 4570290A JP 2844804 B2 JP2844804 B2 JP 2844804B2
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JP
Japan
Prior art keywords
group
acid
oil
salt
salts
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 - Fee Related
Application number
JP2045702A
Other languages
English (en)
Other versions
JPH0347895A (ja
Inventor
新一 秋本
徹 安河内
和夫 古瀬
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.)
NIPPON YUSHI KK
Original Assignee
NIPPON YUSHI KK
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 YUSHI KK filed Critical NIPPON YUSHI KK
Priority to JP2045702A priority Critical patent/JP2844804B2/ja
Priority to BR909001925A priority patent/BR9001925A/pt
Priority to KR1019900005866A priority patent/KR0150003B1/ko
Priority to EP90107994A priority patent/EP0399239B1/en
Priority to ES90107994T priority patent/ES2045624T3/es
Priority to DE9090107994T priority patent/DE69000787T2/de
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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  • Compositions Of Macromolecular Compounds (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

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〕 ポリアルキレングリコール誘導体は潤滑油としていろ
いろ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は作動油、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）アクリレートの重合物は水系潤滑油（特開昭56
−47411号公報）に、ヒ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加工油（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上剤（特
公昭53−44196号公報）、冷凍機油（特開昭57−51795号
公報）等に使用されている。
〔発明が解決しようとする課題〕
ところが、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を目的とする。
〔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
体からなる潤滑油である。
（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、R1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。） 一般式（１）のＺ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、フロログルシン等の多価フエノール；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、オクタデシレングリコー
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、トリメチロ
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、ジベンタエリスリトール、ソルビトール、ソルビタ
ン、ソルバイド、ソルビトール−グリセリン縮合物、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、ラムノース、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、セロビオース、
マルトース、イソマルトース、トレハロース、シユーク
ロース、ラフイノース、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、オキシドデシレン基、オキシテトラデシレン基、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のア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。
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、イソペ
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、イソトリデシル基、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、イソオクタデシル基、オレイル基、オクチルドデシ
ル基、ドコシル基、デシルテトラデシル基、ベンジル
基、クレジル基、ブチルフエニル基、ジブチルフエニル
基、オクチルフエニル基、ノニルフエニル基、ドデシル
フエニル基、ジオクチルフエニル基、ジノニルフエニル
基、ナフチル基、スチレン化フエニル基などがあり、ア
シル基としては、酢酸、プロピオン酸、酪酸、イソ酪
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、ウンデシレン酸、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、パルミトレイン酸、
オレイン酸、リノール酸、リノレン酸、エルカ酸、イソ
パルミチン酸、イソステアリン酸、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。
マレイン酸塩としては、リチウム塩、ナトリウム塩、
カリウム塩、マグネシウム塩、カルシウム塩等のアルカ
リ金属塩、アルカリ土類金属塩のほか、アンモニウム塩
や有機アミン塩がある。
有機アミン塩としては、メチルアミン塩、エチルアミ
ン塩、プロピルアミン塩、ブチルアミン塩、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、デシルアミン塩、ドデシルアミ
ン塩、イソ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、イソヘキサデシルアミン
塩、オクタデシルアミン塩、イソオクタデシルアミン
塩、オクチルドデシルアミン塩、ドコシルアミン塩、デ
シルテトラデシルアミン塩、オレイルアミン塩、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塩、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−プロピレンジアミン塩、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
ミン塩、ジエタノールアミン塩、トリエタノールアミン
塩、モノイソプロパノールアミン塩、ジイソプロパノー
ルアミン塩、トリイソプロパノールアミン塩、これらの
アルキレンオキシド付加物の塩、第一または第二アミン
のア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。
これらのうち、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い。
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、プロパノ
ール、イソプロパノール、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、イソペンタノー
ル、ヘキサノール、ヘプタノール、２−エチルヘキサノ
ール、オクタノール、ノナノール、デカノール、ウンデ
カノール、ドデカノール、イソトリデカノール、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、イソ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
アルキレンオキシド付加物；フエノール、クレゾール、
ブチルフエノール、オクチルフエノール、ノニルフエノ
ール、ドデシルフエノール、カテコール、レゾルシン、
ヒドロキノン、フロログルシン等のフエノール類のアル
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、ドデシレングリコール、オクタデシレ
ングリコール、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、
トリメチロールエタン、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、ソルバイド、ソルビトール−グリセリン縮
