JPS6230240B2 - - Google Patents

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Publication number
JPS6230240B2
JPS6230240B2 JP57036723A JP3672382A JPS6230240B2 JP S6230240 B2 JPS6230240 B2 JP S6230240B2 JP 57036723 A JP57036723 A JP 57036723A JP 3672382 A JP3672382 A JP 3672382A JP S6230240 B2 JPS6230240 B2 JP S6230240B2
Authority
JP
Japan
Prior art keywords
acid
group
oils
phosphite
oil
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
Application number
JP57036723A
Other languages
English (en)
Other versions
JPS57164192A (en
Inventor
Uiriamu Kotsuku Furederitsuku
Rii Masaa Jerii
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.)
Lubrizol Corp
Original Assignee
Lubrizol Corp
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 Lubrizol Corp filed Critical Lubrizol Corp
Publication of JPS57164192A publication Critical patent/JPS57164192A/ja
Publication of JPS6230240B2 publication Critical patent/JPS6230240B2/ja
Granted legal-status Critical Current

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    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/022—Well-defined aliphatic compounds saturated
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/024—Well-defined aliphatic compounds unsaturated
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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Description

【発明の詳細な説明】 この発明は摩擦減少用添加剤を含有する作動流
体に関する。さらに詳しくは、この発明は式 （式中、R1およびR2はそれぞれ低級アルキル基ま
たは置換低級アルキル基である）で表わされる少
なくとも１種のリン化合物と式 （式中、R3は炭素原子10〜20個を有するアルキル
基である）で表わされる少なくとも１種のエポキ
シドとの反応により製造された組成物からなる作
動流体用摩擦変性剤を含有する作動流体に関す
る。
圧力流体および自動伝動流体のような物質等の
動力伝達用作動流体の開発には動力伝達特性を改
良するための新規な添加剤の開発が不可欠となつ
ている。頻繁に変化するはずの特性の１つは流体
の摩擦性である。すなわち、流体はその主成分で
ある基油の摩擦係数よりも実質的に低い摩擦係数
を有することがしばしば好ましい。それ故に改良
された摩擦減少用添加剤に対して多大の関心がこ
れまで寄せられてきた。
この発明の目的は摩擦係数の低い自動伝導流体
および他の作動流体を提供することである。
前記のとおり、この発明の摩擦変性剤は亜リン
酸ジエステルとエポキシドとの反応により製造さ
れた組成物を包含してなるものである。亜リン酸
ジエステルは通常、亜リン酸ジ−（低級アルキ
ル）である。ここにいう「低級アルキル」とは炭
素原子７個以下のアルキル基を意味する。
置換低級アルキル基は低級アルキル基と全く同
等と考えられる。「置換」という語には、その基
の特性または反応性を大きく変更することのない
置換基を含む基を意味する。このような置換基の
例としては、次のものがある。
ハロゲン基（フツ素基、塩素基、臭素基、ヨウ
素基） 水酸基 エーテル基（とくに低級アルコキシ基） ケト基 エステル基（とくに低級カルボアルコキシ基） ニトロ基 チオエーテル基 スルホキシ基 スルホン基 このような置換基が約１個だけ基中に存在する
のが一般である。
上記のエポキシドは炭素原子約12〜22個を含む
ものである。このようなエポキシドの市販混合物
を利用することができ、それらの使用はこの発明
の一部をなすものとする。
任意過剰のいずれの反応体も生成物の性質に実
質的に影響することなく単に生成物中に残留する
のみであるから、２つの反応体の割合には限定は
ない。通常はほぼ等モル量の２つの反応体を、ま
たはわずかに過剰のエポキシドを使用するのが好
ましい。例えば、亜リン酸ジアルキルの１モル当
り約1.0〜1.5モルのエポキシドを使用するのが望
ましい。
反応は強アルカリ性試薬、通常はアルカリ金属
またはそれから誘導されたアルキル、アルコキシ
ドあるいはアミド等の存在下でおこなわれる。ご
く少量、通常は反応体の全重量を基準としてその
約0.01〜0.5％のアルカリ性試薬が一般に必要で
ある。
反応は混合物を約100℃以上でかつその分解温
度以下の温度に、一般には約150〜225℃に単に加
熱することによつておこなわれる。好ましくは窒
