JP3040618B2 - Fluid composition for new viscous coupling - Google Patents

Fluid composition for new viscous coupling

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Publication number
JP3040618B2
JP3040618B2 JP4312190A JP31219092A JP3040618B2 JP 3040618 B2 JP3040618 B2 JP 3040618B2 JP 4312190 A JP4312190 A JP 4312190A JP 31219092 A JP31219092 A JP 31219092A JP 3040618 B2 JP3040618 B2 JP 3040618B2
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Japan
Prior art keywords
group
hydrocarbon group
general formula
acid
phosphorus
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
JP4312190A
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Japanese (ja)
Other versions
JPH06158081A (en
Inventor
法生 矢野
顕一 関根
郁男 福原
行男 湯橋
雅彦 福田
学 遠山
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.)
Cosmo Oil Co Ltd
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Cosmo Oil Co Ltd
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Publication date
Application filed by Cosmo Oil Co Ltd filed Critical Cosmo Oil Co Ltd
Priority to JP4312190A priority Critical patent/JP3040618B2/en
Priority to DE69316847T priority patent/DE69316847T2/en
Priority to EP93118776A priority patent/EP0599251B1/en
Publication of JPH06158081A publication Critical patent/JPH06158081A/en
Application granted granted Critical
Publication of JP3040618B2 publication Critical patent/JP3040618B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/10—Groups 5 or 15
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/12—Groups 6 or 16
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Lubricants (AREA)

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【０００１】[0001]

【産業上の利用分野】本発明は、長期間の使用において
安定なビスカスカップリング用流体組成物に関するもの
である。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a viscous coupling fluid composition which is stable for long-term use.

【０００２】[0002]

【従来の技術】ビスカスカップリングは粘性を利用した
軸継手で、自動車の走行安定性や悪路脱出を目的として
ディファレンシャル機構や四輪駆動車のプロペラシャフ
ト等に装着されるもので、その耐久性は充填されている
ビスカスカップリング用流体の性能に大きく依存してい
る。当該ビスカスカップリングの構成は、ハウジングと
ハブ、このハウジング側とハブ側にそれぞれ取り付けら
れた数十枚の薄い鉄製の環状プレートによりなり、この
中に高粘度のビスカスカップリング用流体が充填されて
いる。ハブとハウジング側の両プレート間に回転差が生
じると、両プレート間にせん断力がかかり、充填流体の
粘性によるトルクが発生し、トルクが伝達され、また回
転差が制御される。ビスカスカップリングの構造につい
ては例えば特公昭５８−４８７７９号公報に記載されて
いる。2. Description of the Related Art A viscous coupling is a shaft coupling that utilizes viscosity and is mounted on a differential mechanism, a propeller shaft of a four-wheel drive vehicle, or the like for the purpose of driving stability of a car and escaping from a rough road. Depends greatly on the performance of the viscous coupling fluid being filled. The configuration of the viscous coupling is composed of a housing and a hub, dozens of thin iron annular plates attached to the housing side and the hub side, respectively, and filled with a high-viscosity viscous coupling fluid. I have. When a rotation difference occurs between the two plates on the hub and the housing side, a shear force is applied between the two plates, a torque is generated due to the viscosity of the filling fluid, the torque is transmitted, and the rotation difference is controlled. The structure of the viscous coupling is described in, for example, Japanese Patent Publication No. 58-48779.

【０００３】このように、ビスカスカップリングは充填
されるビスカスカップリング用流体の粘性抵抗を利用し
たもので、自動車に装着される場合、出来るだけ小型で
必要なトルクを得ることが要求されるため、比較的高粘
度の流体が使われる。また、ビスカスカップリング用流
体としては温度に対する粘度変化の小さいこと、高温で
の熱安定性に優れることが要求され、従来よりシリコー
ンオイル、特に、２５℃での粘度が５０００〜５０００
００センチストークスの（cSt）ジメチルポリシロキサ
ン流体が一般に使われている。しかし、当該流体は、こ
れにかかるせん断力やプレート間の摩擦による発熱で相
当の高温になることもあり、長期間の使用において、粘
度上昇を起こし最終的にはゲル化に至ることが多いとい
う問題点があった。つまり、充填流体が著しく粘度上昇
したり、ゲル化するとビスカスカップリングの初期設定
性能が維持できなくなり、この点の解決が検討されてき
た。一方、充填流体がかなりの高温になった場合、熱分
解により粘度低下を生じ、その結果ビスカスカップリン
グの初期設定性能が維持できなくなることもあった。[0003] As described above, the viscous coupling utilizes the viscous resistance of the viscous coupling fluid to be filled. When the viscous coupling is mounted on an automobile, it is required to obtain a required torque as small as possible. A relatively high viscosity fluid is used. In addition, a viscous coupling fluid is required to have a small change in viscosity with respect to temperature and to have excellent thermal stability at high temperatures, and has conventionally used a silicone oil, particularly a viscosity at 25 ° C of 5,000 to 5,000.
00 centistoke (cSt) dimethylpolysiloxane fluid is commonly used. However, the fluid may be heated to a considerable high temperature due to the shearing force applied to the fluid or the heat generated by friction between the plates. There was a problem. That is, if the viscosity of the filling fluid increases significantly or gels, the initial setting performance of the viscous coupling cannot be maintained, and a solution to this problem has been studied. On the other hand, when the filling fluid is heated to a considerably high temperature, the viscosity is reduced by thermal decomposition, and as a result, the initial setting performance of the viscous coupling may not be maintained.

【０００４】従来よりポリオルガノシロキサンの耐熱性
向上のため種々の耐熱向上剤の添加が検討されており、
また、ビスカスカップリング用流体として硫黄化合物
（特開昭６４−６５１９５号公報）やリン化合物（特開
平２−９１１９６号公報）の添加が提案されている。[0004] Conventionally, the addition of various heat-resistant improvers has been studied to improve the heat resistance of polyorganosiloxanes.
Further, addition of a sulfur compound (Japanese Patent Application Laid-Open No. 64-65195) and a phosphorus compound (Japanese Patent Application Laid-Open No. 2-91196) as a fluid for viscous coupling has been proposed.

【０００５】[0005]

【発明が解決しようとする課題】しかしながら、このよ
うな硫黄化合物やリン化合物の添加のみでは、ポリオル
ガノシロキサンの重合や架橋などによる粘度上昇やゲル
化に対しては大きな効果が認められるものの熱分解によ
る粘度低下を防止することはできなかった。However, the addition of such a sulfur compound or a phosphorus compound alone has a great effect on increasing the viscosity or gelling due to polymerization or crosslinking of the polyorganosiloxane, but is not effective for thermal decomposition. However, it was not possible to prevent the viscosity from decreasing.

【０００６】従って、本発明の目的は、熱分解による粘
度低下の防止と、更に粘度上昇やゲル化を防止する安定
なビスカスカップリング用流体を提供することにある。Accordingly, it is an object of the present invention to provide a stable viscous coupling fluid which prevents a decrease in viscosity due to thermal decomposition and further prevents an increase in viscosity and gelation.

【０００７】[0007]

【課題を解決するための手段】斯かる実状に鑑み本発明
者らは、上記の如き欠点がなく、長期間の使用において
安定なビスカスカップリング用流体を得るべく鋭意研究
を行なった結果、ポリオルガノシロキサン流体を基油と
し、これにスルホネート、フェネート又はサリシレート
を添加すれば、熱分解による粘度低下が防止出来、これ
に、更に硫黄、リン又は塩素化合物を添加すれば、粘度
上昇やゲル化も防止出来る安定なビスカスカップリング
用流体が得られることを見出し本発明を完成した。In view of such circumstances, the present inventors have conducted intensive studies to obtain a fluid for viscous coupling which does not have the above-mentioned disadvantages and is stable over a long period of use. If an organosiloxane fluid is used as a base oil and sulfonate, phenate or salicylate is added thereto, viscosity reduction due to thermal decomposition can be prevented, and if a sulfur, phosphorus or chlorine compound is further added, viscosity increase or gelation may occur. The present inventors have found that a stable viscous coupling fluid can be obtained, and have completed the present invention.

【０００８】すなわち本発明は次の成分（Ａ）及び
（Ｂ）を含有するビスカスカップリング用流体組成物を
提供するものである。 （Ａ）次の平均単位式（１）That is, the present invention provides a fluid composition for viscous coupling containing the following components (A) and (B). (A) The following average unit formula (1)

【０００９】[0009]

【化９】 Embedded image

【００１０】〔式中、Ｒ1は炭化水素基又はハロゲン化
炭化水素基を示し、ａは１．９〜２．１の数を示す〕で
示され、２５℃における粘度が１００〜５００，０００
cStのポリオルガノシロキサン、（Ｂ）スルホネート、
フェネート及びサリシレートから選ばれる１種又は２種
以上。Wherein R 1 represents a hydrocarbon group or a halogenated hydrocarbon group, a represents a number of 1.9 to 2.1, and has a viscosity at 25 ° C. of 100 to 500,000.
cSt polyorganosiloxane, (B) sulfonate,
One or more selected from phenates and salicylates.

