EP1973999A1 - Utilisation d'esters comprenant des groupes alkyle ramifiés, en tant que lubrifiants - Google Patents

Utilisation d'esters comprenant des groupes alkyle ramifiés, en tant que lubrifiants

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Publication number
EP1973999A1
EP1973999A1 EP07700179A EP07700179A EP1973999A1 EP 1973999 A1 EP1973999 A1 EP 1973999A1 EP 07700179 A EP07700179 A EP 07700179A EP 07700179 A EP07700179 A EP 07700179A EP 1973999 A1 EP1973999 A1 EP 1973999A1
Authority
EP
European Patent Office
Prior art keywords
acid
esters
branched alkyl
alkyl groups
sup
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
EP07700179A
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German (de)
English (en)
Inventor
Markus Scherer
Dirk Rettemeyer
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Cognis IP Management GmbH
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Cognis IP Management GmbH
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Publication date
Application filed by Cognis IP Management GmbH filed Critical Cognis IP Management GmbH
Publication of EP1973999A1 publication Critical patent/EP1973999A1/fr
Withdrawn legal-status Critical Current

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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
    • 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
    • C10M105/32—Esters
    • C10M105/36—Esters of polycarboxylic 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
    • 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
    • C10M105/32—Esters
    • C10M105/34—Esters of monocarboxylic 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
    • 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
    • C10M129/68—Esters
    • C10M129/70—Esters of monocarboxylic 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
    • 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
    • C10M129/68—Esters
    • C10M129/72—Esters of polycarboxylic 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C10M2207/2815—Esters of (cyclo)aliphatic monocarboxylic acids 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
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C10M2207/2825—Esters of (cyclo)aliphatic oolycarboxylic acids used as base material
    • 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
    • C10N2020/065—Saturated Compounds
    • 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
    • C10N2020/071—Branched chain compounds
    • 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
    • C10N2030/36—Seal compatibility, e.g. with rubber
    • 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
    • C10N2030/64—Environmental friendly compositions
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or turbines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants

