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
  • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
  • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
  • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
  • C10M107/34—Polyoxyalkylenes
• • 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
  • 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
  • C10M145/38—Polyoxyalkylenes esterified

Definitions

• the present invention relates to a lubricant composition comprising an amount of at least one ester as described in the preamble of the first claim.
• esters of fatty acids as performance lubricants in automotive and industrial applications, both as basic oil or additive to a lubricant composition or a hydraulic oil composition is well known in the art.
• a lubricant should be made exclusively of fatty acid esters.
• the better intrinsic lubricity thereof is attributed to the polar character of the fatty acid ester.
• the swelling of polymer material may be minimized, provided the lubricant composition comprises an ester of:
• the ester according to the invention can comprise different organic carboxylic acids and different alcohols.
• the inventors are of the opinion that the reduced swelling properties of the ester of the present invention can be explained by the fact that when a mono- or polyfunctional alcohol comprising a first alcohol of which at least one OH group is coupled to an an epoxide is used for the ester, an additional branching is added to the ester, thereby increasing the steric hindrance.
• a mono- or polyfunctional alcohol comprising a first alcohol of which at least one OH group is coupled to an an epoxide
• an additional branching is added to the ester, thereby increasing the steric hindrance.
• 'epoxide' a three-membered cyclic ether is meant, having a general formula
• R1 and R2 being indepently from each other H, a hydrocarbon chain being aliphatic or aromatic, saturated or unsaturated, branched, linear, or cyclic, including polycyclic, and containing one or more functional groups.
• esters of the present invention show improved lubricating properties, which are believed to be related to the higher polarity of the esters of this invention when compared to the known materials.
• the organic carboxylic acid may contain one or more carboxylic acid groups.
• the extent of esterification of the carboxylic acid groups is as high as possible to have an acid number that is as low as possible and to minimise the risk to corrosion of the equipment.
• the organic carboxylic acid used in the ester of the present invention comprises at least one COOH group and a hydrocarbon chain having 1-54 carbon atoms, the hydrocarbon chain being aliphatic or aromatic, saturated or unsaturated, branched, linear, or cyclic, including polycyclic, and containing one or more functional groups.
• the organic carboxylic acid is selected from the group of acids comprising 2-24 carbon atoms, more preferably 8-12 carbon atoms, including the so-called short chain fatty acids.
• Short chain fatty acids like octanoic and decanoic acid are preferred, because they are liquid and saturated at room temperature and allow obtaining lubricants with improved cold stability and improved oxidation resistance.
• esters of these short chain carboxylic acids would be suspected to involve polymer swelling because of their polar character, this swelling has been observed to be of minimal extent with esters made from the above described alcohol. Accordingly, this will allow using the short chain fatty acids as the carboxylic acid component of the ester.
• organic carboxylic acids suitable for use with the present invention include synthetic mono-, di- or polycarboxylic acids and dimers or polymers of the above described organic carboxylic acids.
• the first alcohol used in the ester of the present invention contains at least one OH group and a hydrocarbon chain having 1-54 carbon atoms, the hydrocarbon chain being aliphatic or aromatic, saturated or unsaturated, branched, linear, or cyclic, including polycyclic, and containing one or more functional groups.
• the alcohol contains 2-15 OH groups. More preferably, the alcohol corresponds to the following formula: with R1 and R2 being independently of each other a C1-C4 linear or branched alkyl or alkylol, and R3 and R4 being independently of each other a C1-C4 linear or branched chain alkylol.
• the first alcohol is selected from the group comprising trimethylolpropane, pentaerytritol and neopentylglycol. Whereas an ester of such a polyol with an organic carboxylic acid would be suspected to cause polymer swelling because of its polar character, the swelling appears to be minimal when at least one OH group of the first alcohol is coupled to an epoxide.
• suitable first alcohols for the present invention include condensation products of two or more of the above described alcohol monomers.
• the epoxide to which at least one OH group of the first alcohol is coupled is preferably an epoxide having 2-20 carbon atoms.
• the epoxide may be a mono- or polyepoxide, the hydrocarbon chain of the epoxide being aliphatic or aromatic, saturated or unsaturated, and being a branched, linear, or cyclic, including polycyclic, structure and containing one or more functional groups.