【００１１】本発明組成物の基油である平均単位式
（１）で示されるポリオルガノシロキサンにおいて、式
中のＲ1は炭化水素基又はハロゲン化炭化水素基を示す
が、ここで炭化水素基の例としては、炭素数１〜１２の
直鎖又は分岐鎖の飽和又は不飽和の脂肪族炭化水素基
（例えばアルキル基、アルケニル基等）、炭素数６〜１
８の芳香族炭化水素基が挙げられ；ハロゲン化炭化水素
基の例としては上記炭化水素基の少なくとも１個の水素
原子がハロゲン原子（例えばフッ素、塩素、臭素、ヨウ
素）で置換されたものが挙げられる。更に、脂肪族炭化
水素基、ハロゲン化脂肪族炭化水素基としては炭素数１
〜８のものが望ましく、例えばメチル基、エチル基、ブ
チル基、ヘキシル基、オクチル基、トリフルオロプロピ
ル基、オクテニル基などが挙げられる。芳香族炭化水素
基の例としてはフェニル基、トリル基、キシリル基など
が挙げられる。ケイ素原子に結合するこれらの基は同一
または異種のものであってもよい。式（１）のポリオル
ガノシロキサンは基本的に直鎖状の骨格を成しており、
若干の分岐部分を有してもよい。式（１）のポリオルガ
ノシロキサンにおいて、直鎖で分子量の高いものはａが
２．０に近く、分子量が低いものはａが２．０より大き
く、分岐部分を含むものはａが２．０より小さい。In the polyorganosiloxane represented by the average unit formula (1), which is the base oil of the composition of the present invention, R 1 in the formula represents a hydrocarbon group or a halogenated hydrocarbon group. Examples of the group include a linear or branched, saturated or unsaturated aliphatic hydrocarbon group having 1 to 12 carbon atoms (eg, an alkyl group and an alkenyl group), and a carbon number of 6 to 1
Examples of the halogenated hydrocarbon group include those in which at least one hydrogen atom of the above hydrocarbon group is substituted with a halogen atom (eg, fluorine, chlorine, bromine, iodine). No. Further, the aliphatic hydrocarbon group and the halogenated aliphatic hydrocarbon group each have 1 carbon atom.
To 8 are desirable, and examples thereof include a methyl group, an ethyl group, a butyl group, a hexyl group, an octyl group, a trifluoropropyl group and an octenyl group. Examples of the aromatic hydrocarbon group include a phenyl group, a tolyl group, and a xylyl group. These groups attached to the silicon atom may be the same or different. The polyorganosiloxane of the formula (1) basically forms a linear skeleton,
It may have some branches. Among the polyorganosiloxanes of the formula (1), those having a straight chain and a high molecular weight have a close to 2.0, those having a low molecular weight have a larger than 2.0, and those having a branched portion have a of 2.0. Less than.

【００１２】本発明に使用されるポリオルガノシロキサ
ンの例としては、ポリジメチルシロキサン、ポリジメチ
ル・メチルフェニルシロキサン、ポリメチルフェニルシ
ロキサン、ポリジメチル・ジフェニルシロキサン、ポリ
メチルヘキシルシロキサン、ポリメチルオクチルシロキ
サン、ポリメチルトリフルオロプロピルシロキサン、ポ
リジメチル・メチルトリフルオロプロピルシロキサンな
ど単一重合体や共重合体又はこれらの混合物が挙げられ
る。また、分子鎖末端はトリオルガノシリル基で封鎖さ
れていることが望ましく、その例としてはトリメチルシ
リル基、トリエチルシリル基などが挙げられる。Examples of the polyorganosiloxane used in the present invention include polydimethylsiloxane, polydimethylmethylphenylsiloxane, polymethylphenylsiloxane, polydimethyldiphenylsiloxane, polymethylhexylsiloxane, polymethyloctylsiloxane, polymethylsiloxane. Examples include homopolymers and copolymers such as trifluoropropylsiloxane and polydimethylmethyltrifluoropropylsiloxane, or mixtures thereof. Further, it is desirable that the molecular chain terminal is blocked with a triorganosilyl group, and examples thereof include a trimethylsilyl group and a triethylsilyl group.

【００１３】これらのポリオルガノシロキサンの粘度は
２５℃において約１００〜５００，０００、好ましくは
約５，０００〜４００，０００センチストークス（cS
t）の範囲のものが適当である。粘度が低すぎるものは
粘性抵抗が小さくビスカスカップリングの容量を非常に
大きくする必要があり、また粘度が高すぎるものは粘性
抵抗が大きすぎ、発熱が非常に大きくなり耐久性に問題
がでてくる。本発明の組成物において、このポリオルガ
ノシロキサンは基油として配合され、その配合量は組成
物の多割合を占め、通常約９０〜９９．９９重量％（以
下、単に％で示す）、好ましくは約９５〜９９．９５％
である。本発明においては、上記ポリオルガノシロキサ
ンよりなる基油（Ａ）に少量のスルホネート、フェネー
ト及びサリシレートから選ばれる１種又は２種以上
（Ｂ）が配合される。以下これらの成分について述べ
る。The viscosity of these polyorganosiloxanes at 25 ° C. is about 100 to 500,000, preferably about 5,000 to 400,000 centistokes (cS
Those in the range of t) are appropriate. If the viscosity is too low, the viscous resistance is small and the capacity of the viscous coupling needs to be very large.If the viscosity is too high, the viscous resistance is too large, heat generation becomes very large, and there is a problem with durability. come. In the composition of the present invention, the polyorganosiloxane is blended as a base oil, and the blending amount accounts for a large proportion of the composition, usually about 90 to 99.99% by weight (hereinafter simply referred to as%), preferably About 95-99.95%
It is. In the present invention, a small amount of one or more selected from sulfonate, phenate and salicylate (B) is blended with the base oil (A) composed of the polyorganosiloxane. Hereinafter, these components will be described.

【００１４】本発明に用いるスルホネートは、脂肪族ス
ルホン酸（Ｒ14−ＳＯ3Ｈ：Ｒ14はアルキル基）、芳香
族スルホン酸（Ａｒ−ＳＯ3Ｈ：Ａｒはアリール基）の
周期律表第一族、第二族金属の金属塩である。これら金
属塩の例としては、アルカリ金属、アルカリ土類金属例
えばナトリウム、カリウム、カルシウム、マグネシウ
ム、バリウム、ストロンチウムが挙げられる。The sulfonate used in the present invention may be selected from aliphatic sulfonic acids (R 14 —SO 3 H: R 14 is an alkyl group) and aromatic sulfonic acids (Ar—SO 3 H: Ar is an aryl group) in the periodic table. It is a metal salt of Group 1 and Group 2 metals. Examples of these metal salts include alkali metals, alkaline earth metals such as sodium, potassium, calcium, magnesium, barium, strontium.

【００１５】特に本発明に於いて好ましいスルホネート
は、アルキル芳香族炭化水素を、発煙硫酸又はＳＯ3ガ
スとの反応によりスルホン化した後、これを炭酸ガスの
存在下又は不存在下で周期律表第一族、第二族金属の酸
化物、水酸化物と反応させる常法に従い容易に製造でき
る。炭酸ガスの存在下で反応を行なうと過塩基性のスル
ホン酸塩が得られ、炭酸ガスの不存在下に反応を行なう
と中性のスルホン酸塩が得られる。（スルホン酸塩の製
法は、例えば、Ｈｅｎｒｙ Ｄ．Ｄｒｅｗ著、ＮＯＹＥ
Ｓ ＤＡＴＡ社１９７５年発行の“ＭＥＴＡＬＢＡＳＥ
Ｄ ＬＵＢＲＩＣＡＮＴ ＣＯＭＰＯＳＩＴＩＯＮＳ”
３〜６頁、３３〜６１頁に詳述されている。）ここで用
いるアルキル芳香族炭化水素は、一般式Ａｒ（Ｒ15）
（Ｒ16）で示されるもので、ここでＡｒはアリール基を
表わし、Ｒ15は水素又は炭素数１０〜２２個のアルキル
基を表わす。又Ｒ16は、Ｒ15が水素の場合は炭素数８〜
２２個の、Ｒ15がアルキル基の場合は炭素数３〜１０個
のアルキル基であることが好ましい。炭素数１０〜２２
個のアルキル基の例としては、ドデシル基、テトラデシ
ル基、ヘキサデシル基、オクタデシル基、オレイル基、
プロピレン又はブチレン等オレフィンのオリゴマーから
誘導される炭化水素基等があり、炭素数３〜１０個のア
ルキル基の例としては、プロピル基、ブチル基、ヘキシ
ル基、オクチル基、ノニル基等がある。本発明に用いる
フェネートは、フェノール類の塩であり、好ましい例と
しては炭素数約８〜３０のアルキル基が付加されたアル
キルフェノールの硫化物のアルカリ土類金属塩（好まし
くはカルシウム、マグネシウムもしくはバリウム塩）が
挙げられ、例えば特開昭５７−１４２３９３号公報に詳
しく記載されており、商品としてはコスモＰＡＤ２１０
（コスモ石油（株））がある。Particularly preferred in the present invention is a sulfonate obtained by sulfonating an alkyl aromatic hydrocarbon by reaction with fuming sulfuric acid or SO 3 gas, and then subjecting the sulfonate to the presence or absence of carbon dioxide gas in the periodic table. It can be easily produced according to a conventional method of reacting with an oxide or hydroxide of a Group 1 or Group 2 metal. When the reaction is performed in the presence of carbon dioxide, an overbased sulfonic acid salt is obtained, and when the reaction is performed in the absence of carbon dioxide, a neutral sulfonic acid salt is obtained. (Sulfonate is manufactured by, for example, NOYE by Henry D. Drew.
"METALBASE," published by S DATA in 1975
D LUBRICANT COMPOSITIONS "
The details are described on pages 3 to 6 and pages 33 to 61. ) The alkyl aromatic hydrocarbon used herein has a general formula of Ar (R 15 )
(R 16 ), wherein Ar represents an aryl group, and R 15 represents hydrogen or an alkyl group having 10 to 22 carbon atoms. R 16 has a carbon number of 8 to when R 15 is hydrogen.
When 22 R 15 groups are alkyl groups, it is preferably an alkyl group having 3 to 10 carbon atoms. Carbon number 10-22
Examples of alkyl groups include dodecyl, tetradecyl, hexadecyl, octadecyl, oleyl,
There are hydrocarbon groups derived from oligomers of olefins such as propylene and butylene, and the like. Examples of the alkyl group having 3 to 10 carbon atoms include a propyl group, a butyl group, a hexyl group, an octyl group, and a nonyl group. The phenate used in the present invention is a salt of a phenol, and a preferred example thereof is an alkaline earth metal salt of a sulfide of an alkylphenol to which an alkyl group having about 8 to 30 carbon atoms is added (preferably a calcium, magnesium or barium salt). ), Which are described in detail in, for example, JP-A-57-142393.
(Cosmo Oil Co., Ltd.).

