Classifications

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  • 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
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  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
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  • C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
  • C10M125/02—Carbon; Graphite
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  • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
  • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
  • C10M129/04—Hydroxy compounds
  • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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  • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
  • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
  • C10M137/04—Phosphate esters
  • C10M137/10—Thio derivatives
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  • C10M147/00—Lubricating compositions characterised by the additive being a macromolecular compound containing halogen
  • C10M147/02—Monomer containing carbon, hydrogen and halogen only
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  • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
  • C10M2201/04—Elements
  • C10M2201/041—Carbon; Graphite; Carbon black
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  • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
  • C10M2201/04—Elements
  • C10M2201/041—Carbon; Graphite; Carbon black
  • C10M2201/042—Carbon; Graphite; Carbon black halogenated, i.e. graphite fluoride
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  • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
  • C10M2201/06—Metal compounds
  • C10M2201/065—Sulfides; Selenides; Tellurides
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  • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
  • C10M2201/06—Metal compounds
  • C10M2201/065—Sulfides; Selenides; Tellurides
  • C10M2201/066—Molybdenum sulfide
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  • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
  • C10M2201/08—Inorganic acids or salts thereof
  • C10M2201/084—Inorganic acids or salts thereof containing sulfur, selenium or tellurium
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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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  • 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
  • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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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
  • C10M2207/027—Neutral salts thereof
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • 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
  • C10M2213/06—Perfluoro polymers
  • C10M2213/062—Polytetrafluoroethylene [PTFE]
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
  • C10M2219/021—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds used as base material
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
  • C10M2219/0406—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides used as base material
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  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
  • C10M2219/046—Overbased sulfonic acid salts
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
  • C10M2219/061—Thio-acids; Thiocyanates; Derivatives thereof used as base material
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/081—Thiols; Sulfides; Polysulfides; Mercaptals used as base material
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
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  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
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  • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
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  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/04—Groups 2 or 12