• the epoxide is selected from the group comprising propyleneoxide, butyleneoxide, dodecene oxide, styrene oxide, isoamylene oxide.
• the linear monoepoxide namely a reduced tendency to involve polymer swelling has been observed.
• the extent to which the OH group(s) of the first alcohol are coupled to epoxides will be adapted by the man skilled in the art depending on the properties of the lubricant composition aimed at.
• the lower limit of the extent to which the OH group(s) of the first alcohol are coupled to epoxides is determined by the viscosity of the resulting ester which increases with increasing degree of epoxidation.
• the upper limit of the extent to which the OH group(s) of the first alcohol are coupled to epoxides is determined by the emulsion-forming tendency of the ester.
• esters suitable for use in the lubricant composition of this invention are tri octanoate/decanoate esters of propoxylated trimethylolpropane, tri octanoate/decanoate ester of butoxylated trimethylolpropane, tetra octanoate/decanoate ester of propoxylated pentaerytritol, tetra octanoate/decanoate ester of butoxylated pentaerytritol, di octanoate/decanoate ester of propoxylated neopentylglycol, di octanoate/decanoate ester of butoxylated neopentylglycol.
• the lubricant composition may also comprise a mixture of two or more different esters according to the present invention so as to allow adjusting the viscosity and polarity of the lubricant composition.
• the lubricant composition of the present invention preferably comprises the above described ester in an amount which can vary depending on the application and the properties of the ester. Because of the reduced tendency to involve polymer swelling, an increased amount of ester may be incorporated in the lubricant composition, thus allowing to obtain a lubricant composition with enhanced performance. Consequently, a lubricant composition may contain 100% of the above described ester. On the other hand, the above described ester can also be present as an additive in a very low amount in the lubricant composition.
• Comparative Examples I-III and Examples 1-9 describe experiments in which different esters were tested for the swelling they cause when they are contacted with different polymers.
• esters not according to the invention were tested, whereas in the examples esters according to the invention were tested.
• the percent of swelling of the different polymers has been determined according to method ISO6072.
• Comparative Example II the experiment of Comparative Example II was repeated, however, with the tetra octanoate/decanoate ester of pentaerytritol (Penta).
• Example 1 the tri octanoate/decanoate ester of ethoxylated trimethylolpropane (20EO TMP) having 20 moles ethyleneoxide per mole trimethylolpropane, was contacted with acrylonitrile butadiene rubber rubber and the % swelling of acrylonitrile butadiene rubber was measured according to method ISO6072.
• Example 2 the tri octanoate/decanoate ester of propoxylated trimethylolpropane (3PO TMP) having 3 moles propyleneoxide per mole trimethylolpropane, was contacted with either acrylonitrile butadiene rubber, ethylene-propylene rubber or with fluorcarbon rubber and the % swelling of the respective materials was measured according to method ISO6072.
• 3PO TMP propoxylated trimethylolpropane
• Example 3 was conducted similar to Example 2, however using the tri octanoate/decanoate ester of propoxylated trimethylolpropane (4PO TMP) having 4 moles propyleneoxide per mole trimethylolpropane.
• 4PO TMP propoxylated trimethylolpropane
• Example 4 was carried out similar to Example 1, however with the tri octanoate/decanoate ester of propoxylated trimethylolpropane (5PO TMP), having 5 moles propyleneoxide per mole trimethylolpropane.
• 5PO TMP propoxylated trimethylolpropane
• Example 5 was carried out similar to Example 2, using the tri octanoate/decanoate ester of propoxylated trimethylolpropane (7PO TMP), having 7 moles propyleneoxide per mole trimethylolpropane.
• 7PO TMP propoxylated trimethylolpropane
• Example 6 was carried out similar to Example 1, using the tetra octanoate/decanoate ester of propoxylated pentaerytritol (5PO Penta), having 5 moles propyleneoxide per mole Penta.
• 5PO Penta propoxylated pentaerytritol
• Example 7 use was made of the tetra octanoate/decanoate ester of propoxylated pentaerytritol (8.5PO Penta), having 8.5 moles propyleneoxide per mole Penta.
