JPS6035096A - Operating oil - Google Patents

Operating oil

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Publication number
JPS6035096A
JPS6035096A JP59132853A JP13285384A JPS6035096A JP S6035096 A JPS6035096 A JP S6035096A JP 59132853 A JP59132853 A JP 59132853A JP 13285384 A JP13285384 A JP 13285384A JP S6035096 A JPS6035096 A JP S6035096A
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JP
Japan
Prior art keywords
hydraulic
alkyl
formula
oil
hydraulic 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.)
Granted
Application number
JP59132853A
Other languages
Japanese (ja)
Other versions
JPS6046155B2 (en
Inventor
ハーバート・フランク・アスキユウ
コリン・ジヨン・ハーリントン
ジエラルド・ジヨン・ジヨセフ・ジエイン
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.)
Castrol Ltd
Original Assignee
Castrol Ltd
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Filing date
Publication date
Application filed by Castrol Ltd filed Critical Castrol Ltd
Publication of JPS6035096A publication Critical patent/JPS6035096A/en
Publication of JPS6046155B2 publication Critical patent/JPS6046155B2/en
Expired legal-status Critical Current

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    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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    • C10M2227/04Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/08Hydraulic fluids, e.g. brake-fluids

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

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。
(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

【発明の詳細な説明】 シラン誘導体を含有する作動油に関する。[Detailed description of the invention] The present invention relates to a hydraulic fluid containing a silane derivative.

グリコールエーテルをベース油とする作動油1°は車類
のブレーキおよびクラッチ系などに多年にわたって用い
られており最も汎用されている。しかしながら、油田系
の製造業者やザ・ソサイアテイ・オプ・オートモーテイ
プ・エンジニアーズ(the Society of 
Automotive Engineers )、ユ−
・ニス・デパートメント・オブ・トランスポーテイショ
シ( IJ, S.Dopa.rtment ofTr
ansportatlqn)などの公共機関で設定して
いる品質基準はますます厳格になっている。とくに、よ
り高沸点の作動油に対ノーる要求が高まっており、さら
に重要なことは、製造業者1/C.J:5処方される作
動油および水の存在下にも使われる作動油の両方に対し
てより高いペーパーロック温度が要求されている。グリ
コールエーテルベース油は、その吸湿性のために大気よ
り水分を吸収し7、そのような要求に対しては不適であ
ることが知られている。その水分吸収により作動油の沸
点およびペーパーロック温度が降下し、使用とともに作
動油の水分含量は、その沸点鰺よびペーパーロック温度
が危険域までに降下する程の基準にまで達する。もし、
それが強いブレーキをかけたときなどに生じる熱に会え
ば、その作動油は沸騰または気化し、著しいブレーキ機
能不全を起す。
Hydraulic oil 1°, which is based on glycol ether, has been used for many years in automobile brake and clutch systems and is the most widely used oil. However, oil field manufacturers and the Society of Automotive Engineers
Automotive Engineers),
- Varnish Department of Transportation (IJ, S.Dopa.rtment of Tr.
The quality standards set by public institutions such as Ansportatlqn are becoming increasingly strict. In particular, there is an increasing demand for higher boiling point hydraulic fluids and, more importantly, manufacturers are increasing their demand for higher boiling point hydraulic fluids. Higher paper lock temperatures are required for both hydraulic fluids that are formulated as J:5 and those that are also used in the presence of water. Glycol ether-based oils are known to absorb moisture from the atmosphere due to their hygroscopic nature7 and are therefore unsuitable for such requirements. The water absorption lowers the boiling point and paper rock temperature of the hydraulic fluid, and with use, the water content of the hydraulic fluid reaches such a standard that the boiling point and paper rock temperature drop to a dangerous level. if,
When it encounters the heat generated when applying strong brakes, the hydraulic fluid boils or evaporates, causing significant brake malfunction.

この問題を解決するために、グリコールエステル類をベ
ースとした低吸湿性の作動油も開発されている。この作
動油は大気中の水分に対しては比較的感応性が少ないが
、グリコールエーテルベース油に比べて高価であるとと
もに、技術的にも欠点を有し、たとえばその粘度特性が
グリコールエーテルベース油よりも劣っている。したが
って、このような低吸湿注油の使用は、所望の高沸点、
高ペーパーロック温度などの性質がその欠点をこえて重
要であるような場合に限られている.他の水分非感応性
の作動油も開発されている。しかしながら、製造業者ら
は、グリコールエーテルベース油お・よび低吸湿注油の
両者の良好な性質を兼ね備え.さらに低吸湿注油よりも
さら]て高い沸点およびペーパーロック温度を有する新
しい作動油をめている。
In order to solve this problem, low hygroscopic hydraulic fluids based on glycol esters have also been developed. Although this fluid is relatively insensitive to atmospheric moisture, it is more expensive than glycol ether-based oils and has technical drawbacks, such as its viscosity characteristics that differ from glycol ether-based oils. inferior to. Therefore, the use of such a low moisture absorption lubricant can reduce the desired high boiling point,
Only in cases where properties such as high paper rock temperature outweigh the disadvantages. Other moisture-insensitive hydraulic fluids have also been developed. However, manufacturers are trying to combine the good properties of both glycol ether-based oils and low moisture absorption. In addition, new hydraulic oils with even higher boiling points and paper lock temperatures than low-moisture lubrication oils are being introduced.

