EP0397507B1 - Fluides de silicone pour accouplements visqueux - Google Patents

Fluides de silicone pour accouplements visqueux Download PDF

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Publication number
EP0397507B1
EP0397507B1 EP90305069A EP90305069A EP0397507B1 EP 0397507 B1 EP0397507 B1 EP 0397507B1 EP 90305069 A EP90305069 A EP 90305069A EP 90305069 A EP90305069 A EP 90305069A EP 0397507 B1 EP0397507 B1 EP 0397507B1
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EP
European Patent Office
Prior art keywords
fluid
added
wear agent
wear
type
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
EP90305069A
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German (de)
English (en)
Other versions
EP0397507A1 (fr
Inventor
Hirotaka C/O Tonen Corporation Corp. Tomizawa
Noboru C/O Tonen Corporation Corp. Umemoto
Hitoshi C/O Tonen Corporation Corp. Ohenoki
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.)
Tonen General Sekiyu KK
Original Assignee
Tonen Corp
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Publication date
Priority claimed from JP2870090A external-priority patent/JP2930352B2/ja
Application filed by Tonen Corp filed Critical Tonen Corp
Publication of EP0397507A1 publication Critical patent/EP0397507A1/fr
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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
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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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    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
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    • C10M135/20—Thiols; Sulfides; Polysulfides
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    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • the present invention relates to a fluid for use in viscous couplings and which has high durability.
  • a fluid coupling also called a viscous coupling
  • a plurality of inner plates movably disposed on a driving shaft and a plurality of outer plates fixed on a driven shaft with predetermined spacings are combined together alternately and are accommodated in a housing, which contains the viscous operating fluid for torque transmission.
  • shearing force i.e. shear torque
  • shear torque is generated in said groups of plates due to the difference of the revolutions between the driving shaft and the driven shaft, in order to transmit torque to the driven shaft.
  • organopolysiloxane oils such as dimethylpolysiloxane or methylphenylpolysiloxane, have been used as the hydraulic fluid or the operating fluid for fluid couplings.
  • a dimethylpolysiloxane (also called dimethyl-silicone oil) of high viscosity index has been widely used, but it is difficult to maintain stable torque transmission ability for a long period under severe operating condition at high temperature. This is mainly due to the low thermal stability of this fluid at high temperature. Because the operating conditions are becoming increasingly severe in various usages including in viscous couplings, it is desirable to improve the thermal stability of the silicone oil, which constitutes the main component of dimethyl-silicone.
  • antioxidants such as iron octanoate, phenylamine derivatives or ferrocene derivatives
  • an organopolysiloxane oil antioxidants, such as iron octanoate, phenylamine derivatives or ferrocene derivatives, have been added to an organopolysiloxane oil.
  • a certain level of gelation preventive effect can be obtained at high temperature when these antioxidants are added, the viscosity increases when the viscous coupling is used continuously.
  • GB-A-2206887 describes a polyorganosiloxane fluid comprising a sulfur-based additive.
  • the object of this invention is to provide a fluid for viscous couplings, which has good resistance to thermal decomposition and gelation and has high stability.
  • a fluid for viscous couplings comprises an organopolysiloxane as the base oil and as additive a phosphorus type anti-wear agent of one of the formulae (1) to (27) given below.
  • the fluid for viscous coupling according to the present invention, it is possible to increase the heat-resistant property of the fluid and to improve its durability by adding antioxidants together with the anti-wear agent.
  • an anti-wear agent of the sulphur and/or zinc dithiophosphate type each has a certain effect when each is added alone to the fluid for viscous coupling.
  • an agent of the phosphorus, sulphur and/or zinc dithiophosphate type are admixed and blended together, and this gives a cumulative effect to form a film on the new metal surface and to suppress catalytic action thereby, thus almost completely eliminating the thickening of the fluid. This provides a better effect than when a phosphorus type agent is used alone.
  • the phosphorus type, sulphur type and zinc dithiophosphate type anti-wear agents give an adsorption effect on the metal in a specific temperature range according to their respective thermal stability. It appears that various friction and wear conditions occur in the viscous coupling itself during the operation and that the environmental temperature also widely differs. By this invention, the anti-wear agents with different absorption property are combined to cope with such conditions.
