BE1000209A6 - Compositions d'organopolysiloxanes liquides. - Google Patents

Compositions d'organopolysiloxanes liquides. Download PDF

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Publication number
BE1000209A6
BE1000209A6 BE8800452A BE8800452A BE1000209A6 BE 1000209 A6 BE1000209 A6 BE 1000209A6 BE 8800452 A BE8800452 A BE 8800452A BE 8800452 A BE8800452 A BE 8800452A BE 1000209 A6 BE1000209 A6 BE 1000209A6
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Belgium
Prior art keywords
groups
weight
parts
metal
organosiloxane
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BE8800452A
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English (en)
Inventor
Gardiner William
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Dow Corning Ltd
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    • 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
    • C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
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    • C08K5/54—Silicon-containing compounds
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    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
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    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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Abstract

Composition d'organopolysiloxane comprenant (1) un polydiorganosiloxane, (2) un organosiloxane ayant au moins un groupe fixé au silicium choisi parmi les groupes anilinophénoxy et naphthylaminophénoxy et (3) un composé de métal siloxy dans lequel le métal est Ti, Zr ou Hf, ou un sel de zirconium d'un acide monocarboxylique. Les compositions sont stabilisées vis-à-vis d'une dégradation par oxydation aux températures élevées et sont utiles, entre autres comme fluides pour accouplement visqueux dans les embrayages à palettes des automobiles.

Description


   <Desc/Clms Page number 1> 
 



   DESCRIPTION COMPOSITIONS D'ORGANOPOLYSILOXANES LIQUIDES 
L'invention concerne des compositions d'organosiloxanes liquides et elle se rapporte plus particulièrement à ces compositions qui présentent une Variation réduite de la viscosité en fonction du temps et de la temperature. 



   L'emploi d'organosiloxanes liquides comme lubrifiants, fluides pour transfert thermique et fluides visqueux pour accouplement est bien connu. Afin d'agir de manière satisfaisante dans cette dernière application, le fluide doit posséder certaines propriétés, en particulier il doit être stable   vis-à-vis   de l'oxydation et presenter peu ou pas de variation de viscosité dans toute la gamme des temperatures de fonctionnement ni durant sa durée de vie de fonctionnement prévue. Dans de telles applications, on emploie le plus usuellement des   polydiméthylsiloxanes   liquides. Cependant, si ces polydiméthylsiloxanes sont employés seuls à des températures de fonctionnement élevées, ils peuvent présenter une augmentation de la viscosité et une gélification subsequente.

   Cet accroissement de la viscosité peut être retardé en ajoutant certains antioxydants. Par exemple, dans le brevet des E. U. A. no. 3. 328. 350, il est indique que l'addition   p. ex.   du produit de la réaction d'un organosiloxane et de   p-anilinophénol   à des   polydimethylsiloxanes   fluides peut améliorer leur stabilité contre une dégradation par oxydation. Le brevet des   E. U. A. no. 4. 537. 691 décrit   une 

 <Desc/Clms Page number 2> 

 nouvelle composition de silicone fluide utilisable en tant que fluide de travail à des   temperatures elevees,   qui comprend un melange d'un diorganopolysiloxane ayant à la fois des groupes trihydrocarbylsiloxy et des groupes. 
 EMI2.1 
 hydroxy avec des siloxane ayant certains substituants aminoaryles, p. ex. anilinophenoxy. 



   La demande de brevet européen no.   191.456 décrit   un autre développement en cette matière et concerne des fluides d'organopolysiloxane visqueux pour couplage comprenant un   melange   d'un fluide d'organopolysiloxane, d'un compose d'organosiloxane contenant du zirconium et d'un composé d'organosiloxane contenant du cérium. 



   Bien que les fluides connus de la pratique antérieure se comportent de manière satisfaisante en tant que liquides d'embrayage & palettes sous des conditions opératoires normales, le développement de moteurs automobiles A performances plus élevées requiert des liquides ayant une plus grande résistance   ä   la dégradation par oxydation et aux variations de viscosité. 