Definitions

  • esters with branched alkyl groups as lubricants
  • the invention is in the field of oleochemistry. It relates to the use of esters with branched alkyl groups as lubricants and more particularly to the use of the branched esters as a carrier medium for hydraulic fluid and to lubricants containing these esters with branched alkyl groups.
  • the different lubricants such as engine oil, turbine oil; Hydraulic fluid, transmission oil, compressor oil and the like must meet extremely high criteria in addition to high biodegradability such as, high viscosity index, good lubricity, high sensitivity to oxidation, good thermal stability or the like.
  • Criteria are i.a. low toxicity, biodegradability, and at least 50% renewable resources.
  • Ester-based lubricating oils are known per se and have been used for some time (see Ullmanns Enzyklopadie der ischen Chemie, 3rd edition, 15th volume, 1964, pp. 285-294).
  • Common esters are reaction products of dicarboxylic acids with moderate alcohols, e.g. 2-ethylhexanol, or reaction products of polyols, e.g. Trimethylolpropane, and fatty acids, e.g. Oleic acid or a mixture of n-octane and n-decanoic acid.
  • Lower low-temperature viscosities and thus improved handling at lower temperatures have been described in particular for esters with branched alkyl chains.
  • esters are, for example, reaction products of Guerbet alcohols with dicarboxylic acids, which are described as components in lubricants in EP 489809. From DE 2302918 ester oils of polyols with branched acids are also known, which have an improved viscosity temperature behavior over lubricants based on mineral oil. Furthermore, it is known from US Pat. No. 5,488,121, for example, that esters of Guerbet alcohols and Guerbet acids, so-called Di-Guerbet esters, lead to lubricants which have good oxidation stability and good viscosity-temperature properties.
  • esters with fully saturated side chains have an increased oxidation stability.
  • a particular problem is when the lubricants, in addition to increased oxidation stability and low cryogenic viscosity, must have improved compatibility with sealing materials. This problem occurs especially in biodegradable hydraulic fluids.
  • the known lubricants based on linear esters with good oxidation stability are saturated in nature, but lead to softening of the usual sealing materials.
  • unsaturated ester types derived from, for example, oleic acid behave better than sealants, but have greatly reduced oxidation stabilities.
  • sealing materials such as NBR (nitrile-butyl rubber) and their hydrogenated variants (HNBR).
  • lubricants which, in addition to good biodegradability, have high oxidation stability and at the same time good compatibility with sealing materials.
  • lubricants are generally desired that can be obtained based on renewable raw materials. The other properties, in particular the lubricity and rheological properties of the lubricant must not be adversely affected.
  • esters with branched alkyl groups which are reaction products of alcohols of the general formula (I) R 1 OH (I) in which R 1 is a branched alkyl radical having 10 to 40 carbon atoms is: a) aliphatic Dicarboxylic acids of the general formula (II)
  • R 3 is -COOH (III) in which R 3 is a branched alkyl radical of 3 to 39 C atoms, or c) saturated monocarboxylic acids of the general formula (III) in the R 3 for a linear alkyl radical of 3 to 29 C atoms or d) a mixture of at least two of said acid group a) to c) as a lubricant with the proviso that the esters with branched alkyl groups have an oxidation stability of greater than or equal to 1000 hours in a test for oxidation stability, for example according to turbine oil Stability test (TOST test) according to DIN EN ISO 4263-3 have and compatibility with sealing materials (for example, according to ASTM D 471) show.
  • TOST test turbine oil Stability test
  • esters with branched alkyl groups which are reaction products of alcohols of general formula (I) R 1 OH (I) in which R 1 is a branched alkyl radical having 10 to 40 carbon atoms with: aliphatic dicarboxylic acids of the general Formula (II)
  • esters with branched alkyl groups to be used furthermore fulfill the proviso that a biodegradability of the esters with branched alkyl groups of greater than or equal to 60% is present and / or the proviso that in the lubricant the proportion of renewable raw materials is greater or equal to 50 wt .-% is.
  • reaction products as well as the raw materials from which they are made, are compounds known per se.
  • the branched alcohols may branch at any position of the alkyl chain other than Cl, with branching at position C2 being preferred.
  • the branched alcohols are preferably Guerbet alcohols or Guerbet alcohol mixtures.
  • the preferred Guerbet alcohols are those obtainable by guerbetization of fatty alcohols containing from 8 to 12 carbon atoms.
  • the trivial name guercalcohols is understood as meaning 2-alkyl-substituted 1-alkanols whose technical synthesis has been adequately described in the literature. It proceeds via the condensation of primary linear alcohols in the presence of basic catalysts via the intermediates of aldehydes and aldols.
  • the branching of the alcohols with an alkyl group of 10 to 40 carbon atoms consists of an alkyl radical of 3 to 20 carbon atoms.
  • the sum of the C atoms of the entire branched alkyl group consists of alkyl chain and alkyl radical of the branch having 3 to 20 C atoms and is 10 to 40 C atoms.
  • the branched alcohols of 10 to 40 carbon atoms which are selected from the group formed by 2-propylheptanol, 2-butyloctanol, 2-pentylnonanol, 2-hexyldecanol, 2-heptylundecanol, 2-octyldodecanol , 2-nonyltridecanol, 2-decyltetradecanol, 2-undecylpentadecanol, 2-dodecylhexadecanol, 2-tridecylheptadecanol, 2-tetradecyloctadecanol, 2-pentadecylnonadecanol, 2-hexadecoylicosanol and 2-heptadecylheneicosanol.
  • 2-hexyldecanol (C16), 2-heptylundecanol (C18), 2-octyldodecanol (C20), 2-nonyltridecanol (C22), and 2-decyltetradecanol (C24) are 2-hexyldecanol (C16), 2-heptylundecanol (C18) and 2-octyldodecanol (C20).
  • the dicarboxylic acids of the formula (II) are known per se and are commercially available.
  • saturated dicarboxylic acids such as oxal, malonic, succinic, glutaric, adipic, pimelic, cork, azealin, sebacic, brassyl, thapsic, and phellogenic acids are used.
  • the anhydrides of the dicarboxylic acids are also suitable for the reaction according to the invention. Particularly preferred are azelaic acid and sebacic acid and their anhydrides.
  • the saturated monocarboxylic acids of the formula (III) are also known per se and are commercially available. Suitable are both branched saturated with 4 to 40 and linear saturated monocarboxylic acids having 4 to 30 carbon atoms. Typical examples are selected from the group formed by 2,2-dimethylpropionic acid, neoheptanoic acid, neo-offanoic acid, neononanoic acid, isohexanoic acid, neodecanoic acid, 2-ethylhexanoic acid, 3,5,5-trimethylhexanoic acid, isoheptanoic acid, isooctanoic acid, isononanoic acid, isostearic acid , Isopalmitic acid and isodecanoic acid, and of butyric, valeric, caproic, heptanoic, caprylic, pelargonic, capric, undecanoic, lauric, tridecanoic, tetradecanoic
  • the reaction to the reaction products proceeds in known per se for the preparation of esters.
  • esters with branched alkyl groups which have a kinematic viscosity (DIN 51562) in the range from 3 to 500 mm / s, preferably from 10 to 120 mm / s, at 40 ° C.
  • DIN 51562 kinematic viscosity
  • the oxidation stability of the esters is determined according to a standard test, DIN EN ISO 4263-1, which is also referred to as turbine oil stability test (TOST test) or its updated versions, especially DIN EN ISO 4263-3 , At the time of the test, the DIN EN ISO 4263-3 test was still in draft status. However, the opposition period expired on October 31, 2004. It was determined the oxidation stability between saturated linear, saturated branched and unsaturated linear esters.
