JPH0326239B2 - - Google Patents

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Publication number
JPH0326239B2
JPH0326239B2 JP57176029A JP17602982A JPH0326239B2 JP H0326239 B2 JPH0326239 B2 JP H0326239B2 JP 57176029 A JP57176029 A JP 57176029A JP 17602982 A JP17602982 A JP 17602982A JP H0326239 B2 JPH0326239 B2 JP H0326239B2
Authority
JP
Japan
Prior art keywords
formula
carbon atoms
group
same
different
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 - Lifetime
Application number
JP57176029A
Other languages
English (en)
Other versions
JPS5871996A (ja
Inventor
Deyubasu Henrii
Kiruhimaiyaa Rudorufu
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of JPS5871996A publication Critical patent/JPS5871996A/ja
Publication of JPH0326239B2 publication Critical patent/JPH0326239B2/ja
Granted legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/20—Thiols; Sulfides; Polysulfides
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/287—Partial esters
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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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    • C10M2211/08—Halogenated waxes
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2215/064—Di- and triaryl amines
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    • C10M2215/066—Arylene diamines
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    • C10M2215/26—Amines
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Description

【発明の詳細な説明】
本発明は２個の窒素原子を含むポリサルフアイ
ドの潤滑剤添加剤としての用途に関するものであ
る。 鉱物性潤滑剤及び合成潤滑剤に、その作用特性
を改善するため種々の添加物を加えることは通常
なされていることである。特に潤滑することを望
まれている装置を摩耗からまもる添加剤供給に対
する需要がある。これらの摩耗防止剤について要
求されることはそれらが潤滑剤の許容荷重を増加
し、保護される金属部品に対して腐蝕作用を呈し
ないことである。公知の潤滑剤添加物には硫化鯨
ロウ油及び例えば西ドイツ特許公開第2166893号
及び第260610号公報に開示されているような硫化
オレフインがある。このような添加物を含有する
潤滑剤の極圧特性には屡々不満足なものがある。
殊に熱安定性が不十分であり、また腐蝕により
銅、鉄が侵される。 本発明の目的は上述せる公知の組成物の欠点を
有しない潤滑剤組成物を提供することにある。 従つて本発明は、 ａ） 鉱物性基材油及びまたは合成基材油 ｂ） 式： Ａ−（Ｓ）ｎ−Ｇ ……（） ｛式中、ｎは２ないし６の整数を表わし、Ａ
とＧとは同一であるかまたは異なつていて次