  • a metal deactivator and/or corrosion inhibitor is added to the mixture of organopolysiloxane and anti-wear agent.
  • a metal deactivator and/or corrosion inhibitor has lower solubility in the coupling fluid than the anti-wear agent, these substances can prevent increase of viscosity of the fluid when they are added in small quantity. This increases further the heat-resistance and improves the durability of the fluid.
  • the combined use therewith of an anti-wear agent and/or antioxidants is also desirable, so as to increase the heat-resistance and durability of the fluid.
  • An organopolysiloxane which is the base oil of the fluid according to this invention, has the following general formula: wherein R represents the same or different, optionally halogenated, hydrocarbon group having 1 - 18 carbon atoms, and n is an integral number of 1 - 3000.
  • Examples of the group R are an alkyl group such as a methyl, ethyl, n -propyl, i -propyl, n -butyl, i -butyl, t - butyl, n -pentyl, neopentyl, hexyl, heptyl, octyl, decyl or octadecyl group, an aryl group such as a phenyl or naphthyl group, an aralkyl group such as a benzyl, 1-phenylethyl or 2-phenylethyl group, an o -, m -, p -diphenyl group, or a halogenated hydrocarbon group such as an o -, m -, p -chlorphenyl group, o -, m -, p -bromphenyl group, 3,3,3-trifluoro
  • R a fluorinated hydrocarbon group having 1 - 8 carbon atoms other than an aliphatic unsaturated group; or, a mixture of a methylpolysiloxane and phenylpolysiloxane.
  • the phosphorus type anti-wear agent used is one of the following formulae (1) - (27) wherein R may be hydrogen, or an alkyl, aryl or benzyl group. R may be same or different.
  • R may be hydrogen, or an alkyl, aryl or benzyl group. R may be same or different.
  • actual compounds are given for some of the formulae, namely: Formula (1), triaryl phosphates, e.g.
  • benzyldiphenyl phosphate allydiphenylphosphate, triphenyl phosphate, tricresyl phosphate, ethyldiphenyl phosphate, tributyl phosphate, dibutyl phosphate, cresyldiphenyl phosphate, dicresylphenyl phosphate, ethylphenyldiphenyl phosphate, diethylphenylphenyl phosphate, propylphenyldiphenyl phosphate, dipropylphenylphenyl phosphate, triethylphenyl phosphate, tripropylphenyl phosphate, butylphenyldiphenyl phosphate, dibutylphenylphenyl phosphate, tributylphenyl phosphate, a propyl phenyl phenyl phosphate mixture, butyl phenyl phenyl phosphate mixture, or an acid phosphate
  • Formula (2) e.g. di- n -butylhexyl phosphate.
  • Formula (3) e.g. n -butyl-n-dioctyl phosphate.
  • triaryl phosphoro-thionates e. g. triphenyl phosphoro-thionate and alkylaryl phosphoro-thionates
  • Formula (15) e.g. triisopropyl phosphite and diisopropyl phosphite.
  • Formula (19) e.g. trilauryl thiophosphite.
  • the effects are particularly conspicuous in the cases of the compounds with excellent thermal stability having the structure of triaryl phosphate or triaryl phosphoro-thionate.
  • a sulfide such as diphenyl sulfide, diphenyl disulfide, dibenzyl disulfide, di- n -butyl sulfide, di- n -butyl disulfide, di- tert -butyl disulfide, di- tert -dodecyl sulfide or di- tert -dodecyl trisulfide, a sulfurized oil such as sulfurized sperm oil or sulfurized dipentene, or a thiocarbonate such as xanthic disulfide; and as a zinc dithiophosphate anti-wear agent a primary alkyl zinc dithiophosphate, secondary alkyl zinc dithiophosphate, alkyl-aryl zinc dithiophosphate or aryl zinc dithiophosphate.
  • each type of anti-wear agent phosphorus type, sulfur type and/or zinc dithiophosphate
  • each type of anti-wear agent in an amount of 0.01 - 5 wt% of the organopolysiloxane, more preferably 0.1 - 3 wt%.
  • the ratio of phosphorus type anti-wear agent to total anti-wear agents is preferably 5-95 wt%.
  • a compound may be used containing both phosphorus and sulfur, such as having at least one of the following formulae: e.g. benzyl (di- n -pentyl phosphoryl) bisulfide.
