EP3344734B1 - Mélange à action lubrifiante contenant des glycérides - Google Patents
Mélange à action lubrifiante contenant des glycérides Download PDFInfo
- Publication number
- EP3344734B1 EP3344734B1 EP16754476.6A EP16754476A EP3344734B1 EP 3344734 B1 EP3344734 B1 EP 3344734B1 EP 16754476 A EP16754476 A EP 16754476A EP 3344734 B1 EP3344734 B1 EP 3344734B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- lubricating
- mixture
- glycerides
- mixture according
- mass fraction
- 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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Links
- 239000000203 mixture Substances 0.000 title claims description 59
- 230000001050 lubricating effect Effects 0.000 title claims description 41
- 125000005456 glyceride group Chemical group 0.000 title claims description 21
- 239000000314 lubricant Substances 0.000 claims description 33
- 239000007787 solid Substances 0.000 claims description 30
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 21
- 239000008158 vegetable oil Substances 0.000 claims description 21
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 20
- 239000000194 fatty acid Substances 0.000 claims description 20
- 229930195729 fatty acid Natural products 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 13
- 150000003626 triacylglycerols Chemical class 0.000 claims description 13
- 230000005540 biological transmission Effects 0.000 claims description 9
- 239000007791 liquid phase Substances 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 235000019871 vegetable fat Nutrition 0.000 claims description 5
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 4
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 4
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 235000014121 butter Nutrition 0.000 claims 1
- 235000019864 coconut oil Nutrition 0.000 claims 1
- 239000003240 coconut oil Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 22
- 239000003925 fat Substances 0.000 description 17
- 235000019197 fats Nutrition 0.000 description 15
- 239000002994 raw material Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 8
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 8
- 235000019482 Palm oil Nutrition 0.000 description 7
- 239000002540 palm oil Substances 0.000 description 7
- 239000000654 additive Substances 0.000 description 6
- 230000001590 oxidative effect Effects 0.000 description 6
- 239000007790 solid phase Substances 0.000 description 6
- -1 fatty acid esters Chemical class 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000002600 sunflower oil Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- 235000019486 Sunflower oil Nutrition 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000012208 gear oil Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000000149 penetrating effect Effects 0.000 description 3
- 229930003799 tocopherol Natural products 0.000 description 3
- 239000011732 tocopherol Substances 0.000 description 3
- 125000002640 tocopherol group Chemical class 0.000 description 3
- 235000019149 tocopherols Nutrition 0.000 description 3
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 239000010720 hydraulic oil Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 150000003365 short chain fatty acid esters Chemical class 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000000828 canola oil Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001746 carotenes Chemical class 0.000 description 1
- 235000005473 carotenes Nutrition 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- LNSXAHXVHYLJEG-UHFFFAOYSA-N ethyl 2-hydroxypropanoate;2-hydroxy-2-methylbutanoic acid Chemical compound CCOC(=O)C(C)O.CCC(C)(O)C(O)=O LNSXAHXVHYLJEG-UHFFFAOYSA-N 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 235000009048 phenolic acids Nutrition 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004633 phorbol derivatives Chemical class 0.000 description 1
- 239000002644 phorbol ester Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000903 polyhydroxyalkanoate Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 229930003802 tocotrienol Natural products 0.000 description 1
- 239000011731 tocotrienol Substances 0.000 description 1
- 235000019148 tocotrienols Nutrition 0.000 description 1
- 229940068778 tocotrienols Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
-
- 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
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
- C10M2207/2895—Partial esters containing free hydroxy groups 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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/401—Fatty vegetable or animal oils 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
- 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
-
- 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
- C10N2040/25—Internal-combustion engines
Definitions
- the invention relates to a lubricating mixture which contains at least a proportion by mass of ⁇ 50% of glycerides of natural origin and a proportion of fatty acid alkyl esters and is particularly suitable for use in gears, electric motors or internal combustion engines.
- lubricating liquids made from mineral oils, synthetic oils, vegetable oils or water, to which additives are usually added to improve the lubricating properties.
- the task of the liquids is to generate a liquid film on the surface of components, thereby reducing friction losses between components that move against one another and minimizing wear.
