Classifications

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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
  • C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
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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
  • 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
  • C10M133/38—Heterocyclic nitrogen compounds
  • C10M133/40—Six-membered ring containing nitrogen and carbon only
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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
  • C10M169/06—Mixtures of thickeners and additives
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/102—Aliphatic fractions
  • C10M2203/1025—Aliphatic fractions used as base material
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/108—Residual fractions, e.g. bright stocks
  • C10M2203/1085—Residual fractions, e.g. bright stocks used as base material
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  • 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
  • C10M2207/10—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
  • C10M2207/126—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 monocarboxylic
• • 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
  • C10M2207/10—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
  • C10M2207/126—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 monocarboxylic
  • C10M2207/1265—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 monocarboxylic used as thickening agent
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  • 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
  • C10M2207/10—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
  • C10M2207/127—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 polycarboxylic
• • 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
  • C10M2207/10—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
  • C10M2207/127—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 polycarboxylic
  • C10M2207/1276—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 polycarboxylic used as thickening agent
• • 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
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
• • 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
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
  • C10M2207/1415—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic used as thickening agent
• • 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
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/16—Naphthenic acids
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • 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
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/221—Six-membered rings containing nitrogen and carbon only
• • 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
  • 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
  • C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
• • 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
  • 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
  • C10M2223/04—Phosphate esters
  • C10M2223/045—Metal containing thio derivatives
• • 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
• • 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
  • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
• • 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
  • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
• • 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
  • C10N2030/26—Waterproofing or water resistance
• • 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
  • C10N2030/70—Soluble oils
• • 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
  • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
  • C10N2050/10—Semi-solids; greasy

Definitions

• the present invention relates to a method for preparing a lubricating composition, in particular a grease .
• Alkyl -substituted quinolines and polymerized derivatives thereof are known as very effective, low cost antioxidants for several uses, including the use in lubricating compositions.
• WO 94/24235 discloses the use of alkyl -substituted 1 , 2-dihydroquinolines (including monomers, dinners, trimers and tetramers thereof) in motor oils, transmission oils, gear oils, metal working fluids, hydraulic fluids, greases and the like.
• alkyl -substituted 1, 2-dihydroquinolines are 2 , 2 , 4-trimethyl-l, 2-dihydroquinoline, 2-methyl-2 , 4 ⁇ diethyl-1, 2-dihydroquinoline, 2 , 2, 4 , 6-tetramethyl-l, 2 , - dihydroquinoline, 2,2,4, 7-tetramethyl-l, 2, - dihydroquinoline, 6,6' -bis (2,2, 4-trimethyl-l, 2 , - dihydroquinoline) and the like.
• US 5 246 606 discloses that dimeric, trirneric and tetrameric tetrahydroquinoline derivatives are suitable for stabilising organic materials against light-induced, thermal and/or oxidative degradation. US 5 246 606 suggests to use these compounds amongst others in functional fluids such as lubricants and hydraulic fluids.
• alkyl-substituted quinolines such as 2,2,4- trimethyl-1 , 2-dihydroquinoline (also referred to as "TMQ”, “TMDQ” and “TMHQ”) and oligomeric (i.e. dimeric, trimeric and tetrameric ⁇ derivatives thereof, are widely used as antioxidants, they have a number of disadvantages .
• TMQ is in the form of a brittle solid at room temperature and, being usually- in the form of a mixture of monomer and oligomers, it has no well-defined melting point. Although it softens as the temperature increases, it is still a very viscous and stringy material at typical additive addition temperatures of around 80 to 100 0 C.
• TMQ TMQ is added to lubricating compositions such as greases at this typical temperature range of from 80 to 100 0 C, it will not be suitably dispersed into the grease and will result in e.g. filter blockages in grease ⁇ delivery systems. Even if the filter loading of these grease delivery systems is not enough for the filter to block immediately, some of the antioxidant will have been taken out of the grease, which would then suffer from reduced life as a result.
