EP0337425B1 - Antirostadditive für Schmiermittel oder Schmierfette mit Perfluoropolyäthern als Basismaterial - Google Patents

Antirostadditive für Schmiermittel oder Schmierfette mit Perfluoropolyäthern als Basismaterial Download PDF

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EP0337425B1
EP0337425B1 EP89106508A EP89106508A EP0337425B1 EP 0337425 B1 EP0337425 B1 EP 0337425B1 EP 89106508 A EP89106508 A EP 89106508A EP 89106508 A EP89106508 A EP 89106508A EP 0337425 B1 EP0337425 B1 EP 0337425B1
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additives
radical
cfx
end group
groups
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French (fr)
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EP0337425A1 (de
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Ezio Strepparola
Piero Gavezotti
Costante Corti
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Syensqo Specialty Polymers Italy SpA
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Ausimont SpA
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
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    • C10M2211/06—Perfluorinated compounds
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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
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    • C10M2213/06—Perfluoro polymers
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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • C10M2213/062—Polytetrafluoroethylene [PTFE]
    • C10M2213/0623—Polytetrafluoroethylene [PTFE] used as base material
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/16—Nitriles
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/26—Amines
    • C—CHEMISTRY; METALLURGY
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives

Definitions

  • the present invention relates to functionalized fluoropolyether compounds which impart antirust properties to lubricating oils and greases based on perfluoropolyethers.
  • PFPE perfluoropolyethers
  • PFPE utilizable also for formulating lubricating oils and greases are well-known on the market, for example, Fomblin (R) (produced by Montedison), KRYTOX (R) (produced by DuPont), DENNUM (R) (produced by Daikin), and the like.
  • the compounds according to the present invention represent a significant improvement in antirust protection as compared with the anticorrosive products described in EP-A-95825, 165649, 165650 and IT-A-20159 A/86.
  • the additives of the above types 1 and 3 exhibit the drawback of being scarcely soluble in the lubricating perfluoropolyether which causes problems with respect to phase separation, while the additive of type 2, although showing an acceptable solubility at the beginning, results in a certain amount of formed ester compounds in the course of time, whereby the mixture becomes cloudy and tends to form an overfloating layer. i.e., the additive separates from the lubricant.
  • a perfluoropolyether having a sequence of one or more of the following units is used: wherein the groups R′ f , which may be the same or different from each other, are H or fluoroalkyl radicals (preferably having 1 to 3 carbon atoms such as, for example, CF3 and C2F5) and having at least one end group selected from:
  • the other end group may be one of the above groups (a), (b) and (c) but may also represent a perfluoroalkyl radical with 1 to 3 carbon atoms, for example, CF3 or C2F5.
  • a in group (c) is a nitrogen atom
  • the group attached thereto preferably has the same meanings as the groups R1 and R2, particularly H, CH3 and C2H5.
  • preferred antirust additives of the present invention belong to the following classes: wherein at least one of the end groups T and T′ is selected from:
  • the additives of the present invention exhibit a solubility in the PFPE lubricant of at least 1% by weight based on the lubricant.
  • the amount of the above fluoropolyether antirust additives preferably ranges from 1% to 5% by weight, based on the total lubricant amount, even more preferred from 2% to 4% by weight.
  • the lubricant to which the antirust additive is added is a grease based on perfluoropolyethers, it may be prepared as is described in EP-A-92825.
  • such a grease can be formulated by suspending polytetrafluoroethylene particles having, for example, a spherical morphology and being composed of aggregates having a size of from 1 to 200 ⁇ m, in a liquid perfluoropolyether such as Fomblin (R) Y or Fomblin (R) Z.
  • a liquid perfluoropolyether such as Fomblin (R) Y or Fomblin (R) Z.
  • the additives having the above end groups (a), (b) and (c) can be used in combination with small amounts of fluoropolyether compounds having the same chain structure as the compounds of the present invention, for example structures (I) to (XI), but one or two end groups ⁇ CFX-COOH, wherein X is F or CF3.
  • fluoropolyether compounds having the same chain structure as the compounds of the present invention for example structures (I) to (XI), but one or two end groups ⁇ CFX-COOH, wherein X is F or CF3.
  • the latter compounds are employed in amounts ranging from 1/30 to 1/20 (about 3 to about 5%) of the weight of the additive characterized by end groups (a), (b) and/or (c).
  • the fluoropolyether precursors of the additives of the present invention may be prepared as follows:
  • the above end groups can be introduced, for example, by the method described in US-A-3010874.
  • end groups of types (b) and (c) may be effected by reacting the ester compounds indicated above with an amine of the formulae NHR1R2 or to form the corresponding amides and by subsequent reduction of the latter with hydrides.
  • Carbon steel plates (C15) (UNI), superficially treated as described below, were dipped into the oil, allowed to drip and hung in a fog chamber at 50°C and 100% relative humidity for a predetermined number of hours. The oil passes or does not pass the test on the basis of the number of rust stains visible on the surface of the plates.
  • the steel plates were cleaned and degreased by means of a cloth soaked with Delifrene (R) 113 (trichlorotrifluoroethane); the surface was polished by means of emery paper (400 mesh and 600 ⁇ ), washed with water and dried.
  • the utilized plates had the following dimensions: 50 ⁇ 100 ⁇ 2 mm. (Note: polyethylene gloves must be used to handle the plates).
  • the first figure refers to the state of the exposed face;
  • the second figure refers to the non-exposed face (with respect to the sprayer).
  • Lubricants consisting of perfluoropolyethers having perfluoroalkyl end groups (Fomblin (R) Y25), characterized by a viscosity of 250 cSt (250 mm2/s) at 20°C, to which the compounds indicated in the following Table 1 had been added, were subjected to the accelerated corrosion test in a fog chamber according to the method described above.
  • Table 1 shows the weight percentage of the additive with respect to the perfluoropolyether and the results of the corrosion test, expressed by the ratings (figures) outlined above.
  • Example 1 was repeated, using as lubricant perfluoropolyether Fomblin (R) Y25 without additive. The result was a complete corrosion of the plate: 5-5.
  • Lubricants consisting of perfluoropolyethers having perfluoroalkyl end groups (Fomblin (R) Z25), characterized by a viscosity of 250 cSt (250 mm2/s) at 20°C to which the compounds reported in the following Table 2 had been added were subjected to the accelerated corrosion test of example 1.
  • Table 2 shows the results of said tests.
  • Example 2 was repeated, using as lubricant perfluoropolyether Fomblin (R) Z25 without additive. The result was a complete corrosion of the plate: 5-5.
  • lubricants consisting of perfluoropolyethers having perfluoroalkyl end groups (Fomblin (R) YR 140/13), characterized by a viscosity of 1400 cSt (1400 mm2/s) at 20°C to which the following mixture had been added:
  • the result of the corrosion test was 0-0.
  • Example 3 was repeated, using as lubricant perfluoropolyether Fomblin (R) YR 140/13 without additive. The result was a complete corrosion of the plate: 5-5.

