JPS6187793A - グリ−ス組成物 - Google Patents

グリ−ス組成物

Info

Publication number
JPS6187793A
JPS6187793A JP60178685A JP17868585A JPS6187793A JP S6187793 A JPS6187793 A JP S6187793A JP 60178685 A JP60178685 A JP 60178685A JP 17868585 A JP17868585 A JP 17868585A JP S6187793 A JPS6187793 A JP S6187793A
Authority
JP
Japan
Prior art keywords
grease
epoxides
grease composition
composition according
thickener
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
JP60178685A
Other languages
English (en)
Other versions
JPH0579119B2 (ja
Inventor
ジヨン・フイリツプス・ドウナー
アンドリユー・ジーン・ホロドウイツキー
ジヨン・アントン・ケラー、ジユニア
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.)
Mobil Oil AS
Original Assignee
Mobil Oil AS
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 Mobil Oil AS filed Critical Mobil Oil AS
Publication of JPS6187793A publication Critical patent/JPS6187793A/ja
Publication of JPH0579119B2 publication Critical patent/JPH0579119B2/ja
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M169/06—Mixtures of thickeners and additives
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    • C10M117/00—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof
    • C10M117/02—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof having only one carboxyl group bound to an acyclic carbon atom, cycloaliphatic carbon atom or hydrogen
    • C10M117/04—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof having only one carboxyl group bound to an acyclic carbon atom, cycloaliphatic carbon atom or hydrogen containing hydroxy groups
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    • C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/14—Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/14—Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds
    • C10M2201/145—Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds used as thickening agents