  • these agents in amount of 0.01 - 5 wt % to the organopolysiloxane, and more preferably, 0.1 - 3 wt %.
  • benzotriazole benzothiazole, thiadiazole, triazole, dithiocarbamate, indazole, or derivatives of any of these, or organic carboxylic acids including dibasic acids such as adipic acid, sebacic acid or dodecane dioic acid, or monobasic acids such as stearic acid, oleic acid or lauric acid, or amine salts of these compounds may be used.
  • corrosion inhibitors there are isostearate, n -octadecylammonium stearate, a long chain aliphatic diamine e.g. DUOMEEN-T diorate, lead naphthenate, sorbitan oleate, pentaerythrite oleate, oleyl sarcosine, alkyl succinic acid, alkenyl succinic acid, and derivatives of these compounds.
  • a long chain aliphatic diamine e.g. DUOMEEN-T diorate
  • lead naphthenate sorbitan oleate
  • pentaerythrite oleate oleyl sarcosine
  • alkyl succinic acid alkenyl succinic acid, and derivatives of these compounds.
  • Prefered amounts of the metal deactivator and corrosion inhibitors are each 0.001 - 1.0 wt % of the organopolysiloxane, more preferably 0.01 - 0.5 wt %. When the added quantity exceeds 1.0 wt %, it is not desirable because precipitation increases. If it is less than 0.001 wt %, there is no effect.
  • the durability of the fluid can be increased by adding antioxidant when an phosphorus anti-wear agent is added alone, or when a phosphorus type anti-wear agent and sulfur type anti-wear agent and/or zinc dithiophosphate type anti-wear agent are together added, or when a metal deactivator and/or corrosion inhibitor is added alone or together with the above anti-wear agents.
  • Suitable antioxidants are amine type antioxidants such as dioctyldiphenylamine, phenyl- ⁇ -naphthylamine, alkyldiphenylamine, N-nitrosodiphenylamine, phenothiazine, N,N′-dinaphthyl- p -phenylenediamine, acridine, N-methylphenothiazine, N-ethylphenothiazine, dipyrizylamine and diphenylamine, phenol type antioxidants such as 2,6-di- t -butylparacresol, 4,4′-methylenebis (2,6-di- t -butylphenol) and 2,6-di- t -butylphenol, or organic metal compound type antioxidants such as an organic iron salt such as iron octoate, ferrocene or iron naphthoate, an organic cerium salt such as cerium naphthoate or cerium toluate, and an
  • Preferred amounts of the antioxidants are 0.001 - 5 wt % of the organopolysiloxane, more preferably 0.01 - 2 wt %.
  • Viscosities were measured at 25°C.
  • the viscous coupling was placed in a bath kept at a constant temperature of 130°C and was operated for 50 hours.
  • Example 1 was repeated, but with various amounts of tricresyl phosphate (A) and triphenyl phosphorothionate (B) as phosphorus type anti-wear agents in the weight percentage shown below.
  • the four fluids thus prepared were tested as in Example 1; the results are given in the table below: (A) Added quantity (B) Added quantity Viscosity change (%) Torque change (%) Blocking temperature (°C) a) with antioxidant in the fluid 0 1.0 +2 +1 330 0.5 0.5 +1 0 330 b) without antioxidant 0 1.0 +1 +1 290 0.5 0.5 +3 +3 290
  • Examples 1 and 2 show that satisfactory fluids can be prepared even when antioxidant is not added.
  • both sulfur type and phosphorus type agents have almost the same torque stability as anti-wear agents in the fluid.
  • the heat-resistance of the additive itself is inferior to that of the organopolysiloxane, the coking phenomenon occurs, in which black decomposed products of the additive are generated in the hot tube coking test, and the thermal stability of the fluid is thus reduced by the addition of such agent.
  • Example 3 was repeated but using dibenzyl disulfide and a polysulfide respectively as sulfur type anti-wear agents instead of the phosphorus type anti-wear agent tricresyl phosphate.
  • the results are: Cp. Ex. No Agent Addeded quantity of anti-wear agent (wt %) Viscosity change (%) Torque change (%) 2 Dibenzyl disulfide 2.0 -20 -35 1.0 -10 -22 0.5 -8 -17 None 0 Measurement not achievable Measurement not achievable 3 polysulfide 2.0 -22 -25 1.0 -15 -20 0.5 -10 -12
  • both phosphorus type and sulfur type agents exhibit excellent durability in viscosity change and torque change of the fluid for viscous coupling when the temperature is relatively low as in the Examples 1 and 2 and Comparative Example 1, whereas the phosphorus type shows the higher durability at high temperature.