【００１６】本発明に用いるサリシレートはサリチル酸
塩であり、アルカリ土類金属のサリシレートが好まし
い。アルカリ土類金属のサリシレートの代表例として
は、カルシウム塩、マグネシウム塩等があり、一般には
炭素数１４〜１８のα−オレフィンでフェノールをアル
キル化しアリカリ金属塩とし、コルベーシュミット反応
でカルボキシル基を導入し、複分解等によりアルカリ土
類金属塩としたもので特公昭６１−２４５６０号公報、
特公昭６１−２４５６１号公報等に詳しい。The salicylate used in the present invention is a salicylate, preferably an alkaline earth metal salicylate. Representative examples of salicylates of alkaline earth metals include calcium salts, magnesium salts and the like.Generally, phenol is alkylated with an α-olefin having 14 to 18 carbon atoms to form an alkali metal salt, and a carboxyl group is formed by a Kolbeschmitt reaction. Introduced and made into an alkaline earth metal salt by double decomposition, etc.
It is detailed in JP-B-61-24561.

【００１７】これら（Ｂ）成分は、本発明組成物中０．
０１〜１０％、特に０．１〜５％配合することが好まし
い。Ｂ成分の配合量が０．０１％未満であると充分な粘
度低下防止効果が得られず、また２％を超えて配合して
も効果の向上はあまり望めず、好ましくない。特に好ま
しい配合量は０．１〜２．０％である。These components (B) are contained in the composition of the present invention in an amount of 0.1%.
It is preferable that the compounding amount be from 0.1 to 10%, especially from 0.1 to 5%. If the compounding amount of the component B is less than 0.01%, a sufficient effect of preventing the viscosity from decreasing cannot be obtained, and if the compounding amount exceeds 2%, the effect cannot be expected to be improved much, which is not preferable. A particularly preferred amount is 0.1 to 2.0%.

【００１８】本発明の組成物は上記（Ａ）成分及び
（Ｂ）成分のみで粘度低下を防止でき、更に、次の
（イ）〜（ル）に示す硫黄、硫黄化合物、リン化合物及
び塩素化合物から選ばれる１種又は２種以上を添加すれ
ば、粘度上昇やゲル化に対する防止作用が向上する。 （イ）一般式（２）The composition of the present invention can prevent a decrease in viscosity only by the above components (A) and (B), and furthermore, sulfur, sulfur compounds, phosphorus compounds and chlorine compounds shown in the following (a) to (l): Addition of one or more selected from the group improves the effect of preventing viscosity increase and gelation. (B) General formula (2)

【００１９】[0019]

【化１０】 Embedded image

【００２０】〔式中、Ｒ2は炭化水素基、Ｒ3は二価の炭
化水素基、ｘは１以上の整数であり（くり返し単位中に
おいてそれぞれのｘは同一又は異なる数でありうる）、
ｎは０または１以上の整数〕で示される炭化水素硫化
物、 （ロ）油脂と硫黄の反応生成物である硫化油脂、 （ハ）一般式（３）[Wherein, R 2 is a hydrocarbon group, R 3 is a divalent hydrocarbon group, x is an integer of 1 or more (each x may be the same or different in the repeating unit),
n is 0 or an integer of 1 or more], (b) sulfurized fat or oil which is a reaction product of fat and sulfur, (c) general formula (3)

【００２１】[0021]

【化１１】 Embedded image

【００２２】〔式中、Ｒ4、Ｒ5、Ｒ6、Ｒ7は同一又は異
なる炭化水素基〕で示されるジチオリン酸亜鉛。 （ニ）一般式（４）A zinc dithiophosphate represented by the formula: wherein R 4 , R 5 , R 6 and R 7 are the same or different hydrocarbon groups. (D) General formula (4)

【００２３】[0023]

【化１２】 Embedded image

【００２４】〔式中、Ｒ8、Ｒ9、Ｒ10、Ｒ11は同一又は
異なるアルキル基、ＭｅはＺｎ、Ｐｂ、Ｍｏ、Ｓｂの金
属〕で示されるジアルキルジチオカルバミン酸金属塩、 （ホ）単体硫黄、 （ヘ）一般式（５）Wherein R 8 , R 9 , R 10 , and R 11 are the same or different alkyl groups, and Me is a metal of Zn, Pb, Mo, and Sb; a metal salt of dialkyldithiocarbamic acid represented by the formula: Sulfur, (f) general formula (5)

【００２５】[0025]

【化１３】 Embedded image

【００２６】〔式中、Ｒ12、Ｒ13は二価の炭化水素基、
ｘは１以上の整数であり（くり返し単位中においてそれ
ぞれのｘは同一又は異なる数でありうる）、ｍは０又は
１以上の整数〕で示される炭化水素硫化物。 （ト）一般式（６）[Wherein R 12 and R 13 are divalent hydrocarbon groups,
x is an integer of 1 or more (each x may be the same or a different number in the repeating unit, and m is 0 or an integer of 1 or more). (G) General formula (6)

【００２７】[0027]

【化１４】 Embedded image

【００２８】〔式中、Ｒ14は一価の炭化水素基、ｂは
１、２又は３、ｃは０又は１の数、Ｘは酸素原子又は硫
黄原子〕で示されるリン酸エステル、亜リン酸エステ
ル、チオリン酸エステル、あるいはジチオリン酸エステ
ル。Wherein R 14 is a monovalent hydrocarbon group, b is 1, 2 or 3, c is a number of 0 or 1, and X is an oxygen atom or a sulfur atom. Acid esters, thiophosphates, or dithiophosphates.

【００２９】（チ）（ト）で示される酸性リン酸エステ
ル、酸性亜リン酸エステル、酸性チオリン酸エステルあ
るいは酸性ジチオリン酸エステルのアルキルアミン塩、(H) an alkylamine salt of an acid phosphate, acid phosphite, acid thiophosphate or acid dithiophosphate represented by (g);

【００３０】（リ）炭化水素と硫化リンとの反応生成物(I) Reaction product of hydrocarbon and phosphorus sulfide

【００３１】（ヌ）一般式（７）(Nu) General formula (7)

【００３２】[0032]

【化１５】 Embedded image

【００３３】〔式中、Ｒ15は一価の炭化水素基、Ｒ16は
二価の炭化水素基〕で示されるジチオリン酸の水酸基置
換トリエステルとリン酸類、酸化リン類、又はハロゲン
化リン類との反応生成物をアミンで中和して得られるリ
ン及び窒素を含む組成物。[Wherein, R 15 is a monovalent hydrocarbon group and R 16 is a divalent hydrocarbon group] and a hydroxyl-substituted triester of dithiophosphoric acid and phosphoric acid, phosphorus oxide, or halogenated phosphorus A composition comprising phosphorus and nitrogen obtained by neutralizing a reaction product of the above with an amine.