   . Suivant la présente invention, on fournit une composition d'organopolysiloxane comprenant   (1)   100 parties en poids d'un polydiorganosiloxane liquide dans lequel au moins 70 pour cent de la totalité des substituants organiques sont des groupes méthyles, tous les substituants organiques restants étant choisis parmi les groupes alkyles ayant de 2 à y compris 14 atomes de carbone et groupes phényles, (2) de   0, 01 à 7, 5   parties en poids d'un organosiloxane ayant au moins un groupe fixé au silicium choisi parmi les groupes anilinophénoxy et naphthylaminophénoxy et (3) un compose de métal qui est choisi parmi (i) des composés de métal siloxy ayant dans la molecule au moins un atome de métal choisi parmi les atomes de titane, zirconium et hafnium attachés au silicium par une liaison TiOSi, ZrOSi ou HfOSi, et (ii)

   des sels de zirconium d'acides monocarboxyliques, le composant de métal étant present de maniere suffisante pour fournir de 

 <Desc/Clms Page number 3> 

   0, 001 à 0, 25   partie en poids de métal. 



   Les polydiorganosiloxanes   (l)   des compositions 
 EMI3.1 
 de la présente invention peuvent être représentés par la 
 EMI3.2 
 formule générale unitaire moyenne RnSiO, dans laquelle 2 
 EMI3.3 
 R représente les substituants organo fixés au silicium et n a une valeur d'environ 1, 85 ä environ 2, 15, de préfé- rence de   1, 99 à 2, 01.   Les polydiorganosiloxanes sont donc de caractère à prédominance linéaire mais peuvent contenir des proportions relativement faibles d'unités de chaînes latérales (RSiO3/2). Des unités de blocage   d'extrémiste   R3SiO1/2 sont de préférence présentes mais les polydiorganosiloxanes dans lesquels ces unites sont absentes sont aussi opérationnels.

   Ainsi, le polydiorganosiloxane peut être   terminé.   par exemple, par des groupes   = SiOH ou   
 EMI3.4 
 = SiOR. 



   Au moins 70 pour cent de la totalité des groupes R sont des groupes méthyles. Tout groupe R restant peut être, par exemple, éthyle, butyle, triméthylpentyle, dodécycle ou phényle. Des exemples de polydiorganosiloxanes   (1)   sont, par conséquent, polydimethylsiloxanes bloques en extrémité par triméthylsilyle, polydiméthylsiloxanes bloques en   extremiste   par diméthylphénylsilyle, copolymeres d'unités de diméthylsiloxane et de phénylméthylsiloxane bloqués en extrémité par trìméthylsilyle et polydiméthylsiloxanes à terminaison hydroxyle. Le polydiorganosiloxane (1) peut consister en un seul polymere de siloxane ou en un mélange de polymères de siloxane ayant différents substituants, structures ou viscosités.

   Pour emploi suivant cette invention, on préfère des polydiorganosiloxanes qui consistent en un mélange d'environ 70   ä   95 parties en poids d'un polydiméthylsiloxane et de 5   ä   30 parties en poids d'un   polyméthylphénylsiloxane   ou un copolymère de   dimethylsiloxane   et de   methylphenyl-   siloxane. 



   La viscosité du polydiorganosiloxane   (1)   peut 

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 varier dans des limites étendues, p. ex. de   0, 0005 a     0, 1 m2/s à 25"C   pourvu qu'il seit liquide ä 25 .   Généra-   lement, la vicosité particulière sera choisie en fonction des exigences de l'application prévue. Quand le composé est destiné à un emploi dans un accouplement visqueux, comme dans les embrayages à palettes des automobiles, une 
 EMI4.1 
 o viscosité comprise dans la gamme de ,001 à 0,05 m /s est préférée. 



   Le composant (2) des compositions de cette invention est un organosiloxane   ayant. : au   moins un groupe fixe au silicium choisi parmi les groupes anilinophenoxy et naphthylaminophenoxy. Les substituants restants fixes au silicium sont choisis parmi les groupes alkyles,   p. ex.   groupes méthyle, ethyle, isopropyle et phenyle, les organosiloxanes dans lesquels les substituants restants sont substantiellement tous des groupes méthyles étant particulièrement préférés. L'organosiloxane (2) est aussi de préférence un polydiorganosiloxane substantiellement   l aire.   



   Au moins un groupe   CHeNHCeH. O- et/ou   
 EMI4.2 
 C. HgNHCgH. O- doit etre präsent dans (2). Ces groupes peuvent être pendants a partir des atomes de silicium le long de la chaine siloxane, attachés ä un atome de silicium terminal ou bien se presenter selon les deux manières. Les organosiloxanes (2) peuvent être des homopolymeres ou des copolymères. Ils sont des substances connues et peuvent être   prepares   par la reaction des acyloxy siloxanes et du phenol approprie, p. ex. le   p-anilinophénol,   comme décrit dans le brevet des   E. U. A.   no. 3.328.350. Un autre procédé de préparation de ces organosiloxanes comprend la réaction du phénol avec un organosiloxane ayant des atomes de chlore fixes au silicium, en-presence d'un accepteur pour le HCl sousproduit.