式： （式中、R1及びR2は同一または異なり、直
鎖状若しくは分岐鎖状の炭素原子数１ないし24
のアルキル基、炭素原子数３ないし18のアルケ
ニル基、炭素原子数３ないし12のシクロアルキ
ル基または核中に６ないし10個の炭素原子を含
有するアリール基または炭素原子数７ないし30
のアルキル基で、各々が未置換であるか、また
は−Cl，−ZR5，−ZCN，−NCZ，CZZ1R5，−
ZCZ1R5，−CZNR7R8，−NR7R8または−
CZZ1Eで置換されていてＺ及びZ1の各々が相互
に独立して−Ｏ−，−Ｓ−，−S2，−SO−，−
SO2，または−SO3を表わし、そしてR5は水素
原子または炭素原子数１ないし18のアルキル基
または炭素原子数３ないし18のアルケニル基を
表わし、各々が未置換であるかまたは−Cl，−
ZCN，−NCZまたは−CNで置換され、Ｅは
Na，Ｋまたは−NR7R8R9を表わし、式中、R7
ないしR9はR5で定義したと同じ意味を表わし、
同一でも異なつていてもよい。） で表わされるか、；またはＡ及びまたはＧは５
ないし12の環員と、飽和または未飽和の−（Ｓ）
ｎ基に連なる原子としての窒素原子を含有する
核とを含有し更に複素原子として−Ｏ−，−Ｓ
−または第二の窒素原子を含有することがで
き、そして核中ではR1及びR2によつて４回迄
置換することのできる複素環基を表わし、但
し、もしもＡがモルホリノであるならば、Ｇは
同様にモルホリノであつてはならない。｝ で表わされる化合物の一種以上、及び ｃ） 所望により更に他の潤滑剤添加物を含有
し、基材油(a)が該基材油に対して0.001ないし
５重量％の式で表わされる化合物を含有する
潤滑剤組成物を提供するものである。 アルキル基としてのR1及びR2にはメチル、
イソプロピル、ｎ−ブチル、第二ブチル、第三
ブチル、第三アミル、２−エチルヘキシル、ｎ
−オクチル、第三オクチル、ｎ−ドデシル、
１，１，７，７−テトラメチルオクチル、ｎ−
オクチルデシルが挙げられ、２−エチルヘキシ
ルが好ましい。 シクロアルキルとしてのR1及びR2にはシク
ロプロピル、シクロペンチル、シクロヘキシ
ル、シクロヘプチル、シクロオクチルまたはシ
クロドデシルがあげられシクロペンチル及びシ
クロヘキシルが好ましい。 アルアルキルとしてのR1及びR2はベンジル、
フエニルエチル及び２−フエニル−イソプロピ
ルが挙げられる。 アルカリールとしてのR1及びR2はトリル、
キシリル、２，６−ジエチルフエニルまたは４
−第三−ブチルフエニルが挙げられる。 アリールとしてのR1及びR2はフエニル、α
−ナフチルまたはβ−ナフチルが挙げられる。 Ａ及びまたはＧとして表わされる複素環基には
モルホリノ、ピペラジノ、ピペリジノ、ピロリジ
ノ、ヘキサメチレンイミノ、イミダゾリジノ、イ
ミダゾまたはピロロが挙げられ、Ａがもしもモル
ホリノであるならば、Ｇは同様にモルホリノであ
つてはならない。 上記の基R1及びR2または複素環基Ａ及びまた
はＧの置換基として選ばれるものは：メチル、エ
チル、イソプロピル、ｎ−ブチル、ビニル、アリ
ル、塩素、メルカプト、メチルチオ、メチルスル
ホキシド、ドデシルチオ、ドデシルジチオ、スル
ホ、スルホネート、スルフアモイル、メトキシス
ルフイニル、ヒドロキシ、メトキシ、エトキシ、
アリルオキシ、ｎ−オクチルオキシ、３，６，
９，12，15−ペンタオキサ−ヘプタデシルオキ
シ、シアノ、シアネート、チオシアネート、イソ
チオシアネート、メトキシカルボニル、イソオク
チルオキシカルボニル、カルボキシ、ナトリウム
カルボキシレート、アセトキシ、２−エチルヘキ
サノイルオキシ、ブタノイル、ジメチルアミノ、
ビス−（２，2′）ジヒドロキシエチルアミノ、ジ
ドデシルアミノである。いずれにしても本発明は
上記の置換基のリストにより制約されるものでは
ない。 潤滑剤組成物で好ましいものは式においてＡ
とＧとが同一または異なり次式： （式中、R1及びR2は同一または異なり、未置
換または−Cl，−ZR5，−ZCN，−NCZ，−
CZZ1R5，−ZCZ1R5，−CZNR7R8，−NR7R8または
−CZZ1Eで置換された直鎖状若しくは分岐鎖状の
炭素原子数１ないし24のアルキル基を表わし、但
しＡのみが上記の意味を有するならば、Ｇは前述
したように５ないし12員環の複素環基を表わす。） で表わされる基を表わす化合物(b)を含有するもの
である。 式においてＡとＧとが同一または異なり次
式： （式中、R1及びR2は同一または異なり、R5も
同様に、未置換または−Cl，−ZR5，ZCN，−
NCZ，−CZZ1R5，NR7R3，−ZCZ1R5，−