【００３４】（ル）一般式（８）(R) General formula (8)

【００３５】[0035]

【化１６】 Embedded image

【００３６】〔式中、Ｒ17はアルキル基〕で示されるジ
エステルWherein R 17 is an alkyl group

【００３７】これら硫黄化合物リン化合物及び塩素化合
物について更に詳細に説明する。まず（イ）で示される
イオウ化合物において、基Ｒ2は炭化水素基であり、炭
化水素基の例としては、炭素数２〜２０の直鎖又は分岐
の飽和又は不飽和の脂肪族炭化水素基（例えばアルキル
基、アルケニル基）、炭素数６〜２６の芳香族炭化水素
基が挙げられる。これら炭化水素基の具体例としてはエ
チル基、プロピル基、ブチル基、ノニル基、ドデシル
基、プロペニル基、ブテニル基、ベンジル基、フェニル
基、トリル基、ヘキシルフェニル基等が挙げられる。基
Ｒ3は二価の炭化水素基であり、その例は、炭素数２〜
２０の直鎖又は分岐の脂肪族炭化水素基、炭素数６〜２
６の芳香族炭化水素基がある。これら二価の炭化水素基
の具体例はエチレン基、プロピレン基、ブチレン基、フ
ェニレン基などがある。（イ）のイオウ化合物の代表的
なものは、硫化オレフィン、及び一般式Ｒ2−Ｓｘ−Ｒ2
（ｘは２以上の整数）で示されるポリサルファイド化合
物である。（イ）の具体例としてはジイソブチルジサル
ファイド、ジオクチルポリサルファイド、ジターシャリ
ノニルポリサルファイド、ジターシャリブチルポリサル
ファイド、ジベンジルポリサルファイド、そしてポリイ
ソブチレン、テルペン類等のオレフィン類をイオウ等の
硫化剤で硫化した硫化オレフィン類、イソブチレンとイ
オウとの化合物で式The sulfur compound phosphorus compound and chlorine compound will be described in more detail. First, in the sulfur compound shown in (a), the group R 2 is a hydrocarbon group, and examples of the hydrocarbon group include a linear or branched saturated or unsaturated aliphatic hydrocarbon group having 2 to 20 carbon atoms. (For example, an alkyl group and an alkenyl group) and an aromatic hydrocarbon group having 6 to 26 carbon atoms. Specific examples of these hydrocarbon groups include ethyl, propyl, butyl, nonyl, dodecyl, propenyl, butenyl, benzyl, phenyl, tolyl, hexylphenyl and the like. The group R 3 is a divalent hydrocarbon group, examples of which are
20 linear or branched aliphatic hydrocarbon groups, having 6 to 2 carbon atoms
There are six aromatic hydrocarbon groups. Specific examples of these divalent hydrocarbon groups include an ethylene group, a propylene group, a butylene group, and a phenylene group. A typical sulfur compound of (a) is a sulfurized olefin and a general formula R 2 —Sx—R 2
(X is an integer of 2 or more). Specific examples of (a) include sulfided olefins obtained by sulfided olefins such as diisobutyl disulfide, dioctyl polysulfide, ditertiarynonyl polysulfide, ditertiary butyl polysulfide, dibenzyl polysulfide, and polyisobutylene and terpenes with a sulfurizing agent such as sulfur. , A compound of isobutylene and sulfur with the formula

【００３８】[0038]

【化１７】 Embedded image

【００３９】（ロ）で示される成分は油脂と硫黄の反応
生成物である硬化油脂で、油脂としてはラード、牛脂、
鯨油、パーム油、ヤシ油、ナタネ油などの動植物油脂が
ある。この反応生成物は化学構造が単一ではなく種々の
混合物であり、化学構造そのものは明確ではない。
（ハ）で示されるジチオリン酸亜鉛において、式中、基
Ｒ4、Ｒ5、Ｒ6、Ｒ7は同一又は異なる炭化水素基であ
り、炭化水素基の例としては炭素数３〜２０、特に３〜
１２の直鎖もしくは分岐の飽和もしくは不飽和の脂肪族
炭化水素基（例えばアルキル基、アルケニル基）、炭素
数６〜２０の芳香族炭化水素基が挙げられる。これら炭
化水素基の具体例としてはプロピル基、ブチル基、ノニ
ル基、ドデシル基、オクテニル基、フェニル基、トリル
基等がある。（ハ）の具体例としてはジイソブチルジチ
オリン酸亜鉛、ジペンチルジチオリン酸亜鉛、ジ−１−
メチルヘプチルジチオリン酸亜鉛、ジ−２−エチルヘキ
シルジチオリン酸亜鉛、ジフェニルジチオリン酸亜鉛等
がある。（ニ）で示されるジアルキルジチオカルバメー
ト類において、式中、Ｒ8、Ｒ9、Ｒ10、Ｒ11は同一又は
異なるアルキル基で、その炭素数は３〜２０、特に３〜
１２のものが好ましく、その例としてはプロピル基、ブ
チル基、ノニル基、ドデシル基等がある。（ニ）の化合
物において、式中、ＭｅはＺｎ、Ｐｂ、ＭｏまたはＳｂ
の金属である。（ヘ）の具体例としては、ジイソブチル
ジチオカルバミン酸亜鉛、ジアミルジチオカルバミン酸
亜鉛、ジドデシルジカルバミン酸鉛等がある。（ホ）の
成分である硫黄は粉末で、ポリオルガノシロキサン中に
入れ、約１５０〜２５０℃の温度で加熱撹拌することに
より溶解もしくは均一に分散する。（ヘ）で示される環
状のイオウ化合物において、基Ｒ12、Ｒ13は二価の炭化
水素基であり、炭化水素基の例としては、炭素数２〜２
０の直鎖もしくは分岐の脂肪族炭化水素基、炭素数６〜
２６の芳香族炭化水素基がある。これらの二価の炭化水
素基の具体例はエチレン基、プロピレン基、ブチレン
基、フェニレン基等がある。一般式（ヘ）のイオウ化合
物の例としてThe component represented by (b) is a hardened oil or fat which is a reaction product of oil and fat with sulfur, such as lard, beef tallow,
There are animal and vegetable fats and oils such as whale oil, palm oil, coconut oil, and rapeseed oil. The reaction product is not a single chemical structure but various mixtures, and the chemical structure itself is not clear.
In the zinc dithiophosphate represented by (C), in the formula, the groups R 4 , R 5 , R 6 , and R 7 are the same or different hydrocarbon groups, and examples of the hydrocarbon group include 3 to 20 carbon atoms, 3 ~
Examples thereof include 12 linear or branched saturated or unsaturated aliphatic hydrocarbon groups (eg, an alkyl group and an alkenyl group) and an aromatic hydrocarbon group having 6 to 20 carbon atoms. Specific examples of these hydrocarbon groups include propyl, butyl, nonyl, dodecyl, octenyl, phenyl, and tolyl groups. Specific examples of (c) include zinc diisobutyl dithiophosphate, zinc dipentyl dithiophosphate, and di-1-
Zinc methylheptyldithiophosphate, zinc di-2-ethylhexyldithiophosphate, zinc diphenyldithiophosphate and the like. In the dialkyldithiocarbamates represented by (d), in the formula, R 8 , R 9 , R 10 , and R 11 are the same or different alkyl groups, and have 3 to 20, particularly 3 to 3, carbon atoms.
Twelve are preferable, and examples thereof include a propyl group, a butyl group, a nonyl group, and a dodecyl group. In the compound of (d), Me represents Zn, Pb, Mo or Sb.
Metal. Specific examples of (f) include zinc diisobutyldithiocarbamate, zinc diamyldithiocarbamate, and lead didodecyldicarbamate. Sulfur, which is a component of (e), is a powder and is dissolved or uniformly dispersed in polyorganosiloxane by heating and stirring at a temperature of about 150 to 250 ° C. In the cyclic sulfur compound represented by (f), the groups R 12 and R 13 are divalent hydrocarbon groups, and examples of the hydrocarbon groups include those having 2 to 2 carbon atoms.
0 linear or branched aliphatic hydrocarbon group, having 6 to 6 carbon atoms
There are 26 aromatic hydrocarbon groups. Specific examples of these divalent hydrocarbon groups include an ethylene group, a propylene group, a butylene group, and a phenylene group. Examples of sulfur compounds of the general formula (f)

【００４０】[0040]

【化１８】 Embedded image

【００４１】の化合物がある。上記環状のイオウ化合物
は、例えば米国特許第３，９２５，４１４号に記載され
た合成方法によって調製でき、イソブチレンのようなオ
レフィンとイオウモノハライドとから得られる反応物を
更にアルカリメルカプチドと反応させて得られる。There are the following compounds: The cyclic sulfur compound can be prepared, for example, by a synthesis method described in U.S. Pat. No. 3,925,414, in which a reactant obtained from an olefin such as isobutylene and a sulfur monohalide is further reacted with an alkali mercaptide. Obtained.