  • TOST test turbine oil stability test
  • the branched esters to be used according to the invention show an oxidation stability of more than 1000 hours.
  • the esters according to the invention preferably have an oxidation stability determined after the test which is greater than 2000 hours and in particular greater than 4000 hours.
  • esters to be used according to the invention Another property of the esters to be used according to the invention is the good hydrolytic stability. This was determined by the acid number measurement on 12-day reaction with water at 100 ° C.
  • the acid number (measured according to DIN ISO 660) of the branched esters to be used according to the invention after a 12-day test is preferably less than or equal to 1, particularly preferably less than or equal to 0.5.
  • the branched esters to be used according to the invention show a high compatibility with sealing materials which are commonly used.
  • the test for compatibility with sealing materials can be carried out, for example, according to the standard test ASTM D 471, for example for 168 h at 100 ° C.
  • the branched esters to be used according to the invention show an increase in volume of not more than 20%, preferably not more than 10%, a hardness loss of less than 15%, preferably less than 10% and a decrease in elongation at break of less than 50%, preferably less 30%.
  • the compatibility of the branched alkyl ester esters to be used with sealing materials selected from the group consisting of NR (natural rubber), NBR (nitrile-butadiene rubber), HNBR (hydrogenated nitrile rubber), Butyl rubber), FPM (fluororubber), ACM (acrylate rubber), PTFE (Teflon), PU (polyurethane), silicone, polyacrylate and neoprene, especially preferred over NBR, HNBR and ACM.
  • the stability of the sealing materials to esters with branched alkyl groups is determined by the abovementioned test ASTM D 471 and the stated criteria are met.
  • esters to be used according to the invention or of the lubricants containing the esters with branched alkyl groups is the good biodegradability. This is determined, for example, according to the standard test methods according to OECD 301 or according to the test EPA 560 / 6-82-003. The determination according to the test is preferably OECD 301 B. In these tests, the esters with branched alkyl groups to be used must show a biodegradability of at least 60%. Preference is given to a biodegradability of at least 70% and in particular of at least 75%.
  • esters with branched alkyl groups which are used according to the invention or the lubricants containing the esters with branched alkyl groups should consist of at least 50% by weight of renewable raw materials. Particularly preferably, the proportion of renewable raw materials of greater than or equal to 70 wt .-% and in particular a proportion of greater than or equal to 90 wt .-%.
  • renewable raw materials are compounds which are obtained either by direct isolation or by refinement such as, for example, esterification from raw materials taken from living nature.
  • These raw materials are, for example, plants or animal fats.
  • the esters with branched alkyl groups to be used have a flash point which is greater than 200.degree. Preferably, the flash point is greater than 250 ° C.
  • the inventive ester with branched alkyl groups as a base liquid for fire-resistant lubricants and especially as a carrier medium for fire-resistant hydraulic fluid and in particular for the production of fire-resistant hydraulic fluids of the class HFDU.
  • the esters with branched alkyl groups according to the above-mentioned reaction products and the provisos that they show an oxidation stability of greater than 1000 hours and a compatibility with sealing materials are used as the basis for lubricating oils, as a carrier medium for hydraulic fluid, as a carrier medium for cooling lubricant, as a carrier medium for industrial gear oil, as a carrier medium for compressor oil, as a carrier medium for turbine oil, as a carrier medium for motor oil, as a carrier medium for axle oil, as a carrier medium for shock absorber fluid or as a carrier medium for vehicle transmission oil.
  • a carrier medium for hydraulic fluid in particular the use for the production of hydraulic fluids of the ISO classes ISO VG 10, VG 22, VG 32, VG, 46, VG, 68 and VG 100.
  • lubricant is understood to mean in particular the said lubricating oils, liquids, lubricating liquids and oils.
  • the invention is not limited to the use of these particular lubricants.
  • esters with branched alkyl groups in amounts of 0.1 to 100 wt .-%, based on the total amount of lubricant in the lubricant.
  • a proportion of esters with branched alkyl groups is preferably between 5 and 99% by weight. In the case of the hydraulic fluid, a proportion of 95 to 99.5 wt .-% is preferred.
  • further lubricating liquids may be contained in the lubricant, which are selected from the group consisting of mineral oils, highly refined mineral oils, alkylated mineral oils, poly- ⁇ -olefins, polyalkylene glycols, phosphate esters, Silicone oils, diesters and esters of polyhydric alcohols and mineral oils of classes Solvent Neutral and mineral oils of classes XHVI, VHVI, Group II and Group III.
  • the lubricant according to the invention may contain further additives which are selected from the group formed by thickeners, viscosity index improvers, antioxidants, corrosion inhibitors, demulsifiers, defoamers, dyes, wear protection additives, EP (Extreme Pressure) and AW (Antiwear) additives and friction modifiers.
  • Essential for the invention are therefore also as a further subject of the invention lubricants containing esters with branched alkyl groups, which meet the criteria of oxidation stability and compatibility with sealing materials, in amounts of from 0.1 to 99.5 wt .-%, based on the total amount of lubricant. Again, it is preferred that an amount of 5 to 99 wt .-% and in the case of hydraulic fluids, an amount of 95 to 99.5 wt .-% of the esters with branched alkyl groups in the lubricant is included. These lubricants may also contain the said further lubricating fluids and / or additives, wherein the sum of the amounts add up to 100 wt .-%. Examples
  • Bl Example 1, saturated branched ester of 2-octyldodecanol with azelaic acid VB1: Comparative Example 1, saturated linear ester of trimethylolpropane (TMP) and linear C8 / C10 acid (available, for example, under the product name Synative ES 3157).
  • TMP trimethylolpropane
  • VB2 Comparative Example 2, unsaturated linear esters of trimethylolpropane (TMP) and oleic acid (available, for example, under the product name Synative ES TMP 05)
  • TMP trimethylolpropane
  • oleic acid available, for example, under the product name Synative ES TMP 05
  • the investigated hydraulic fluids consist of 96.8% of the stated esters.
  • the additive mixture used has been used in each product at 3.2% and covers the usual requirements for finished formulated hydraulic oils. Contains antioxidants, corrosion inhibitors for non-ferrous metals and steel, additives for adjusting the air separation capacity, foaming behavior and demulsibility, and EP / AW additives
  • NBR 1 nitrile-butadiene rubber, in accordance with DIN ISO 6072: 2002 E) as the sealing material and the esters mentioned in Example 1 were used.
  • hydraulic fluid Bl with the saturated ester with branched alkyl groups achieves excellent values with regard to the change in volume and all the other criteria also show the desired values.
  • the hydraulic fluid with VBl which has proven to be good in the oxidation behavior, but here shows poor values.