- natural raw materials are increasingly being used, which are often modified before being used as a lubricant (e.g. cellulose in the DE202009018507U1 ) and/or additives can be added.
- Very high demands are placed on gear or engine oils in the lubricant sector in particular, since they should be chemically stable over a long period of time and are often exposed to high temperature fluctuations, which can affect the lubricating properties. Those high In many cases, requirements cannot be met by either synthetic or natural fats and oils.
- viscosity index describes the temperature dependency of the kinematic viscosity of a lubricating oil. Oils with a low viscosity index show a greater change in viscosity with temperature than those with a high viscosity index. The latter are particularly desirable in lubricating applications.
- Vegetable oils are an environmentally friendly alternative to products based on Petroleum based and based on renewable natural resources.
- the use of vegetable oils as lubricants is limited by the property of some oils to solidify at low temperatures, due to a low viscosity index and because of the often lacking oxidative stability.
- EP2350240A1 describes the use of vegetable oil with a high proportion of unsaturated fatty acids as gear oil or hydraulic fluid to improve the viscosity properties, the oil having a natural viscosity index (VI) of greater than or equal to 200 and a proportion of monounsaturated fatty acids of greater than 80%, a proportion twice unsaturated fatty acids of a maximum of 1-10% and a proportion of triunsaturated fatty acids of less than 1%.
- a part of the vegetable oil can be used in the form of an unsaturated ester of the vegetable oil.
- gear oils or hydraulic oils should be thin at low temperatures ( ⁇ 40°C) in order to be easier to pump, which is achieved by using vegetable oil such as rapeseed or sunflower oil with a high proportion of unsaturated fatty acids.
- vegetable oil such as rapeseed or sunflower oil with a high proportion of unsaturated fatty acids.
- the occurrence of a solid phase in the lubricating medium should be avoided according to the description.
- Industrial oils should also exhibit high oxidative stability, which is generally related to the unsaturated fatty acids present in vegetable fatty acid alkyl chains.
- the reaction of a vegetable oil with oxygen can lead to polymerization and crosslinking of the fatty acid alkyl chains and reduced oxidative stability.
- Oils based on saturated hydrocarbons contain little or no unsaturated fatty acids and therefore have high oxidative stability.
- DE60031505T2 describes a method for increasing the oxidative stability and improving the lubricating properties of a vegetable oil.
- the vegetable oil is transesterified with a short-chain fatty acid ester and volatile components are separated after transesterification.
- the vegetable oil can have a monounsaturated fatty acid content of at least 50% and can be selected, for example, from the group consisting of corn oil, rapeseed oil, soybean oil and sunflower oil.
- the short chain fatty acid ester can be saturated and is four to 10 carbon atoms in length. This type of transesterification with different synthetic components is an expensive process and therefore has economic disadvantages.
- Hydraulic oils based on mineral oil are known. These usually have a viscosity index of around 100. Additives are added to the mineral oil to ensure protection against corrosion and increase its resistance to aging.
- viscosity index improvers are added. These are long-chain synthetic hydrocarbon compounds that are homogeneously distributed in cold oils and only slightly increase viscosity, but unfold at higher operating temperatures and increase in volume when dissolved in the oil. This thickens the oil and increases the viscosity index.
- Such viscosity index improvers have the disadvantage, however, that the long-chain hydrocarbon compounds are broken down into smaller fragments under stress, as a result of which their original thickening effect is sometimes significantly altered. This effect is also known as permanent shear loss.
- a lubricant based on fatty acid esters is described.
- vegetable or animal fats are transesterified with monohydric alcohols, which have a chain length of between three and six carbon atoms.
- glycerol is a by-product and is separated because it is insoluble in the fatty acid alkyl esters.
- the Indian DE20305164U1 The lubricant described therefore contains no glycerides.
- the lubricant consists of natural or synthetic triglycerides, one organic solvent and an antioxidant. Lactic acid ethyl ester (ethyl lactate), mineral oils and mixtures of both are suggested as solvents.
- fatty acid methyl esters from soybean oil can optionally be added.
- partial glycerides is not described. Since this lubricant is explicitly a penetrating oil, i.e. a medium with low viscosity and good penetration properties, a solids content is undesirable.
- a lubricant consisting of palm oil and palm oil by-products.
