JPS6319538B2 - - Google Patents

Info

Publication number
JPS6319538B2
JPS6319538B2 JP58064095A JP6409583A JPS6319538B2 JP S6319538 B2 JPS6319538 B2 JP S6319538B2 JP 58064095 A JP58064095 A JP 58064095A JP 6409583 A JP6409583 A JP 6409583A JP S6319538 B2 JPS6319538 B2 JP S6319538B2
Authority
JP
Japan
Prior art keywords
formula
component
silicone oil
weight
parts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
JP58064095A
Other languages
English (en)
Other versions
JPS59189167A (ja
Inventor
Shigeru Mori
Yoshiaki Kudo
Satoshi Kuwata
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.)
Shin Etsu Chemical Co Ltd
Original Assignee
Shin Etsu Chemical Co Ltd
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 Shin Etsu Chemical Co Ltd filed Critical Shin Etsu Chemical Co Ltd
Priority to JP58064095A priority Critical patent/JPS59189167A/ja
Priority to US06/597,455 priority patent/US4515702A/en
Publication of JPS59189167A publication Critical patent/JPS59189167A/ja
Publication of JPS6319538B2 publication Critical patent/JPS6319538B2/ja
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound containing silicon
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    • C10M155/00—Lubricating compositions characterised by the additive being a macromolecular compound containing atoms of elements not provided for in groups C10M143/00 - C10M153/00
    • C10M155/02—Monomer containing silicon
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    • C10M169/04—Mixtures of base-materials and additives
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    • C10M2229/02—Unspecified siloxanes; Silicones
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    • C10M2229/025—Unspecified siloxanes; Silicones used as base material
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    • C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
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    • C10M2229/0435—Siloxanes with specific structure containing carbon-to-carbon double bonds used as base material
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    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/053—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/053—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing sulfur
    • C10M2229/0535—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing sulfur used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/054—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/054—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing phosphorus
    • C10M2229/0545—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing phosphorus used as base material

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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)
  • Lubricants (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Description