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/1245—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof used as thickening agent
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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】 本発明はヒドロキシル基含有石鹸増粘剤及びエポキシド
ホウ酸塩からなるグリース組成物に関する。
米国特許第４，４１０，４３８号明細書はホウ素が過剰
に存在するホウ酸エポキシドを含有するグリースを含め
た潤滑剤組成物を記載している。また特定の他の形形の
エポキシドが潤滑剤に使用されている０例えば、米国特
許第４，２４４．８２９号明細書は潤　　゛滑油の潤滑
剤としてのエポキシ化した脂肪酸エステルの使用を記載
している。
本発明は主要量のグリース、及び一般式［式中、Ｒ，Ｒ
１、Ｒ２及びＲ３はそれぞれ水素またはＣ２〜Ｃ３゜の
炭化水素基（ハイドロカルビル基）であって、Ｒ，Ｒ’
　、Ｒ２またはＲ３の少なくとも１個が炭化水素基であ
る］で表わされるエポキシドと、ホウ素化合物、特にメ
タホウ酸塩、または他のホウ素給源、ホウ酸、ホウ素酸
化物または一般式（Ｒ’　０）ｘＢ（ＯＨ）ｙ（式中、
Ｘは１または２または３であり、ｙはＯまたは１または
２であり、Ｘとｙの合計が３であり、Ｒ４すなわち各Ｒ
４は１〜６個の炭素原子を含有するアルキル基である）
で表わされるアルキルホウ酸塩を反応させることによっ
て調製した少量の化合物とからなるグリース組成物にお
いて、グリースが少なくとも１５重量％のヒドロキシル
基金、有石鹸用増粘剤と含有する増粘剤を含むことを特
徴とするグリース組成物を提供するにある。
好適なエポキシドは過ホウ酸含有、すなわち化学量論量
以上のホウ素を含有するホウ酸塩生成物である。
ホウ酸エポキシドはエポキシドとホウ素酸化物、ホウ酸
、ホウ酸アルキルまたはそれらの混合物のような適当な
ホウ素化合物を反応させることによって造ることができ
る。得られた生成物は主としてモノホウ酸エステル類で
あるが、他の使用可能な生成物はエポキシオクタンまた
はより高級なオリゴマー類と、対応するホウ酸エステル
類を形成するためのホウ素化合物との反応生成物である
。エポキシドの炭化水素基は炭素原子８〜３０個、好適
には１０〜２２個をもつアルキル基、アリール基、シク
ロアルキル基またはシクロアルケニル基である。好適な
炭化水素基はアルキル基である。
適当なエポキシドは例えば１．２−エポキシオクタン、
１．２−エポキシデカン、１．２−エポキシドデカン、
１．２−エポキシテトラデカン、１．２−エポキシペン
タデカン、１，２−エポキシヘキサデカン、１．２−エ
ポキシヘプタデカン、１，２−エポキシオクタデカン、
１．２−エボキシエイコサン及びそれらの混合物、並び
に池のエポキシドとの混合物である。これらは０２！〜
Ｃ３゜オレフィン類の混合物のエポキシド及びＣ２４〜
Ｃ２，オレフィン類の混合物のエポキシドを包含する。
また、上述のエポキシドに包含されるものはオクテンの
二量体、デセンの二量体、オクテンとデセンの混合物の
二量体から誘導されたエポキシド、デセンの三量体から
誘導されたエポキシド、プロピレンの三量体または四量
体、及びブチレンの二量体、三量体及び四量体等から誘
導されたエポキシドなどである。
上述のように、ホウ素化合物はホウ酸、ホウ素酸化物ま
たはホウ酸アルキルであり、ホウ酸が好適である。ホウ
酸アルキルはホウ酸モノエチル、ホウ酸ジエチル及びホ
ウ酸トリエチルのようなホウ酸モノアルキル、ホウ酸ジ
アルキル及びホウ酸トリアルキルを包含する。
ホウ酸エステルを形成するための反応は約８０℃へ約２
６０℃、好適には約り１０℃〜約１８０℃の温度で行な
われる。温度の選択は大部分反応剤及び溶媒を使用する
が否かに依存する。この反応を行なう際に、エポキシド
／ホウ素化合物のモル比が約０．２／１〜約１／１、好
適には約０．５７１〜約０．９／１となるように反応剤
の量を選択することが好適である。エポキシドは約０．
１重量％から１０重置部またはそれ以上のホウ素を含有
