EP0184713A2 - Lubrifiants stabilisés à base de polyéther - Google Patents

Lubrifiants stabilisés à base de polyéther Download PDF

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Publication number
EP0184713A2
EP0184713A2 EP85114960A EP85114960A EP0184713A2 EP 0184713 A2 EP0184713 A2 EP 0184713A2 EP 85114960 A EP85114960 A EP 85114960A EP 85114960 A EP85114960 A EP 85114960A EP 0184713 A2 EP0184713 A2 EP 0184713A2
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EP
European Patent Office
Prior art keywords
alkyl
group
radical
cycloalkyl
formula
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.)
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Application number
EP85114960A
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German (de)
English (en)
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EP0184713A3 (fr
Inventor
Hans-Josef Dr. Buysch
Siegfried Dipl.-Ing. Kussi
Günther Dr. Boehmke
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Bayer AG
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Bayer AG
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Publication of EP0184713A2 publication Critical patent/EP0184713A2/fr
Publication of EP0184713A3 publication Critical patent/EP0184713A3/fr
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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
    • 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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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • 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
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
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    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/18—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/24—Polyethers
    • C10M145/26—Polyoxyalkylenes
    • C10M145/36—Polyoxyalkylenes etherified
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    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
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    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
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    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • 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
    • 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
    • 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
    • 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
    • C10M2221/041—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving sulfurisation of macromolecular compounds, e.g. polyolefins
    • 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
    • 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
    • C10M2221/043—Polyoxyalkylene ethers with a thioether group
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties

Definitions

  • the present invention relates to polyether-based lubricants stabilized with special diphenylamine derivatives.
  • Polyether-based lubricants are known. They are characterized by excellent lubricity, good viscosity behavior, high flash point, low volatility, low pour point and low impact on metals and sealing materials. They can be used over a wide temperature range, for example from -20 to + 220 ° C. Because of these properties, lubricants based on polyether are used in particular as hydraulic fluids, brake fluids, metalworking fluids, lubricants for compressors and refrigeration machines and as bearing and gear oils for thermally and mechanically highly stressed units in the paper, textile and plastics industries.
  • polyether-based lubricants often have insufficient thermal and oxidation stability and therefore do not always meet all the requirements placed on high-quality lubricants.
  • additives In order to improve the properties of lubricants based on polyethers, additives have already been proposed, such as aromatic amines, e.g. Phenyl-ctnaphthylamine, phenothiazine derivatives and certain diphenylamine derivatives (see Ullmann's Encyclopedia of Industrial Chemistry, 4th edition, volume 20, page 510, DE-OS 22 11 805 and DE-OS 28 06 133).
  • aromatic amines e.g. Phenyl-ctnaphthylamine, phenothiazine derivatives and certain diphenylamine derivatives
  • Such polyethers are generally oils which have molecular weights of, for example, 500 to 20,000. They preferably have molar masses of 1000 to 7000. They can be prepared by methods known per se, for example by an alkali-catalyzed or acid-catalyzed polymerization of the cyclic ethers, it being possible to use monoalcohols, polyalcohols or amines as starter molecules.
  • the OH end groups of the polyethers thus produced can be closed by a conventional alkylation or acylation, i.e. be converted into ether or ester end groups.
  • Polyethers which are particularly suitable for the stabilization according to the invention are oils with molecular weights of 500 to 20,000, preferably with molecular weights of 1,500 to 7,000, which are obtained by alkali-catalyzed addition of propylene oxide and optionally ethylene oxide to alcohols, for example ethanol, butanol, propanediol, glycerol, trimethylolpropane or Pentaerythritol.
  • the diphenylamine derivatives of the formula (VII) can be present, for example, in amounts of 0 to 10% by weight, based on the mixture. This amount is preferably 0.1 to 5% by weight.
  • the metal deactivators of the formula (VIII) can be present, for example, in an amount of 0 to 4% by weight, based on the mixture. This amount is preferably 0.5 to 2% by weight.
  • the other additives can, for example, each be present in amounts of 0 to 10% by weight, based on the mixture. This amount is preferably 0 to 5% by weight.
  • the lubricants according to the invention can be produced in various ways.
  • diphenylamine derivatives of the formula (I) and, if appropriate, further additives can be added to polyethers in the desired proportions and, if appropriate with heating, for example at 80 to 100 ° C., dissolved therein.
  • Another possibility is to first produce concentrates from the stabilizers using a suitable medium and to add these to the polyether lubricant to be stabilized in accordance with the desired proportions.
  • suitable concentrations for Such concentrates are, for example, those from 20 to 90% by weight, suitable media for their production are, for example, higher alcohols, such as 2-ethylhexanol and octaethylene glycol, but especially polyether lubricants. You can also mix the stabilizers or their concentrates first in the desired proportions and add this mixture to the lubricant to be stabilized.
  • a commercial polypropylene ether with a molecular weight of 5500 and started on trimethylolpropane was mixed with 2% by weight, based on the mixture, of the specified stabilizers and the mixture was tested for oxidation stability in accordance with DIN 51 352 Part 2.
  • the oil to be tested was aged in a glass vessel with 0.1% by weight of ferric oxide as a catalyst while introducing 15 l / h of air at 200 ° C. for 24 hours.
  • the viscosity of the aged samples was determined at 40 ° C. and compared with the viscosity of the non-aged sample.
  • Table 1 shows the stabilizers tested, and Table 2 the results obtained.
  • the (kinetic) viscosity measurements were carried out in accordance with DIN 51562, Part 1 (Ubbelohde method).
  • Table 4 shows good resistance to degradation for all products at the lower temperatures and short exposure times. At higher temperatures and especially with long exposure times, the formulations according to the invention prove to be significantly more stable. Also noteworthy is the low or even constant loss of evaporation of samples A and B over a period of 3 hours with increasing temperatures.
  • the amount of stabilizer applied is significantly less than in comparative experiment C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP85114960A 1984-12-08 1985-11-26 Lubrifiants stabilisés à base de polyéther Withdrawn EP0184713A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3444884 1984-12-08
DE3444884A DE3444884A1 (de) 1984-12-08 1984-12-08 Stabilisierte schmierstoffe auf der basis von polyethern