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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)

Abstract

La présente invention concerne l'utilisation d'esters comprenant des groupes alkyle modifiés, qui sont des produits de la réaction d'alcools de formule générale (I) R1OH, dans laquelle R1 est un radical alkyle ramifié comprenant de 10 à 40 atomes de C, avec : a) des acides dicarboxyliques aliphatiques de formule générale (II) HOOC-R2-COOH, dans laquelle R2 est un radical alkyle saturé, ramifié ou non, comprenant de 0 à 34 atomes de C ; ou b) des acides monocarboxyliques saturés de formule générale (III) R3-COOH, dans laquelle R3 est un radical alkyle ramifié comprenant de 3 à 39 atomes de C ; et c) des acides monocarboxyliques saturés de formule générale (III) dans laquelle R3 est un radical alkyle linéaire comprenant de 3 à 29 atomes de C ; ou d) un mélange d'au moins deux groupes acides mentionnés a)-c). Ces esters sont employés comme lubrifiants à la condition qu'ils aient une stabilité à l'oxydation supérieure ou égale à 1000 heures dans le cadre du test relatif à la stabilité à l'oxydation (par exemple selon DIN EN ISO 4263-3), et une certaine tolérance aux matériaux d'étanchéité (par exemple selon ASTM D 471). L'invention concerne aussi des lubrifiants qui contiennent les esters mentionnés en des quantités de 0,1 à 99,5 % en poids rapportés à la quantité totale de lubrifiant.
EP07700179A 2006-01-12 2007-01-04 Utilisation d'esters comprenant des groupes alkyle ramifiés, en tant que lubrifiants Withdrawn EP1973999A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006001768A DE102006001768A1 (de) 2006-01-12 2006-01-12 Verwendung von Estern mit verzweigten Alkylgruppen als Schmiermittel
PCT/EP2007/000034 WO2007082639A1 (fr) 2006-01-12 2007-01-04 Utilisation d'esters comprenant des groupes alkyle ramifiés, en tant que lubrifiants

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EP1973999A1 true EP1973999A1 (fr) 2008-10-01

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US (2) US20100261628A1 (fr)
EP (1) EP1973999A1 (fr)
JP (1) JP5412116B2 (fr)
CA (1) CA2637401A1 (fr)
DE (1) DE102006001768A1 (fr)
WO (1) WO2007082639A1 (fr)

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Publication number Publication date
CA2637401A1 (fr) 2007-07-26
JP5412116B2 (ja) 2014-02-12
DE102006001768A1 (de) 2007-07-19
US20130137614A1 (en) 2013-05-30
US8921289B2 (en) 2014-12-30
WO2007082639A1 (fr) 2007-07-26
JP2009523182A (ja) 2009-06-18
US20100261628A1 (en) 2010-10-14

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