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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 (10)

1. Rostschutzadditive für Schmiermittel auf Perfluorpolyetherbasis, umfassend eine oder mehrere Fluorpolyetherverbindungen, die eine oder mehrere der folgenden Einheiten aufweisen:
Figure imgb0018
 worin R′f H oder einen Fluoralkylrest darstellt,
und mindestens eine Endgruppe aufweisen, die ausgewählt ist aus:
(a)   ―CFX-CN;
(b)   ―CFX-CH₂-NR₁R₂, worin R₁ und R₂, gleich oder verschieden, C₁₋₈-Alkyl, C₇₋₁₁-Alkylaryl oder C₆₋₁₀-Cycloalkylgruppen, gegebenenfalls mit C₁₋₃-Alkylgruppen substituiert, darstellen, wobei R₁ und R₂ gegebenenfalls Heteroatome enthalten, die aus O, N und S ausgewählt sind;
Figure imgb0019
 worin A = O, N oder S und R H oder eine C₁₋₃-Alkylgruppe bedeutet;
wobei der Rest X in (a), (b) und (c) F oder CF₃ representiert;
während die andere Endgruppe die oben für die erste Endgruppe angegebene Bedeutung hat oder einen Perfluoralkylrest mit 1 bis 3 Kohlenstoffatomen darstellt;
mit der Maßgabe, daß im Fall von Fluorpolyetherverbindungen, die lediglich die Einheiten (CF₂CF₂O) und (CF₂O) und eine Endgruppe (a) oder (b) aufweisen, die andere Endgruppe einen Perfluoralkylrest mit 1 bis 3 Kohlenstoffatomen darstellt.
2. Additive nach Anspruch 1, umfassend eine oder mehrere der folgenden Fluorpolyetherverbindungen:
Figure imgb0020
worin mindestens eine der Endgruppen T und T′ ausgewählt ist aus:
(a)   ―CFX-CN;
(b)   ―CFX-CH₂-NR₁R₂;
Figure imgb0021
 worin X, R₁, R₂, A und R wie in Anspruch 1 definiert sind;
die andere Endgruppe T oder T′ ebenfalls ein Perfluoralkylrest mit 1 bis 3 Kohlenstoffatomen sein kann, und im Fall der Verbindung (I) ein Perfluoralkylrest mit 1 bis 3 Kohlenstoffatomen sein muß;
g, h, m, n, k, j, p, q, s, t, r, u, v, z, x, y ganze Zahlen sind, derart ausgewählt, daß das durchschnittliche Molekulargewicht der Polyoxyfluoralkylenkette 600 bis 6000 beträgt; Rf ein Fluoralkylenrest ist; R′f H oder einen Fluoralkylrest bedeutet;
die Oxyfluoralkyleneinheiten statistisch entlang der Kette verteilt sind;
wobei die Additive eine Löslichkeit im PFPE-Schmiermittel von mindestens 1 Gew.-%, bezogen auf das Schmiermittel, aufweisen.
3. Additive nach Anspruch 2 mit einer Formel vom Typ (I), einer Endgruppe vom Typ (a) und einem durchschnittlichen Molekulargewicht von etwa 2000.
4. Additive nach Anspruch 2 mit einer Formel vom Typ (VII), Endgruppen vom Typ (c) und einem durchschnittlichen Molekulargewicht von etwa 1000.
5. Verwendung von Fluorpolyetherverbindungen als Rostschutzadditive für Schmiermittel auf Perfluorpolyetherbasis, die eine oder mehrere der folgenden Einheiten aufweisen:
Figure imgb0022
 worin R′f H oder einen Fluoralkylrest darstellt,
und mindestens eine Endgruppe aufweisen, die ausgewählt ist aus:
(a)   ―CFX-CN;
(b)   ―CFX-CH₂-NR₁R₂, worin R₁ und R₂, gleich oder verschieden, C₁₋₈-Alkyl, C₇₋₁₁-Alkylaryl oder C₆₋₁₀-Cycloalkylgruppen, gegebenenfalls mit C₁₋₃-Alkylgruppen substituiert, darstellen, wobei R₁ und R₂ gegebenenfalls Heteroatome enthalten, die aus O, N und S ausgewählt sind;
Figure imgb0023
 worin A = O, N oder S und R H oder eine C₁₋₃-Alkylgruppe bedeutet;
wobei der Rest X in (a), (b) und (c) F oder CF₃ repräsentiert;