【００４２】一般式（６）で示されるリン系添加剤にお
いて、基Ｒ14は一価の炭化水素基であり、炭化水素基の
例としては、炭素数５〜２０の直鎖もしくは分岐の飽和
もしくは不飽和の脂肪族炭化水素基（例えばアルキル
基、アルケニル基）、炭素数６〜２６の芳香族炭化水素
基、シクロアルキル基があり、これらの具体例としては
リン酸モノオクチル、リン酸ジオクチル、リン酸トリオ
クチル、亜リン酸ジオクチル、亜リン酸トリオクチル、
チオリン酸ジオクチル、チオリン酸トリオクチル、リン
酸ジデシル、亜リン酸ジデシル、リン酸ジドデシル、リ
ン酸トリドデシル、亜リン酸ジドデシル、亜リン酸トリ
ドデシル、チオリン酸トリドデシル、リン酸トリヘキサ
デシル、亜リン酸トリヘキサデシル、チオリン酸トリヘ
キサデシル、リン酸トリオクタデセニル、亜リン酸トリ
オクタデセニル、チオリン酸トリオクタデセニル、リン
酸トリ（オクチルフェニル）、亜リン酸トリ（オクチル
フェニル）、チオリン酸トリ（オクチルフェニル）、リ
ン酸トリ（オクチルシクロヘキシル）、ジチオリン酸ト
リデシル等が挙げられる。In the phosphorus additive represented by the general formula (6), the group R 14 is a monovalent hydrocarbon group, and examples of the hydrocarbon group include straight-chain or branched saturated hydrocarbon groups having 5 to 20 carbon atoms. Or an unsaturated aliphatic hydrocarbon group (for example, an alkyl group or an alkenyl group), an aromatic hydrocarbon group having 6 to 26 carbon atoms, or a cycloalkyl group. Specific examples thereof include monooctyl phosphate and dioctyl phosphate , Trioctyl phosphate, dioctyl phosphite, trioctyl phosphite,
Dioctyl thiophosphate, trioctyl thiophosphate, didecyl phosphate, didecyl phosphite, didodecyl phosphate, tridodecyl phosphate, didodecyl phosphite, tridodecyl phosphite, tridodecyl thiophosphate, trihexadecyl phosphate, trihexa phosphite Decyl, trihexadecyl thiophosphate, trioctadecenyl phosphate, trioctadecenyl phosphite, trioctadecenyl thiophosphate, tri (octylphenyl) phosphate, tri (octylphenyl) phosphite, Tri (octylphenyl) thiophosphate, tri (octylcyclohexyl) phosphate, tridecyl dithiophosphate and the like.

【００４３】（チ）で示される成分は（ト）で示される
酸性リン酸エステル、酸性亜リン酸エステル、酸性チオ
リン酸エステルあるいは酸性ジチオリン酸エステルアル
キルアミン塩である。上記成分のうちビスカスカップリ
ング用流体には特に、酸性リン酸エステルが好適であ
り、これらの化合物の具体例としては、ブチルアシッド
ホスフェート、２−エチルヘキシルアシッドホスフェー
ト、オクチルアシッドホスフェート、ラウリルアシッド
ホスフェート、オレイルアシッドホスフェート、トリー
ルアシッドホスフェート等がある。それを中和するため
に用いられるアルキルアミンとしては一般式：The component represented by (h) is an acidic phosphoric ester, acidic phosphite, acidic thiophosphate or acidic dithiophosphate alkylamine salt represented by (g). Among the above components, the acid phosphoric acid ester is particularly preferable for the viscous coupling fluid. Specific examples of these compounds include butyl acid phosphate, 2-ethylhexyl acid phosphate, octyl acid phosphate, lauryl acid phosphate, and oleyl. Acid phosphate, tolyl acid phosphate and the like. The alkylamine used to neutralize it has the general formula:

【００４４】ＮＲ18Ｒ19Ｒ20（Ｒ18、Ｒ19及びＲ20は一
価の炭化水素基又は水素原子であり、そのうち少なくと
も一つは炭化水素基）で表わされ、これら化合物の具体
例としては、ジブチルアミン、オクチルアミン、ジオク
チルアミン、ラウリルアミン、ジラウリルアミン、ココ
ナッツアミン、牛脂アミン等が含まれる。上記の塩とし
て市販されているものとしては商品名「Ｏｒｔｈｏｌｅ
ｕｍ ５３５」（デュポン社製）、「Ｖａｎｌｕｂｅ
６７２」（バンダビルド社製）、「Ｉｒｇａｌｕｂｅ
３４９」（チバガイギー社製）などがある。NR 18 R 19 R 20 (R 18 , R 19 and R 20 are monovalent hydrocarbon groups or hydrogen atoms, at least one of which is a hydrocarbon group), and specific examples of these compounds Examples include dibutylamine, octylamine, dioctylamine, laurylamine, dilaurylamine, coconutamine, tallowamine, and the like. Commercially available salts as the above include “Orthole”
um 535 "(manufactured by DuPont)," Vanlube "
672 "(manufactured by Banda Build)," Irgalube
349 "(manufactured by Ciba-Geigy).

【００４５】（リ）で示される成分の原料炭化水素は二
重結合を一個以上含有し、かつ約５〜２０個の炭素原子
を含有する炭化水素であり、硫化リンとしては例えばＰ
2Ｓ5 、Ｐ2Ｓ4 、Ｐ2Ｓ3 などであり、炭化水素と硫化リ
ンとの反応生成物としては例えばテルペン類、低分子量
ポリブチレン又はオレフィンをリン硫化したもの等が挙
げられる。The raw material hydrocarbon of the component shown in (i)
Containing one or more heavy bonds and about 5-20 carbon atoms
And the phosphorus sulfide is, for example, P
TwoSFive , PTwoSFour, PTwoSThreeSuch as hydrocarbons and sulfides
Examples of the reaction product with terpene, low molecular weight
Examples include polybutylene or olefins that have been phosphorus-sulfurized.
I can do it.

【００４６】（ヌ）で示される反応生成物の原料である
（７）式中Ｒ15は一価の炭化水素基であり、例えば炭素
数１〜２５の直鎖もしくは分岐の飽和もしくは不飽和の
脂肪族炭化水素基（例えばアルキル基、アルケニル
基）、炭素数６〜２６の芳香族炭化水素基、シクロアル
キル基である。Ｒ16は炭素数が約２０より少ない二価の
炭化水素基例えばアルキレン基、アリール置換アルキレ
ン基等である。アミンは約５〜２０個の炭素原子を有す
る脂肪族、芳香族又は脂環族の第１級アミンである。In the formula (7), which is a raw material of the reaction product represented by (nu), R 15 is a monovalent hydrocarbon group, for example, a linear or branched saturated or unsaturated C 1 -C 25 group. An aliphatic hydrocarbon group (for example, an alkyl group or an alkenyl group), an aromatic hydrocarbon group having 6 to 26 carbon atoms, or a cycloalkyl group. R 16 is a divalent hydrocarbon group having less than about 20 carbon atoms such as an alkylene group and an aryl-substituted alkylene group. The amine is an aliphatic, aromatic or cycloaliphatic primary amine having about 5 to 20 carbon atoms.

【００４７】上記リン及び窒素を含む組成物の具体例と
してはヒドロキシエチル−Ｏ，Ｏ′−ジヘキシルジチオ
リン酸エステルと五酸化リンとの反応物をドデシルアミ
ンで中和したもの、ヒドロキシプロピル−Ｏ，Ｏ′−ジ
ヘキシルジチオリン酸エステルと五酸化リンとの反応物
をオクタデシルアミンで中和したもの、ヒドロキシヘキ
シル−Ｏ，Ｏ′−ジヘキシルジチオリン酸エステルと五
酸化リンとの反応物をドデシルアミンで中和したもの、
フェニルヒドロキシエチル−Ｏ，Ｏ′−ジヘキシルジチ
オリン酸エステルと五酸化リンとの反応物をドデシルア
ミンで中和したもの、ヒドロキシプロピル−Ｏ，Ｏ′−
ジフェニルジチオリン酸エステルと五酸化リンとの反応
物をオクタデシルアミンで中和したもの等が挙げられ
る。これらリン及び窒素を含む組成物は例えば通常無機
リン薬剤１モルに約１〜５モルのジチオリン酸トリエス
テルを反応させて酸性の中間物を作り、この中間物をア
ミンにより実質的に中和することにより製造することが
できる。上述した炭化水素硫化物は分子量が低すぎると
蒸発によるロスが起り、分子量が大きすぎると効果が不
十分になる。他方リンを含む有機化合物は炭化水素置換
基の炭素数が小さすぎるものは効果が不十分であり、炭
素数の大きすぎるものは入手が困難である。Specific examples of the composition containing phosphorus and nitrogen include a product obtained by neutralizing a reaction product of hydroxyethyl-O, O'-dihexyldithiophosphate with phosphorus pentoxide with dodecylamine, hydroxypropyl-O, A reaction product of O'-dihexyldithiophosphate and phosphorus pentoxide neutralized with octadecylamine, and a reaction product of hydroxyhexyl-O, O'-dihexyldithiophosphate with phosphorus pentoxide neutralized with dodecylamine What did
A product obtained by neutralizing a reaction product of phenylhydroxyethyl-O, O'-dihexyldithiophosphate and phosphorus pentoxide with dodecylamine, hydroxypropyl-O, O'-
Examples include a product obtained by neutralizing a reaction product of diphenyldithiophosphate with phosphorus pentoxide with octadecylamine. These phosphorus and nitrogen containing compositions, for example, typically react about 1 to 5 moles of a dithiophosphoric acid triester with 1 mole of an inorganic phosphorus drug to form an acidic intermediate which is substantially neutralized with an amine. It can be manufactured by the following. If the molecular weight of the above-mentioned hydrocarbon sulfide is too low, loss due to evaporation occurs, and if the molecular weight is too high, the effect becomes insufficient. On the other hand, when the organic compound containing phosphorus has too small a carbon number of the hydrocarbon substituent, the effect is insufficient, and those having too large a carbon number are difficult to obtain.