  • This is attributable to the fact that, because a sulfur type anti-wear agent was a lower heat-resistant property, the reaction with dimethylsilicone or with the plates in the viscous coupling proceeded excessively at high temperature, which the phosphorus type anti-wear agent was higher heat-resistant property.
  • Example 3 As for the odor of the coupling fluids that of Example 3 is odorless and did not have a strong sulfur odor as did the fluids of the comparative examples. A phosphorus type of anti-wear agent is thus more convenient in use than a sulfur type anti-wear agent.
  • Example 6 the phosphorus type agent in Example 6 was stable to dimethylsilicone and this may be attributed to the high heat-resistant property of this agent.
  • the viscous coupling was maintained in a bath kept at constant temperature of 130°C and was operated for 100 hours.
  • Example 7 sulfurized sperm oil was added in the percentages given below as sulfur type anti-wear agent instead of dibenzyl disulfide (sulfur type) anti-wear agent.
  • the fluid thus prepared was tested as in Example 7 and the results were: Examples 8 to 11 and 14 to 15 respectively describe modifications of the samples of Examples 7 or 14 which contained an antioxidant.
  • Added quantity of phosphorus type wt %)
  • Added quantity of sulfur type wt %)
  • Viscosity change (%) Torque change (%)
  • Wear fragment iron (ppm) 0 0.5 +5 +7 450 0.25 0.25 +3 +3 200
  • Example 7 In the specimen of Example 7, an aminedibutyl phosphonate (phosphorus type agent) anti-wear agent was added in the percentages given below instead of tricresyl phosphate (phosphorus type) anti-wear agent.
  • the fluid was tested as in Example 7, and the results were: Added quantity of phosphorus type (wt %) Added quantity of sulfur type (wt %) Viscosity change (%) Torque change (%) Wear fragment iron (ppm) 0.5 0 +7 +5 450 0.25 0.25 +1 +1 200
  • di-sec-butyl zinc dithiophosphate (zinc dithiophosphate type amount) was added in the percentages below instead of dibenzyl disulfide (sulfur type).
  • the fluid thus prepared was tested as in Example 7, and the results were: Added quantity of phosphorus type (wt %) Added quantity of zinc thiophosphate (wt %) Viscosity change (%) Torque change (%) Wear fragment iron (ppm) 0 0.5 +8 +7 350 0.25 0.25 +3 +3 250
  • triphenyl phosphorothionate (phosphorus type) anti-wear agent was added in the percentage as given below instead of tricresyl phosphate (phosphorus type) anti-wear agent.
  • the fluid prepared was tested as in Example 7, and the results were: Added quantity of phosphorus type (wt %) Added quantity of sulfur type (wt %) Viscosity change (%) Torque change (%) Wear fragment iron (ppm) 0.5 0 +5 +3 350 0.25 0.25 +1 0 130
  • the viscous coupling was placed in a bath at constant temperature of 130°C and was operated for 100 hours. After the operation, viscosity change and torque change were measured; the results were: Anti-wear agent (wt %) Metal deactivator (wt %) Viscosity change (%) Torque change (%) 0 0 Measurement not achievable* Measurement not achievable* 0 0.1 +10 +10 0 0.4 +8 +7 0 0.8 +5 +5 0.5 0.1 +2 +2 * Stopped before the expiration of 100 hours due to sudden increase of torque.
  • Example 12 Each fluid was tested as in Example 12 with the results: Anti-wear agent (wt %) Metal deactivator (wt %) Viscosity change (%) Torque change (%) (a) with antioxidant 0 0 Measurement not achievable* Measurement not achievable* 0 0.1 +8% +8% 0 0.4 +5% +5% 0 0.8 +3% +3% 0.5 0.1 ⁇ 0 ⁇ 0 (b) without antioxidant 0 0 Measurement not achievable Measurement not achievable 0 0.1 +10% +10% 0 0.4 +7% +5% 0 0.8 +5% +4% 0.5 0.1 +2% ⁇ 0% * Measurement stopped before the expiration of 100 hours due to sudden increase in torque.