合物、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、セロビ
オース、マルトース、イソマルトース、トレハロース、
シユークロース、ラフイノース、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、あるいはそれらのアルキレンオキ
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、アミルアミン、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、イソトリデシルアミン、テトラデ
シルアミン、ヘキサデシルアミン、イソヘキサデシルア
ミン、オクタデシルアミン、イソオクタデシルアミン、
オクチルドデシルアミン、ドオシルアミン、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、オクタデシル
−プロピレンジアミン、オレイル−プロピレンジアミ
ン、ジエチレントリアミン、トリエチレンテトラミン、
テトラエチレンペンタミン、ペンタエチレンヘキサミン
等のポリアミンのアルキレンオキシド付加物；モノエタ
ノールアミン、ジエタノールアミン、トリエタノールア
ミン、モノイソプロパノールアミン、ジイソプロパノー
ルアミン、トリイソプロパノールアミン等のアルカノー
ルアミンやそれらのア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
とによって得ることができるが、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
共重合させるときの比は、重合性の二重結合を基準にし
た当量比で3:7〜7:3、とくに約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％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、これらの一価または二価の金属
塩、アンモニウム塩、有機アミン塩、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
かスチレン、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、イソブチレン、ジイソブチレンなどのオレフ
イン、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。
ｌ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。
l,m,nの関係であるが、ｎは０〜２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、l,m,nの関係はn/（ｌ＋ｍ）≦1/2が好ましい。
また、a,bおよびｃはａ≧０、ｂ≧０、ｃ≧０で、al
＋bm＋cn＝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）のア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、油に溶けるが水には溶けないもの、
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（トリクロロ
モノフルオロメタン）、フロンＲ−12（ジクロロジフル
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−134a（1,1,1,2−テトラフルオロエ
タン）、フロンＲ−152a（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
％以下）、そのモノ−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種以上のア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
ど、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〕
以下に実施例を記載する。
表１に以下の実施例に使用した共重合体を構成する単
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１のNo.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 18.00重量％ プロピレングリコール 37.00 〃 イオン交換水 40.00 〃 オレイン酸 3.45 〃 モルホリン 0.60 〃 ベンゾトリアゾール 0.10 〃 水酸化カリウム 0.85 〃 ジメチルシロキサン（粘度 上記合計量に対して350c
st） 100ppm 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。
実施例 2. 表１のNo.3、No.4、No.6、No.7、No.8およびNo.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（JIS B−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 20.0 〃 切削加工試験の条件 切削される材料 快削ステンレス鋼（SAE51−416F） 40φ×300（mm） 切削工具 SKH−4B（JIS G−4403） 切削速度 70m/min 加工速度 ８μ/min 切削油流量 １/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本のバイトで切削され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
効果が大きいことがわかる。
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。
実施例 3. 表５に示す組成物について、フロン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を耐圧ガ
ラス溶器にとり、−５〜60℃の範囲で白濁が生ずるかど
うかを目視により観察し、白濁を生じる場合を溶解しな
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溶解性
にすぐれ、潤滑性能にも優れていることがわかる。
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ１０Ｎ 40:08 40:22 40:24

Claims (1)

    (57)【特許請求の範囲】
  1. 【請求項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。 （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、R1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
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.
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
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.
US07/801,633 US5250205A (en) 1989-04-26 1991-12-04 Lubricating oil

Applications Claiming Priority (3)

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

Publications (2)

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

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

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO2005042679A1 (en) * 2003-10-21 2005-05-12 Union Carbide Chemicals & Plastics Refrigerant composition
BR112013028516A2 (pt) * 2011-05-06 2017-01-10 Chemetall Gmbh fluido metalúrgico sem voc sem amina
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
US4471100A (en) * 1981-01-16 1984-09-11 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

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KR900016439A (ko) 1990-11-13
EP0399239A1 (en) 1990-11-28
DE69000787D1 (de) 1993-03-04
DE69000787T2 (de) 1993-07-01
BR9001925A (pt) 1991-07-30
ES2045624T3 (es) 1994-01-16
KR0150003B1 (ko) 1998-10-01
JPH0347895A (ja) 1991-02-28
EP0399239B1 (en) 1993-01-20

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