【００４８】（ル）で示される（８）式中Ｒ17は、好ま
しくは炭素原子数４〜８個のアルキル基である。ジエス
テルの具体例としてジブチルクロレンデート、ジヘキシ
ルクロレンデート、ジオクチルクロレンデート、ジ−２
−エチルヘキシルクロレンデート等がある。In the formula (8) represented by (II), R 17 is preferably an alkyl group having 4 to 8 carbon atoms. Specific examples of diesters include dibutylchlorendate, dihexylchlorendate, dioctylchlorendate, and di-2.
-Ethylhexylchlorendate and the like.

【００４９】上記のジエステルはクロレンデン酸のカル
ボキシル基と分子中に４〜８個の炭素原子を有するアル
コールとの反応によりつくられる。クロレンデン酸は別
の命名法では１，４，５，６，７，７−ヘキサクロルビ
シクロ−（２，２，１）−ヘプト−５−エン−２，３−
ジカルボン酸と表わされ、対応する塩素化シクロペンタ
ジエン及び無水マレイン酸のディールス−アルダー（Ｄ
ｉｅｌｓ−Ａｌｄｅｒ）付加として知られている方法に
より製造することができる。The above diesters are prepared by reacting the carboxyl group of chlorendic acid with an alcohol having 4 to 8 carbon atoms in the molecule. Chlorendenic acid is another nomenclature for 1,4,5,6,7,7-hexachlorobicyclo- (2,2,1) -hept-5-ene-2,3-.
Dicarboxylic acids, represented by the corresponding chlorinated cyclopentadiene and maleic anhydride Diels-Alder (D
ies-Alder) addition.

【００５０】前記（イ）で示されるイオウ化合物は、本
発明ビスカスカップリング用流体組成物中に約０．０１
〜１０重量％（以下単に％で示す）、特に約０．１〜５
％配合するのが好ましい。（イ）に示される成分の配合
量が少なすぎると効果が小さいし、配合量が多すぎると
（Ａ）や（イ）の成分自体の熱劣化の影響が大きくなり
望ましくない。このことは（ロ）〜（ル）の成分に対し
ても同じである。また、（ホ）の成分である単体硫黄に
ついては、特に好ましい配合量は約０．０１〜５．０
％、ことに約０．０５〜２．０％である。本発明組成物
において、配合する（Ｂ）成分は基油のポリオルガノシ
ロキサン中に溶解することが好ましいが、必ずしも溶解
しなくてもよい、基油の粘度が高いことにより単に分散
していてもよいし、また基油と反応していてもよい。
（Ａ）に示されるポリオルガノシロキサンに加える
（イ）〜（ル）の成分はそれぞれ単独で用いて効果を有
するが、（イ）〜（ル）のなかから２〜６成分を併用し
て加えてもさしつかえない。この場合、（イ）〜（ル）
の成分の全量が約０．０１〜１０重量％の範囲にあるこ
とが望ましい。尚本発明組成物において配合量は特に断
らない限り、組成物全量を基準とする。The sulfur compound represented by the above (A) is added to the fluid composition for viscous coupling of the present invention in an amount of about 0.01%.
To 10% by weight (hereinafter simply indicated as%), especially about 0.1 to 5%
% Is preferred. If the amount of the component shown in (A) is too small, the effect is small, and if the amount is too large, the effect of thermal deterioration of the components (A) and (A) itself is undesirably large. This is the same for the components (b) to (lu). With respect to elemental sulfur which is a component of (e), a particularly preferable blending amount is about 0.01 to 5.0.
%, Especially about 0.05 to 2.0%. In the composition of the present invention, the component (B) to be blended is preferably dissolved in the polyorganosiloxane of the base oil, but may not necessarily be dissolved, and may be simply dispersed due to the high viscosity of the base oil. Or it may have reacted with the base oil.
The components (A) to (L) added to the polyorganosiloxane shown in (A) have an effect when used alone, but the components (A) to (L) are used in combination with 2 to 6 components. I don't mind. In this case, (a) to (le)
Is desirably in the range of about 0.01 to 10% by weight. In the composition of the present invention, the amount is based on the total amount of the composition unless otherwise specified.

【００５１】また、本発明の組成物に従来公知の耐熱向
上剤やその他慣用の添加剤を添加してもさしつかえな
い。特に、ビスカスカップリング用流体として種々の過
酷な条件下にさらされることを考えると、従来公知の耐
熱向上剤をも添加した方が望ましい場合もある。このよ
うな添加剤としては、上記の特開平２−９１１９６号公
報記載のリン化合物及び塩素化合物の他、公知の酸化防
止剤、さび止め剤、金属不活性化剤が挙げられる。本発
明の組成物は、ビスカスカップリング用流体組成物とし
て有用なものであるが、ファンカップリングなどの流体
継手にも適用できるものである。The composition of the present invention may be added with a conventionally known heat resistance improver or other conventional additives. In particular, considering that the viscous coupling fluid is exposed to various severe conditions, it may be desirable to add a conventionally known heat resistance improver. Examples of such additives include known antioxidants, rust inhibitors, and metal deactivators in addition to the phosphorus compounds and chlorine compounds described in JP-A-2-91196. The composition of the present invention is useful as a fluid composition for viscous coupling, but can also be applied to fluid couplings such as fan couplings.

【００５２】[0052]

【発明の効果】本発明のビスカスカップリング用流体組
成物は、長時間の使用において、熱分解による粘度の低
下の防止及び粘度上昇やゲル化を防止できるため、安定
である。また、本発明のビスカスカップリング用流体を
使用することにより、上記の点以外にプレート板の耐摩
耗性も改善されるという効果を有し、ビスカスカップリ
ングの耐久性、さらには自動車の信頼性を高めることが
できる。The fluid composition for viscous coupling of the present invention is stable because it can prevent a decrease in viscosity due to thermal decomposition and prevent an increase in viscosity and gelation when used for a long time. In addition, by using the fluid for viscous coupling of the present invention, in addition to the above-described points, the wear resistance of the plate plate is also improved, and the durability of the viscous coupling and the reliability of the automobile are further improved. Can be increased.

【００５３】[0053]

【実施例】以下、実施例を挙げて本発明を更に詳細に説
明するが本発明はこれらに限定されるものではない。 実施例１〜１１ 以下の組成のビスカスカップリング用流体を常法により
製造し、下記の試験を行なった。この結果を表３に示
す。。EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto. Examples 1 to 11 Fluids for viscous coupling having the following compositions were produced by a conventional method, and the following tests were conducted. Table 3 shows the results. .

【００５４】なお、これらの組成物は、比較例１を除い
て全て表１と表２に示す割合で６０℃で１時間混合攪拌
することにより調製した。実施例１〜１１及び比較例１
〜３で用いたポリジメチルシロキサンは全て分子鎖末端
をトリメチルシリル基で封鎖したものである。また、実
施例１〜１１のＣａスルホネートは比重（１５／４℃）
１．１２５ Ｃａ １２．０（重量％）〔日本ルブリゾ
ール（株），ルブリゾール７４〕、Ｃａサリチレートは
比重（１５／４℃）１．０２５ Ｃａ ６．０（重量
％）〔シェル化学（株），シェルＡＣ６０Ｃ〕、Ｃａフ
ィネートは比重（１５／４℃）１．０１ Ｃａ ５．２
（重量％）〔オロナイトジャパン（株），オロア２１８
Ａ〕のものを用いた。実施例２、１０及び比較例３にお
けるジターシャリーノニルポリサルファイドは比重（１
５℃／４℃）１．０４５、硫黄分３７．５重量％のもの
で、日本チオケミカル株式会社の商品名「ＴＮＰＳ」の
ものを用いた。実施例３、６、１１と比較例２における
硫化オレフィンは比重（１５℃／４℃）１．１４、硫黄
分４６．５重量％、粘度（cSt／１００℃）９．０のも
ので、日本クーパー株式会社の商品名「ＨＩＴＥＣ ０
５３」のものを用いた。These compositions were prepared by mixing and stirring at 60 ° C. for 1 hour at the ratios shown in Tables 1 and 2 except for Comparative Example 1. Examples 1 to 11 and Comparative Example 1
All of the polydimethylsiloxanes used in Nos. 1 to 3 were obtained by blocking the molecular chain terminals with trimethylsilyl groups. The Ca sulfonates of Examples 1 to 11 have a specific gravity (15/4 ° C.)
1.125 Ca 12.0 (% by weight) [Japan Lubrizol Co., Ltd., Lubrizol 74], Ca salicylate is specific gravity (15/4 ° C) 1.025 Ca 6.0 (% by weight) [Shell Chemical Co., Ltd. Shell AC60C], Ca finate is specific gravity (15/4 ° C.) 1.01 Ca 5.2
(% By weight) [Oronite Japan Co., Ltd., Oroa 218
A) was used. The ditertiary nonyl polysulfides in Examples 2, 10 and Comparative Example 3 had specific gravity (1
(5 ° C./4° C.) 1.045, sulfur content: 37.5% by weight, trade name “TNPS” of Nippon Thiochemicals Co., Ltd. was used. The sulfurized olefin in Examples 3, 6, 11 and Comparative Example 2 has a specific gravity (15 ° C./4° C.) of 1.14, a sulfur content of 46.5% by weight, and a viscosity (cSt / 100 ° C.) of 9.0. Cooper Corporation product name "HITEC 0
53 ".