• alkyl-substituted quinolines are usually added to greases at temperatures above 150 0 C, usually between 150-160 0 C after the grease has completed its critical cooling phase after establishing the thickener system in the base oil .
• an associated problem of the known method is that the window of opportunity for adding the alkyl- substituted quinolines is usually narrow, if they are to be dispersed' properly in the grease. If the alkyl- substituted quinolines are added e.g. ten minutes later, this may be too late as the grease may have been cooled too much.
• a further problem of the known method of adding the alkyl-substituted quinolines to the grease at relatively high temperatures is that more severe health and safety issues need to be taken into account, relating e.g. to the dangers of grease at high temperature and the danger of fumes when the manufacturing vessel has to be opened. It is an object of the present invention to avoid the above problems .
• a method for preparing a lubricating composition in particular a grease, the method at least comprising the steps of: a) providing a base oil composition optionally containing one or more additives; b) providing a solution of one or more alkyl- substituted quinolines or oligomeric derivatives thereof in a solvent; and c) adding the solution of step b) to the base oil composition of step a) at a temperature below 150 0 C.
• the alkyl- .substituted quinolines or oligomeric derivatives thereof
• they can be added at a lower temperature, whilst still obtaining a proper dispersing thereof in the base oil composition.
• an important advantage of the present invention is that the alkyl-substituted quinolines (or oligomeric derivatives thereof) can be added at a lower temperature, resulting in less severe safety requirements. Also, there is more flexibility in the moment of adding the alkyl ⁇ substituted quinolines (or oligomeric derivatives thereof) , as the specific temperature for adding thereof is less critical than in the case where no solvent is used.
• the solution of step b) is added at a temperature below 120 0 C, preferably in the range of from 10 to HO 0 C, more preferably from 15 to 100 0 C.
• the one or more alkyl-substituted quinolines are alkyl-substituted 1, 2-dihydroquinolines (or oligomeric derivatives thereof) .
• the one or more alkyl -substituted 1, 2-dihydroquinolines have the general formula (I)
• R 1 -?. 8 are independently selected from hydrogen or an alkyl group having 1-8 carbon atoms; and n is 0, 1, 2 or 3.
• R 3 ⁇ -R 8 are independently selected from hydrogen or an alkyl group having 1-4 carbon atoms, preferably having 1-2 carbon atoms.
• R 4 is H. It is even more preferred that R 4 -R 8 are all H. Also it is preferred that R 1- -R 3 are all a methyl group.
• one or more alkyl substituted 1,2- dihydroquinolines preferably have an average value for n of from 1.0 to 2.0, preferably from 1.3 to 1.6.
• the one or more alkyl substituted quinolines provided in the solution have a solubility of below 0.1% as determined using ASTM D893.
• alkyl substituted quinoline compounds (or oligomeric derivatives thereof) as used in the present invention are either commercially available or can be prepared by various reactions that are known in the art . Examples of preparation methods have been given in the above-mentioned WO 94/24235 and US 5 246 606 and references cited therein, the teaching of which is hereby incorporated by reference. Other examples are given in US 4 692 258 and US 3 910 918 and references cited therein, the teaching of which is hereby incorporated by reference as well.
• the solvent comprises a polyglycol, more preferably a polyalkylene glycol.
• Polyglycols are well known in the art and are not further discussed here in detail.
• the polyalkylene glycols may exhibit alkylene oxide units with 1 to 6 carbon atoms (-
• the polyalkylene glycols may exhibit hydrogen end groups, alkyl, aryl, alkylaryl, aryloxy, alkoxy, alkylaryloxy and/or hydroxy end groups.
• Alkylaryloxy groups should also be understood to mean arylalkyl (ene)oxy groups and alkylaryl groups to mean arylalkyl (ene) groups (e.g. aryl CH 2 CH 2 -).