CZNR7R8または−CZZ1Eで置換された直鎖状も
しくは分岐鎖状の炭素原子数１ないし18のアルキ
ル基を表わし、但しＡのみが上記の意味を有する
ならば、Ｇは前述したように５ないし12員環の複
素環基を表わす。） で表わされる基を表わす化合物(b)を含有する潤滑
剤組成物もまた好ましい。 更に、式においてＡがモルホリノ基を意味
し、Ｇは次式： （式中、R1及びR2は上記の意味を有する。） で表わされる基を表わす化合物(b)を含有する潤滑
剤組成物も好ましい。 なお更に、式で表わされ、ｎが２を表わす化
合物(b)を含有する潤滑剤組成物も好ましい。 下記の三種の潤滑剤組成物は、本発明を具体的
に示すものとして特に好ましいものである。 １ 式で表わされ、式中ＡとＧとが同一である
かまたは異なつていて次式： （式中、R1及びR2は同一または異なり直鎖
状若しくは分岐鎖状の未置換の炭素原子数１な
いし18のアルキル基を表わす。） で表わされる基を表わす化合物(b)を含有する潤
滑剤組成物。 ２ 式で表わされ、式中Ａ及びＧが次式： （式中、R1とR2は同一の基で炭素原子数５
ないし15のアルキル基を表わす。） で表わされる基を表わす化合物(b)を含有する潤
滑剤組成物。 ３ 式で表わされ、式中Ａ及びＧが同一で、上
記で定義したような同一の５ないし12員環の複
素環を表わす化合物(b)を含有する潤滑剤組成
物。 本発明の実施に使用され式で表わされる化
合物は公知であり、米国特許第3359247号明細
書中に加硫剤として、またゴムの加硫促進剤と
して記載されている。それらはここで詳細に記
すには及ばぬ公知の方法により調製することが
できる。例えば第二アミンを塩化硫黄及び塩基
と２：１：２のモル比で溶媒中で反応させるこ
とができる。 式で表わされる化合物の例： １ ビス−（ジイソオクチルアミノ）−ジサルフア
イド ２ ビス−（ジシクロヘキシルアミノ）−ジサルフ
アイド ４ ビス−（Ｎ−フエニル−Ｎ−エチルアミノ）−
ジサルフアイド ５ 〔CH3CH2−（OCH2CH2）5〕2−Ｎ−Ｓ−Ｓ−
Ｎ−〔（CH2CH2O）5CH2CH3〕2 ６ （H25C12SCH2CH2）2N−Ｓ−Ｓ−Ｎ−
（CH2CH2SC12H15）2 ８ ビス−（Ｎ−２−エチルヘキシル−Ｎ−２−
シアノエチルアミノ）−ジサルフアイド ９ ビス−（ジ−２−アセトキシエチルアミノ）−
ジサルフアイド 10 ビス−（２−トリクロロメトキシカルボニル
ピロリジノ）−ジサルフアイド 11 ビス−（ジ−ｐ−メチルピペラジノ）−ジサル
フアイド 12 ビス−（ジピペリジノ）−ジサルフアイド 13 ビス−（ジシクロヘキシルアミノ）−テトラサ
ルフアイド 14 （ジシクロヘキシルアミノモルホリノ）−ジ
サルフアイド 15 ジチオ−テトラ−ｎ−ブチル ビス−（イミ
ノジアセテート） 更に特定の作用性を改善するために所望により
潤滑剤組成物に添加することのできる潤滑剤添加
剤(c)で好ましいものは酸化防止剤、金属奪活剤、
防錆剤、粘度指数改良剤、流動点降下剤及び分散
剤／洗浄剤である。 酸化防止剤の例： ａ） アルキル化及び未アルキル化芳香族アミン
及びその混合物、例えば：ジオクチルジフエニ
ルアミン、モノ−第三−オクチルフエニル−α
及び−β−ナフチルアミン、フエノトリアジ
ン、ジオクチルフエノチアジン、フエニル−α
−ナフチルアミン、Ｎ，N′−ジ−第二ブチル
−ｐ−フエニレンジアミン。 ｂ） 立体障害性フエノール、例えば： ２，６−ジ−第三−ブチル−ｐ−クレゾー
ル、４，4′−ビス−（２，６−ジイソプロピル
フエノール）、２，４，６−トリイソプロピル
フエノール、２，2′−チオ−ビス−（４−メチ
ル−６−第三ブチルフエノール）、４，4′−メ
チレン−ビス−（２，６−ジ−第三−ブチルフ
エノール）。 ｃ） アルキル、アリールまたはアルカリールホ
スフアイト、例えば： トリノニルホスフアイト、トリフエニルホス
フアイト、ジフエニルデシルホスフアイト。 ｄ） チオジプロピオン酸またはチオジ酢酸のエ
ステル、例えば： ジラウリルチオジプロピオネートまたはジオ
クチルチオジアセテート。 ｅ） カルバミン酸及びジチオ燐酸の塩、例え
ば： ジアミルジチオカルバミン酸アンチモン、 ジアミルジチオ燐酸亜鉛 ｆ） 上記酸化防止剤の２種以上の配合物、例え
ば： アルキル化アミンと立体障害性フエノール。 金属奪活剤の例： ａ） 銅に対しては例えば：ベンゾトリアゾー
ル、テトラヒドロベンゾトリアゾール、２−メ
ルカプトベンゾトリアゾール、２，５−ジメル
カプトチアゾール、サリサイクリデンプロピレ