素のような不活性ガスの雰囲気中で反応をおこな
う。不活性な希釈剤を使用してもよいが、通常は
必要としない。
上記の反応に続いて、例えばストリツピングに
より通常減圧の下で、揮発物を除去し、残留物を
過して所望の生成物を得る。必要に応じて、常
法により生成物を精製してもよいが、通常精製す
ることなく生成物をそのまゝこの発明の目的に使
用することができる。
この発明の組成物は簡単な化合物というよりは
むしろ恐らく各種の化合物の混合物である。それ
故にその製造方法によつてのみ完全にこの組成物
を定義することができるのである。しかし、亜リ
ン酸塩とエポキシドとの反応は主として簡単な付
加反応であること、および主生成物は式 （式中、R1、R2およびR3は上記定義のとおりであ
る）を有することの証拠がある。この式の化合物
をクロマトグラフイーのような通常の分離手段に
より生成物中に存在する他の物質から分離するこ
とができ、こうした化合物はこの発明の一部をな
すものとする。
以下の例によりこの発明に用いられる摩擦変性
剤用組成物の製造を説明する。全ての部および％
は重量基準である。
例 １ 亜リン酸ジ−ノルマルブチル194部（１モル）、
C14およびC16の直鎖α−オレフインの市販混合物
から誘導されたエポキシド239部（１モル）、およ
びナトリウムメトキシド0.2部からなる混合物を
190〜200℃で８時間加熱した。さらにエポキシド
60部（0.25モル）を追加し、200〜205℃で８時間
加熱を続けた。その後、揮発物を150℃で真空ス
トリツピングにより除去し、残留物を過助剤を
通して過し、リン6.28％を含有する所望の生成
物を得た。
例 ２ 亜リン酸ジ−ノルマルブチル776部（４モル）
と例１のエポキシド1195部（５モル）との混合物
を窒素で空気置換をし、これに金属ナトリウム
4.6部を加えた。この混合物を窒素雰囲気中で160
〜170℃で10時間加熱し、その後過助剤を通し
て過した。所望の生成物である液はリン6.30
％を含んでいた。
例 ３ 亜リン酸ジ−ノルマルブチルの代りに亜リン酸
ジ−イソヘキシルを同モル量で使用した以外は、
例２の操作をくりかえし、類似の生成物を得た。
例 ４ 使用したエポキシドがプロペン四量体から誘導
されたエポキシドであるほかは例２の操作をくり
かえして類似の生成物を得た。
本文に戻つて、先に記載したように、この発明
の組成物は作動流体における摩擦変性用添加剤と
して有用である。このような添加剤として、この
組成物は天然の、および合成の潤滑油あるいはそ
れらの混合物のような潤滑粘性をもつ各種の油を
基礎とする種々の潤滑組成物に使用されうる。こ
こに意図する潤滑組成物には主として自動伝動機
流体、伝動軸用潤滑剤および圧力流体などが含ま
れるが、他の潤滑油およびグリース組成物もまた
この発明組成物の混入によつて利益を受けうる。
天然油には動物油および植物油（例えば、ひま
し油、ラード油）ならびに溶媒精製または酸精製
されたパラフイン系、ナフテン系、あるいは混合
パラフイン−ナフテン系の鉱物性潤滑油が含まれ
る。石炭または頁岩から誘導された潤滑粘性をも
つ油もまた有用な基油である。合成潤滑油には重
合および相互重合オレフインのような炭化水素油
およびハロゲン置換炭化水素油（例えば、ポリブ
チレン、ポリプロピレン、プロピレン−イソブチ
レン共重合体、塩素化ポリブチレン等）；アルキ
ルベンゼン類（例えば、ドデシルベンゼン、テト
ラデシルベンゼン、ジノニルベンゼン、ジ−（２
−エチルヘキシル）ベンゼン等）、ポリフエニル
類（例えば、ビフエニル、ターフエニル等）など
が含まれる。酸化アルキレンの重合体および共重
合体ならびにその誘導体であつて、その末端水酸
基がエステル化、エーテル化等により変性された
ものは公知の合成潤滑油の別な一群を構成する。
これらの例は酸化エチレンまたは酸化プロピレン
の重合によつて製造される油、これらのポリオキ
シアルキレン重合体のアルキルおよびアリールエ
ーテル（例えば、平均分子量1000のメチルポリイ
ソプロピレングリコールエーテル、分子量500〜
1000のポリエチレングリコールのジフエニルエー
テル、分子量1000〜1500のポリプロピレングリコ
ールのジエチルエーテル等）、またはこれらのモ
ノおよびポリカルボン酸エステル、例えば、酢酸
エステル、混合C3〜C8脂肪酸エステル、あるい
はテトラエチレングリコールのC13オキソ酸ジエ
ステルである。合成潤滑油の別な好適な群はジカ
ルボン酸（例えば、フタル酸、コハク酸、マレイ
ン酸、アゼライン酸、スベリン酸、セバシン酸、
フマル酸、アジピン酸、リノール酸二量体等）と
種々のアルコール（例えば、ブチルアルコール、
ヘキシルアルコール、ドデシルアルコール、２−
エチルヘキシルアルコール等）とのエステルを含
む。これらのエステルの具体的な例はアジピン酸
ジブチル、セバシン酸ジ（２−エチルヘキシ
ル）、フマル酸ジ−ノルマルヘキシル、セバシン
酸ジオクチル、アゼライン酸ジイソオクチル、ア
ゼライン酸ジイソデシル、フタル酸ジオクチル、
フタル酸ジデシル、セバシン酸ジエイコシル、リ
ノール酸二量体の２−エチルヘキシルジエステ
ル、セバシン酸１モルとテトラエチレングリコー
ル２モルおよび２−エチルヘキサン酸２モルとの
反応により生成された複合エステル等である。ポ
リアルキルシロキサン油、ポリアリールシロキサ
ン油、ポリアルコキシシロキサン油、またはポリ
アリールオキシシロキサン油およびケイ酸塩油の
ようなシリコン系の油は合成潤滑剤の別の有用な
る群をなす。その例を挙げると次のとおりであ
る。ケイ酸テトラエチル、ケイ酸テトライソプロ
ピル、ケイ酸テトラ−（２−エチルヘキシル）、ケ
イ酸テトラ−（４−メチル−２−テトラエチル）、
ケイ酸テトラ−（パラ第３−ブチルフエニル）、ヘ
キシル−（４−メチル−２−ペントキシ）−ジシロ
キサン、ポリ（メチル）−シロキサン、ポリ（メ
チルフエニル）−シロキサン等。他の合成潤滑油
にはリン含有酸の液状エステル（例えばリン酸ト