  • Example 13 a corrosion inhibitor n-octadecyl ammonium stearate was added in the percentage given below instead of the metal deactivator. Each fluid sample was tested as in Example 13, and the results are below. In the table, the added quantity of the anti-wear agent is not given. Added quantity of corrosion inhibitor (wt%) Viscosity change (%) Torque change (%) 0 Measurement not achievable Measurement not achievable 0.1 +12% +12% 0.4 +8% +10% 0.8 +4% +5% 0.1 +3% +3% (b) without antioxidant 0 Measurement not achievable Measurement not achievable Measurement not achievable 0.1 +14% +14% 0.4 +10% +10% 0.8 +5% +6% 0.1 +3% +3%
  • Example 13 was repeated but the amount of the metal deactivator was 0.1 wt % and the corrosion inhibitor 0.2 wt %.
  • the viscosity change was ⁇ 0%, and torque change was +3%.

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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)

Claims (5)

  1. Fluide pour couplage visqueux, comprenant comme base huileuse un organopolysiloxane de formule générale :
    Figure imgb0013
        dans laquelle les R représentent des groupes hydrocarbonés, éventuellement halogénés, identiques ou différents possédant de 1 à 18 atomes de carbone et n est un nombre entier allant de 1 à 3000, possédant une viscosité à 25°C voisine de 50000 mm²/s ou plus, et ayant comme additif au moins un des agents anti-usure à base de phosphore choisi parmi les substances possédant les formules (1) à (27):
    Figure imgb0014
    Figure imgb0015
        dans lesquelles les R sont des atomes d'hydrogène, des radicaux alcoyles, aryles ou benzyles identiques ou différents.
  2. Fluide selon la revendication 1 qui contient aussi un désactivateur métallique et/ou un inhibiteur de corrosion.
  3. Fluide selon la revendication 2 qui contient aussi un antioxydant.
  4. Fluide selon les revendications 1, 2 ou 3, qui contient aussi un agent anti-usure à base de soufre et/ou un agent anti-usure à base de dithiophosphate de zinc.
  5. Utilisation comme fluide pour couplage visqueux d'un fluide comprenant, comme base huileuse, un organopolysiloxane de formule générale :
    Figure imgb0016
        dans laquelle les R représentent des groupes hydrocarbonés, éventuellement halogénés, identiques ou différents possédant de 1 à 18 atomes de carbone et n est un nombre entier allant de 1 à 3000, et ayant comme additif au moins un des agents anti-usure à base de phosphore choisi parmi les substances de formules (1) à (27) comme il est exposé dans la revendication 1.
EP90305069A 1989-05-10 1990-05-10 Fluides de silicone pour accouplements visqueux Expired - Lifetime EP0397507B1 (fr)

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JP11626589 1989-05-10
JP116265/89 1989-05-10
JP31270089 1989-11-30
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JP2870090A JP2930352B2 (ja) 1990-02-07 1990-02-07 ビスカスカップリング用流体
JP28700/90 1990-02-07
JP30990/90 1990-02-09
JP3099090 1990-02-09
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ATE142250T1 (de) * 1990-06-29 1996-09-15 Tonen Corp Hydraulik-, schmier- und kupplungsmittelzusammensetzung, die einen organopolysiloxan und einen phosphor enthaltenden additiv enthält.
JP3040618B2 (ja) * 1992-11-20 2000-05-15 コスモ石油株式会社 新規ビスカスカップリング用流体組成物
DE4310593C2 (de) * 1993-03-31 1996-11-28 Wacker Chemie Gmbh Stabilisierte Organopolysiloxanöle und deren Verwendung
DE69420796T2 (de) * 1993-07-30 2000-01-13 Tonen Corp Flüssige Zusammensetzung für Flüssigkeitsreibungskupplung
EP3607033A1 (fr) 2017-04-03 2020-02-12 Solvay Specialty Polymers Italy S.p.A. Compositions de fluide de travail

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* Cited by examiner, † Cited by third party
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CN101023333B (zh) * 2004-08-27 2011-01-12 E.G.O.电气设备制造股份有限公司 预老化的工作流体在恒温器中的用途以及预老化恒温器用的工作流体的方法

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