EP0283922B1 - Fluide hydraulique à base de siloxane et de polyalphaoléfine - Google Patents

Fluide hydraulique à base de siloxane et de polyalphaoléfine Download PDF

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Publication number
EP0283922B1
EP0283922B1 EP88104211A EP88104211A EP0283922B1 EP 0283922 B1 EP0283922 B1 EP 0283922B1 EP 88104211 A EP88104211 A EP 88104211A EP 88104211 A EP88104211 A EP 88104211A EP 0283922 B1 EP0283922 B1 EP 0283922B1
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EP
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Prior art keywords
weight
parts
blend
viscosity
fluid
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EP88104211A
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German (de)
English (en)
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EP0283922A3 (en
EP0283922A2 (fr
Inventor
Eugene Dale Groenhof
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Dow Silicones Corp
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Dow Corning Corp
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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
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • C10M107/18—Hydrocarbon polymers modified by oxidation
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    • 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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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/12—Oxidised hydrocarbons, i.e. oxidised subsequent to macromolecular formation
    • C10M2205/123—Oxidised hydrocarbons, i.e. oxidised subsequent to macromolecular formation used as base material
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044—Acids; Salts or esters thereof
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    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
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    • C10M2229/02—Unspecified siloxanes; Silicones
    • C10M2229/025—Unspecified siloxanes; Silicones used as base material
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    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • the present invention relates to hydraulic fluid compositions which may be used over a wide temperature range and yet exhibit relatively high flash points. More particularly, the fluids of this invention consist essentially of a dimethylsiloxane/alkylmethylsiloxane copolymer blended with a synthetic hydrogenated polyalphaolefin. This invention further relates to the use of said compositions as hydraulic fluid in a hydraulic system transmitting force.
  • silicone fluids are known for their superior resistance to shear, thermal and oxidative degradation. Moreover, unlike typical hydrocarbon lubricating oils or hydraulic fluid, they maintain a relatively flat viscosity-temperature profile. On the other hand, these silicones generally do not possess the high degree of lubricity in steel-to-steel contact that is exemplified by hydrocarbons such as mineral oil, a property vital in many hydraulic applications. This problem can be resolved to some extent by the incorporation of certain lubricity additives in the silicone "base fluid.”
  • compositions comprising mineral oil and, as a viscosity index improver therefor, a homopolymeric diorganopolysiloxane in which the majority of the organo groups are methyl groups.
  • the remaining organo groups may be selected from alkyl, alkaryl or aralkyl groups having from 6 to 30 carbon atoms in amount sufficient to render them soluble in the mineral oil.
  • a lubricating oil composition comprising 1 % to 50% by weight of a polydimethylsiloxane having a viscosity of 100,000 to 1,000,000 mm 2 /s (cS) at 38°C (100°F), the remainder of the mixture being a hydrocarbon oil having a viscosity of less than 40,000 mm 2 /s (cS) at -53.9°C (-65°F)
  • a major contribution to the art asserted by this disclosure is the dissolution of high viscosity polydimethylsiloxane in the hydrocarbon oil to provide a lubricating composition having improved viscosity-temperature properties in which the siloxane component does not separate from the mixture at low temperatures.
  • EP-A-0,177,825 published April 16, 1986, describes lubricating oil preparations comprising silicone copolymers containing organomethylsiloxane units wherein the organo group is selected from alkyl groups having 1 to 7 carbon atoms or the phenyl radical and alkylmethylsiloxane units wherein the alkyl group can have from 6 to 16 carbon atoms.
  • copolymers have the further restrictions in that they must have a pour point below -15°C. and must be miscible with mineral oil, synthetic lubricating oils and the lubricity additives commonly employed in such oils.
  • the high flash point of the MIL-H-83282 fluid would not be compatible with the above low temperature viscosities and compromise target values of at least 163°C. and 191°C. were set for the flash point and fire point, respectively. Additionally, a major requirement of a successful candidate fluid was that this fluid be compatible with the existing military fluids (i.e., MIL-H5606 and MIL-H-83282) so as to make "drain-and-fill" replacement in current hydraulic systems possible.
  • MIL-H5606 and MIL-H-83282 existing military fluids
  • the invention provides a homogeneous blend consisting of:
  • the blend contains 40 to 90 parts by weight of the siloxane copolymer of (A) and 60 to 10 parts by weight of a synthetic hydrogenated polyalphaolefin (B) represented by the formula said blend having a total of 100 parts by weight of said components (A) and (B).