   La proportion de (2) employee dans les compositions de l'invention dependra largement de l'importance de l'effet désiré et de la proportion des substituants 

 <Desc/Clms Page number 5> 

 aminophénoxy spécifiés dans la molécule par rapport aux substituants restants. Au moins 0, 01 et jusqu'à 7, 5 parties pour 100 parties de   (1)     peuvent. etre utilisees,   de   0, 1 ä 2, 5   parties étant généralement préférées. 



   Le composant (3) des compositions de cette invention est (i) un compose de métal siloxy dans lequel le métal est Zr, Ti ou Hf et dans lequel l'atome. de métal est joint au silicium par un atome d'oxygène,    ou.   (ii) un sel de zirconium d'un acide monocarboxylique ou ä la fois (i) et (ii). 



   Les composés de métal siloxy (i) sont des composes d'organosilicium, p. ex : des organosilanes et des organosiloxanes, ayant au moins une liaison ZrOSi, TiOSi, HfOSi par molécule. Les valences restantes des atomes de silicium peuvent ôtre satisfaites par d'autres liaisons métal-oxygène, par des groupes d'hydrocarbures monovalents, par exemple méthyle, propyle, octyle, vinyle, phényle ou benzyle, ou par des atomes d'oxygène divalents liés   ä   leur tour aux autres atomes de silicium pour 
 EMI5.1 
 former des liaisons siloxane -31031-.

   Toutes les valences des atomes Zr, Ti ou Hf qui ne sont pas satisfaites par des groupes siloxy sont satisfaites par des groupes organiques fixés à l'oxygène, par exemple des groupes alkoxy, p. ex. méthoxy, ethoxy, butoxy et décoxy, des groupes arylox, p.ex. phénoxy, des groupes acyloxy,   p. ex :   acetoxy, propionoxy et octanoxy, et des groupes de chelation tels que éthylacétoacétate et acétylacétonate. Ainsi, un type de composé de métal siloxy (i) est celui qui peut 
 EMI5.2 
 être représenté par la-formule generale 
 EMI5.3 
 - j. (CHS10jxM= 
 EMI5.4 
 dans laquelle M représente Zr, Ti ou Hf, et les valences restantes de M sont satisfaites par d'autres siloxy, p. ex. des groupes -(CH3)2SiO-, ou par des groupes organiques fixés à l'oxygène comme spécifié ci-dessus.

   Un autre type de composé de métal siloxy peut être représenté par le 
 EMI5.5 
 compose C (CH) siol M. 



  3 3. 4 

 <Desc/Clms Page number 6> 

 
Les composes de métal siloxy sont des substances connues et peuvent etre préparées, par exemple, en chauffant un mélange de   polydimthylsiloxane et d'un composé   organométallique ayant des liaisons métal-oxygène-carbone. 



  D'une autre manière, ils peuvent être préparés en faisant réagir l'alkoxyde de métal avec un organosiloxane   ä   terminaison silanol ou en faisant réagir l'halogénure de métal avec un silanolate de métal alcalin. 



   11 est généralement préférable d'utiliser comme Composant (3) des compositions de l'invention les composes de métal siloxy (i), particulièrement des organosiloxanes dans lesquels au moins 80 pour cent de la totalité des groupes organiques fixés au silicium sont des groupes méthyles. Ces organosiloxanes sont plus solubles dans le polydiorganosiloxane   (1),   et par consequent plus aisément dispersés dans celui-ci. Cependant, les carboxylates de zirconium, par exemple acétate de zirconium, butyrate de zirconium et octoate de zirconium peuvent aussi être employés au lieu du, ou en combinaison avec le, compose de métal siloxy. 



   Le Composant (3) doit   etre   present en une quantite suffisante pour fournir de   0, 001 ä 0, 25 partie,   de préférence   de 0, 005 ä 0, 1 partie   en poids de métal pour 100 parties en poids du polydiorganosiloxane (1). 



   Les compositions de cette invention. peuvent etre préparées en mélangeant simplement les Composants   (l),     (2)   et (3) dans n'importe quel ordre. Habituellement, cependant, le procédé le plus approprié consiste a ajouter (2) et (3)   ä   (1). 