リクレジル、リン酸トリオクチル、デカンホスホ
ン酸のジエチルエステル等）、重合テトラヒドロ
フラン等が含まれる。
一般にこの発明の組成物約0.05〜20.0（重量）
部を油100部に溶解して満足すべき流体が得られ
る。また、この発明の生成物と組合わせて他の添
加剤を用いることをもできる。このような添加剤
には、例えば、灰分含有または無灰の清浄剤およ
び分散剤、酸化防止剤、流動点降下剤、極圧剤、
色安定剤および消泡剤が含まれる。
灰分含有清浄剤の例はアルカリ金属またはアル
カリ土類金属とスルホン酸、カルボン酸、または
少なくとも１つの炭素−リン直接結合を有する有
機リン含有酸（例えば分子量1000のポリイソブテ
ンのようなオレフイン重合体を例えば三塩化リ
ン、七硫化リン、五硫化リン、三塩化リンと硫
黄、黄リンとハロゲン化イオウ、またはホスホロ
チオン酸クロライドのようなリン化剤で処理する
ことにより製造された有機リン含有酸）との油溶
性の中性および塩基性塩である。最も一般に使用
されるこのような酸の塩類はナトリウム、カリウ
ム、リチウム、カルシウム、マグネシウム、スト
ロンチウムおよびバリウムのそれである。
「塩基性塩」という語は金属が有機酸基よりも
化学量論的に多量に存在する金属塩をさすことを
意味する。この塩基性塩を製造するために一般に
使用される方法としては酸の鉱油溶液を例えば金
属の酸化物、水酸化物、炭酸塩、重炭酸塩または
硫化物のような金属中和剤の化学量論的過剰量と
ともに50℃以上の温度で加熱し、得られた物質を
過するものがある。その中和工程において大過
剰の金属の混入を助けるために「助触媒」を使用
することもまた知られている。助触媒として有用
な化合物の例はフエノール、ナフトール、アルキ
ルフエノール、チオフエノール、硫化アルキルフ
エノール、およびホルムアルデヒドとフエノール
系物質との縮合生成物のようなフエノール性物
質、メタノール、２−プロパノール、オクチルア
ルコール、セロソルブ、カルビトール、エチレン
グリコール、ステアリルアルコール、およびシク
ロヘキシルアルコールのようなアルコール類、お
よびアニリン、フエニレンジアミン、フエノチア
ジン、フエニル−β−ナフチルアミン、あるいは
ドデシルアミンのようなアミン類である。塩基性
塩を製造するのにとくに有効な方法は、酸に過剰
の塩基性アルカリ土類金属中和剤と少なくとも１
種のアルコール助触媒とを混合し、この混合物を
60〜200℃のような高められた温度で炭酸化する
ことを含む。
無灰清浄剤および分散剤の例としては油溶解化
単量体（例えばメタアクリル酸デシル、ビニルデ
シルエーテルまたは高分子量オレフイン）と極性
置換基を含む単量体（例えばアミノアルキルアク
リレートまたはポリ−（オキシエチレン）−置換ア
クリレート）との相互重合体あるいはステアリン
酸、オレイン酸、トール油酸、および高分子量の
アルキルまたはアルケニル置換コハク酸のような
油溶性モノカルボン酸またはジカルボン酸のアミ
ン塩、アミドあるいはイミドがある。無灰分清浄
剤としてとくに有用なものとしては、米国特許第
3272746号に記載されているようなアシル化ポリ
アミンおよび少なくとも炭素原子約54個を含む類
似の窒素化合物や、このような化合物とホウ素化
合物、リン化合物、エポキシド、アルデヒド、有
機酸等の他の反応体との反応生成物、および米国
特許第3381022号に記載されているような炭化水
素置換コハク酸のエステルがある。
補助的な極圧剤ならびに腐食防止剤および酸化
防止剤の例としては、塩素化ワツクスのような塩
素化脂肪族炭化水素、有機硫化物および多硫化
物、例えば二硫化ベンジル、二硫化ビス（クロロ
ベンジル）、四硫化ジブチル、オレイイン酸の硫
化メチルエステル、硫化アルキルフエノール、硫
化ジペンテン、および硫化テルペン、ホスホ硫化
炭化水素、例えば硫化リンとテレビンまたはオレ
イン酸メチルとの反応生成物、主に亜リン酸ジ炭
化水素および亜リン酸トリ炭化水素（例えば亜リ
ン酸ジブチル、亜リン酸ジヘプチル、亜リン酸ジ
シクロヘキシル、亜リン酸ペンチルフエニル、亜
リン酸ジペンチルフエニル、亜リン酸トリデシ
ル、亜リン酸ジステアリル、亜リン酸ジメチルナ
フチル、亜リン酸オレイル４−ペンチルフエニ
ル、亜リン酸ポリプロピレン（分子量500）置換
フエニル、亜リン酸ジイソブチル置換フエニル）
のようなリン含有エステル、金属チオカルバメー
ト、例えばジオクチルジチオカルバミン酸亜鉛お
よびヘプチルフエニルジチオカルバミン酸バリウ
ム、ホスホロジチオ酸の周期律表第族金属塩
類、例えばジシクロヘキシルホスホロジチオ酸亜
鉛、ジオクチルホスホロジチオ酸亜鉛、ジ（ヘプ
チルフエニル）ホスホロジチオ酸バリウム、ジノ
ニルホスホロジチオ酸カドミウム、および五硫化
リンとイソプロピルアルコールおよびノルマルヘ
キシルアルコールの等モル混合物との反応により
製造されたホスホロジチオ酸の亜鉛塩がある。
種々の添加剤またはその油溶液を直接鉱油中に
溶解することによりこの発明の流体をつくること
ができる。しかし、２種またはそれ以上の所望の
添加剤を含む添加剤濃縮物を製造し、こらの濃縮
物を鉱油中に溶解して作動流体を形成することが
しばしば一層便利である。
この発明の代表的な自動伝動流体は次の組成を
有する。全ての％は重量基準である。
鉱油（自動伝動流体基油） 92.25％ 例１の生成物 0.13％ 無水ポリイソブテニルコハク酸−ポリエチレンポ
リアミン（３〜７アミノ基）反応生成物 1.75％ 無水ポリイソブテニルコハク酸−ポリエチレンポ
リアミン反応生成物とホウ酸との反応生成物
0.67％ ジ−（イソオクチル）ホスホロジチオ酸亜鉛
0.64％ 牛脂油置換ジエタノールアミン 0.10％ 無水マレイン酸とスチレンの共重合体の混合エス
テル−アミド（トルエン中12％溶液） 1.20％ 炭化水素樹脂シール膨潤剤 3.00％ 置換ジフエニルアミン 0.20％ グリシドール（２モル）とC12第１アミン混合物
（１モル）との反応生成物 0.04％ シリコーン消泡剤 0.02％