【００５５】実施例４、８と比較例３におけるトリクレ
ジルホスフェートは、比重（１５℃／４℃）１．１７、
リン分８．４重量％、全酸価０．０５mg KOH／ｇのもの
で、大八化学（株）のものを用いた。実施例５における
ジアルキルジチオリン酸亜鉛（１）のアルキル基は炭素
数６のアルキル基で、比重（１５℃／４℃）１．１０、
亜鉛分８．５重量％、硫黄分１７．０重量％のもので、
日本クーパー株式会社の商品名「ＨＩＴＥＣ ０５３」
のものを用いた。実施例１１における芳香族基を有する
シロキサンは、芳香族基を有するシロキサン〔比重（２
５℃）１．０８０，粘度１１５cSt 〕であり、エチル７
０２は、エチル社の「ＨＩＴＩＣ ４７１０」（商品
名）であり、金属不活性剤はアモコ社の「アモコ ８０
８７」（商品名）を用いた。The tricresyl phosphate in each of Examples 4 and 8 and Comparative Example 3 had a specific gravity (15 ° C./4° C.) of 1.17,
It had a phosphorus content of 8.4% by weight and a total acid value of 0.05 mg KOH / g, and was manufactured by Daihachi Chemical Co., Ltd. The alkyl group of the zinc dialkyldithiophosphate (1) in Example 5 was an alkyl group having 6 carbon atoms, and had a specific gravity (15 ° C./4° C.) of 1.10;
8.5% by weight of zinc and 17.0% by weight of sulfur
Product name "HITEC 053" of Nippon Cooper Corporation
Was used. The siloxane having an aromatic group in Example 11 was a siloxane having an aromatic group [specific gravity (2
5 ° C.) 1.080, viscosity 115 cSt] and ethyl 7
02 is "HITIC 4710" (trade name) of Ethyl, and the metal deactivator is "Amoco 80" of Amoco.
87 "(trade name).

【００５６】[0056]

【表１】 （重量％） 実施例１ ポリジメチルシロキサン（３００，０００cSt） バランス Ｃａスルホネート ０．２ 実施例２ ポリジメチルシロキサン（３００，０００cSt） バランス ジターシャリーノニルポリサルファイド ０．５ Ｃａスルホネート ０．３ 実施例３ ポリジメチルシロキサン（３００，０００cSt） バランス 硫化オレフィン ０．５ Ｃａスルホネート ０．３ 実施例４ ポリジメチルシロキサン（３００，０００cSt） バランス トリクレジルホォスフェート １．０ Ｃａスルホネート ０．３ 実施例５ ポリジメチルシロキサン（３００，０００cSt） バランス ジアルキルジチオリン酸亜鉛 １．０ Ｃａスルホネート ０．５ 実施例６ ポリジメチルシロキサン（３００，０００cSt） バランス 硫化オレフィン １．０ Ｃａサリチレート ０．５ 実施例７ ポリジメチルシロキサン（３００，０００cSt） バランス Ｃａサリチレート ０．３ 実施例８ ポリジメチルシロキサン（３００，０００cSt） バランス トリクレジルホスフェート １．０ Ｃａサリチレート ０．５ 実施例９ ポリジメチルシロキサン（３００，０００cSt） バランス Ｃａフィネート ０．５ 実施例１０ ポリジメチルシロキサン（３００，０００cSt） バランス ジターシャリーノニルポリサルファイド １．０ Ｃａフィネート ０．５ 実施例１１ ポリジメチルシロキサン（３００，０００cSt） バランス 硫化オレフィン ０．５ Ｃａスルホネート ０．３ 芳香族を有するシロキサン ０．５ エチル７０２ ０．２ 金属不活性剤 ０．１Table 1 (% by weight) Example 1 Polydimethylsiloxane (300,000 cSt) Balanced Ca Sulfonate 0.2 Example 2 Polydimethylsiloxane (300,000 cSt) Balanced Ditertiary Nonyl Polysulfide 0.5 Ca Sulfonate 0.3 Example 3 Polydimethylsiloxane (300,000 cSt) Balance Sulfurized Olefin 0.5 Ca Sulfonate 0.3 Example 4 Polydimethylsiloxane (300,000 cSt) Balance Tricresylphosphate 1.0 Ca Sulfonate 0.3 Example 5 Polydimethylsiloxane (300,000 cSt) Balanced zinc dialkyldithiophosphate 1.0 Ca sulfonate 0.5 Example 6 Polydimethylsiloxane (300,000 cSt) Balance Sulfurized olefin 1.0 Ca salicylate 5.5 Example 7 Polydimethylsiloxane (300,000 cSt) Balanced Ca Salicylate 0.3 Example 8 Polydimethylsiloxane (300,000 cSt) Balanced Tricresyl Phosphate 1.0 Ca Salicylate 0.5 Example 9 Polydimethylsiloxane ( 300,000 cSt) Balanced Ca Finate 0.5 Example 10 Polydimethylsiloxane (300,000 cSt) Balanced Ditertiary Nonyl Polysulfide 1.0 Ca Finate 0.5 Example 11 Polydimethylsiloxane (300,000 cSt) Balanced Sulfurized Olefin 0. 5 Ca sulfonate 0.3 Aromatic siloxane 0.5 Ethyl 702 0.2 Metal deactivator 0.1

【００５７】[0057]

【表２】 比較例１ ポリジメチルシロキサン（３００，０００cSt） １００．０ 比較例２ ポリジメチルシロキサン（３００，０００cSt） バランス 硫化オレフィン ０．５ 比較例３ ポリジメチルシロキサン（３００，０００cSt） バランス ジターシャリーノニルポリサルファイド ０．５ トリクレジルホスフェート ０．５Table 2 Comparative Example 1 Polydimethylsiloxane (300,000 cSt) 100.0 Comparative Example 2 Polydimethylsiloxane (300,000 cSt) Balance Sulfurized olefin 0.5 Comparative Example 3 Polydimethylsiloxane (300,000 cSt) Balance Ditertiary nonyl Polysulfide 0.5 Tricresyl phosphate 0.5

【００５８】以上の実施例及び比較例に示す組成のもの
をビスカスカップリング用流体として、下記の如く評価
した。その結果を表３及び表４に示す。熱安定度評価
は、５０ccのビーカー（内径３cm）に試料油を約４０ｇ
とり、これを回転式空気循環恒温槽中に水平に置き、１
８０℃で１２０時間加熱し、粘度変化を測定した。実機
評価は３１枚のプレートから成るビスカスカップリング
に充填率が８２容積％になるよう封入し２０回転／分の
差速で流体温度を１３５℃に保持しながら４００時間連
続運転したときの運転前後のトルク変化と粘度変化を測
定した。The fluids having the compositions shown in the above Examples and Comparative Examples were evaluated as follows as fluids for viscous coupling. The results are shown in Tables 3 and 4. Thermal stability evaluation is about 40g of sample oil in a 50cc beaker (3cm inside diameter)
And place it horizontally in a rotary air circulation thermostat.
It heated at 80 degreeC for 120 hours, and measured the viscosity change. The actual machine was evaluated before and after running for 400 hours with a viscous coupling consisting of 31 plates filled at a filling rate of 82% by volume and continuously operated at a differential speed of 20 revolutions / minute and a fluid temperature of 135 ° C. The change in torque and the change in viscosity were measured.