ンジアミン、サリチルアミノグアニジンの塩。 ｂ） 鉛に対しては例えば：セバシン酸誘導体、
キニザリン、プロピルガレート。 ｃ） 上記添加物の２種以上の配合物 防錆剤の例： ａ） 有機酸、そのエステル、金属塩及び無水
物、例えば：Ｎ−オレイルサルコシン、ソルビ
タンモノオレエート、ナフテン酸鉛、ドデセニ
ルコハク酸無水物。 ｂ） 含窒素化合物、例えば： 一級、二級または三級の脂肪族もしくは環状
脂肪族のアミン及び有機酸、無機酸のアミン
塩、例えば油溶性アルキルアンモニウムカル
ボキシレート。 複素環化合物、例えば置換イミダゾリン及び
オキサゾリン。 ｃ） 含燐化合物、例えば：燐酸部分エステルの
アミン塩。 ｄ） 含硫黄化物、例えば：ジノニルナフタレン
スルホン酸バリウム、芳香族（石油）スルホン
酸カルシウム。 ｅ） 上記添加物の二種以上の配合物。 粘度指数改良剤の例： ポリメタクリレート、ビニルピロリドン／メ
タクリレートコポリマー、ポリブテン、オルフ
インコポリマー、スチレン／アクリレートコポ
リマー 流動点降下剤の例： アルキル化ナフタレン、アルキル化フエノー
ル、ポリメタクリレート。 洗浄剤と分散剤の例： ポリアルケニルサクシンイミド、油溶性金属石
鹸例えばカルシウム、バリウム、マグネシウム及
びアルミニウムのカルボキシレート、フエノレー
トまたはスルホネート。 他の耐摩耗性添加物の例： 硫黄及びまたは燐及びまたはハロゲン原子を含
有する化合物、例えば硫化植物油、ジアルキルジ
チオ燐酸亜鉛、トリトリルホスフエート、塩素化
パラフイン、アルキル及びアリールジサルフアイ
ド。更に本発明の潤滑剤組成物中の潤滑剤添加物
(c)の濃度は、どのような型の添加物が使用される
かにより著しく変化する。しかしながらこれらの
濃度は当業者にとり極めて公知なので、特に詳細
に述べることを省く。 式で表わされる化合物を潤滑剤添加物として
使用することもまた、さらに本発明の目的を構成
するものである。 数種の式で表わされる化合物を同時に使用す
るときはこれらの化合物を基材油に個別にまたは
混合物の形で添加する。 式で表わされる化合物は極く微量用いても潤
滑剤に対する有効な極圧添加物である。そこで潤
滑剤を基準として0.001ないし５重量％、好まし
くは0.02ないし３重量％の式で表わされる化合
物を添加された鉱物性潤滑油、合成潤滑油及びそ
の混合物は優れた極圧潤滑性を有し、そのことは
潤滑された摩擦面における摩耗と引裂の著しい減
少によつて観察することができる。適切な潤滑油
は当業者には公知のもので例えば“シユミエルミ
ツテル タツシエンブツフ（Schmiermittel
Taschenbuch）”｛ヒユツテイツヒ フエアラー
ク、ハイデルベルク（Hu¨thig Verlag，
Heidelberg），1974｝に記載されている。 本発明を下記の実施例により説明する。 実施例 添加物１のために下に記した方法に従つて製品
を調整する。“部”は重量部を示し、化合物の番
号は第15頁乃至第17頁の記載の事項と対応する。 式で表わされる添加物１の製造 ジイソオクチルアミン10部をエーテル67部に加
え、この混合物に先ず１ないし３℃で50分かけ
て、エーテル10部中塩化硫黄28部の溶液の半分と
次に水酸化ナトリウムの25％水溶液３容量部を加
える。次に塩化硫黄溶液の残部と水酸化ナトリウ
ム25％水溶液を更に３容量部、１ないし３℃で40
分かけて同時に加える。水溶液相の分離後、有機
溶媒相を３分割した水25部で洗浄し、次に乾燥濃
縮して黄色油状物11部を得る。 実施例１乃至３、および５乃至９ 潤滑剤組成物８種を、試験法IP239／69（油及
びグリースのための極圧及び摩耗潤滑試験、四球
装置）によりシエル四球装置を用いて試験する。
その結果を第１表に総括する。
【表】
【表】 実施例 10 ローム アンド ハース（Rohm＆Haas）か
ら“プライメン（PRIMENE） ”（登録商標）
81−Ｒとして市販されている第一アミン混合物を
高温でアクリロニトリルと反応させ第二アミンの
混合物を得る。次にこの生成物を塩化硫黄と反応
させる。石油蒸溜物を溶媒として用うることを除
き、反応条件は式で表わされる添加物の調製の
ために述べたと同じである。シエル四球装置を用
い下記の結果を得た： 添加物濃度：１％ 基 材 油：ビトレア41 ISL ：80Kg WL ：220Kg WSD ：0.5mm 実施例 11 １重量％の添加物１を含有するビトレア41 の
腐蝕性をDIN（ドイツ国工業標準）51 585に従つ
て測定した。結果：腐蝕度０−１、すなわち腐蝕
なし。