するホウ酸エステルを形成するために過量のホウ酸エス
テル化剤と反応させることができる。
大気圧が通常好適であるが、反応は約１００　　゛ｋＰ
ａ〜約５００ｋＰａの圧力条件下で好都合に行なうこと
ができる。更に、条件が正常である場合、溶媒を使用す
ることができる。ベンゼン、トルエン、キシレン及び１
．４−ジオキサンを含む比較的極性のない非反応性溶媒
を使用することができる。プロパツール及びブタノール
を含む他の炭化水素溶媒及びアルコール溶媒を使用でき
る。アルコール溶媒と炭化水素溶媒の混合物もまた使用
できる。
反応時間は臨界的なものではない、従って、操作のいず
れの段階も約１時間〜約２０時間の期間内に行なうこと
ができる。
本発明のグリース組成物を造るために使用する増粘剤は
１分子当り１２〜約３０個の炭素原子をもつヒドロキシ
ル基含有脂肪酸類、ヒドロキシル基含有脂肪酸グリセリ
ド類及びヒドロキシル基含有脂肪酸エステルのアルカリ
金属塩（石鹸）、アルカリ土類金属塩（石鹸）またはア
ミン塩（石鹸）を少なくとも部分的に含有する増粘剤で
ある。ナトリウム、リチウム、カルシウム及びバリウム
が金属の代表例である。リチウムが好適である。上述の
脂肪酸及び脂肪酸物質の中で好適なものは１２−ヒドロ
キシステアリン酸及び１２−ヒドロキシステアリン酸塩
、１４−ヒドロキシステアリン酸、１６−ヒドロキシス
テアリン酸及び６−ヒドロキシステアリン酸を含むグリ
セリド類である。
これらの増粘剤はグリース組成物中の増粘剤の全量を構
成する必要はない、全増粘剤を基準として約１５重量％
程度の少量でも上述の増粘剤を使用すれば顕著な利点が
達成できる。増粘剤の残余量、すなわち約８５重量％ま
でが種々の他の増粘剤を本発明のグリース組成物中に使
用することができる。有用な他の増粘剤に包含されるも
のはメチル−１２−ヒドロキシステアリン酸のアルカリ
金属塩（石鹸）及びアルカリ土類金属塩（石鹸）、０４
〜ＣＩ２ジカルボン酸類のジエステル類の石鹸、及びタ
ル油脂肪酸の石鹸である一０１２〜３ｏの炭・　素原子
をもち、且つ遊離のヒドロキシル基が存在しない他の脂
肪質のアルカリ金属塩またはアルカリ土類金属塩を使用
することができる。これらはステアリン酸及びオレイン
酸の金属塩（石鹸）２包含する。
他の増粘剤はステアリン酸−酢酸カルシウム（米国特許
第２，１９７，２６３号）、ステアリン酸−酢酸バリウ
ム（米国特許第２，５６４，５６１号）、ステアリン酸
−力プリル酸−酢酸カルシウム外体（米国特許第２：９
９９．０６５号）、カプリル酸−酢酸カルシウム（米国
特許第２，９９９，０６６号）、及び因分子Ｍ酸類、中
分子量酸類及び高分子量酸類及び堅果油酸類のカルシウ
ム塩及び石鹸のような塩及び石鹸錯体を包含する。
他のグループの増粘剤は置換尿素、フタロシアニン、イ
ンダスレン、ペリルイミド（ｐｅｒｙｌｉｍｉｄｅ）、
ピロメリ・ントジイミド（ｐｙｒｏ＋＊ｅｌｌｉｔｄｉ
ｉ＋＊１ｄｅ）、及びアンメリン（ａｍｍｅｌｉｎｅ）
のような顔料、並びに疎水性粘土よりなる。上述の増粘
剤は初めから親水性の粘土から、グリース組成物の成分
として使用する前に、該粘土粒子の表面に長鎖炭化水素
残基を導入することによって、例えば粘土をオニウム化
合物のような有機質カチオン界面活性剤で予備処理する
ことによって疎水状聾に変換することによって調製する
ことができる０代表的なオニウム化合物はジメチルジオ
クタデシルアンモニウムクロリドのようなテトラアルキ
ルアンモニウムクロリド、′ジメチルジベンジルアンモ
ニウムクロリドまたはそれらの混合物である。
本発明において、増粘剤はヒドロキシル基含有金属石鹸
または含有ヒドロキシル基含有非金属石鹸を少なくとも
１５重量％含有し、全増粘剤は全グリース組成物の約３
重量％〜約２０！ｉ量％を構成することが好ましい。
また、グリースはエポキシドと少なくとも等モル量のホ
ウ素化合物との反応により好都合に得ることができるホ
ウ酸エポキシドを約０．０１重量％〜約１０重量％、好
適には約０．１重量％〜約２重量％含有する。
ヒドロキシル基含有増粘剤及びホウ酸エポキシドを含有
する本発明のグリース組成物は同じグリースビヒクル、
同じホウ酸エポキシド及び異なる増粘剤、例えばヒドロ
キシル基未含有増粘剤から誘導されたグリースの滴点よ