   Les compositions comprenant   (1),     (2)   et (3) sont résistantes à la degradation sous des conditions de cisaillement élevé aux hautes températures. Elles sont done particulièrement utiles comme fluides pour accouplement visqueux, par exemple dans les embrayages   a   palettes des automobiles, oü la rétention d'une viscosité de travail stable est requise durant de longues périodes. 

 <Desc/Clms Page number 7> 

 



   L'Exemple suivant, dans lequel toutes les parties sont exprimées en poids, est une illustration de   11 invention.   



   A 89 parties de polydiméthyulsiloxane bloque en extrémité par trimethylsilyl, ayant une viscosite de 9 x   10-3,     m2/s   (9. 000 cS) à 25OC, on a ajouté   9, 9   parties d'un copolymère, bloqué en extrémité par triméthylsilyl, 
 EMI7.1 
 consistant en 90 % d'unités de dimethylsiloxane et 10 % d'unites de   méthylphénylsiloxane   ayant une vicosité de 10-4 mis (100 cS) à 25 C.

   A ce mélange on a ensuite ajouté, en agitant,   0, 5   partie de polydimethylsiloxane ayant un groupe   p-anilinophenoxy fixe ä   chacun de ses atomes de silicium terminaux et un poids moléculaire d'environ 2. 000, puls 0, 6 partie de   methylsiloxane   contenant du zirconium, contenant 3 % en poids de zirconium et obtenu en chauffant ensemble du polydiméthylsiloxane et de   l'octoa. te   de zirconium, L'agitation a été poursuivie jusqu'à ce que le   mé1ange   devienne homogène. 



   Le mélange obtenu ci-dessus presente une stabilite de sa viscosité au travail durant une longue période quand il est employé comme fluide pour accouplement visqueux dans l'embrayage à palettes d'un moteur automobile ä performance élevée. 



   Quatre mélanges d'organosiloxanes A, B, C et   0,   contenant respectivement 0,   0, 6, 1, 0   et 2, 0 parties de méthylsiloxane contenant du zirconium ont été préparés comme décrit ci-dessus. Chaque mélange a été ensuite soumis ä une analyse de thermogravimétrie en utilisant un appareil d'analyse thermogravimétrique Perkin Eimer TCS-2 dont la température a té augmentée à une vitesse de   300C   par minute. Pour   l'Echantillon   A, le début d'une perte rapide du poids (indiquant une dégradation du polymere) a commencé   ä   492 C, la perte totale du poids de l'échantil-   lon   se produisant ä environ 650 C.

   Dans les cas des Echantillons B, C et D, le début d'une perte rapide du poids ne s'est pas produit avant que la temperature 

 <Desc/Clms Page number 8> 

   n'atteigne environ 6000C et la disparition totale des échantillons (perte de poids de 100 %) s'est produite à   des températures d'environ 700 à   750 C.

Claims (7)

  1. REVENDICATIONS 1. Composition d'organopolysiloxane comprenant (1) 100 parties en poids d'un polydiorganosiloxane liquide dans lequel au moins 70 pour cent de la totalité des substituants organiques sont des groupes méthyles, tous les substituants organiques restants étant choisis parmi les groupes alkyles ayant de 2 à y compris 14 atomes de carbone et les groupes phényles, (2) de 0, 01 ä 7, 5 parties en poids d'un organosiloxane ayant au moins un groupe fixé au silicium choisi parmi les groupes anilinophénoxy et naphthylajninophenoxy et (3) un composé de métal qui est choisi parmi (i) des composés de métal siloxy ayant dans la molecule au moins un atome de métal choisi parmi les atoms de titane, de zirconium et de hafnium fixé au silicium par une liaison TiOSi, ZrOSi ou HfOSi,
    et (ii) des sels de zirconium d'acides monocarboxyliques, le composé de métal étant present de maniere suffisante pour fournir de 0, 001 ä 0, 25 partie en poids de metal.
  2. 2. Composition suivant la revendication 1, dans laquelle le polydiorganosiloxane liquide (1) consiste en 70 à 95 parties en poids d'un polydiméthylsiloxane et en 5 ä 30 parties en poids d'un polyméthylphénylsiloxane et/ou d'un copolymere de dimethylsiloxane et de methyl- phenylsiloxane.
  3. 3. Composition suivant la revendication 1 ou 2, dans laquelle le polydiorganosiloxane (1) a une viscosité EMI9.1 p comprise dans la gamme de 0, 001 ä 0, 05 m/s.
  4. 4. Composition suivant n'importe laquelle des revendications précédentes, dans laquelle le composé de métal siloxy (3) est un organosiloxane dans lequel au moins 80 pour cent des groupes organiques fixés au silicium sont des groupes méthyles. <Desc/Clms Page number 10>
  5. 5. Composition suivant n'importe laquelle des revendications précédentes, dans laquelle l'organosiloxane (2) est present en une quantité de 0, 1 â 2, 5 parties en poids.
  6. 6. Composition d'organosiloxane qui est substantiellement comme décrite en se référant à l'Exemple.
  7. 7. Embrayage contenant comme fluide pour accouplement visqueux une composition d'organosiloxane suivant n'importe laquelle des revendications précédentes.
BE8800452A 1987-04-24 1988-04-20 Compositions d'organopolysiloxanes liquides. BE1000209A6 (fr)