【発明の詳細な説明】
本発明は耐熱性シリコーンオイル組成物、特に
は200℃以上の高温における耐久性のすぐれた耐
熱性シリコーンオイル組成物に関するものであ
る。 シリコーンオイルが他の鉱物油、動植物油にく
らべて耐熱性のすぐれたものであるということは
よく知られているところであるが、このシリコー
ンオイルも200℃以上の高温下では徐々に酸化反
応が進行するため、比較的高温に曝される潤滑
油、作動油に使用されるシリコーンオイルはそれ
だけでは充分な耐久性を示さないという不利があ
る。そのため、高温で使用されるシリコーンオイ
ルについては、その耐久性を向上させるために酸
化防止剤を添加するということも行なわれている
が、この酸化防止剤はその多くのものがシリコー
ンオイルに溶解しないものであるため、これを添
加したものは均一なオイル組成物にならないし、
加熱などによつて強制的に溶解分散させたものも
高温に曝されたときにこの酸化防止剤が揮散され
てしまうために、これらのシリコーンオイル組成
物は満足すべく耐熱性を示さないという欠点があ
つた。 本発明はこのような不利を解決した耐熱性シリ
コーンオイル組成物に関するものであり、これは １ 一般式
【式】（こゝにR1はアルキル 基またはフエニル基、ａ＝1.95〜2.25）で示され
る、粘度が10〜1000000cSであるオルガノポリシ
ロキサン100重量部と、 ２ 一般式 または （こゝにR1は前記に同じ、R2は式
【式】または
【式】 で示される基、ｌは１〜50の整数、ｍは０〜47
の整数、ｎは１〜10の整数、ｍ＋ｎ＝１〜48）
で示される芳香族アミン変性オルガノポリシロ
キサン0.01〜５重量部からなることを特徴とす
るものである。 これを説明すると、本発明者らはシリコーンオ
イルの耐熱性向上策について種々検討の結果、シ
リコーンオイルに芳香族アミン変性オルガノポリ
シロキサンを添加すればこれがシリコーンオイル
と相溶性をもつものであることから容易に均一な
オイル組成物が得られ、このものが200℃以上の
高温における耐久性を大巾に向上したものとなる
こと、また開放加熱条件での増粘速度が極めて小
さくなるということを見出し、これについてさら
に研究を進め、この芳香族アミン変性オルガノポ
リシロキサンとしては上記した一般式で示された
ものが特に有効であること、これによれば高温耐
久性がすぐれており、高温で長時間使用後におい
ても良好な流動性を保持するシリコーンオイル組
成物を容易に得ることができることを確認して本
発明を完成させた。 本発明の組成物を構成する第１成分としてのシ
リコーンオイルは一般式
【式】で示され るものであり、これはそのR1がメチル基、エチ
ル基、プロピル基、デシル基などのアルキル基ま
たはフエニル基でこのａが1.95〜2.25で示される
ものであるが、これは本発明の組成物が特に耐熱
性のすぐれたものとされることからこのR1のう
ちの少なくとも80％がメチル基であるものとする
ことがよい。また、このものはその粘度が10cS
以下では蒸気圧が高く、揮発性も大きいので耐熱
用途に適さず、 1000000cS以上では流動性が乏しくて潤滑油、
作動油としての用途に適さないので、これは25℃
における粘度が10〜1000000cSの範囲のものとさ
れる。 また、この第１成分に添加される第２成分とし
ての芳香族アミン変性オルガノポリシロキサン
は、上記したように一般式
【式】または で示されるものとされるが、このR2については
これをＮ―（ｐ―アニリノフエニル）アミノフエ
ニル基 Ｎ―（α―ナフチル）アミノフエニル基
【式】およびＮ―（β― ナフチル）アミノフエニル基
【式】から選ばれる基とす ることがよい。また、上記の式におけるｌは１〜
50とする必要があり、このｍ＋ｎについては、こ
れを49以上とするとこの第２成分中におけるアミ
ノフエニル基の含有量が小さくなりすぎて第２成
分の添加量を多くさせる必要が生じるし、このｎ
を10以上にすると第２成分の第１成分への溶解性
が低下するので、これらはｍ＝０〜47、ｎ＝１〜
10、ｍ＋ｎ＝１〜48とすることが必要とされる。
なお、この第２成分の第１成分に対する添加量は
第１成分100重量部に対し第２成分を0.01〜５重
量部とすればよく、これが0.01重量部以下では耐
熱性の向上が充分にならず、これを５重量部以上
とすると、第２成分の第１成分への溶解性が乏し
くなつて均一な組成物を得ることが困難になると
いう不利が生じるおそれがある。 この第２成分としての芳香族アミン変性オルガ
ノポリシロキサンは、上記したアミノフエニル基
をもつアミノフエノール類、例えば
【式】
【式】と、反応性基をも つアルキルポリシロキサンとを反応させることに
よつて容易に得ることができ、この反応に当つて
は例えば塩素化アルキルポリシロキサンと上記フ
エノールとを反応当モルでトルエン溶媒中にて塩
酸捕捉剤、例えばピリジン、トリエチルアミンな
どの共存下に、室温あるいは加温下で撹拌後、塩
酸塩を除去し、減圧下にストリツピングするとい
う方法で行なえばよい。 本発明の耐熱性シリコーンオイル組成物は上記
した第１成分としてのオルガノポリシロキサンと
第２成分としての芳香族アミン変性オルガノポリ
シロキサンを単純に混合することによつて得るこ
とができるが、この混合は空気雰囲気下、窒素ガ
ス雰囲気下のいずれで行なつてもよく、またこれ
には加熱あるいは空気の吹き込みなどを併用して
もよい。 このようにして得られた本発明の組成物はその
まゝで潤滑油、作動油などに使用することができ
るが、これはまたこれをシリコーングリースの基
油として、これに通常使用される増稠剤や各種の
添加剤を混合して高温の使用に潤滑グリースとし
ても使用することができる。 つぎに本発明の実施例をあげる。 実施例１〜８、比較例１〜２ 両末端がトリメチルシリル基で封鎖された25℃
での粘度が7800cSであるジメチルポリシロキサ
ン100重量部に、下記Ａ）〜Ｆ）で示される芳香
族アミノ変性オルガノポリシロキサンを第１表に
示した配合量で添加し、窒素ガス雰囲気において
250℃で３時間撹拌してシリコーンオイル組成物
を作つた。 つぎに、この組成物30ｇを100mlの硬質ガラス
ビーカーに採取して250℃の熱風循環式恒温槽で
加熱下に放置し、所定時間経過後に取り出して、
その25℃における粘度を測定したところ、第１表
に併記したとおりの結果が得られた。 （芳香族アミノ変性ポリオルガノシロキサンの種
類） また、比較のため、上記において芳香族アミノ
変性オルガノポリシロキサンを添加しないジメチ
ルポリシロキサン（比較例１）およびこのジメチ
ルポリシロキサン100重量部に下記 の芳香族アミノ変性オルガノポリシロキサンを
0.6重量部添加したシリコーンオイル組成物（比
較例２）について上記と同様に処理してその粘度
変化を測定したところ、第１表に併記したとおり
の結果が得られた。
【表】
【表】