während die andere Endgruppe die oben für die erste Endgruppe angegebene Bedeutung hat oder einen Perfluoralkylrest mit 1 bis 3 Kohlenstoffatomen darstellt.
6. Verwendung nach Anspruch 5, worin eine oder mehrere der folgenden Fluorpolyetherverbindungen eingesetzt werden:
Figure imgb0024
 worin mindestens eine der Endgruppen T und T′ ausgewählt ist aus:
(a)   ―CFX-CN;
(b)   ―CFX-CH₂-NR₁R₂;
Figure imgb0025
 worin X, R₁, R₂, A und R wie in Anspruch 1 definiert sind;
die andere Endgruppe T oder T′ ebenfalls ein Perfluoralkylrest mit 1 bis 3 Kohlenstoffatomen sein kann;
g, h, m, n, k, j, p, q, s, t, r, u, v, z, x, y ganze Zahlen sind, derart ausgewählt, daß das durchschnittliche Molekulargewicht der Polyoxyfluoralkylenkette 600 bis 6000 beträgt; Rf ein Fluoralkylenrest ist; R′f H oder einen Fluoralkylrest bedeutet;
die Oxyfluoralkyleneinheiten statistisch entlang der Kette verteilt sind;
wobei die Additive eine Löslichkeit im PFPE-Schmiermittel von mindestens 1 Gew.-%, bezogen auf das Schmiermittel, aufweisen.
7. Verwendung nach Anspruch 6, worin Fluorpolyetherverbindungen mit einer Formel vom Typ (I), Endgruppen vom Typ (a) und einem durchschnittlichen Molekulargewicht von etwa 2000 eingesetzt werden.
8. Schmiermittel auf Perfluorpolyetherbasis mit Rostschutzeigenschaften, welche die Additive nach irgendeinem der Ansprüche 1 bis 7 enthalten.
9. Schmiermittel nach Anspruch 8, worin die Additive in einer Menge von 1 bis 5 Gew.-%, vorzugsweise 2 bis 4 Gew.-%, bezogen auf die Gesamtmenge des Schmiermittels, anwesend sind.
10. Schmiermittel nach irgendeinem der Ansprüche 8 und 9, die zusätzlich Fluorpolyetherverbindungen umfassen, welche dieselbe Kettenstruktur wie die Additive der Ansprüche 1 bis 7 aufweisen, mit der Ausnahme, daß sie 1 oder 2 Endgruppen der Formel ―CFX-COOH haben, worin X F oder CF₃ ist, wobei die zusätzlichen Additive in einer Menge von 1/30 bis 1/20 des Gewichts der Additive nach Anspruch 1 bis 7 vorhanden sind.
EP89106508A 1988-04-13 1989-04-12 Antirostadditive für Schmiermittel oder Schmierfette mit Perfluoropolyäthern als Basismaterial Expired - Lifetime EP0337425B1 (de)

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IT20183/88A IT1218217B (it) 1988-04-13 1988-04-13 Additivi antirust per lubaificanti o grassi a base di perfluoropolieteri

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JPH03126790A (ja) * 1989-10-13 1991-05-29 Nippon Oil Co Ltd 潤滑油組成物
IT1237887B (it) * 1989-12-12 1993-06-18 Ausimont Spa Lubrificanti perfluoropolieterei aventi proprieta' antiusura
CN102676275B (zh) * 2012-05-07 2014-01-15 中国石油化工股份有限公司 润滑油添加剂及其制备方法和用途
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US4113772A (en) * 1975-07-21 1978-09-12 Lagow Richard J Method for producing perfluoroether oligomers having terminal carboxylic acid groups
US4132660A (en) * 1978-03-01 1979-01-02 The United States Of America As Represented By The Secretary Of The Air Force Grease compositions
US4194983A (en) * 1979-02-06 1980-03-25 The United States Of America As Represented By The Secretary Of The Air Force Perfluorinated polyalkylether based lubricant composition
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