- Base fluid for this lubricating medium is palm olein, a liquid fraction of palm oil.
- the iodine value of the palm olein used must be at least 56 in order to avoid the formation of fat crystals.
- Other lubricant components are tocopherols from palm oil and fatty acid alkyl esters. The latter are synthesized from free fatty acids and hindered polyhydric alcohols. Neopentyl glycol, trimethylolpropane, pentaerythritol and dipentylerythritol are used as hindered alcohols. Thus, the resulting esters are not mono- and diglycerides. Due to the use of palm olein, the lubricant has no solid fraction.
- WO 2010/118891 A1 describes a lubricating fluid and a method for its production. This is a mixture of mono-, di- and triacylglycerides, free fatty acids and fatty acid alkyl esters. This lubricant is explicitly a liquid. A solid content is not described.
- the object of the present invention is to provide a lubricating medium with a high viscosity index, which can be used advantageously in gears, engines or other units to be lubricated, which can be produced inexpensively and can also consist entirely of renewable raw materials and thus does not present a high hazard potential if released into the environment.
- the proposed mixture contains at least a mass fraction of ⁇ 50% natural glycerides Origin and a proportion of fatty acid alkyl esters with 1 to 4 carbon atoms in the alkyl group.
- the glycerides are at least partly mono- and/or diglycerides, which form a mass fraction of ⁇ 10% in the mixture, and the mixture has a temperature range of > 10°C to at least 15°C, preferably to at least 20°C, a liquid phase with a solids content of ⁇ 1% by volume, which is formed from a proportion of the glycerides and/or the fatty acid alkyl esters.
- the occurrence of the solid phase is characterized by the fact that the light transmission of the mixture is 10% to 90% lower than that of a completely liquid reference of the same composition at a correspondingly higher temperature.
- the proportion of solids is preferably selected in such a way that the light transmission is 10% to 50%, ideally 10% to 20%, lower than that of the reference.
- Methods for determining the light transmission are, for example, photometers or measuring devices that work according to the TURBISCAN ® principle.
- the lubricating mixture according to the invention also referred to below as lubricant, thus fulfills the lubricating effect of two systems at once by combining the properties of lubricating oils (liquid phase) and lubricating greases (solid phase).
- the mixture has a predominantly liquid consistency, so the volume fraction of liquid in the mixture is >40%, advantageously >80%, especially advantageously >90%.
- the mixture can also be formed or produced entirely from renewable raw materials, in particular vegetable oils and fats.
- the proportion of solids does not impair the properties of the lubricant, or only insignificantly, but leads to better chemical resistance of the lubricant than when using pure vegetable oils.
- the lubricant can therefore be used in technical lubrication applications without any problems.
- the size of the solid particles that form the solids content of the proposed mixture have an edge length in the range between 4 ⁇ m and 5 mm. They show a good lubricating effect, since they get into the space between the gear wheels in transmissions, for example, and can develop an advantageous lubricating effect there. This significantly reduces the wear between the metal surfaces compared to other non-lubricating solid particles in the lubricant and prevents abrasive components from penetrating between the gears or into gaps and developing their abrasive effect there.
- the lubricant according to the invention consists predominantly of triglycerides and partial glycerides natural oils and fats and fatty acid alkyl esters with 1 to 4 carbon atoms in the alkyl group.
- Particularly advantageous properties result when the mass fraction of the triglycerides in the lubricant is >30%, preferably >40%, ideally >50%.
- the mass fraction of fatty acid alkyl esters is >10%, ideally >15%.
- Particularly advantageous properties result when the proportion of diglycerides is >10%, ideally >15%, and that of monoglycerides is >5%.
- the lubricant contains a proportion of unbound monohydric or polyhydric alcohol. This proportion is preferably between 0.1 and 4%, ideally between 0.1 and 2%.
- the solids content will advantageously consist of components that are contained in the natural raw material (fat, oil) from which the glycerides for the mixture are obtained or that are obtained from this raw material.
- the lubricant contains, in addition to the above-mentioned solids based on fats and oils and/or fatty acid alkyl esters, other organic or inorganic components which do not come from the natural raw material and which remain active even at high temperatures of at least 90°C are always fixed.