Publications (2)

Publication Number Publication Date
EP0184713A2 true EP0184713A2 (fr) 1986-06-18
EP0184713A3 EP0184713A3 (fr) 1987-02-04

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US (1) US4627929A (fr)
EP (1) EP0184713A3 (fr)
JP (1) JPS61138696A (fr)
BR (1) BR8506132A (fr)
DE (1) DE3444884A1 (fr)
ES (1) ES8705510A1 (fr)

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US6797677B2 (en) 2002-05-30 2004-09-28 Afton Chemical Corporation Antioxidant combination for oxidation and deposit control in lubricants containing molybdenum and alkylated phenothiazine
US8202829B2 (en) * 2004-11-04 2012-06-19 Afton Chemical Corporation Lubricating composition
EP2691498A1 (fr) * 2011-03-29 2014-02-05 Dow Global Technologies LLC Compositions lubrifiantes comprenant un diéther de polyalkylène glycol à basse volatilité noack
US10287418B2 (en) 2015-12-22 2019-05-14 Eastman Chemical Company Compounds with antidegradant and antifatigue efficacy and compositions including said compounds
US10428009B2 (en) 2015-12-22 2019-10-01 Eastman Chemical Company Methods of making compounds and mixtures having antidegradant and antifatigue efficacy
US10167252B2 (en) * 2015-12-22 2019-01-01 Eastman Chemical Company Compounds and mixtures with antidegradant and antifatigue efficacy and compositions including such compounds
US10260017B2 (en) 2015-12-22 2019-04-16 Eastman Chemical Company Compounds and mixtures with antidegradant and antifatigue efficacy and compositions including said compounds
US10160718B2 (en) * 2015-12-22 2018-12-25 Eastman Chemical Company Methods of making compounds having antidegradant and antifatigue efficacy
WO2018226372A1 (fr) * 2017-06-09 2018-12-13 Eastman Chemical Company Procédés de fabrication de composés ayant un effet protecteur et une efficacité anti-fatigue
MX2021003642A (es) * 2018-11-14 2021-05-27 Sika Tech Ag Composicion curable para sustratos alcalinos.

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DE2806133A1 (de) * 1978-02-14 1979-08-16 Hoechst Ag Schmiermittel
EP0070436A1 (fr) * 1981-07-14 1983-01-26 Bayer Ag Stabilisateurs contenant des composantes réactives pour mousse de PU, stabilisateurs et un procédé servant à leur préparation

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Publication number Priority date Publication date Assignee Title
DE2806133A1 (de) * 1978-02-14 1979-08-16 Hoechst Ag Schmiermittel
EP0070436A1 (fr) * 1981-07-14 1983-01-26 Bayer Ag Stabilisateurs contenant des composantes réactives pour mousse de PU, stabilisateurs et un procédé servant à leur préparation

Also Published As

Publication number Publication date
ES549665A0 (es) 1987-05-01
DE3444884A1 (de) 1986-06-12
US4627929A (en) 1986-12-09
EP0184713A3 (fr) 1987-02-04
JPS61138696A (ja) 1986-06-26
ES8705510A1 (es) 1987-05-01
BR8506132A (pt) 1986-08-26

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