り予想外に高い滴点をもつ。
通常、ホウ酸エポキシドは所望の程度の摩擦低減、耐摩
耗活性、酸化防止活性、高温安定性または錆防止活性を
付与するために有効な任意の量で使用することができる
。
本発明のグリース組成物は鉱油、合成油またはそれらの
混合物から造ることができる０通常、パラフィン質鉱油
、ナフテン質鉱油またはそれらの混合物は例えば３８℃
で約４５５ＵＳ〜３８℃で約６００Ｏ３ＵＳ、好適には
９９℃で約５０ＳＵＳ〜約２５Ｏ８ＵＳのような所定の
潤滑油粘度範囲のものであることができる。これらの油
は約１００またはそれ以上の粘度指数範囲をもつことが
ある。約７０〜約９５の粘度指数が好適である。上述の
油の平均分子量は約２５０〜約８００の範囲であること
ができる。グリースを製造する際に、増粘剤及び他の添
加剤成分の所望の量を添加後、全グリース組成物の釣り
合いをとるために充分な量のグリース調製用の潤滑油を
通常使用する。
鉱油の代わりに合成油を使用する場合、この夕４イブの
種々の化合物が利用できる０代表的な合成ビヒクルはポ
リインブチレン、ポリイソブチン類、水素化ポリデセン
類、ポリプロピレングリコール、ポリエチレングリコー
ル、トリメチロールプロパンエステル類、ネオペンチル
エステル及びペンタエリトリトールエステル、ジ（２−
エチルヘキシル）セバケートメ、ジ（２−エチルヘキシ
ル）アジベートメ、ジブチルフタレート練、フｌレオロ
カーボン類、珪酸エステル類、シラン類、リン含有酸類
のエステル類、液体尿素、フェロセン誘導体類。
水素化合成油類、鎖状ポリフェニル類、シロキサン類及
びシリコーン類（ポリシロ午サン類）、ブチル置換ビス
（ｐ−フェノキシフェニル）エーテル類により代表され
るアルキル置換ジフェニルエーテル類、フェノキシフェ
ニルエーテル類を包含する。
本発明のグリース組成物は周知のグリースでは得られな
い増大した滴点及び改善されたグリース稠度特性の利点
をもつ０本発明のグリース組成物はホウ酸エポキシドの
添加量と鹸化完了後の完全に形成した石鹸グリースとを
単に混合することによって製造できる付加的な利点をも
つ。
以下に、実施例（以下、特記しない限り単に「例」と記
載する）を挙げ、本発明を更に説明する。
１．２−エポキシヘキサデカン［ユニオン・カーバイド
社（Ｕ　ｎ１ｏｎ　Ｃａｒｂｉｄｅ）から市販されてい
る］約１４４０ｙ、トルエン５００１１及びホウ酸５０
０９を加熱装置、撹拌装置及びコンデンサー付デイ−ン
ースターク管を備えたガラス製５１反応器に装入した。
内容物を水の蒸発が停止するまで撹拌しながら１４４℃
へ加熱した；これには約１０特開を要した。溶媒を約１
６０℃で減圧蒸留することにより除去し、生成物な約１
２０℃で珪藻土に。
通すことによってろ過すると透明琥珀色の流体が得られ
、冷却すると琥珀色のロウ質流体となった。
匠−りじ」」江 密閉容器中、約１７７℃及び最終圧力約８６０ｋＰａで
、鉱油ビヒクル（約７６重量％）中に１２−ヒドロキシ
ステアリン酸約８重量％、１２−ヒドロキシステアリン
酸のグリセリド９重量％並びに水酸化リチウム・１水和
物２．５重量％を含有する混合物を鹸化することによっ
てヒドルキシステアリン酸リチウムグリース増粘剤を調
製した。
医−」− 例２の増粘剤を開放型反応器中で脱水し、例１で調製し
たホウ酸エポキシド１．４重量％をグリース濃縮物へ添
加した。
桝−コしけり【湾上 基準グリースをステアリン酸及びｉ＜ルミチン酸の５０
１５０重量％混自物のリチウム塩（石鹸）（ヒドロキシ
ル基未含有増粘剤ンで増粘しな。
伝−」トΩ１考」０− ５０１５０重量％ヒドロキシル基含有増粘剤／ヒドロキ
シル基未含有増粘剤混含物を形成するために例２の基準
グリースと例４の基準グリースを混きした。
医−」Ｌす【ムＪｉｌ− 例４の基準グリースと例１のホウ酸エポキシド２重量％
を混合した。
九−二 例５の基準グリースと例１のホウ酸エポキシド（ａ）１
％及び（ｂ）２％を混合した。
上述のグリース組成物を使用してＡＳＴＭ　　Ｄ２２６
５−７８グリ一ス滴点試験を行なった結果を以下の表に
記載する。
ホウ酸エポキシドが不在である脱水したしドロキシステ
アリン酸塩増粘剤の滴点は１９９℃であった。該増粘剤
ヘエボキシドホウ酸塩１．４重量％を添加すると、滴点
は８外にも２５７℃へ上昇した。