- These particles preferably have a diameter of 0.1 to 1.5 ⁇ m, ideally 0.2 to 1 ⁇ m, and surprisingly improve the running-in properties of gears.
- the proportion of this solid fraction in the lubricant is preferably between 0.1 and 3%, ideally between 0.15 and 2%.
- foreign particles are non-oxidative metals and metal compounds such as iron or aluminum oxides, inert silicon-based compounds such as silicon oxide, and synthetic and natural polymers such as polystyrene, polyethylene, polyethylene terephthalate, polypropylene, polycarbonate, polyhydroxyalkanoates, polylactic acid, proteins, starches, Celluloses and their derivatives.
- the composition of the solid particles from the glycerides differs from the composition of the liquid phase.
- the monoglyceride content in the solid phase is ideally higher by a factor of >1.5, advantageously by a factor of >2, particularly advantageously by a factor of >5, than in the liquid phase.
- fats containing a high proportion of saturated fatty acids being used at least in part as the raw material.
- These can be vegetable fats such as palm oil, palm kernel oil or coconut fat or other fats that contain a high proportion of saturated fatty acids >30% by mass, particularly advantageously >80% by mass and are still solid at a temperature of 20°C.
- a very oxidation-stable lubricant is obtained, which is largely liquid at a temperature of 20°C, so that pumping is possible and a surprisingly high lubricating effect is achieved . This is not the case with untreated vegetable fat.
- the use of unrefined or only partially refined vegetable oils and fats as raw material is particularly advantageous.
- the lubricant obtained from this has particularly good oxidation stability.
- the lubricant has particularly advantageous properties if only the hydratable phospholipids are removed in the refining process or if fat components, which are usually separated off in vegetable oil refining, are not removed or added back.
- examples of such compounds are carotenoids, non-hydratable lecithins, phenols and phenolic acids, tocopherols, phorbol esters, etc.
- the mixture of triglycerides and partial glycerides and fatty acid esters according to the invention has a higher viscosity index of >200 compared to the untreated oils and fats.
- oils that are liquid at this temperature and contain long-chain unsaturated fatty acids in addition to the fat components that are still solid at a temperature of 20°.
- This can be achieved by adding oils that a contain a high content of unsaturated fatty acids, such as rapeseed or sunflower oil, with the proportion of these oils being selected to be less than 50% by mass, advantageously less than 10% by mass, in order to maintain oxidation stability. It is possible to add the low-viscosity oil before the conversion of the triglycerides or after the conversion.
- Such mixtures can also be fractions of vegetable oils in the form of pumpable residues which are separated off as minor components during the winterization of oils. At a temperature of 20°C, these contain both liquid and solid components, which have a surprisingly good lubricating effect. Further configurations can be mixtures of these winterization residues with fats or oils, which are optionally also subjected to a partial transesterification.
- antioxidant substances to further increase the oxidation stability.
- plant ingredients are used to advantage, which are also contained in natural fats and are also soluble there. These can be carotenes, tocopherols, tocotrienols and other oil-soluble substances with an antioxidant effect.
- antioxidant plant substances between 0.1 and 10% by mass of antioxidant plant substances should be used for technical applications.
- the lubricant has particularly advantageous properties if it has a low proportion of inorganic particles ( ⁇ 1.5 ⁇ m). These serve as nuclei for fat crystallization and accelerate the formation of the solid phase.
- composition and application of the proposed lubricant are shown below using an example.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Claims (18)
- Mélange à action lubrifiante, notamment destiné à être utilisé dans les transmissions et les moteurs, qui contient au moins- une fraction massique en glycérides d'origine naturelle de ≥ 50 %, dans lequel au moins une partie des glycérides est issue de matières grasses végétales, qui contiennent une fraction massique en acides gras saturés d'au moins 30 % et sont solides à une température de 20°C, et- une fraction d'esters alkyliques d'acides gras avec 1 à 4 atomes C dans le groupe alkyle,dans lequel- les glycérides sont au moins en partie des mono et/ou diglycérides, qui forment une fraction massique de ≥ 10 % dans le mélange, et- le mélange présente dans une plage de température > 10°C à au moins 15°C, une phase liquide avec une fraction solide de ≥ 1 % en volume,- qui est formé par une fraction des glycérides et/ou des esters alkyliques d'acide gras et par des particules solides, qui présentent une extension comprise entre 4 µm et 5 mm, et- dans lequel une fraction de liquide dans le mélange s'élève à > 40 % en volume dans la plage de température de > 10°C à au moins 15°C.