最近、別々の油圧系で操作していたパワーステアリング
、ショックアブソーバ−、フ゛レ−キなとを単一油圧系
にて操作するような車を設計する傾向がみられる。この
ことは好適な作動油の処方に重要な影響を与えている。
Recently, there has been a tendency to design cars in which power steering, shock absorbers, and brakes, which used to be operated by separate hydraulic systems, are operated by a single hydraulic system. This has important implications for the formulation of suitable hydraulic fluids.

これまでパワ御名テアリシグ系やショックアブソーバ−
に用いられている鉱油ベース油はその系のシールやガス
ケットに用いているニトリルゴム、クロロプロピレンゴ
ムには充分用いられうるが、油圧ブレーキやクラッチ系
((用いられている天然ゴム、スチレン/プタジエシゴ
ムなどには著しく有害である。そのため、後者のシール
が異常(て膨張し、ブレーキやクラッチ系の著しい機能
不全をもたらす。したがって、これまでブレーキやクラ
ッチ系に充分使用されてきた、グリコ−ル類、グリコー
ルエーテル類、グリコールエーテルエステル類をベース
とする作動油は、パワーステアリング、ショックアブソ
ーバ−に用いられるニトリルゴム、クロロプレシゴムに
有害で、それらの系の機能不全をもたらす。車輛運転に
おいては、運転の確実性(それはあらゆる機械装置にお
いて望まれることであるが)が安全性の観点より必須の
条件として重要視されている。したがって、この要求は
、各種の装置の運転をコントロールする中枢系に充分満
足して使用されつる作動油に対しても与えられる。
Up until now, we have used Power Gonna Tea Risig series and shock absorbers.
Mineral oil-based oils used in systems can be used satisfactorily for nitrile rubber and chloropropylene rubber used for seals and gaskets in these systems, but hydraulic brakes and clutch systems (natural rubber, styrene/puttadiene rubber used in As a result, the seals of the latter expand abnormally, resulting in significant malfunction of brake and clutch systems. Hydraulic fluids based on , glycol ethers, and glycol ether esters are harmful to nitrile rubber and chloropress rubber used in power steering and shock absorbers, causing malfunction of these systems. Reliability of operation (which is desired in all mechanical devices) is emphasized as an essential condition from a safety perspective.Therefore, this requirement is imposed on the central system that controls the operation of various devices. It is also given for hydraulic fluids that are used satisfactorily.

本発明者らは、ある種のケイ素化合物が、油圧ブレーキ
、クラッチ系および中枢油圧系に用いられる作動油の成
分として有用であることを見出した。これらの化合物は
、油田系の構造体に用いられる各種の天然および合成ゴ
ムの膨張性全改良し、また比較的水に対する感応性が少
ない。
The inventors have discovered that certain silicon compounds are useful as components of hydraulic fluids used in hydraulic brakes, clutch systems, and central hydraulic systems. These compounds improve the expansibility of various natural and synthetic rubbers used in oilfield structures and are relatively water-insensitive.

該化合物は式 rt−^i、−R4(■) (’)It3 〔式中、 (a) Rif、 it; −(OR5)ITl−Of
(!’−で示される基。
The compound has the formula rt-^i, -R4(■) (')It3 [wherein (a) Rif, it; -(OR5)ITl-Of
(Group indicated by !'-.

(b) It!およびTL2は各々低級アルキル、−0
R3またはH,’−(Oltu 1m−□IL6−で示
される基:(C) I(pij、同一47’c fd 
A 71 ッテ、R’−(ORPIB、−テ示される基
(b) It! and TL2 are each lower alkyl, -0
R3 or H,'-(Oltu 1m-□IL6- group: (C) I(pij, same 47'c fd
A 71 te, R'-(ORPIB, -te group).

(6,) +t’は、同一ま7ヒは異なって、炭素数1
〜18のアルキル; (e) ](4は、同一または異なって、エチレンまた
はプロピレン; (f) R6は、同一または異なって、炭素数6までの
アルキレジ; ()l;) mは、同一′TFたは異なって、0または
1〜4の整数。
(6,) +t' is the same or 7hi is different, and the number of carbon atoms is 1
-18 alkyl; (e) ] (4 is the same or different, ethylene or propylene; (f) R6 is the same or different, an alkylene having up to 6 carbon atoms; ()l;) m is the same' TF or different, 0 or an integer from 1 to 4.

で示されるシラン誘導体である。mが0以外の式(i)
のシラン誘導体は新規な化合物である。
This is a silane derivative represented by Formula (i) where m is other than 0
The silane derivative of is a new compound.