• the end groups of the alkyl type, including the alkoxy type, or of the aryl types, including the alkylaryl type, aryloxy type and alkylaryloxy type preferably exhibit 6 to 24 carbon atoms, particularly preferably 6 to 18 carbon atoms, based on the aryl types, and preferably 1 to 12 carbon atoms, based on the alkyl types.
• polyalkylene glycols according to the invention may be either homopolymers, namely polypropylene glycol - S -
• the monomer units may exhibit a random distribution or a block structure.
• the polyalkylene glycols are not homopolymers , preferably at least 20%, preferably at least 40% of all monomer units are producible from polypropylene oxide (PO) , and also preferably, at least 20% of all monomer units of these polyalkylene glycols are producible by using ethylene oxide (EO) (PO/EO copolymers ⁇ .
• PO polypropylene oxide
• EO ethylene oxide
• preferably at- least 20%, preferably at least 40% of all monomer units are obtainable from butylene oxide (BO) and, moreover, preferably at least 20% of all monomer units of these polyalkylene glycols are obtainable by using ethylene oxide (BO/EO copolymers) .
• BO butylene oxide
• preferably at least 20% of all monomer units of these polyalkylene glycols are obtainable by using ethylene oxide (BO/EO copolymers) .
• (poly) alcohols the starting compound is incorporated into the polymer and, according to the meaning of the invention, also referred to as end group of the polymer chain.
• Suitable starting groups consist of compounds comprising active hydrogen such as e.g.
• n ⁇ butanol propylene glycol, ethylene glycol, neopentyl glycols such as pentaerythritol , ethylene diamine, phenol, cresol or other (Cl to C16 (mono, di or tri) alkyl) aromatics, (hydroxyalkyl) aromatics, hydroquinone , aminoethanolamines, triethylenetetramines, polyamines, sorbitol or other sugars.
• C-H acidic compounds such as carboxylic acids or carboxylic anhydrides can also be used as starting compounds.
• the polyalkylene glycols comprise aryl groups or corresponding heteroaromatic groups, e.g. inserted into the polymer chain, as side groups or end groups; the groups may, if necessary, be substituted with linear or branched alkyl groups or alkylene groups, the alkyl groups or alkylene groups overall exhibiting preferably 1 to 18 carbon atoms.
• Cyclic ether alcohols such as hydroxyfurfuryl or hydroxytetrahydrofuran, nitrogen heterocyclics or sulphur heterocyclics can also be used as starting groups.
• Such polyalkylene glycols are disclosed in WO 01/57164, the teaching of which is herewith incorporated by reference.
• the polyalkylene glycols according to ⁇ the invention have an average molecular weight (number average) of 200 to 3000 g/raole, more preferably 400 to 2000 g/mole.
• the kinematic viscosity of the polyalkylene glycols is preferably 10 to 400 mm 2 /s (cSt) measured at 4O 0 C according to DIN 51562.
• the polyalkylene glycols used according to the invention can be produced by reacting alcohols, including polyalcohols, as starting compounds with oxiranes such as ethylene oxide, propylene oxide and/or butylene oxide. Following the reaction, these possess only one free hydroxy group as end group. Polyalkylene glycols with only one hydroxy group are preferred over those with two free hydroxy groups. Polyalkylene glycols which, e.g. after a further etherification step, comprise no free hydroxy groups any longer are particularly preferred regarding the stability, hygroscopicity and compatibility. The alkylation of terminal hydroxyl groups leads to an increase in the thermal stability.
• the PAG base oil comprises end-capped PAG, i.e. where no free hydroxyl groups are present.
• neopentyl polyolesters instead of the polyalkylene glycols described above.
• the esters of neopentyl polyols such as neopentyl glycol, pentaerythritol and trimethylol propane with linear or branched C4 to C 1 2 mono ⁇ arboxylic acids, e.g. with addition of corresponding dicarboxylic acids are suitable neopentyl polyolesters.