- Mélange à action lubrifiante selon la revendication 1, caractérisé en ce que
le mélange contient la phase liquide avec la fraction solide de ≥ 1 % en volume dans la plage de température de > 10°C à au moins 20°C. - Mélange à action lubrifiante selon la revendication 1 ou 2, caractérisé en que
le mélange présente une phase liquide avec une fraction solide de ≥ 50 % en volume dans la plage de température de > 10°C à au moins 15°C ou jusqu'à au moins 20°C. - Mélange à action lubrifiante selon la revendication 1 ou 2, caractérisé en ce que
la phase liquide dans la plage de température de > 10°C à au moins 15°C ou à au moins 20°C présente une fraction de ≥ 80 % en volume du mélange. - Mélange à action lubrifiante selon une des revendications 1 à 4,
caractérisé en ce que
le mélange contient > 30 % en masse de triglycérides. - Mélange à action lubrifiante selon une des revendications 1 à 5,
caractérisé en ce que
le mélange contient > 10 % en poids de diglycérides et > 5 % en poids de monoglycérides. - Mélange à action lubrifiante selon la revendication 5 ou 6, caractérisé en ce que
la fraction massique en triglycérides est > 40 %, de préférence > 50 %. - Mélange à action lubrifiante selon la revendication 6 ou 7, caractérisé en ce que
la fraction massique en diglycérides s'élève à > 15 %. - Mélange à action lubrifiante selon une des revendications 1 à 8,
caractérisé en ce que
le mélange contient une fraction massique > 10 %, de préférence > 15 %, en esters alkyliques d'acides gras. - Mélange à action lubrifiante selon une des revendications 1 à 9,
caractérisé en ce que
le mélange contient une fraction massique comprise entre 0,1 % et 4 % d'alcool mono ou polyhydrique non lié. - Mélange à action lubrifiante selon une des revendications 1 à 10,
caractérisé en ce que
le mélange, en plus de la fraction solide des glycérides et/ou esters alkyliques d'acides gras, contient des particules solides d'autres substances organiques et/ou inorganiques qui sont encore solides même à une température d'au moins 90°C. - Mélange à action lubrifiante selon la revendication 11,
caractérisé en ce que
les particules solides des autres substances organiques et/ou inorganiques sont contenues dans le mélange dans une fraction massique comprise entre 0,1 % et 3 %. - Mélange à action lubrifiante selon la revendication 11 ou 12, caractérisé en ce que
les particules solides issues des autres substances organiques et/ou inorganiques présentent une extension dans la plage comprise entre 0,1 µm et 1,5 µm. - Mélange à action lubrifiante selon une des revendications 1 à 13,
caractérisé en ce que
les glycérides de la fraction solide ont une fraction de monoglycérides au moins 1,5 fois supérieure aux glycérides de la phase liquide. - Mélange à action lubrifiante selon une des revendications 1 à 14,
caractérisée en ce qu'
au moins une partie des glycérides est obtenue à partir de graisse de palme et/ou de graisse de coco. - Mélange à action lubrifiante selon une des revendications 1 à 15, caractérisé en ce que
certains des glycérides sont obtenus à partir d'huiles végétales liquides à une température de 20°C. - Utilisation du mélange à action lubrifiante selon une ou plusieurs des revendications précédentes comme lubrifiant.