このシラン誘導体を油圧ブレーキおよびクラッチ系に用
いる場合には、その系に用いられるシールやガスケット
のゴム膨張を最小限に押えるために、その末端アルキル
基は比較的短鎖のもの、たとえば、炭素数1〜4、さら
に好ましくは1または2のアルキルが好ましい。しかし
、中枢系に用いる場合には、各種シールやガスケット類
の各々に要求される、しばしば競合するような、要件を
満たすことが望ましい。この場合には、末端アルキル基
のいくつかあるいは全部をより長鎖のアルキル、たとえ
ば炭素数6個まで、ときには8個くらいのものにしても
よい、さらl/C1鉱油t”−スとする作動油において
は、さらに長鎖の末端アルキル基、たとえば炭素数16
個、ときには18個のものを用いることが、油溶性の点
から要求される、末端アルキル基は直鎖または分枝鎖の
いずれでもよいが、油溶性の点でくことに鉱油に対して
)分枝鎖アルキルが好ましい。
When this silane derivative is used in hydraulic brake and clutch systems, the terminal alkyl group must have a relatively short chain, e.g. 1 to 4, more preferably 1 or 2 alkyl is preferred. However, for central system applications, it is desirable to meet the often competing requirements of each type of seal or gasket. In this case, some or all of the terminal alkyl groups may be longer chain alkyls, such as those having up to 6, sometimes as many as 8 carbon atoms. In oils, even longer chain terminal alkyl groups, e.g.
The terminal alkyl group may be either straight chain or branched, but from the viewpoint of oil solubility, it is necessary to use 18, sometimes 18, especially for mineral oil). Branched alkyls are preferred.

本発明のシラン誘導体は適当なハロアルキルシランから
公知の方法により容易に製造される。
The silane derivative of the present invention can be easily produced from a suitable haloalkylsilane by a known method.

このシラン誘導体は、作動油の添加物、ベース油あるい
はベース油混合物の1成分として用いられる。月数は広
範囲にわたり、作動油の全量に基いて05〜99%(重
量係、以下同じ)の範囲である。ベース油として用いる
場合には、このシラン誘導体は作動油の主構成成分とな
り、その全重量に基いて、たとえば75または80〜9
9チの範囲で含まれる。その残部は公知の作動油添加剤
および/または他の作動油用ベース油である。
The silane derivatives are used as additives in hydraulic fluids, base oils or as a component of base oil mixtures. The number of months varies over a wide range, ranging from 0.5% to 99% (by weight, the same applies hereinafter) based on the total amount of hydraulic fluid. When used as a base oil, this silane derivative becomes the main constituent of the hydraulic fluid and, based on its total weight, is e.g.
Included in the range of 9. The remainder is known hydraulic fluid additives and/or other hydraulic fluid base oils.

ベース油混合物の1成分として用いる場合には、その全
ベース油混合物が作動油の主構成成分となり、この場合
は、該ベース油は主として1以上のシラン誘導体からな
り、これに・そのシラン誘導体の性質を改質するために
より少ない量の他のベース油1種または2種以上を配合
する、しかして、該作動油は、1種以上のシラン誘導体
を、全重量に基いて、たとえば、55〜75%含有する
。、また他の1種以−ヒのベース油の性質を改質するた
めにより少量のシラン誘導体を混合してもよく、この場
合、該作動油はシラン誘導体をたとえば20〜40%含
有する。さらに、シラン誘導体と他のベース油の性質を
折合せるように、それらをほぼ等量ずつ混合して、シラ
ン誘導体含量が40〜55%となるようにしてもよい。
When used as a component of a base oil mixture, the entire base oil mixture becomes the main component of the hydraulic fluid, in which case the base oil consists primarily of one or more silane derivatives, including: Incorporating smaller amounts of one or more other base oils to modify the properties, the hydraulic oil may contain one or more silane derivatives, e.g. Contains 75%. A smaller amount of a silane derivative may also be mixed in to modify the properties of one or more other base oils, in which case the hydraulic oil contains, for example, 20 to 40% of the silane derivative. Furthermore, in order to balance the properties of the silane derivative and other base oils, they may be mixed in approximately equal amounts so that the silane derivative content is 40 to 55%.

また、作動油の、ことにその沸点およびペーハーロック
温度に関し、水に対する感応性を抑えるために用いる場
合には、7ラン誘導体は20〜50%、さらに好ましく
は20〜40%の範囲で用いるのが望ましい。さらに、
より少量、たとえば0.5〜15%あるいは20%まで
のシラン誘導体を用いても改良効果はあるが、上記の高
用量がより好ましい。この場合の作動油の主構成成分は
後記の如き他のベース油の1種または2種以上である。
In addition, when used to suppress the sensitivity of hydraulic oil to water, especially regarding its boiling point and pH lock temperature, the 7-run derivative is used in a range of 20 to 50%, more preferably 20 to 40%. is desirable. moreover,
Although smaller amounts of the silane derivative, such as 0.5-15% or even up to 20%, can have an improved effect, the higher doses mentioned above are more preferred. The main component of the hydraulic oil in this case is one or more of the other base oils described below.

シラン誘導体をベース油混合物の1成分として用いる場
合には、実質的にシラン誘導体からなるベース油の場合
と同様に、公知の作動油添加剤を配合してもよい。同様
に、添加剤として用いる場合にも、所望ならば、シラン
誘導体を他の公知の作動油添加剤と併用してもよい。
When a silane derivative is used as one component of a base oil mixture, known hydraulic oil additives may be added, as in the case of a base oil consisting essentially of a silane derivative. Similarly, when used as additives, silane derivatives may be used in combination with other known hydraulic fluid additives, if desired.