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GB878709745A GB8709745D0 (en) 1987-04-24 1987-04-24 Liquid organosiloxane compositions

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DE (1) DE3813660C2 (fr)
FR (1) FR2614308B1 (fr)
GB (2) GB8709745D0 (fr)

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JP2683547B2 (ja) * 1988-09-09 1997-12-03 東燃株式会社 耐熱安定性に優れたシリコーン油組成物
JP2671146B2 (ja) * 1989-01-31 1997-10-29 スズキ株式会社 アイドル回転数制御装置
EP0397507B1 (fr) * 1989-05-10 1995-03-15 Tonen Corporation Fluides de silicone pour accouplements visqueux
US4898956A (en) * 1989-06-27 1990-02-06 Dow Corning Corporation Method to prepare thermo-oxidatively stable phenylmethylsiloxane fluids
EP0462777B1 (fr) * 1990-06-18 1995-01-18 Tonen Corporation Composition hydraulique, lubrifiante et d'engrenage
US5130041A (en) * 1990-06-21 1992-07-14 Dow Corning Corporation Silicone fluid compositions having reduced viscosity temperature coefficient
JPH06158076A (ja) * 1992-11-20 1994-06-07 Cosmo Oil Co Ltd ビスカスカップリング用流体組成物
US5599778A (en) * 1994-01-28 1997-02-04 Dow Corning Toray Silicone Co., Ltd. Organosiloxane lubricant compositions
JPH08143883A (ja) * 1994-11-17 1996-06-04 Dow Corning Asia Ltd 耐熱性グリース組成物
GB9613756D0 (en) * 1996-07-01 1996-09-04 Bingley Michael S Additive composition
US6623399B2 (en) 2001-12-28 2003-09-23 Dow Corning Corporation Traction fluids
WO2021141836A1 (fr) 2020-01-09 2021-07-15 Dow Silicones Corporation Polysiloxanes ramifiés et leurs procédés de préparation et d'utilisation en tant que fluides de transfert de chaleur
CN113755226B (zh) * 2021-10-21 2022-04-29 华亿金卫(杭州)能源有限公司 一种油溶性有机锆减摩剂及其制备方法

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US3328350A (en) * 1966-07-05 1967-06-27 Union Carbide Corp Stabilized organosilicon polymers
US4193885A (en) * 1977-08-02 1980-03-18 Dow Corning Corporation Method for preparing a thermal-stability additive and a thermally stabilized methylpolysiloxane and compositions therefrom
US4379094A (en) * 1981-12-30 1983-04-05 Union Carbide Corporation Ferrosiloxane thermal stabilizers for diorganopolysiloxanes
JPS60106891A (ja) * 1983-11-14 1985-06-12 Shin Etsu Chem Co Ltd 作動流体
JPS61185597A (ja) * 1985-02-12 1986-08-19 Toray Silicone Co Ltd 粘性流体継手用オルガノポリシロキサン組成物

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CA1314280C (fr) 1993-03-09
US4840743A (en) 1989-06-20
GB2203750A (en) 1988-10-26
DE3813660C2 (de) 1998-09-24
FR2614308A1 (fr) 1988-10-28
FR2614308B1 (fr) 1992-10-09
JP2595294B2 (ja) 1997-04-02
GB8709745D0 (en) 1987-05-28
GB8807574D0 (en) 1988-05-05
JPS63275665A (ja) 1988-11-14
GB2203750B (en) 1991-04-24
DE3813660A1 (de) 1988-11-17

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