  • a synthetic hydrogenated polyalphaolefin represented by the formula said blend having a total of 100 parts by weight of said components (A) and (B).
  • component (B) is represented by the formula
  • component (B) is selected from the dimer, trimer or tetramer of decene-1, and said homogeneous hydraulic fluid has a vicosity of at most 2500mm 2 /s (2500 cS) at -54°C., a viscosity of at least 3.5mm 2 /s (3.5 cS) at 100°C. and an open cup flash point of at least 163°C.
  • This invention also relates to the use of said hydraulic fluid for transmitting force in a hydraulic system.
  • the present invention relates to hydraulic fluid compositions consisting essentially of a homogeneous blend of (A) a dimethylsiloxane/alkylmethylsiloxane copolymer and (B) a synthetic hydrogenated polyalphaolefin.
  • Component (A) of the present invention is a copolymer which may be represented by the average formula wherein Me denotes the methyl radical and R is a linear or branched alkyl group having 4 to 10 carbon atoms, such as n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, diisobutyl, n-nonyl or n-decyl. Straight chain alkyl groups are preferred over branched structures. It is further preferred that R is selected from the n-hexyl or n-octyl radicals.
  • the R' groups on the terminal silicon atoms are identical or different short chain alkyl groups having from one to 10 carbon atoms, such as methyl, ethyl, propyl, butyl, hexyl, octyl or decyl, with methyl being preferred.
  • x in the above formula may range from about 5 to 15, preferably from 6 to 12.
  • the value of y may correspondingly range from about 0.5 to 4, preferably from 0.5 to 3.
  • the value of y is, however, restricted such that the ratio y/x is at most 0.3.
  • x and y are chosen such that the viscosity of the copolymer fluid ranges from 5 to 50mm 2 /s (centistokes) at 25°C.
  • the viscosity is 1G-20mm 2 /s (cS).
  • the copolymers may be prepared by methods which are well known in the art. For example, they may be synthesized by the cohydrolysis, and subsequent condensation, of the appropriate diorganodialkoxy- silanes or diorganodichlorosilanes. In this approach, a desired quantity of an end-capping reactant, (R') 3 SiZ, is included in the reaction mixture to regulate the molecular weight of the product (i.e., more end- capping reactant yields a lower molecular weight product).
  • the R' groups of said end-capping reactant are the same as those set forth above for component (A).
  • the Z group is a hydrolyzable species such as halide (e.g., chlorine, fluorine or bromine) or alkoxy (e.g., methoxy, ethoxy).
  • Another procedure which may be followed in the synthesis of the subject copolymers is the acid or base catalyzed equilibration of diorganocyclosiloxanes in the presence of the aforementioned end-capping reactant.
  • Yet another, and preferred, method comprises the steps of preparing an SiH-functional copolymer intermediate of the general formula wherein Me represents the methyl radical and R' has been previously defined.
  • These intermediates are well known in the art and may be prepared by the acid equilibration of a commercially available polymethylhydrogensiloxane with cyclic dimethylsiloxanes in various ratios. Molecular weight of the intermediate may be controlled by incorporating the proper level of an endcapping monomer, such as hexamethyldisiloxane.
  • the SiH-functional intermediate is then reacted with about a 25% excess of the desired alkene to chemically add the latter to the SiH groups of the former. This addition reaction is catalyzed by platinum complexes known in the art.
  • Component (B) of the present invention is at least one synthetic hydrogenated polyalphaolefin (PAO) selected from the dimer, trimer or tetramer of decene-1, whichmay be represented by the following formulae:
  • PAO synthetic hydrogenated polyalphaolefin
  • component (B) is the PAO trimer. It is, however, possible to achieve the high flash point and viscosity-temperature profile needed to meet the requirements of the Low-Temperature MIL-H-83282 target by blending component (A) with mixtures of the above dimer, trimer and tetramer, as may be determined by routine experimentation.
  • the PAO fluids are well known in the art and can be prepared from the monomer decene-1 by catalytic polymerization and hydrogenation. The interested reader is directed, for example, to methods outlined by Cupples et al. in the October 1981 government report number AFWAL-TR-81-4109 (Materials Laboratory, Air Force Wright Aeronautical Laboratories, Wright-Patterson Air Force Base). These fluids are commercially available from the Gulf Oil Chemicals Co., Houston, Texas, under the trade name SYNFLUID @.
  • compositions of the present invention may be prepared by simply blending components (A) and (B) to form a homogeneous mixture therebetween.
  • the method of mixing is not critical and any of the commonly employed methods known in the art may be used.
  • the blend so formed is referred to as a "base fluid" in that it is ordinarily combined with lubricity additives and other adjuvants, described infra, to form a fully formulated hydraulic fluid.