公知の添加剤は、通常、005〜10%の範囲、たとえ
ば01〜2%の少量で用いられる。
Known additives are usually used in small amounts in the range 0.05-10%, for example 0.1-2%.

シラン誘導体と混合されつるあるいはシラン誘導体を添
加剤として配合しうるベース油としては、鉱油、ポリオ
キシアルキレングリコール類およびそのエーテル類、モ
ノ−、ジーまたはポリカルボン酸またはホウ酸のアルキ
ルおよびポリオキシアルキレジグリコールエーテルエス
テル類、ホルマール類、アセタール類、りん酸エステル
類、シリコーン類、ジーまたはポリアルコールのモノカ
ルボン酸エステル類、その他の公知のベース油が含まれ
る。
Examples of base oils that can be mixed with silane derivatives or in which silane derivatives can be used as additives include mineral oils, polyoxyalkylene glycols and their ethers, mono-, di- or polycarboxylic acids, or alkyl and polyoxyalkylene boronic acids. Included are resin glycol ether esters, formals, acetals, phosphate esters, silicones, monocarboxylic acid esters of di- or polyalcohols, and other known base oils.

本発明の好ましい1つの態様においては、前記式(T)
のシラン誘導体の少なくとも1種5〜30%と次式 %式% () () 〔式中、allはアルキル(好ましくは炭素数1〜18
のアルキル)またはアリール(好ましくはフェニル) 
、 B+2はアルキル(好ましくは炭素数1〜18のア
ルキル)、アリール(好ましくはフェニル)、アルカリ
ール(好ましくは炭素数1〜12のアルキルで置換され
たフェニル)、アラルキル(好ましくはベンジル)また
はR1−(OR5)□−で示される基、 B+3はアル
キル(好ましくは炭素数1〜18のアルキル)、アリー
ル(好ましくはフェニル)、アルカノール(好ましくは
炭素数1〜12のアルキルで置換されたフェニル)、ア
ラルキル(好ましくはベンジル)またはR’−(OR5
)□−〇−で示される基:14、R5およびmは前記式
(I) I/Cついて定義したものと同じ〕 で示される公知のベース油化合物の少なくとも1種5〜
30%とラフリコールエーテルベース油に配合してなる
作動油を提供する。
In one preferred embodiment of the present invention, the formula (T)
5 to 30% of at least one silane derivative of the following formula % () () [wherein all is alkyl (preferably carbon number 1 to 18
alkyl) or aryl (preferably phenyl)
, B+2 is alkyl (preferably alkyl having 1 to 18 carbon atoms), aryl (preferably phenyl), alkaryl (preferably phenyl substituted with alkyl having 1 to 12 carbon atoms), aralkyl (preferably benzyl), or R1 -(OR5)□-, B+3 is alkyl (preferably alkyl having 1 to 18 carbon atoms), aryl (preferably phenyl), alkanol (preferably phenyl substituted with alkyl having 1 to 12 carbon atoms) , aralkyl (preferably benzyl) or R'-(OR5
) A group represented by □-〇-: 14, R5 and m are the same as those defined for formula (I) I/C] At least one of the known base oil compounds represented by 5-
To provide a hydraulic oil which is blended with 30% Lafrycol ether base oil.

さらに他の好ましい態様においては、実質的に式(1)
のシラン誘導体の少なくとも1種10〜90チと式(n
)、(III)または(IT)の化合物の少なくとも1
種90・〜10q6からなる作動油全提供する。
In yet another preferred embodiment, substantially the formula (1)
At least one silane derivative of formula (n
), (III) or (IT)
Hydraulic oils consisting of species 90-10q6 are provided.

いずれの組成物においても、本発明の作動油は一40″
Oでの動粘度が5000 cat、なかんづぐ2000
 cstを越えないことが望ましい。さらに本発明の作
動油は少なくとも260℃の沸点を有することが好まし
い。
In either composition, the hydraulic oil of the present invention is
Kinematic viscosity at O is 5000 cat, Nakanzugu 2000
It is desirable not to exceed cst. Furthermore, it is preferred that the hydraulic oil of the present invention has a boiling point of at least 260°C.

本発明のさらに他の態様においては、前記のような作動
油を機能’fi (functional fluid
 )として含む、油圧手段にて動力全伝達するための油
圧系を提供するものである。
In yet another aspect of the invention, the above-mentioned hydraulic fluid is used as a functional fluid.
), it provides a hydraulic system for transmitting all power by hydraulic means.

さらに他の態様においては、前記のような作動油を油圧
系に導入し、該作動油に圧力を与えて動力を伝達するこ
とからなる油圧系の運転方法を提供する。
In yet another aspect, there is provided a method for operating a hydraulic system, which comprises introducing the above-mentioned hydraulic oil into the hydraulic system, applying pressure to the hydraulic oil, and transmitting power.

つぎして実施例をあげて本発明をさらに具体的に説明す
る。
Next, the present invention will be explained in more detail with reference to Examples.