Claims (1)

  1. 【特許請求の範囲】 １ ａ） 鉱物性基材油または合成基材油 ｂ） 式： Ａ−（Ｓ）o−Ｇ …（） ｛式中、ｎは２ないし６の整数を表わし、Ａと
    Ｇとは同一であるかまたは異なつていて次式： （式中、R1及びR2は同一または異なり、直鎖
    状若しくは分岐鎖状の炭素原子数１ないし24のア
    ルキル基、炭素原子数３ないし18のアルケニル
    基、炭素原子数３ないし12のシクロアルキル基ま
    たは核中に６ないし10個の炭素原子を含有するア
    リール基または炭素原子数７ないし30のアルアル
    キル基で、各々が未置換であるか、または−Cl，
    −ZR5，−ZCN，−NCZ，CZZ1R5，−ZCZ1R5，−
    CZNR7R8，−NR7R8または−CZZ1Eで置換され
    ていてＺ及びZ1の各々が相互に独立して−Ｏ−，
    −Ｓ−，−S2，−SO−，−SO2，または−SO3を表
    わし、そしてR5は、水素原子または炭素原子数
    １ないし18のアルアルキル基または炭素原子数３
    ないし18のアルケニル基を表わし、各々が未置換
    であるかまたは−Cl，−ZCN，−NCZまたは−CN
    で置換され、ＥはNa，Ｋまたは−NR7はR8R9を
    表わし、式中、R7ないしR9はR5で定義したと同
    じ意味を表わし、同一でも異なつていてもい。） で表わされるか；または、Ａ及びまたはＧは５な
    いし12の環員と、飽和または未飽和の−（Ｓ）ｎ
    基に連なる原子としての窒素原子を含有する核と
    を含有し更に複素原子として−Ｏ−，−Ｓ−また
    は第二の窒素原子を含有することができ、そして
    核中ではR1及びR2によつて４回迄置換すること
    のできる複素環基を表わし、 但し、もしもＡがモルホリノであるならば、Ｇ
    は同様にモルホリノであつてはならない。｝
JP57176029A 1981-10-06 1982-10-06 潤滑剤組成物 Granted JPS5871996A (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH6416/81-7 1981-10-06
CH641681 1981-10-06