- Utilisation selon la revendication 17 comme lubrifiant pour transmissions ou moteurs.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102015011148 | 2015-08-31 | ||
PCT/EP2016/069395 WO2017036785A1 (fr) | 2015-08-31 | 2016-08-16 | Mélange à action lubrifiante contenant des glycérides |
Publications (2)
Publication Number | Publication Date |
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EP3344734A1 EP3344734A1 (fr) | 2018-07-11 |
EP3344734B1 true EP3344734B1 (fr) | 2022-10-26 |
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ID=56787459
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Application Number | Title | Priority Date | Filing Date |
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EP16754476.6A Active EP3344734B1 (fr) | 2015-08-31 | 2016-08-16 | Mélange à action lubrifiante contenant des glycérides |
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Country | Link |
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US (1) | US10640722B2 (fr) |
EP (1) | EP3344734B1 (fr) |
JP (1) | JP7053454B2 (fr) |
KR (1) | KR102604851B1 (fr) |
CN (1) | CN108138065B (fr) |
AU (1) | AU2016315409B2 (fr) |
BR (1) | BR112018002095B1 (fr) |
CA (1) | CA2992150C (fr) |
ES (1) | ES2933622T3 (fr) |
MX (1) | MX2018002472A (fr) |
MY (1) | MY191237A (fr) |
PH (1) | PH12018500243A1 (fr) |
RU (1) | RU2018111249A (fr) |
SG (1) | SG11201800960XA (fr) |
WO (1) | WO2017036785A1 (fr) |
Families Citing this family (2)
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CN108130157A (zh) * | 2017-11-15 | 2018-06-08 | 泰州市艾瑞斯克模具有限公司 | 一种基于天然脂肪的可降解生物基质润滑剂的制备方法 |
DE102019210061A1 (de) * | 2019-07-09 | 2021-01-14 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Auf Gleitreibung beanspruchtes System |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI66899C (fi) | 1983-02-11 | 1984-12-10 | Kasvisoeljy Vaextolje Ab Oy | Smoerjmedel med triglycerider som huvudkomponent |
US6278006B1 (en) | 1999-01-19 | 2001-08-21 | Cargill, Incorporated | Transesterified oils |
US6624124B2 (en) * | 2001-07-13 | 2003-09-23 | Renewable Lubricants, Inc. | Biodegradable penetrating lubricant |
JP2003055299A (ja) | 2001-08-17 | 2003-02-26 | Sumitomo Chem Co Ltd | 脂肪酸エステルの製造方法および脂肪酸エステルを含む燃料 |
DE20305164U1 (de) | 2003-03-28 | 2003-09-04 | Falk, Oliver, 85356 Freising | Biologisch schnell abbaubares Schmierstoffgrundöl |
MY141241A (en) | 2003-11-20 | 2010-03-31 | Malaysia Palm Oil Board | Lubricant base from palm oil and its by-products |
DE102005002700A1 (de) * | 2005-01-19 | 2006-07-27 | Cognis Deutschland Gmbh & Co. Kg | Zusammensetzungen verwendbar als Biotreibstoff |
AT502218B1 (de) * | 2005-07-25 | 2010-09-15 | Bdi Biodiesel Internat Ag | Verfahren zur herstellung von carbonsäurealkylestern |
US20070082299A1 (en) * | 2005-10-11 | 2007-04-12 | Lam Research Corp. | Methods and apparatus for fabricating conductive features on glass substrates used in liquid crystal displays |
JP5603013B2 (ja) * | 2006-01-12 | 2014-10-08 | ザ ボード オブ トラスティーズ オブ ザ ユニバーシティ オブ アーカンソー | ナノ粒子組成物およびその製法並びに使用法 |
AU2008286538B2 (en) * | 2007-08-13 | 2012-09-13 | Fraunhofer-Gesellschaft Zur Forderung Der Angewandten Forschung E.V. | Liquid biofuel made of esters and bound glycerides, and also process for production thereof |
FI20075619L (fi) * | 2007-09-07 | 2009-03-08 | Teknillinen Korkeakoulu | Rasvahapon ja rasvahappoesterin tuottaminen |
DE102008011781A1 (de) | 2008-02-28 | 2009-09-03 | Carl Bechem Gmbh | Niedrigviskos bis hochviskos eingestellte wasserbasierte Schmierstoffzusammensetzung |