Claims (1)

  1. 【特許請求の範囲】 １ 潤滑油、および本質的に式 （ここで、R1およびR2はそれぞれ同種の低級アル
    キル基、並びにR3は10ないし20個の炭素原子を
    有するアルキル基）で表わされる少なくとも１種
    のリン含有化合物よりなる摩擦変性剤を該潤滑油
    100重量部につき約0.05ないし20.0重量部の割合
    で含有してなる作動流体。
JP57036723A 1973-10-04 1982-03-10 Functional fluid Granted JPS57164192A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/403,373 US3932290A (en) 1973-10-04 1973-10-04 Phosphorus-containing friction modifiers for functional fluids

Publications (2)

Publication Number Publication Date
JPS57164192A JPS57164192A (en) 1982-10-08
JPS6230240B2 true JPS6230240B2 (ja) 1987-07-01

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JP (2) JPS5946239B2 (ja)
CA (1) CA1031318A (ja)
GB (1) GB1464456A (ja)
IT (1) IT1019461B (ja)

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US3932290A (en) 1976-01-13
CA1031318A (en) 1978-05-16
JPS5065483A (ja) 1975-06-03
GB1464456A (en) 1977-02-16
JPS5946239B2 (ja) 1984-11-10
IT1019461B (it) 1977-11-10
JPS57164192A (en) 1982-10-08

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