実施例1 1フイートの充填カラムを付けたガラスフラスコ中テ、
トリス(メトキシ)−310+=+7”oビルシラシフ
94g(4モル)とメチルトリグリコール2296gC
14モル)の混合物を、該混合物からメタノール188
.1 、!li’が除去されるまで、窒素雰囲気下に加
熱する。該カラi・をはずI−て、最低温度200℃に
てさらに加熱を続け、反応物317.4g(理論値38
4g)をうる。
Example 1 In a glass flask fitted with a 1 foot packed column,
Tris(methoxy)-310+=+7” 94g (4 moles) of methyl triglycol and 2296gC
14 mol) of methanol is extracted from the mixture with 188 mol of methanol
.. 1,! Heat under nitrogen atmosphere until li' is removed. The drain was removed and heating was continued at a minimum temperature of 200°C to yield 317.4 g of reactant (theoretical value: 38
4g).

メチルトリグリコール100100O,1モル)にナト
リウム101.2g(4,4グラム原子)を溶かし、え
られたスラリーを上記反応混合物に加えたのち、100
℃で3時間保持する。生成物を炉取し、最低温度180
℃、01酊HgVcて蒸留し、再度沖過する。
After dissolving 101.2 g (4.4 gram atoms) of sodium in methyl triglycol (100 O, 1 mole) and adding the resulting slurry to the above reaction mixture, 100
Hold at ℃ for 3 hours. The product is taken out of the furnace and the minimum temperature is 180℃.
Distilled at 0.01°C and filtered again.

S1含量420%〔トリス(メチルトリグリコール)−
3−メチルトリグリコールプロピルシランの理論S1含
量:388%〕の暗色液体をうる。
S1 content 420% [Tris (methyl triglycol)-
A dark liquid with theoretical S1 content of 3-methyltriglycolpropylsilane: 388% is obtained.

この生成物は沸点320°C1粘度(−40″0)23
06 c8を有する。このものを5BRG、(42%)
およびナチュラルR32(−10%)についてゴム膨張
t’lテストしたところ良好な結果をえた。
This product has a boiling point of 320°C1 a viscosity of (-40″0)23
Has 06 c8. This thing is 5BRG, (42%)
Rubber expansion t'l test was performed on Natural R32 (-10%) and good results were obtained.

実施例2 前記と同様にして、トリス(メトキシ)−3−クロロプ
ロピルシラン198.5.!i!(1モル)、メチルジ
グリコール398g(3,3モル)およびナトリウム2
!l(1,1グラム原子)のメチルジグリコール401
(3,4モル)中スラリーを用いて、トリス(メチルジ
グリコール)−3−メチルシクリコールグロピルシラン
をうる。
Example 2 Tris(methoxy)-3-chloropropylsilane 198.5. ! i! (1 mol), methyl diglycol 398 g (3.3 mol) and sodium 2
! l (1,1 gram atom) of methyl diglycol 401
(3.4 mol) to obtain tris(methyldiglycol)-3-methylcycricolglopylsilane.

最初の工程でメタノール77g(理論量=96g)が収
集される。Si含量6092%(理論値:512%)、
クロル含量0.2%の生成物409g(75%)をうる
。この生成物は、粘度(−40’0) 1051c8.
沸点310°Cを有し、8BRG9(8,9%)および
ナチュラルR32(2,0%)でのゴム膨張性テストで
良好な結果を与えた。
77 g of methanol (theoretical amount = 96 g) are collected in the first step. Si content 6092% (theoretical value: 512%),
409 g (75%) of product with a chlorine content of 0.2% are obtained. This product has a viscosity (-40'0) of 1051c8.
It has a boiling point of 310°C and gave good results in rubber expansibility tests with 8BRG9 (8.9%) and Natural R32 (2.0%).

実施例3 前記と同様にして、3−クロロプロピル−トリメトキシ
シラン397g(2モル)、トリデカノール1400g
(7モル)、p−トルエンスルホン酸082gおよびナ
トリウム50.6 g(2,2グラム原子)のトリデカ
ノール8oO=<(4モル)中スラリーを用いて、トリ
ス(トリメトキシ)−3−トリデカツキジプロピルシラ
ンをうる。メタノール16 B 、!i+ ’(理論量
:192g)かえられる。
Example 3 In the same manner as above, 397 g (2 mol) of 3-chloropropyl-trimethoxysilane and 1400 g of tridecanol were added.
(7 mol), p-toluenesulfonic acid 082 g and sodium 50.6 g (2,2 gram atoms) in tridecanol 8oO=<(4 mol) to prepare tris(trimethoxy)-3-tridekatsuki dipropyl Take silane. Methanol 16 B,! i+' (theoretical amount: 192g) can be changed.

S1含量3.46%(理論値:323%)の生成物71
1g(82%)かえられる。
Product 71 with S1 content of 3.46% (theoretical value: 323%)
1g (82%) can be exchanged.

この生成物(50%)とDTD585鉱油(50%)と
のブレンド物は粘度(−40℃)2313 asを有し
、これを0.5%H20とともに100℃で72時間加
熱したのちのペーパーロック温度は225°Cであった
A blend of this product (50%) with DTD 585 mineral oil (50%) has a viscosity (-40°C) of 2313 as, and after heating with 0.5% H20 at 100°C for 72 hours, the paper lock The temperature was 225°C.