  • component (B) is the decene trimer from 40 to 90 parts by weight of component (A) is blended with 60 to 10 parts of component (B) to form 100 parts of the compositions of the present invention. It is preferred, however, that from 40 to 60 parts by weight of component (A) is blended with 60 to 40 parts of the decene trimer. Most preferably, equal weights of the decene trimer and the dimethylsiloxane/ alkylmethylsiloxane copolymer fluid of component (A) are employed wherein the dimethylsiloxane/alkylmethylsiloxane copolymer component is delineated by the preferred ranges described above.
  • component (B) is the decene tetramer
  • component (A) is blended with 20 to 10 parts of component (B) to form 100 parts of the compositions of the present invention.
  • compositions of the present invention may be defined in terms of the key physical properties required by the Low-Temperature MIL-H-83282 target.
  • 100 parts by weight of the blend consists of 10 to 90 parts by weight of component (A) and 90 to 10 parts by weight of at least one synthetic hydrogenated polyalphaolefin selected from the dimer, trimer or tetramer of decene-1, such that the homogeneous blend has a viscosity at most 2500mm 2 /s (cS) at -54°C., a viscosity of at least 3.5mm 2 /s (cS) at 100°C. and an open cup flash point of at least 163°C.
  • 40 to 60 parts by weight of component (A) is blended with 60 to 40 parts of component (B).
  • additives are generally incorporated into the base fluids of this invention to prepare completely formulated hydraulic fluids.
  • Antiwear, or lubricity, additives such as tricresyl phosphate, dibutylchlorendate and antimony dialkyl-dithiocarbamate are preferably incorporated at 1 to 10 percent by weight.
  • Rubber swell additives such as di(2-ethylhexyl) sebecate or tributyl phosphate, may be incorporated at 1 to 5% by weight. These are typically employed with polydimethylsiloxanes since these base fluids tend to shrink rubber components by leaching out plasticizers from the latter. Generally, less swell additive is needed as alkyl content, or size of the alkyl group, of component (A) is increased or a greater amount of component (B) is utilized.
  • Antioxidants such as p,p'dioctyldiphenylamine and butylated hydroxytoluene at concentrations of 0.1 to 0.5% by weight are generally required to protect the alkyl groups from oxidation at elevated operating temperatures. Dyes may also be incorporated at low levels, mainly for identification purposes.
  • non-essential additives such as fire retardants, defoamers and corrosion inhibitors may also find utility in combination with the base fluids of the present invention.
  • component (A) Increasing the alkylmethylsiloxane content of component (A) towards 100% resulted in polymers which were unsatisfactory in that these base fluids could not be formulated to conform to the viscosity requirements of the Low-Temperature MIL-H-83282 target. Furthermore, as alkyl content is increased, swell of any rubber components in the hydraulic system also increases, an undesirable consequence in some systems.
  • This invention also relates to an improved process for transmitting hydraulic force (pressure) in a hydraulic system, wherein the hydraulic fluid which is used consists essentially of one of the siloxane copolymer-PAO blends described above.
  • the fluid-containing portions of the hydraulic components of said hydraulic system are filled with the compositions of this invention, as disclosed above.
  • hydraulic components envisioned herein include pumps, fluid coupling devices, such as diaphragms, hydraulic line means, valves and hydraulic actuating means, such as hydraulic motors, pistons and servo- valves.
  • the hydraulic systems which benefit most from the use of the hydraulic base fluids of this invention are those which are required to operate between the temperature extremes of -54°C. and 135°C. and simultaneously require improved fire resistance over systems using mineral oil as the hydraulic fluid.
  • the process of the present invention is, therefore, most appropriately employed in conjunction with military aircraft hydraulic systems.
  • Other hydraulic systems wherein the process of the present invention may be advantageously employed include those of civilian aircraft, military transport and combat vehicles for land and sea, space vehicles and machinery for use in arctic regions or other cold environments.
  • a mixture of 400 grams of the copolymer prepared in Example 1, above, 500 grams of a siloxane having the average formula 100 grams of a mixture of dimethylcyclosiloxanes having 3,4 and 5 dimethylsiloxy units and 1 gram of KOH was stirred and heated to about 160°C. under a nitrogen atmosphere. About 20 ml of volatile products were removed by distillation. The remaining mixture was further reacted at 160°C. for 4 hours, after which it was cooled to room temperature. One gram of trimethylchlorosilane was added and the resulting combination stirred for an additional 30 minutes. The product was pressure-filtered to remove the KCI formed during neutralization of the base catalyst. Finally, the product was stripped to a pot temperature of 250°C. (208°C.
  • a homogeneous blend was prepared by mixing equal portions of the fluid prepared in Example 2 and a 4 mm 2 /s (cS) SYNFLUID @ (Gulf Oil Chemicals Co., Houston, TX).
  • the latter fluid is described as a trimer of jecene havina the formula
  • a siloxane copolymer having the average structure was prepared according to the method described in Example 1, above. This fluid was blended in equal amount with 4 mm 2 /s (cS) SYNFLUID @ as in Example 3 and the blend viscosity and flash point determined. These results also appear in Table 1.