• pentaerythritol is obtainable as technical grade pentaerythritol which is a mixture of monopentaerythritol, dipentaerythritol and tripentaerythritol .
• dipentaerythritol and/or tripentaerythritol are also suitable as alcohol components.
• Pentaerythritol or mixtures with dipentaerythritol and/or tripentaerythritol, preferably mixtures comprising predominantly dipentaerythritol are particularly suitable.
• Complex esters can be produced by proportional esterification of polyhydric alcohols with monovalent and divalent acids such as C 4 to Ci 2 dicarboxylic acids. In this way, dimers and oligomers are formed. When using neopentyl glycol and/or trimethylol propane as alcohol group, complex esters are preferred.
• base oil composition used in the method according to the present invention, and various conventional mineral oils and synthetic oils may be conveniently used.
• base oil is meant to also include a grease base stock.
• the base oil composition used in the present invention may conveniently comprise mixtures of one or more mineral oils and/or one or more synthetic oils.
• Mineral oils include liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oil of the paraffinic, naphthenic, or mixed paraffinic/naphthenic type which may be further refined by hydrofinishing processes and/or dewaxing.
• Suitable base oils for use in the lubricating oil composition of the present invention are Group I, Group II or Group III base oils, polyalphaolefins, Fischer- Tropsch derived base oils and mixtures thereof.
• Group I base oil By “Group I” base oil, “Group II” base oil and “Group III” base oil in the present invention are meant lubricating oil base oils according to the definitions of American Petroleum Institute (API) categories I, II and III. Such API categories are defined in API Publication 1509, 15th Edition, Appendix E, April 2002.
• API American Petroleum Institute
• Suitable Fischer-Tropsch derived base oils that may be conveniently used as the base oil in the lubricating oil composition of the present invention are those as for example disclosed in EP 0 776 959, EP 0 668 342, WO 97/21788, WO 00/15736, WO 00/14188, WO 00/14187, WO 00/14183, WO 00/14179, WO 00/08115, WO 99/41332, EP 1 029 029, WO 01/18156 and WO 01/57165.
• Synthetic oils include hydrocarbon oils such as olefin oligomers (PAOs) , dibasic acid esters, polyol esters, and dewaxed waxy raffinate. Synthetic hydrocarbon base oils sold by the Shell Group under the designation "XHVI” (trade mark) may be conveniently used.
• PAOs olefin oligomers
• XHVI XHVI
• the total amount of base oil incorporated in the lubricating composition of the present invention is preferably present in an amount in the range of from 60 to 92 wt. %, more preferably in an amount in the range of from 75 to 90 wt . % and most preferably in an amount in the range of from 75 to 88 wt.%, with respect to the total weight of the lubricating composition.
• the final lubricating composition may further comprise one or more additives such as anti- oxidants, anti-wear agents, dispersants, detergents, friction modifiers, viscosity index improvers, pour point depressants, tackifying agents, corrosion inhibitors, demulsifiers, defoaming agents and seal fix or seal compatibility agents, etc.
• additives such as anti- oxidants, anti-wear agents, dispersants, detergents, friction modifiers, viscosity index improvers, pour point depressants, tackifying agents, corrosion inhibitors, demulsifiers, defoaming agents and seal fix or seal compatibility agents, etc.
• the additives may be added to the base oil composition before or after the one or more alkyl- substituted quinolines are added in step c) . Also, if appropriate, the additives may also be added at the same time with the one or more alkyl-substituted quinolines.
• Said additives are typically present in an amount in the range of from 0.01 to 12.5 wt.%, based on the total weight of the lubricating composition, preferably in an amount in the range of from 0.05 to 10.0 wt.%, more preferably from 1.0 to 9.0 wt . % and most preferably in the range of from 2.0 to 5.0 wt.%, based on the total weight of the lubricating composition.