Definitions

• machine bearings and gearboxes are known to be provided with a lubricant that enables the solid bodies that are moved against each other to be separated as completely as possible during operation.
• the lubricants can be divided into lubricating oils and greases.
• Mineral oils and synthetic oils such as polyalkylene glycols, ester oils, phosphoric acid esters and silicones are used as lubricating oils (see overview in Ullmanns Enzykl. Der technical chemistry, 4th edition, vol. 20). Modern lubricating oils contain a number of additives that affect both the physical and chemical properties. These are, in particular, oxidation inhibitors, detergents, high-pressure additives, friction reducers, anti-foaming agents and corrosion inhibitors.
• the energy losses and signs of wear occurring in a friction pairing depend in a complex manner on the material of the machine element itself, the properties of the lubricating oil, such as its viscosity and its interactions with the material, and on the pressure and speed conditions. Closed support films, such as occur in the hydrodynamic area of plain bearings or in the elastohydrodynamic area of rolling bearings, are favorable. High friction losses - and the signs of wear that correlate with them in general - occur particularly in plain bearings in the mixed friction area (cf. VDI reports 680, Das ⁇ l als Konstrutechnischsement, VDI-Verlag, Düsseldorf 1988).
• Lubrication with greases is widespread. These consist of a lubricating oil and a solid which is dispersed in fine form, the so-called thickener, which has only a minor influence on the tribological properties, and in primarily has the function of a reservoir for the lubricating oil.
• the known lubricants are in need of improvement because many friction pairings can only be operated with high friction losses.
• DE 33 32 955 gives compounds of the formula I as components for liquid-crystalline phases for electro-optical displays.
• DE 28 19 822 describes additions of less than 1% of tris and tetrakis [alkylthio] benzenes as antioxidants to conventional lubricants.
• the object of the invention was to find a new, stable lubricant by means of which friction pairings in gears and bearings can be operated with particularly low friction losses.
• the lubricant according to the invention may contain other compounds in addition to one or more compounds of the formula I. These can include antioxidants, such as derivatives of 2,6-di- tert -butylphenol, high-pressure additives, such as zinc dialkyl dithiophosphate, friction reducers, light stabilizers, emulsifiers or demulsifiers. However, organic compounds for varying the viscosity can also be used, such as compounds whose molecules contain benzene or naphthalene nuclei which are substituted several times by alkyl groups. If the lubricant according to the invention is a lubricating oil, these additives are present in the homogeneous liquid in a molecularly disperse form. The content of the molecularly dispersed additives in the compounds of the formula I in the lubricating oil according to the invention is at most 30%.
• This lubricating oil can be converted in a generally known manner (cf. Ullmanns Enzykl.) By adding thickeners which are not present in the form of a molecule into a lubricating grease which is also included in the present invention.
• Particularly suitable thickeners are lithium 12-hydroxystearate and powder made of polytetrafluoroethylene (eg microteflon powder 5 ⁇ , Dr. Tillwich GmbH, Horb).
• polymers serving for the formation of gels such as so-called side chain polymers (H. Ringsdorf et al., Angew. Chem.
• molybdenum disulfide is also described or graphite, one of the thickeners.
• An inventive grease can contain up to 35% of such thickeners.
• the distinction between molecularly disperse and non-molecularly disperse substances can be made by an ultracentrifugation (for example with the Beckman L8-M ultracentrifuge at a centrifugal acceleration between 7x10 5 and 6x10 5 m / s 2 at 25 ° C., 10 min) in a manner known per se.
• the compounds of the formula I comprise the preferred sub-formulas Ia to Id (Y independently of one another means -SR, -SO 2 R or -SOR, Z independently of one another means -H, -Cl, -F, -R, -OH, -SH, -OR, -COOR or -OOCR):
• sub-formulas Ia and Ib are particularly preferred.
• the alkyl radicals -R in the substituents Y in one and the same compound can be the same or different. It can be unbranched or branched residues. Unbranched alkyl radicals are preferred. Of these, radicals having 6 to 18 carbon atoms are preferred, in particular hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl and octadecyl.
• substituents Z in the partial formulas Ia to Id are preferred, with -H being particularly preferred.
• the alkyl radicals -R in the substituents Z are each independent of one another and preferably unbranched. They mean in particular methyl, ethyl, propyl, butyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl and octadecyl.
• the compounds of sub-formula Ic include 1,2,4,5-tetrakis [alkylthio] benzenes the 2,3,5,6-tetrakis [alkylthio] terephthalic acid alkyl esters and the 2,3,5,6-tetrakis [alkylthio] -1,2-dialkoxy-benzenes among which the terephthalic acid esters are preferred.
• the compounds of the formula I are prepared by methods known per se, as described in the literature (for example in standard works such as Houben-Weyl, Methods of Organic Chemistry, Georg-Thieme-Verlag, Stuttgart), and under reaction conditions which are suitable for the mentioned implementations are known and suitable.
• Compounds of the sub-formulas Ia and Ib are obtained by reacting hexachlorobenzene or pentachlorobenzene or hexafluorobenzene or pentafluorobenzene with a sodium alkylthiolate RSNa in an aprotic solvent, N, N-dimethylformamide, N-methyl-2-pyrrolidinone or preferably tetraethylene glycol dimethyl ether at 50 to 180 ° C.
• the thiolate is first prepared in one of the solvents mentioned from the mercaptan RSH with sodium hydride or sodium amide.
• mixtures of mercaptans can also be used, so that a mixture of compounds which are included in the sub-formulas is formed. It is assumed within the scope of the invention that the reactivity of the various thiolates towards the halogenobenzenes is the same, so that the compounds have a random substitution pattern for the various alkylthio groups. Mixtures of this type are distinguished by particularly low melting points, which results in a low pour point which is advantageous compared to known lubricants (definition see Ullmanns Enzykl.).
• the lubricant according to the invention is excellently suitable for the lubrication of gears and machine bearings. It has also surprisingly been found that lower friction losses can be achieved in internal combustion engines when using the lubricating oil according to the invention as an engine oil than when using conventional mineral and synthetic oils. This is particularly noticeable by the lower fuel consumption of motors used in racing with a rotation frequency of> 8000 rpm.
• percent means percent by mass.
• the solvent is largely distilled off in vacuo (oil rotary pump) at a bath temperature of 130 ° C.
• the residue is cooled and a total of 1 liter of 5% hydrochloric acid is added dropwise and then rapidly.
• the resulting emulsion is first extracted with 600 ml and then twice with 200 ml of diethyl ether.
• the combined organic phases are extracted three times with 75 ml of saturated NaCl solution and once with 100 ml of water and then dried with MgSO 4 .
• the oily crude product of 426 g is mixed with 500 ml of acetone.
• the isotropic melt can be subcooled to about -10 ° C (polarization microscopic observation in a heating table from Lincam).
• a lubricant A consisting of 99% of this compound and 1.0% of the high pressure additive Irgalube 349 (Ciba-Geigy Ltd.) was compared on various devices with conventional lubricants: a) In a two-disk test stand for measuring the coefficient of friction ⁇ under elastohydrodynamic conditions (TU Kunststoff, see K. Michaelis et al., Proc. 10th Intern. Coll. Tribology - Solving Friction and Wear Problems, Vol. 2, p .
• Example 2 In the manner shown in Example 1, 6.9 g of NaH (289 mmol) in 80 ml of tetraglyme, a solution of 11.0 g of hexyl mercaptan (96.3 mmol), 13.7 g of octyl mercaptan (96.3 mmol) and 16.3 g of decyl mercaptan (96.3 mmol) in 120 ml of tetraglyme and 12.4 g of hexachlorobenzene (43.6 mmol) produced a mixture of hexakis [alkylthio] benzenes.
• the crude product is not crystallized, but is purified by column chromatography (200 g of silica gel 60 (Merck), petroleum ether-toluene mixture). The solvent is first spun off and the residue is freed from volatile impurities at 200 ° C. and in an oil pump vacuum at 0.2 mbar.
• Example 1b The mixture is examined without the addition of additives in the test bench described in Example 1b. In the speed range from 0 to 1500 min -1, lower friction torques result than with the Tellus C 100 reference oil.
• Pentakis [octylthio] benzene (melting point 12 ° C.) was prepared in the same manner and with the same molar ratios, starting from pentachlorobenzene and octyl mercaptan.
• Example 1b In the test bench described in Example 1b, the compound showed lower coefficients of friction at 60 ° C. in the speed range from 0 to 1500 min ⁇ 1 than the comparative oil Tellus C 100 at the same temperature.

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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)
• Inorganic Chemistry (AREA)
• Lubricants (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 1996
  • 1996-03-25 DE DE19611466A patent/DE19611466A1/de not_active Withdrawn
• 1997
  • 1997-02-25 EP EP97102997A patent/EP0798366A3/fr not_active Withdrawn
  • 1997-03-14 US US08/818,602 patent/US5866522A/en not_active Expired - Lifetime

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