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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)

Claims (4)

1. Un mélange homogène constitué de:
(A) 10 à 90 parties en poids d'un copolymère de siloxanes représenté par la formule moyenne
Figure imgb0025
dans laquelle Me représente le groupe méthyle, R' est choisi indépendamment parmi les radicaux alkyles ayant 1 à 10 atomes de carbone, R représente un groupe alkyle ayant 4 à 10 atomes de carbone, x est 5 à 15, y est 0,5 à 4 et le rapport y/x est d'au plus 0,3; et
(B) 90 à 10 parties en poids d'au moins une polyalpha-oléfine hydrogénée synthétique choisie parmi le dimère, le trimère et le tétramère de décène-1, ledit mélange ayant un total de 100 parties en poids desdits composants (A) et (B) et ayant une viscosité d'au plus 2500mm2/s (2500 cS) à -54,C une viscosité d'au, moins 3,5mm2/s (3,5 cS) à 100°C et un point d'éclair en vase ouvert d'au moins 163°C.
2. Le mélange de la revendication 1, dans lequel le mélange contient 40 à 90 parties en poids du copolymère de siloxanes de (A) et 60 à 10 parties en poids d'une polyalpha-oléfine hydrogénée synthétique (B) représentée par la formule
Figure imgb0026
ledit mélange ayant un total de 100 parties en poids desdits composants (A) et (B).
3. Le mélange de la revendication 1, dans lequel le mélange contient 80 à 90 parties en poids du copolymère de siloxanes de (A) et 20 à 10 parties en poids d'une polyalpha-oléfine hydrogénée synthétique (B) représentée par la formule
Figure imgb0027
ledit mélange ayant un total de 100 parties en poids desdits composants (A) et (B).
4. Utilisation du mélange selon l'une quelconque des revendications 1 à 3 comme fluide hydraulique dans un système hydraulique transmetteur de force.
EP88104211A 1987-03-23 1988-03-17 Fluide hydraulique à base de siloxane et de polyalphaoléfine Expired - Lifetime EP0283922B1 (fr)

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US2895087A 1987-03-23 1987-03-23
US28950 1987-03-23

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Cited By (3)

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DE4204200A1 (de) * 1992-02-13 1993-08-19 Daimler Benz Ag Fluessigkeit und deren verwendung
CN106414680A (zh) * 2014-05-30 2017-02-15 道达尔销售服务公司 低粘度润滑聚烯烃
US20170226441A1 (en) * 2014-05-30 2017-08-10 Total Marketing Services Method for preparing low-viscosity lubricating polyolefins

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JP3341318B2 (ja) * 1992-10-21 2002-11-05 エヌオーケー株式会社 低温作動油
JP3344852B2 (ja) * 1994-10-28 2002-11-18 東レ・ダウコーニング・シリコーン株式会社 液状組成物
GB201214473D0 (en) * 2012-08-14 2012-09-26 Dow Corning Lubricant compostion
FR3037968A1 (fr) * 2015-06-29 2016-12-30 Total Marketing Services Polyolefines comme fluide special
FR3037969B1 (fr) * 2015-06-29 2017-08-11 Total Marketing Services Polyolefines lubrifiantes de basse viscosite
FR3037949B1 (fr) * 2015-06-29 2017-08-11 Total Marketing Services Polyolefines lubrifiantes de basse viscosite
CN105754692A (zh) * 2016-04-14 2016-07-13 上海禾泰特种润滑科技股份有限公司 一种空气压缩机油组合物及其制备方法
SG11201910241QA (en) * 2017-06-22 2020-01-30 Exxonmobil Res & Eng Co Low viscosity lubricants based on methyl paraffin containing hydrocarbon fluids

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4204200A1 (de) * 1992-02-13 1993-08-19 Daimler Benz Ag Fluessigkeit und deren verwendung
CN106414680A (zh) * 2014-05-30 2017-02-15 道达尔销售服务公司 低粘度润滑聚烯烃
US20170226441A1 (en) * 2014-05-30 2017-08-10 Total Marketing Services Method for preparing low-viscosity lubricating polyolefins

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AU1337588A (en) 1988-09-22
DE3861601D1 (de) 1991-02-28
CA1334966C (fr) 1995-03-28
EP0283922A3 (en) 1988-10-26
AU597804B2 (en) 1990-06-07
EP0283922A2 (fr) 1988-09-28
JPS63254161A (ja) 1988-10-20
JPH0563509B2 (fr) 1993-09-10

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