Classifications

• • 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
  • 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
  • C10M129/24—Aldehydes; Ketones
• • 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
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
  • C10M105/20—Aldehydes; Ketones
• • 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
  • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
  • C10M159/12—Reaction products
  • C10M159/18—Complexes with metals
• • 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
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/08—Aldehydes; Ketones
  • C10M2207/085—Aldehydes; Ketones used as base material
• • 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
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/09—Metal enolates, i.e. keto-enol metal complexes
• • 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
  • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
  • C10M2227/09—Complexes with metals
• • 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
  • C10N2020/079—Liquid crystals
• • 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
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure

Definitions

• This invention relates to lubricants containing mesogenic compounds.
• Lubricants which contain mesogenic compounds have long been known (EP 0 330 068). It is assumed that a mesophase, that is to say a nematic, smectic or discotic liquid-crystalline phase, can be induced therein by increasing the pressure or by a lubricating action in machine bearings.
• a mesophase that is to say a nematic, smectic or discotic liquid-crystalline phase
• Such phases which are formed by compounds with elongated bar-shaped or discoid molecules are generally known (H Kelker, R Hatz, Handbook of Liquid Crystals, Verlag Chemie, Weinheim 1980). Such phase transitions make it possible to avoid in particular in the lubrication gap of plain bearings contacts between the solid bodies which are moving relative to each other. In comparison with conventional lubricants it is possible therewith to achieve an enormous reduction in frictional losses.
• the invention concerns a lubricant containing between 20 and 99.9% by mass of one or more compounds of the general formula 1
• X denotes H, F, Cl, —CH 3 , —C 2 H 5 , —OCH 3
• R 1 respectively denote independently of each other H, an alkyl residue having a total of between 1 and 18 C-atoms, in which also one or two non-adjacent CH 2 groups can be replaced by —O—, —S— or —CO— and two adjacent CH 2 groups can be replaced by —COO— or —OOC—,
• R 2 respectively denote independently of each other an alkyl residue having a total of between 1 and 18 C-atoms, in which also one or two non-adjacent CH 2 groups can be replaced by —O—, —S— and two non-adjacent CH 2 groups can be replaced by —COO— or —OOC—, or the residue
• the object of the present invention was to find the lubricant which can be economically produced from inexpensive starting materials and which nonetheless permits particularly low coefficients of friction in comparison with conventional lubricants, in particular in plain bearings.
• the compounds of formula 1 above have admittedly been recorded by a Markus formula of an earlier invention (DE 38 10 626) but because of the low ratio of length and diameter of their molecules no liquid-crystalline properties can be assumed by the man skilled in the art, and also a liquid-crystalline phase was never observed in such compounds.
• the compounds of the general formula 1 can advantageously be produced by a single synthesis step from inexpensive compounds.
• an acetophenone which is dissolved in a carboxylic acid ester can be condensed under the effect of sodium (see DE 29 18 775, synthesis diagram 1).
• R 1 in general formula 1 preferably denotes an alkyl or an alkoxy group with between 1 and 7 C-atoms. They are preferably unbranched.
• R 2 in general formula 1 preferably denotes an alkyl or alkoxy group with between 1 and 12 C-atoms, wherein the chains are preferably unbranched.
• X in general formula 1 preferably denotes H or —CH 3 , of which H is particularly preferred.
• the compounds of general formula 1 include the following preferred sub-formulae 1a, 1b and 1c, wherein in the formulae 1b and 1c the significances of X and R 1 are respectively independent of each other.
• the lubricant according to the invention can contain up to 80% of one or more additives.
• additives can be known lubricating oils such as mineral oils produced from crude oil or synthetic oils (see Ullmann's Encyclopaedia of Industrial Chemistry, 5th Edition, Vol A15, page 423 ff) and the additives known in tribology such as anti-wear substances, anti-oxidants or anti-seizure substances.
• additives which as is known involve a grease-like consistency such as metal soaps or polymers also apply as additives.
• the latter can act as gel-forming agents or can be present in the form of finely distributed particles such as for example PTFE (polytetrafluoroethylene).
• PTFE polytetrafluoroethylene
• the lubricants according to the invention also include lubricating greases.
• keto compounds of the general formula 1 are referred to in a simplifying fashion as 1,3-diketones and thus also in Example 1 hereinafter.
• metal compounds metal complexes
• Those compounds are embraced by the present invention.
• Their general formula can be reproduced as follows:
• M m is a m-valent metal atom and m is a number between 1 and 4.
• Preferred metal compounds are those of lithium, magnesium, titanium, zirconium, chromium, molybdenum, manganese, iron, nickel, copper, zinc and tin, of which those of lithium, magnesium and zinc are particularly preferred.
• Those compounds are preferably produced by the acetate, the acetyl acetonate complex or an alcoholate of the metal in question being heated with one or more compounds of formula 1 and by the acetic acid which is liberated in that respect or the acetyl acetone or the alcohol being evaporated.
• Those metal compounds produced from compounds of the general formula 1 can be present in a dissolved form but also in the form of a solid body if the lubricant according to the invention is a lubricating grease.
• metal compounds with different ligands there can be metal compounds with different ligands.
• a proportion of those metal compounds deemed to be within the present invention is that which is obtained when the compounds of formula 1 and possibly also volatile additives are removed from the lubricant by distillation at 180° C. sump temperature under an adequate reduced pressure.
• the residue comprises the metal compounds according to the invention which are most stable at the sump temperature, and possibly further non-volatile additives.
• the distinction which is possibly necessary between the metal compounds from the compounds of formula 1 and further non-volatile additives is effected in accordance with generally known analytical methods.
• a distinction which is possibly necessary between compounds of formula 1 and other volatile additives is also effected in the distillate.
• the compounds of general formula 1 can be mixed with other components which are usual in the lubrication art, by simple stirring at ambient temperature.
• the lubricant according to the invention contains between 20 and 99.9, preferably between 50 and 99.9 and quite preferably between 70 and 99.9% of compounds of general formula 1 and/or metal compounds produced from those compounds.
• the lubricant according to the invention can advantageously be used in the generally known machine bearings which as is known are divided into plain bearings or rolling bearings. Particular advantages are achieved in the lubrication of plain bearings, more specifically those in machines in the textile industry, for example in regard to the needle guides of sewing machines, but also for lubricating pistons of high-speed internal combustion engines.
• the compound produced in accordance with synthesis diagram 1, 1-(4-ethylphenyl)-3-hexyl-1,3-propandion, has a melting point of ⁇ 1° C. and above that temperature is an isotropic fluid with a kinematic viscosity of 11.7 mm/s 2 at 23° C. 0.2% of the anti-oxidant 2,6-di-tert.-butyl-p-kresol was dissolved therein.
• a lubricant (lubricating grease) produced from:
• 30% PTFE powder, 5 ⁇ m (Dr Tillwich GmbH, Horb) presents particularly low coefficients of friction in plain bearings.
• a lubricant comprising
• a lubricant comprising
• the lubricant freed of ethanol (a lubricating grease) is of the composition

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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)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Lubricants (AREA)

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Cited By (4)

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Citations (2)

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• 2007
  • 2007-11-21 DE DE102007055554.9A patent/DE102007055554B4/de active Active
• 2008
  • 2008-11-14 US US12/743,885 patent/US20110086784A1/en not_active Abandoned
  • 2008-11-14 WO PCT/EP2008/065608 patent/WO2009065785A2/de active Application Filing

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