BRPI0908289A2 (pt) | 2008-05-06 | 2015-07-21 | Archer Daniels Midland Co | "processo para a produção de um aditivo lubrificante com base biológica e composição de lubrificante" |
DE102009022593A1 (de) * | 2008-06-13 | 2009-12-17 | KLüBER LUBRICATION MüNCHEN KG | Schmierstoffzusammensetzung auf der Basis natürlicher und nachwachsender Rohstoffe |
FR2936812B1 (fr) * | 2008-10-03 | 2010-10-15 | Total France | Compositions lubrifiantes pour transmissions. |
CH699659B1 (de) | 2008-10-14 | 2012-10-15 | Natoil Ag | Hydraulikflüssigkeit und Getriebeöl auf Pflanzenölbasis. |
WO2010118891A1 (fr) * | 2009-04-17 | 2010-10-21 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Liquide lubrifiant, et procédé pour sa fabrication |
DE102010009030A1 (de) | 2010-02-24 | 2011-08-25 | Audi Ag, 85057 | Kraftfahrzeug mit Einrichtungen zur Erwärmung von Getriebeöl durch Abwärme einer Brennkraftmaschine |
US8535398B1 (en) * | 2012-05-09 | 2013-09-17 | Perlman Consulting, Llc | Chemical complexes comprising glycerine and monoglycerides for thickening purposes |
FR3000497B1 (fr) * | 2012-12-28 | 2015-04-03 | Total Raffinage Marketing | Concentre d'additifs biodegradable ameliorant la lubrifiance des boues a l'eau, son utilisation et boue a l'eau pour le forage |
EP2964737A1 (fr) * | 2013-03-08 | 2016-01-13 | Elevance Renewable Sciences, Inc. | Compositions de graisse à base d'huile naturelle et procédés pour produire ces compositions |
EP3094712B1 (fr) * | 2014-01-15 | 2019-06-12 | Elevance Renewable Sciences, Inc. | Composants épaississants à base d'un dérivé d'huile naturelle, utilisés dans des compositions de graisse |
-
2016
- 2016-08-16 EP EP16754476.6A patent/EP3344734B1/fr active Active
- 2016-08-16 US US15/755,250 patent/US10640722B2/en active Active
- 2016-08-16 RU RU2018111249A patent/RU2018111249A/ru unknown
- 2016-08-16 BR BR112018002095-8A patent/BR112018002095B1/pt active IP Right Grant
- 2016-08-16 CN CN201680050244.8A patent/CN108138065B/zh active Active
- 2016-08-16 MY MYPI2018700456A patent/MY191237A/en unknown
- 2016-08-16 CA CA2992150A patent/CA2992150C/fr active Active
- 2016-08-16 ES ES16754476T patent/ES2933622T3/es active Active
- 2016-08-16 JP JP2018511104A patent/JP7053454B2/ja active Active
- 2016-08-16 MX MX2018002472A patent/MX2018002472A/es unknown
- 2016-08-16 KR KR1020187002151A patent/KR102604851B1/ko active IP Right Grant
- 2016-08-16 SG SG11201800960XA patent/SG11201800960XA/en unknown
- 2016-08-16 WO PCT/EP2016/069395 patent/WO2017036785A1/fr active Application Filing
- 2016-08-16 AU AU2016315409A patent/AU2016315409B2/en active Active
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Also Published As
Publication number | Publication date |
---|---|
RU2018111249A (ru) | 2019-10-04 |
RU2018111249A3 (fr) | 2019-10-04 |
MX2018002472A (es) | 2018-06-15 |
JP2018526511A (ja) | 2018-09-13 |
KR102604851B1 (ko) | 2023-11-21 |
SG11201800960XA (en) | 2018-03-28 |
MY191237A (en) | 2022-06-10 |
BR112018002095A2 (pt) | 2018-09-18 |
WO2017036785A1 (fr) | 2017-03-09 |
BR112018002095B1 (pt) | 2020-11-24 |
US20180245009A1 (en) | 2018-08-30 |
ES2933622T3 (es) | 2023-02-10 |
PH12018500243A1 (en) | 2018-07-30 |
CA2992150C (fr) | 2023-06-27 |
AU2016315409B2 (en) | 2019-07-18 |
JP7053454B2 (ja) | 2022-04-12 |
CA2992150A1 (fr) | 2017-03-09 |
EP3344734A1 (fr) | 2018-07-11 |
US10640722B2 (en) | 2020-05-05 |
CN108138065B (zh) | 2021-01-12 |
KR20180044880A (ko) | 2018-05-03 |
AU2016315409A1 (en) | 2018-03-08 |
CN108138065A (zh) | 2018-06-08 |
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