Claims (1)

  1. 【特許請求の範囲】 １、主要量のグリース、及び一般式 ▲数式、化学式、表等があります▼ （式中、Ｒ、Ｒ＾１、Ｒ＾２及びＲ＾３はそれぞれ水素
    またはＣ＿１〜Ｃ＿３＿０の炭化水素基であって、Ｒ、
    Ｒ＾１、Ｒ＾２またはＲ＾３の少なくとも１個が炭化水
    素基である）で表されるエポキシドとホウ素化合物の反
    応生成物を０．０１〜１０重量％含有してなるグリース
    組成物において、グリースが少なくとも１５重量％のヒ
    ドロキシル基含有石鹸増粘剤を含有する増粘剤を含むこ
    とを特徴とするグリース組成物。 ２、増粘剤が炭素原子１２〜３０個をもつヒドロキシル
    基含有脂肪酸、ヒドロキシル基含有脂肪酸グリセリドま
    たはヒドロキシル基含有脂肪酸エステルのアルカリ金属
    塩、アルカリ土類金属塩またはアミン塩である特許請求
    の範囲第１項記載のグリース組成物。 ３、金属塩がナトリウム塩、リチウム塩、カルシウム塩
    またはバリウム塩である特許請求の範囲第２項記載のグ
    リース組成物。 ４、ヒドロキシル基含有増粘剤を１２−ヒドロキシステ
    アリン酸、１６−ヒドロキシステアリン酸、６−ヒドロ
    キシステアリン酸、またはそれらのグリセリドまたはエ
    ステルから誘導する特許請求の範囲第２項または第３項
    記載のグリース組成物。 ５、エポキシドを１，２−エポキシオクタン、１，２−
    エポキシデカン、１，２−エポキシドデカン、１，２−
    エポキシテトラデカン、１，２−エポキシペンタデカン
    、１，２−エポキシヘキサデカン、１，２−エポキシオ
    クタデカン、１，２−エポキシエイコサン、Ｃ＿２＿２
    〜Ｃ＿３＿０オレフィン類の混合物のエポキシド、Ｃ＿
    ２＿４〜Ｃ＿２＿８オレフィン類の混合物のエポキシド
    、デセン三量体のエポキシド、オクタン二量体のエポキ
    シド、デセン二量体のエポキシド、オクタン及びデセン
    の混合物の二量体のエポキシド、プロピレンの三量体及
    び四量体のエポキシド、及びブチレンの三量体及び四量
    体のエポキシドから選択する特許請求の範囲第１項から
    第４項までのいずれか１項に記載のグリース組成物。 ６、ホウ素化合物がメタホウ酸塩、ホウ酸、ホウ素酸化
    物または一般式（Ｒ＾４Ｏ）ｘＢ（ＯＨ）ｙ（式中、ｘ
    は１または２または３であり、ｙは０または１または２
    であり、ｘとｙの合計が３であり、Ｒ＾４すなわち各Ｒ
    ＾４は炭素原子１〜６個をもつアルキル基である）で表
    されるアルキルホウ酸塩である特許請求の範囲第１項か
    ら第５項までのいずれか１項に記載のグリース組成物。 ７、ホウ素化合物がホウ酸である特許請求の範囲第６項
    記載のグリース組成物。 ８、グリースビヒクルが鉱油である特許請求の範囲第１
    項から第７項までのいずれか１項に記載のグリース組成
    物。 ９、グリースビヒクルが合成油である特許請求の範囲第
    １項から第７項までのいずれか１項に記載のグリース組
    成物。 １０、グリースビヒクルが鉱油と合成油の混合物である
    特許請求の範囲第１項から第７項までのいずれか１項に
    記載のグリース組成物。
JP60178685A 1984-08-15 1985-08-15 グリ−ス組成物 Granted JPS6187793A (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/641,079 US4582617A (en) 1983-08-03 1984-08-15 Grease composition containing borated epoxide and hydroxy-containing soap grease thickener
US641079 1984-08-15