• Lubricating ester of % swelling of acrylonitrile butadiene rubber % swelling of ethylene-propylene rubber % swelling of fluorcarbon rubber 1 20EO TMP 19.4 - - 2 3PO TMP 19 22.5 0.31 3 4PO TMP 18.4 - - 4 5PO TMP 15.5 - - 5 7PO TMP 9.8 10.6 0.007 6 5PO Penta 15.06 - - 7 8.5PO Penta 11.11 - - -
• Table 2 shows that the swelling caused by tri octanoate/decanoate ester of ethoxylated trimethylolpropane having 20 moles ethyleneoxide per mole trimethylolpropane (20EO TMP) of Example 1 is inferior to the swelling caused by the non-ethoxylated tri octanoate/decanoate ester of trimethylolpropane (TMP) of comparative example I. This is attributed to a dilution effect of the polar ester groups in Example 1.
• Table 2 further shows that the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 3 moles propyleneoxide per mole trimethylolpropane (3PO TMP) of Example 2 causes a reduced swelling of acrylonitrile butadiene rubber, ethylene-propylene rubber and fluorcarbon rubber as compared to the non-ethoxylated tri octanoate/decanoate ester of trimethylolpropane (TMP) of comparative example I.
• TMP trimethylolpropane
• Table 2 further shows that that the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 4 moles propyleneoxide per mole trimethylolpropane (4PO TMP) of Example 3 causes a reduced swelling of acrylonitrile butadiene rubber as compared to the non-ethoxylated tri octanoate/decanoate ester of trimethylolpropane (TMP) of comparative example I or as compared to the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 3 moles propyleneoxide per mole trimethylolpropane (3PO TMP) of Example 2.
• TMP trimethylolpropane
• the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 5 moles propyleneoxide per mole trimethylolpropane (5PO TMP) of Example 4 causes a reduced swelling of acrylonitrile butadiene rubber as compared to the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 4 moles propyleneoxide per mole trimethylolpropane (4PO TMP) of Example 3, and consequently also as compared to the esters with a lower degree of propoxylation of examples 2 and 3 and as compared to the ester without propoxylation of Comparative Example I.
• the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 7 moles propyleneoxide per mole trimethylolpropane (7PO TMP) of Example 5 causes a reduced swelling of acrylonitrile butadiene rubber as compared to the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 5 moles propyleneoxide per mole trimethylolpropane (5PO TMP) of Example 4, and consequently also as compared to the esters with a lower degree of propoxylation of examples 2 and 3 and as compared to the ester without propoxylation of Comparative Example I.
• the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 7 moles propyleneoxide per mole trimethylolpropane (7PO TMP) of Example 5 causes a reduced swelling of ethylene-propylene rubber and of fluorcarbon rubber as compared to the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 3 moles ethyleneoxide per mole trimethylolpropane (3PO TMP) of Example 2, and as compared to the ester without propoxylation of Comparative Example I.
• Table 2 further shows that the tetra octanoate/decanoate ester of propoxylated pentaerytritol having 5 moles propyleneoxide per mole pentaerytritol (5PO Penta) of Example 6 causes a reduced swelling of acrylonitrile butadiene rubber as compared to the non-ethoxylated tetra octanoate/decanoate ester of pentaerytritol (Penta) of comparative example II.
• the tetra octanoate/decanoate ester of propoxylated pentaerytritol having 8.5 moles propyleneoxide per mole pentaerytritol (8.5PO Penta) of Example 7 causes a reduced swelling of acrylonitrile butadiene rubber as compared to the tetra octanoate/decanoate ester of propoxylated pentaerytritol having 5 moles propyleneoxide per mole pentaerytritol (5PO Penta) of Example 6, and consequently also as compared to the non-ethoxylated tetra octanoate/decanoate ester of pentaerytritol (Penta) of comparative example II.
• Comparative Example III the tri octanoate/decanoate ester of glycerol was contacted with acrylonitrile butadiene rubber and the % swelling of acrylonitrile butadiene rubber was measured according to method ISO6072.