実施例4〜26 本発明の作動油を以下のテストに付した。Examples 4-26 The hydraulic oil of the present invention was subjected to the following tests.

(a)動粘度(−40°c)−eセンチストーク(cs
)にて5AE1703C仕様書に記載の方法にて測定し
た。
(a) Kinematic viscosity (-40°c) - e centistokes (cs
) was measured using the method described in the 5AE1703C specifications.

(b)コム膨張性iスチレン/ブタジェンゴム(SBJ
、ニトリルゴムおよびエチレン/プロピレンゴムにてテ
ストした。SBRの場合は、FMVS S l l 5
DOT3/4仕様@に記載の方法にて、標準SAE 5
I3Rカツプを用いて行なった。ニトリルゴムについて
のゴム膨張性は、ニド!J/I/ニア’)、試験片(2
54α角、2朋厚さ)を試験液5〇−中にて120°C
で70時間保持した際の容量増加により決定した。エチ
レン/プロピレンゴムについては・航空機産業において
用いられているようなエチレン/プロピレンゴムリング
シールを用いた以外は、ニトリルゴムの場合と同様にし
て行なった。
(b) Comb expandable i-styrene/butadiene rubber (SBJ
, nitrile rubber and ethylene/propylene rubber. For SBR, FMVS S l l 5
Standard SAE 5 by the method described in DOT3/4 specifications @
This was done using an I3R cup. The rubber expansibility of nitrile rubber is Nido! J/I/Near'), test piece (2
54α angle, 2mm thickness) in test solution 50-120°C.
This was determined by the increase in capacity when held for 70 hours. For ethylene/propylene rubber, the procedure was the same as for nitrile rubber, except that an ethylene/propylene rubber ring seal such as that used in the aircraft industry was used.

(C)ペーパーロック温度は、前記試験液をFMVss
l16仕様書に記載されるような湿度試験に付したのち
(但し対照液は用いない)に測定した。
(C) Paper lock temperature is FMVss of the test liquid.
Measurements were made after subjecting the sample to a humidity test as described in the 116 specification (without using a control solution).

クリコールエーテルベース油からなる作動油の場合は、
シリコーンブレーキ油に関するSAE J1705仕様
書に記載の装置および方法によって行なわれるマーキイ
・ペーパーロックテスト(Ma、rkey Vapou
r Lock Te5t ) VCよッテペーパーロツ
ク温度を測定した。非グリコールエーテルベース油のペ
ーパーロック温度は、SAEペーパー710 253に
記載(表題:作動油水分含量により影響を受ける自動車
ブレーキ系の操作)のギルビン・ペーパーロックテスト
((311pin ’VapourLock Te5t
 )により測定した。ギルビシ・ペーパーロック温度は
気泡3@が生じる温度である。
For hydraulic fluids made of glycol ether base oil,
The Markey Vapou Test is conducted by the equipment and method described in the SAE J1705 Specification for Silicone Brake Fluids.
r Lock Te5t ) The VC lock temperature was measured. The PaperLock temperature of non-glycol ether-based oils is determined by the Gilvin PaperLock test ((311pin'VapourLock Te5t
). The Girbishi paper rock temperature is the temperature at which bubbles 3@ occur.

(、i)加水分解安定性をつぎのようにして測定した。(,i) Hydrolytic stability was measured as follows.

すなわち、試験液に水10%加え、密封アンプル中で1
00°Cにて24時間加熱したのち冷却し、ゲル化また
は分離の発現をチェックした。式(n)、(III)ま
たは(mV)のシラン単独、またはそれとグリコールエ
ーテルベース油との混合液はこのような条件下では一般
にゲル化する。
That is, add 10% water to the test solution, and add 10% water in a sealed ampoule.
After heating at 00°C for 24 hours, the mixture was cooled and checked for gelation or separation. Silanes of formula (n), (III) or (mV) alone or in mixtures with glycol ether base oils generally gel under such conditions.

これらの結果を第1表から第3表に示す。表中の略称お
よび市販品はつぎのものを意味する。
These results are shown in Tables 1 to 3. The abbreviations and commercially available products in the table mean the following.

ブチルモノグリコール:エチレングリコールモノブチル
エーテル DPM: ジブロピレングリコールモノメチルエーテル MTG: )!Jエチレングリコールモノメチルエーテ
ル MDG 、ジエチレングリコールモノメチルエーテル 鉱油A: ナフテン酸鉱油、粘度: 130 cs(−
40°F)、3.5Q8(100°F)、1.31cS
(210°F);流動点:〉−70°F:沸点:248
°C:引火点:208℃ニアニリン点ニア6℃ 鉱油D: ジトリデシル・ドデカンジオエート冷媒油B
:市販の冷媒油(Br1tish Petroleum
製ZERICE 853)、アルキ ル化ベンゼンの混合物と考えられる。
Butyl monoglycol: Ethylene glycol monobutyl ether DPM: Dibropylene glycol monomethyl ether MTG: )! J ethylene glycol monomethyl ether MDG, diethylene glycol monomethyl ether mineral oil A: naphthenic acid mineral oil, viscosity: 130 cs (-
40°F), 3.5Q8 (100°F), 1.31cS
(210°F); Pour point: 〉-70°F: Boiling point: 248
°C: Flash point: 208 °C near aniline point 6 °C Mineral oil D: Ditridecyl dodecanedioate refrigerant oil B
: Commercially available refrigerant oil (Br1tish Petroleum
ZERICE 853), which is considered to be a mixture of alkylated benzenes.