Publications (2)

Publication Number Publication Date
JPS6187793A true JPS6187793A (ja) 1986-05-06
JPH0579119B2 JPH0579119B2 (ja) 1993-11-01

Family

ID=24570856

Family Applications (1)

Application Number Title Priority Date Filing Date
JP60178685A Granted JPS6187793A (ja) 1984-08-15 1985-08-15 グリ−ス組成物

Country Status (8)

Country Link
US (1) US4582617A (ja)
EP (1) EP0173505A1 (ja)
JP (1) JPS6187793A (ja)
AU (1) AU578300B2 (ja)
BR (1) BR8503862A (ja)
CA (1) CA1264729A (ja)
NZ (1) NZ213005A (ja)
ZA (1) ZA856213B (ja)

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US5211863A (en) * 1983-01-10 1993-05-18 Mobil Oil Corporation Grease composition
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US5084194A (en) * 1984-03-07 1992-01-28 Mobil Oil Corporation Grease composition
US4780227A (en) * 1984-08-22 1988-10-25 Mobil Oil Corporation Grease composition containing borated alkoxylated alcohols
US4828734A (en) * 1985-08-27 1989-05-09 Mobil Oil Corporation Grease compositions containing borated oxazoline compounds and hydroxy-containing soap thickeners
US4858534A (en) * 1986-04-23 1989-08-22 Amoco Corporation Ballistic lubricating and process
US4735146A (en) * 1986-04-23 1988-04-05 Amoco Corporation Ballistic lubricating grease, ammunition and process
US4873008A (en) * 1987-08-21 1989-10-10 International Lubricants, Inc. Jojoba oil and jojoba oil derivative lubricant compositions
US4906393A (en) * 1988-12-30 1990-03-06 Mobil Oil Corporation Mixed phenol/dimercaptothiadiazole-derived hydroxythioether borates as antioxidant/antiwear multifunctional additives
US5487839A (en) * 1991-04-18 1996-01-30 The Lubrizol Corporation Grease compositions
US5652201A (en) * 1991-05-29 1997-07-29 Ethyl Petroleum Additives Inc. Lubricating oil compositions and concentrates and the use thereof
US5256320A (en) * 1992-07-10 1993-10-26 The Lubrizol Corporation Grease compositions
US5256321A (en) * 1992-07-10 1993-10-26 The Lubrizol Corporation Grease compositions
US5362409A (en) * 1992-07-10 1994-11-08 The Lubrizol Corporation Grease compositions
JPH07258671A (ja) * 1994-03-24 1995-10-09 Lubrizol Corp:The 無灰の低リン潤滑剤
US6100226A (en) * 1998-05-20 2000-08-08 The Lubrizol Corporation Simple metal grease compositions
US6063742A (en) * 1999-03-01 2000-05-16 The Lubrizol Corporation Grease compositions
JP4283491B2 (ja) * 2002-04-26 2009-06-24 新日本石油株式会社 グリース組成物
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Also Published As

Publication number Publication date
EP0173505A1 (en) 1986-03-05
JPH0579119B2 (ja) 1993-11-01
CA1264729A (en) 1990-01-23
BR8503862A (pt) 1986-05-27
NZ213005A (en) 1989-01-27
ZA856213B (en) 1987-03-25
AU4585585A (en) 1986-02-20
AU578300B2 (en) 1988-10-20
US4582617A (en) 1986-04-15

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