• Example 8 was carried out similar to Comparative Example III, using the tri octanoate/ decanoate ester of propoxylated glycerol having 8 moles propyleneoxide per mole glycerol (8PO).
• Example 9 was carried out similar to Comparative Example III, using the tri octanoate/ decanoate ester of ethoxylated glycerol having 9 moles ethyleneoxide per mole glycerol (9EO).
• Table 3 shows that the tri octanoate/decanoate ester of propoxylated glycerol having 8 moles propyleneoxide per mole glycerol (8PO) of Example 8 causes a reduced swelling of acrylonitrile butadiene rubber as compared to the non-propoxylated tri octanoate/decanoate ester of glycerol of Comparative Example III.
• This can be explained by the fact that the propoxylation of glycerol adds an additional branching in the resulting ester, thereby increasing the steric hindrance of the ester. This steric hindrance prevents close interaction of the polar ester groups with the polymers, thereby avoiding the swelling of the polymers.
• table 3 shows that the tri octanoate/decanoate ester of ethoxylated glycerol having 9 moles ethyleneoxide per mole glycerol (9EO) of Example 9 causes a reduced swelling of acrylonitrile butadiene rubber as compared to the non-ethoxylated tri octanoate/decanoate ester of glycerol of Comparative Example III. This can be attributed to a dilution effect of the polar ester groups in Example 9.
• Examples 10-14 describe experiments in which esters according to the invention were tested for various parameters such as viscosity at 40°C and the extent to which they form an emulsion.
• Example 10 the viscosity at 40°C and the tendency for the formation of an emulsion of the tri octanoate/decanoate ester of ethoxylated trimethylolpropane (20EO TMP) having 20 moles ethyleneoxide per mole trimethylolpropane was tested.
• Example 11 was carried out similar to Example 10 using the tri octanoate/decanoate ester of propoxylated trimethylolpropane (3PO TMP) having 3 moles propyleneoxide per mole trimethylolpropane.
• 3PO TMP propoxylated trimethylolpropane
• Example 12 the viscosity at 40°C of the tri octanoate/decanoate ester of propoxylated trimethylolpropane (4PO TMP) having 4 moles propyleneoxide per mole trimethylolpropane was tested.
• Example 13 was carried out similar to Example 12 using the tri octanoate/decanoate ester of propoxylated trimethylolpropane (5PO TMP), having 5 moles propyleneoxide per mole trimethylolpropane.
• 5PO TMP propoxylated trimethylolpropane
• Example 14 was carried out similar to Example 10 using the tri octanoate/decanoate ester of propoxylated trimethylolpropane (7PO TMP), having 7 moles propyleneoxide per mole trimethylolpropane.
• 7PO TMP propoxylated trimethylolpropane
• the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 7 moles propyleneoxide per mole trimethylolpropane (7PO TMP) of Example 14 show a low tendency to form an emulsion.
• the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 7 moles propyleneoxide per mole trimethylolpropane (7PO TMP) of Example 14 has a higher viscosity as compared to the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 5 moles propyleneoxide per mole trimethylolpropane (5PO TMP) of Example 13, the latter having a higher viscosity than the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 4 moles propyleneoxide per mole trimethylolpropane (4PO TMP) of Example 12, in its turn having a higher viscosity than the tri octanoate/decanoate ester of propoxylated trimethylolpropane having 3 moles propyleneoxide per mole trimethylolpropane (3PO TMP) of Example
• viscosity increases as the degree of propoxylation increases.
• Lubricating ester of Viscosity (cSt) Emulsion test oil/water/emulsion
• Example 10 20EO TMP 71.4 24/0/56
• Example 11 3PO TMP 28.9 39/38/3
• Example 12 4PO TMP 30.9 -
• Example 13 5PO TMP 34.8 -
• Example 14 7PO TMP 42.1 42/37/0

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• Chemical Kinetics & Catalysis (AREA)
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• Oil, Petroleum & Natural Gas (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Lubricants (AREA)

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• 2002
  • 2002-01-23 EP EP02447010A patent/EP1335015A1/de not_active Withdrawn
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  • 2003-01-23 AU AU2003203061A patent/AU2003203061A1/en not_active Abandoned
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