• the base oil as contained in the lubricating composition may contain or be compounded with one or more thickeners such as metallic soaps, organic substances or inorganic substances, for example, lithium soaps, lithium complex soaps, sodium terephthalate, urea/urethane compounds and clays .
• thickeners such as metallic soaps, organic substances or inorganic substances, for example, lithium soaps, lithium complex soaps, sodium terephthalate, urea/urethane compounds and clays .
• the lubricating composition has a kinematic viscosity in the range of from 2 to 80 mm 2 /s at 100 0 C, more preferably in the range of from 3 to
• the lubricating compositions of the present invention may be conveniently prepared by admixing the one or more base oils and, optionally, one or more additives that are usually present in lubricating compositions, for example as herein before described, with mineral and/or synthetic base oil.
• the one or more alkyl- substituted quinoline compounds (or oligomeric derivatives thereof) have a sufficiently small particle size (e.g. below 50 ⁇ m, preferably below 20 ⁇ m) to allow easy dispersion thereof in the lubricating composition.
• the present invention provides a lubricating composition, in particular a grease, obtained by the method according to the present invention.
• the present invention is described below with reference to the following Examples, which are not intended to limit the scope of the present invention in any way. Examples
• a 500 ml 50 % na/m solution of oligomeric 2,2,4- trimethyl-1, 2-dihydroquinoline (solid; available from Rhein Ghemie Rheinau GmbH under the trade designation "Additin RC7010”) in polyalkylene glycol (available from The Dow Chemical Company, USA under the trade designation "Oxilube 504") was prepared by heating the polyalkylene glycol to 100 0 C before adding the oligomeric 2,2,4- trimethyl-1, 2-dihydroquinoline.
• the oligomeric 2,2,4- trimethyl-1 , 2-dihydroquinoline was added slowly over about two minutes, allowing it to disperse throughout the fluid before adding more. The mixture thus obtained was stirred for a further 30 minutes at 100 0 C. A stable, homogeneous solution was formed.
• Solution B Similar to Solution A, a 500 ml 50 % m/m solution of oligomeric 2 , 2 , 4 -trimethyl-1 , 2 ⁇ dihydroquinoline in polyglycol (available from The Dow Chemical Company, USA under the trade designation "Synalox 50-50B") was prepared. A stable, homogeneous solution was formed.
• Synynalox 50-50B polyglycol
• a grease was prepared using the above mentioned Solution A (50 ml) and a conventional grease base stock (4950 g) .
• the conventional grease base stock contained about 10% m/m lithium complex thickener and about 90% m/m paraffinic mineral base oil blended from SN 500 and bright stock (viscosity at 40 0 C of 180 ⁇ nm 2 /s according to ASTM D445) .
• the conventional grease base stock also contained an antiwear additive (a zinc dialkyl dithiophosphate) , an extreme pressure additive (a sulphurised ester) and a rust inhibitor (a zinc naphthenate) .
• the grease base stock and Solution A were simply mixed during 30 minutes using a laboratory paddle mixer, after both had been previously heated to 80 0 C before mixing.
• a grease was prepared using the same amount of oligomeric 2 , 2 ,4-trimethyl- 1, 2-dihydroquinoline ⁇ without the solvent) and the same grease base stock of Examples 1 and 2.
• the grease base stock was heated to about 16O 0 C. Then, a part of the solid oligomeric 2 , 2, 4-trimethyl-l, 2- dihydroquinoline was added to the heated grease base stock and left at this temperature for about 10 minutes. Mixing took place using a laboratory paddle mixer until the mixture had reached the temperature of about 6O 0 C.
• the present invention allows adding the alkyl-substituted quinolines or oligomeric derivatives thereof at a significant lower temperature, whilst still obtaining a stable grease having desired properties. It goes without saying that this is highly desired from a health and safety perspective as well as from a practical manufacturing perspective .

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• Chemical & Material Sciences (AREA)
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• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Organic Chemistry (AREA)
• Lubricants (AREA)

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• 2009
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