【００５９】[0059]

【表３】 [Table 3]

【００６０】[0060]

【表４】 [Table 4]

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ Ｃ１０Ｍ 129:54 137:10 137:02 137:04 131:12 135:34 135:04 135:06 137:10 135:18 125:06 159:12） Ｃ１０Ｎ 10:04 10:08 10:10 10:12 20:02 30:02 40:04 40:08 (72)発明者 福原 郁男 埼玉県草加市花栗４−20 ４−306 (72)発明者 湯橋 行男 埼玉県北埼玉郡北川辺町栄70−２ (72)発明者 福田 雅彦 栃木県宇都宮市双葉１−９−28 (72)発明者 遠山 学 神奈川県中郡二宮町二宮1459−１ シテ ィーハイム201号 (56)参考文献 特開 昭64−65195（ＪＰ，Ａ) 特開 平３−231994（ＪＰ，Ａ) 特開 平２−298580（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C10M 169/04 C10M 159/12 - 159/24 C10M 107/50 C10M 135/10 C10M 129/10 C10M 129/54 C10N 40/04 ＷＰＩ／Ｌ（ＱＵＥＳＴＥＬ)──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification code FI C10M 129: 54 137: 10 137: 02 137: 04 131: 12 135: 34 135: 04 135: 06 137: 10 135: 18 125 : 06 159: 12) C10N 10:04 10:08 10:10 10:12 20:02 30:02 40:04 40:08 (72) Inventor Ikuo Fukuhara 4-20 4-306, Hanaguri, Soka-shi, Saitama 72) Inventor Yukio Yubashi 70-2 Sakae Kitagawabe-cho, Kita-Saitama-gun, Saitama (72) Inventor Masahiko Fukuda 1-9-28, Futaba, Utsunomiya-shi, Tochigi 1459-1 Citiheim 201 (56) References JP-A-64-65195 (JP, A) JP-A-3-231994 (JP, A) JP-A-2-298580 (JP, A) (58) field (Int.Cl. 7, DB name) C10M 169/04 C10M 159/12 - 159/24 C10M 107/50 C10M 135/10 C10M 129/10 C10M 129/54 C10N 40/04 WPI / L (QUES EL)

Claims (2)

(57)【特許請求の範囲】(57) [Claims] 【請求項１】 次の成分（Ａ）及び（Ｂ）を含有するビ
スカスカップリング用流体組成物。 （Ａ）次の平均単位式（１） 【化１】 〔式中、Ｒ1は炭化水素基又はハロゲン化炭化水素基を
示し、ａは１．９〜２．１の数を示す〕を有し、２５℃
における粘度が１００〜５００，０００cStのポリオル
ガノシロキサン、 （Ｂ）スルホネート、フェネート及びサリシレートから
選ばれる１種又は２種以上。1. A viscous coupling fluid composition comprising the following components (A) and (B): (A) The following average unit formula (1) Wherein R 1 represents a hydrocarbon group or a halogenated hydrocarbon group, and a represents a number of 1.9 to 2.1.
And (B) one or more selected from sulfonates, phenates and salicylates. 【請求項２】 更に次の（イ）〜（ル）に示す硫黄、硫
黄化合物、リン化合物及び塩素化合物から選ばれる１種
又は２種以上を含有することを特徴とする請求項１記載
のビスカスカップリング用流体組成物。 （イ）一般式（２） 【化２】 〔式中、Ｒ2は炭化水素基、Ｒ3は二価の炭化水素基、ｘ
は１以上の整数であり（くり返し単位中においてそれぞ
れのｘは同一又は異なる数でありうる）、ｎは０または
１以上の整数〕で示される炭化水素硫化物、 （ロ）油脂と硫黄の反応生成物である硫化油脂、 （ハ）一般式（３） 【化３】 〔式中、Ｒ4、Ｒ5、Ｒ6及びＲ7は同一又は異なる炭化水
素基〕で示されるジチオリン酸亜鉛。 （ニ）一般式（４） 【化４】 〔式中、Ｒ8、Ｒ9、Ｒ10及びＲ11は同一又は異なるアル
キル基、ＭｅはＺｎ、Ｐｂ、Ｍｏ、Ｓｂの金属〕で示さ
れるジアルキルジチオカルバミン酸金属塩、 （ホ）単体硫黄、 （ヘ）一般式（５） 【化５】 〔式中、Ｒ12、Ｒ13は二価の炭化水素基、ｘは１以上の
整数であり（くり返し単位中においてそれぞれのｘは同
一又は異なる数でありうる）、ｍは０又は１以上の整
数〕で示される炭化水素硫化物。 （ト）一般式（６） 【化６】 〔式中、Ｒ14は一価の炭化水素基、ｂは１、２又は３、
ｃは０又は１の数、Ｘは酸素原子又は硫黄原子〕で示さ
れるリン酸エステル、亜リン酸エステル、チオリン酸エ
ステル、あるいはジチオリン酸エステル。 （チ）（ト）で示される酸性リン酸エステル、酸性亜リ
ン酸エステル、酸性チオリン酸エステルあるいは酸性ジ
チオリン酸エステルのアルキルアミン塩、 （リ）炭化水素と硫化リンとの反応生成物 （ヌ）一般式（７） 【化７】 〔式中、Ｒ15は一価の炭化水素基、Ｒ16は二価の炭化水
素基〕で示されるジチオリン酸の水酸基置換トリエステ
ルとリン酸類、酸化リン類、又はハロゲン化リン類との
反応生成物をアミンで中和して得られるリン及び窒素を
含む組成物。 （ル）一般式（８） 【化８】 〔式中、Ｒ17はアルキル基〕で示されるジエステル2. The viscous liquid according to claim 1, further comprising one or more selected from the group consisting of sulfur, sulfur compounds, phosphorus compounds and chlorine compounds shown in the following (a) to (l). Fluid composition for coupling. (A) General formula (2) [Wherein, R 2 is a hydrocarbon group, R 3 is a divalent hydrocarbon group, x
Is an integer of 1 or more (each x may be the same or a different number in the repeating unit), and n is 0 or an integer of 1 or more.] (B) Reaction of oil and fat with sulfur (Iii) the general formula (3): [Wherein R 4 , R 5 , R 6 and R 7 are the same or different hydrocarbon groups]. (D) General formula (4) [Wherein R 8 , R 9 , R 10 and R 11 are the same or different alkyl groups, Me is a metal of Zn, Pb, Mo, and Sb], a metal salt of dialkyldithiocarbamate represented by the following formula: F) General formula (5) [Wherein, R 12 and R 13 are divalent hydrocarbon groups, x is an integer of 1 or more (each x may be the same or different in the repeating unit), and m is 0 or 1 or more. Hydrocarbon sulfide represented by an integer. (G) General formula (6) Wherein R 14 is a monovalent hydrocarbon group, b is 1, 2 or 3,
c is a number of 0 or 1, X is an oxygen atom or a sulfur atom], a phosphite, a thiophosphate or a dithiophosphate. (H) an alkylamine salt of an acid phosphate, acid phosphite, acid thiophosphate or acid dithiophosphate shown in (g), (iii) a reaction product of a hydrocarbon with phosphorus sulfide General formula (7) [Wherein, R 15 is a monovalent hydrocarbon group, and R 16 is a divalent hydrocarbon group] Reaction of a hydroxyl-substituted triester of dithiophosphoric acid with phosphoric acid, phosphorus oxide, or phosphorus halide A composition comprising phosphorus and nitrogen obtained by neutralizing the product with an amine. (R) General formula (8) [Wherein R 17 is an alkyl group]
JP4312190A 1992-11-20 1992-11-20 Fluid composition for new viscous coupling Expired - Lifetime JP3040618B2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP4312190A JP3040618B2 (en) 1992-11-20 1992-11-20 Fluid composition for new viscous coupling
DE69316847T DE69316847T2 (en) 1992-11-20 1993-11-22 Use in a viscous coupling of a mixture which contains a polyorganosiloxane and a viscosity inhibitor
EP93118776A EP0599251B1 (en) 1992-11-20 1993-11-22 Use in viscous coupling of a fluid comprising a polyorganosiloxane and a viscosity inhibitor

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP4312190A JP3040618B2 (en) 1992-11-20 1992-11-20 Fluid composition for new viscous coupling

Publications (2)

Publication Number Publication Date
JPH06158081A JPH06158081A (en) 1994-06-07
JP3040618B2 true JP3040618B2 (en) 2000-05-15

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ID=18026304

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Application Number Title Priority Date Filing Date
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Country Status (3)

Country Link
EP (1) EP0599251B1 (en)
JP (1) JP3040618B2 (en)
DE (1) DE69316847T2 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1276799B1 (en) * 1995-06-29 1997-11-03 Dow Corning FORMULATIONS OF F-SILICONE
US6764982B2 (en) 2001-02-07 2004-07-20 The Lubrizol Corporation Lubricating oil composition
JP2012046730A (en) * 2010-07-28 2012-03-08 Cosmo Oil Lubricants Co Ltd Fluid composition for fan clutch
JP5840233B2 (en) 2011-02-17 2016-01-06 ザ ルブリゾル コーポレイションＴｈｅ Ｌｕｂｒｉｚｏｌ Ｃｏｒｐｏｒａｔｉｏｎ Lubricant with good TBN retention
JP2020515697A (en) 2017-04-03 2020-05-28 ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． Working fluid composition

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3759827A (en) * 1970-09-29 1973-09-18 Dow Corning Lubricant compositions
JPS59129294A (en) * 1983-01-17 1984-07-25 Idemitsu Kosan Co Ltd High temperature lubricant
JPH0631389B2 (en) * 1987-05-30 1994-04-27 コスモ石油株式会社 Fluid composition for viscous coupling
JP2579806B2 (en) * 1988-09-28 1997-02-12 ダウコーニングアジア株式会社 Fluid composition for viscous coupling
JPH064850B2 (en) * 1989-04-21 1994-01-19 キング、インダストリーズ、インコーポレーテッド Thermo-oxidatively stable composition
DE69017749T2 (en) * 1989-05-10 1995-07-06 Tonen Corp Silicone fluids for viscous couplings.

Also Published As

Publication number Publication date
DE69316847T2 (en) 1998-06-18
EP0599251B1 (en) 1998-02-04
JPH06158081A (en) 1994-06-07
DE69316847D1 (en) 1998-03-12
EP0599251A1 (en) 1994-06-01

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