冷媒油C:ナフテン酸鉱油の1商品、相対密度:0.9
20;粘度+ 63.0cS(100°F)、6.1c
S(210°F);引火点=183℃:流動点ニー流動
点ニ ー3フ ( Dow Corning製02−1062)E55
5:市販のエチレン/プロピレングリコ19 一ルエーテル( DOW Ohemj.cal Co.
製)、分子量:約243:末端エーテ ルアルギル基は主としてメチルと考 えられるが1部はエチルと考えられ る。
Refrigerant oil C: 1 product of naphthenic acid mineral oil, relative density: 0.9
20; Viscosity + 63.0cS (100°F), 6.1c
S (210°F); Flash point = 183°C: Pour point knee Pour point knee 3f (Dow Corning 02-1062) E55
5: Commercially available ethylene/propylene glyco-19 ether (DOW Ohemj.cal Co.
), molecular weight: approximately 243: The terminal ether argyl group is thought to be mainly methyl, but a portion is thought to be ethyl.

A79ニトリルゴム二市販のニトリルゴムでガーリング
( Girling) ブレーキ系に用いられている。
A79 Nitrile Rubber 2 A commercially available nitrile rubber used in Girling brake systems.

(ホ) (21) に) (23) (別) 第3表 (25) 第1頁の続き QlnL、CI、’ 識別記号 庁内整理番号0発 明
 者 ジエラルド・ジョン・ イギリス国インピジョセ
フ・ジエイン ム、バークバーl−゛ランド、バークシ
ャー、ウオーキンガ・・ドライブ6番
(e) (21) ni) (23) (separate) Table 3 (25) Continuation of page 1 QlnL, CI,' Identification code Office reference number 0 Inventor Gerald John British Impi Joseph Giane 6 Walkingga Drive, Berkshire, Berkshire

Claims (4)

【特許請求の範囲】[Claims] (1)式 %式%() 〔式中、几はR4(on51m−on%−で示される基
;R1およびR2は各々低級アルキル、−0R3または
w−(OR5+m−or−で示される基;Wは、同一ま
たは異なって、Ti’−(OR5)Irl−で示される
基、 fi、4 ハ、同一または異なって、炭素数1〜
18のアルキル、 115は・同一または異なって、エ
チレンまたはプロピレジ、 R6は、同一または異なっ
て、炭素数6までのアルキレシ二mは、同一または異な
って、Oまたは1〜4の整数を意味する〕 で示されるシラシ誘導体の少なくとも1種を全量に基い
て05〜99重量%含有することを特徴とする作動油。
(1) Formula % Formula % () [In the formula, 几 is a group represented by R4 (on51m-on%-; R1 and R2 are each lower alkyl, -0R3 or w-(OR5+m-or-); W is the same or different and is a group represented by Ti'-(OR5)Irl-;
18 alkyl, 115 is the same or different, ethylene or propylene, R6 is the same or different, alkylene having up to 6 carbon atoms, the same or different, means O or an integer from 1 to 4] A hydraulic oil containing at least one type of Shirashi derivative represented by 05 to 99% by weight based on the total amount.
(2)少なくとも1種の公知の作動油添加物および/ま
たはベース油を含有する特許請求の範囲第(1)項の作
動油。
(2) Hydraulic oil according to claim (1), containing at least one known hydraulic oil additive and/or base oil.
(3)該化合物(I)の少なくとも1種5〜30重量%
と式 %式%(1) 〔式中、B11はアルキルまたはアリール、RI2はア
ルキル、アリール、アルカリール、アラルキルまたはR
4(ORE)□−で示される基:R13はアルキル、ア
リール、アルカリール、アラルキルまたはR4−(OR
’l□−0−テ示される基:B、4 、 H,5および
mFi特許請求の範囲第(1)項に記載と同じ〕で示さ
れる化合物の少なくとも1種5〜30重量%をグリコー
ルエーテルベース油に配合してなる特許請求の範囲第(
1)項の作動油。
(3) 5 to 30% by weight of at least one of the compound (I)
and formula % formula % (1) [wherein B11 is alkyl or aryl, RI2 is alkyl, aryl, alkaryl, aralkyl or R
Group represented by 4(ORE)□-: R13 is alkyl, aryl, alkaryl, aralkyl or R4-(OR
5 to 30% by weight of at least one of the compounds represented by 'l□-0-te group: B, 4, H, 5 and mFi (same as described in claim (1))] is added to a glycol ether. Claim No.
1) Hydraulic oil.
(4)該化合物(【)の少なくとも1種10〜90重量
%および式(11)、(■)または(IT)の化合物の
少なくとも1種90〜10重量%からなる特許請求の範
囲第(3)項の作動油。
(4) Claim No. 3 consisting of 10 to 90% by weight of at least one of the compounds () and 90 to 10% by weight of at least one of the compounds of formula (11), (■) or (IT) ) Hydraulic oil.
JP59132853A 1975-11-21 1984-06-26 hydraulic oil Expired JPS6046155B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB48009/75A GB1577715A (en) 1975-11-21 1975-11-21 Hydraulic fluids
GB48009/75 1975-11-21