Claims (1)

  1. 【特許請求の範囲】 １ １ 一般式【式】（こゝにR1はアル キル基またはフエニル基、ａ＝1.95〜2.25）で示
    される、粘度が10〜1000000cSであるオルガノポ
    リシロキサン100重量部と、 ２ 一般式【式】または （こゝにR1は前記に同じ、）R2は 【式】または 【式】で示される基、は１ 〜50の整数、ｍは０〜47の整数、ｎは１〜10の整
    数で、ｍ＋ｎ＝１〜48である）で示される芳香族
    アミン変性オルガノポリシロキサン0.01〜５重量
    部 からなることを特徴とする耐熱性シリコーンオイ
    ル組成物。
JP58064095A 1983-04-12 1983-04-12 耐熱性シリコ−ンオイル組成物 Granted JPS59189167A (ja)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP58064095A JPS59189167A (ja) 1983-04-12 1983-04-12 耐熱性シリコ−ンオイル組成物
US06/597,455 US4515702A (en) 1983-04-12 1984-04-05 Heat-resistant silicone fluid compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP58064095A JPS59189167A (ja) 1983-04-12 1983-04-12 耐熱性シリコ−ンオイル組成物

Publications (2)

Publication Number Publication Date
JPS59189167A JPS59189167A (ja) 1984-10-26
JPS6319538B2 true JPS6319538B2 (ja) 1988-04-22

Family

ID=13248168

Family Applications (1)

Application Number Title Priority Date Filing Date
JP58064095A Granted JPS59189167A (ja) 1983-04-12 1983-04-12 耐熱性シリコ−ンオイル組成物

Country Status (2)

Country Link
US (1) US4515702A (ja)
JP (1) JPS59189167A (ja)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0680148B2 (ja) * 1985-11-08 1994-10-12 東レ・ダウコーニング・シリコーン株式会社 粘性流体継手用オルガノポリシロキサン組成物
JPS62283194A (ja) * 1986-05-30 1987-12-09 Shin Etsu Chem Co Ltd 流体継手用シリコ−ン作動流体
JP2793228B2 (ja) * 1989-02-27 1998-09-03 日本ケーブル・システム株式会社 コントロールケーブル用潤滑剤およびそれを用いてなるコントロールケーブル
JPH07119358B2 (ja) * 1989-04-25 1995-12-20 信越化学工業株式会社 シリコーン組成物
US5445751A (en) * 1993-03-03 1995-08-29 Dow Corning Toray Silicon Co., Ltd. Fluorosilicone lubricant compositions
JP4226726B2 (ja) 1999-05-24 2009-02-18 千葉製粉株式会社 有機変性オルガノポリシロキサン、その製造方法及び組成物
JP4619710B2 (ja) * 2004-07-02 2011-01-26 東レ・ダウコーニング株式会社 シリコーン系感圧接着剤および粘着テープ
JP5532600B2 (ja) * 2008-12-19 2014-06-25 信越化学工業株式会社 ダイカスト用離型剤組成物およびそれを用いるエマルジョン型ダイカスト用離型剤
JP6902233B2 (ja) * 2016-12-06 2021-07-14 株式会社ニッペコ グリース組成物及び可動継手

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5518457A (en) * 1978-07-26 1980-02-08 Nitto Electric Ind Co Ltd Preparation of acrylic low molecular weight polymer

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3026263A (en) * 1959-03-05 1962-03-20 Du Pont High temperature mechanical fluid compositions
US3714044A (en) * 1971-08-19 1973-01-30 Dow Chemical Co Fluorosilicone lubricants containing nitrophenyl substituted organopolysiloxanes
DE2161813C3 (de) * 1971-12-13 1980-10-23 Wacker-Chemie Gmbh, 8000 Muenchen Gleitmittel auf Grundlage von Diorganopolysiloxanen für organische Fasern
US4327140A (en) * 1981-02-05 1982-04-27 Rca Corporation High density information disc lubricants

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5518457A (en) * 1978-07-26 1980-02-08 Nitto Electric Ind Co Ltd Preparation of acrylic low molecular weight polymer

Also Published As

Publication number Publication date
JPS59189167A (ja) 1984-10-26
US4515702A (en) 1985-05-07

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