Publications (2)

Publication Number Publication Date
JPS5871996A JPS5871996A (ja) 1983-04-28
JPH0326239B2 true JPH0326239B2 (ja) 1991-04-10

Family

ID=4309250

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Application Number Title Priority Date Filing Date
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EP (1) EP0076784B1 (ja)
JP (1) JPS5871996A (ja)
CA (1) CA1244469A (ja)
DE (1) DE3276907D1 (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4959167A (en) * 1988-02-12 1990-09-25 Ciba-Geigy Corporation Asymmetric disulfides in lubricant compositions
GB9405903D0 (en) * 1994-03-24 1994-05-11 Exxon Chemical Patents Inc Lubricating compositions

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2343524A (en) * 1940-02-17 1944-03-07 Monsanto Chemicals Process of preparing morpholine sulphides
US2351657A (en) * 1942-12-26 1944-06-20 Carbide & Carbon Chem Corp Lubricant
US2364122A (en) * 1943-06-17 1944-12-05 Carbide & Carbon Chem Corp Oil additive
US2598333A (en) * 1950-09-29 1952-05-27 Monsanto Chemicals Nu-thio bis nu-tetrahydrofurfuryland tetrahydrothenyl-amines
US2648673A (en) * 1950-10-10 1953-08-11 Monsanto Chemicals Nu-thio pyrrolidines
US2649470A (en) * 1951-10-10 1953-08-18 Monsanto Chemicals Cyanoalkyl substituted amine sulfides
US3251811A (en) * 1961-10-02 1966-05-17 Phillips Petroleum Co Process for the preparation of polysulfide polymers
US3394185A (en) * 1964-09-09 1968-07-23 Rohm & Haas Nu, nu'-bis (t-alkylamino) disulfides
US3577459A (en) * 1968-05-20 1971-05-04 Procter & Gamble N-alkyl and n,n-dialkyl alkanesulfonamide bis(alkylimines)and n-alkyl and n,n-dialkyl alkylimines and processes for preparing same
US4039552A (en) * 1975-03-05 1977-08-02 Exxon Research And Engineering Company Two phase process for the preparation of azole and azoline disulfides
US4110234A (en) * 1975-11-05 1978-08-29 Uniroyal, Inc. Antioxidant stabilized lubricating oils
US4096078A (en) * 1977-06-28 1978-06-20 Texaco Inc. Synthetic aircraft turbine oil

Also Published As

Publication number Publication date
US4482463A (en) 1984-11-13
CA1244469A (en) 1988-11-08
EP0076784A3 (en) 1985-01-09
JPS5871996A (ja) 1983-04-28
EP0076784A2 (de) 1983-04-13
EP0076784B1 (de) 1987-08-05
DE3276907D1 (en) 1987-09-10

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