Publications (2)

Publication Number Publication Date
JPS6035096A true JPS6035096A (en) 1985-02-22
JPS6046155B2 JPS6046155B2 (en) 1985-10-14

Family

ID=10447043

Family Applications (2)

Application Number Title Priority Date Filing Date
JP51140066A Expired JPS6019318B2 (en) 1975-11-21 1976-11-20 silane derivative
JP59132853A Expired JPS6046155B2 (en) 1975-11-21 1984-06-26 hydraulic oil

Family Applications Before (1)

Application Number Title Priority Date Filing Date
JP51140066A Expired JPS6019318B2 (en) 1975-11-21 1976-11-20 silane derivative

Country Status (17)

Country Link
JP (2) JPS6019318B2 (en)
AT (1) AT358701B (en)
AU (1) AU506008B2 (en)
BE (1) BE848576A (en)
CA (1) CA1083593A (en)
CH (1) CH629250A5 (en)
DE (1) DE2652719A1 (en)
DK (1) DK154024C (en)
FR (1) FR2332281A1 (en)
GB (1) GB1577715A (en)
IE (1) IE44233B1 (en)
IT (1) IT1121743B (en)
NL (1) NL174467C (en)
NO (1) NO155623C (en)
NZ (1) NZ182641A (en)
SE (1) SE431987B (en)
ZA (1) ZA766833B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1595701A (en) * 1977-06-24 1981-08-19 Castrol Ltd Fluids suitable for use as hydraulic fluids electrical oils heat transfer fluids and refrigerant oils
US4226794A (en) * 1979-05-21 1980-10-07 Olin Corporation Low-foaming alkoxy-bis(trialkoxysiloxy)-silane surfactants
DE3908791A1 (en) * 1989-03-17 1990-09-20 Huels Chemische Werke Ag METHOD FOR PRODUCING SILICON ORGANIC COMPOUNDS
DE102004049427A1 (en) * 2004-10-08 2006-04-13 Degussa Ag Polyether-functional siloxanes, polyethersiloxane-containing compositions, processes for their preparation and their use
US9193875B2 (en) 2005-07-14 2015-11-24 The United States Of America, As Represented By The Secretary Of The Navy Solvent-free, self-polishing polyurethane matrix for use in solvent-free antifoulings
JP6930484B2 (en) * 2018-04-17 2021-09-01 信越化学工業株式会社 Organosilicon compounds and their manufacturing methods
CN121712781A (en) * 2023-08-07 2026-03-20 巴斯夫欧洲公司 Methods for preparing organosilicon compounds

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2835690A (en) * 1953-12-31 1958-05-20 Gen Electric Base-catalyzed addition ot vinyl-silicon compositions
DE1644945B1 (en) * 1964-07-10 1974-03-14 Ruhrchemie Ag Synthetic power transmission fluids based on polyalkylene glycol di-orthosilicic acid (polyoxyalkylene glycol ether) esters
US3814691A (en) * 1970-09-25 1974-06-04 Olin Corp Alkyl(polyalkoxy)silanes as components in hydraulic fluids
CA975347A (en) * 1970-09-25 1975-09-30 David A. Csejka Alkyl (polyalkoxy) silanes as components in hydraulic fluids
BE789152A (en) * 1971-09-22 1973-01-15 Ceskoslovenska Akademie Ved
GB1464712A (en) * 1973-01-10 1977-02-16 Castrol Ltd Hydraulic fluids
GB1480738A (en) * 1973-09-25 1977-07-20 Castrol Ltd Hydraulic fluids
GB1506844A (en) * 1974-03-27 1978-04-12 Castrol Ltd Hydraulic fluid compositions

Also Published As

Publication number Publication date
DK154024C (en) 1989-02-20
DE2652719A1 (en) 1977-05-26
DK523976A (en) 1977-05-22
GB1577715A (en) 1980-10-29
SE431987B (en) 1984-03-12
SE7612899L (en) 1977-05-22
JPS6046155B2 (en) 1985-10-14
AT358701B (en) 1980-09-25
NO155623B (en) 1987-01-19
NL7612915A (en) 1977-05-24
DK154024B (en) 1988-10-03
NZ182641A (en) 1979-01-11
BE848576A (en) 1977-03-16
JPS5265227A (en) 1977-05-30
NL174467C (en) 1984-06-18
IE44233B1 (en) 1981-09-23
IE44233L (en) 1977-05-21
JPS6019318B2 (en) 1985-05-15
IT1121743B (en) 1986-04-23
ZA766833B (en) 1978-06-28
AU506008B2 (en) 1979-12-13
ATA862776A (en) 1980-02-15
NL174467B (en) 1984-01-16
NO763957L (en) 1977-05-24
FR2332281B1 (en) 1982-12-17
NO155623C (en) 1987-04-29
DE2652719C2 (en) 1988-04-14
CH629250A5 (en) 1982-04-15
AU1982376A (en) 1978-05-25
FR2332281A1 (en) 1977-06-17
CA1083593A (en) 1980-08-12

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