EP3841190B1 - Use of a lubricant composition - Google Patents
Use of a lubricant composition Download PDFInfo
- Publication number
- EP3841190B1 EP3841190B1 EP19752696.5A EP19752696A EP3841190B1 EP 3841190 B1 EP3841190 B1 EP 3841190B1 EP 19752696 A EP19752696 A EP 19752696A EP 3841190 B1 EP3841190 B1 EP 3841190B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- esters
- hydroxytyrosol
- use according
- weight
- base oil
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 109
- 239000000314 lubricant Substances 0.000 title claims description 60
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 claims description 108
- 235000003248 hydroxytyrosol Nutrition 0.000 claims description 54
- 229940095066 hydroxytyrosol Drugs 0.000 claims description 54
- 150000002148 esters Chemical class 0.000 claims description 52
- 239000002199 base oil Substances 0.000 claims description 32
- -1 C22 carboxylic acids Chemical class 0.000 claims description 25
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 11
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 239000003921 oil Substances 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- 238000005461 lubrication Methods 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 229920013639 polyalphaolefin Polymers 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000010695 polyglycol Substances 0.000 claims description 3
- 229920000151 polyglycol Polymers 0.000 claims description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 229920013636 polyphenyl ether polymer Polymers 0.000 claims description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 description 43
- 238000007254 oxidation reaction Methods 0.000 description 43
- 230000000052 comparative effect Effects 0.000 description 34
- 239000003963 antioxidant agent Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 15
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- 230000003078 antioxidant effect Effects 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 235000015165 citric acid Nutrition 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 5
- GQBHYWDCHSZDQU-UHFFFAOYSA-N 4-(2,4,4-trimethylpentan-2-yl)-n-[4-(2,4,4-trimethylpentan-2-yl)phenyl]aniline Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)CC(C)(C)C)C=C1 GQBHYWDCHSZDQU-UHFFFAOYSA-N 0.000 description 4
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- 238000005259 measurement Methods 0.000 description 4
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- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
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- 229920001155 polypropylene Polymers 0.000 description 3
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- 239000005642 Oleic acid Substances 0.000 description 2
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- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 235000011180 diphosphates Nutrition 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
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- 150000002500 ions Chemical class 0.000 description 2
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- 238000003878 thermal aging Methods 0.000 description 2
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 2
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- DIOYAVUHUXAUPX-ZHACJKMWSA-N 2-[methyl-[(e)-octadec-9-enoyl]amino]acetic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)N(C)CC(O)=O DIOYAVUHUXAUPX-ZHACJKMWSA-N 0.000 description 1
- DHTAIMJOUCYGOL-UHFFFAOYSA-N 2-ethyl-n-(2-ethylhexyl)-n-[(4-methylbenzotriazol-1-yl)methyl]hexan-1-amine Chemical compound C1=CC=C2N(CN(CC(CC)CCCC)CC(CC)CCCC)N=NC2=C1C DHTAIMJOUCYGOL-UHFFFAOYSA-N 0.000 description 1
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 1
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 1
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Images
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- 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
- C10M129/04—Hydroxy compounds
- C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
- C10M129/14—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring containing at least 2 hydroxy groups
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- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
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- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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- C10M2207/124—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof
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- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/401—Fatty vegetable or animal oils used as base material
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- C10M2209/1055—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only used as base material
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
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- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
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- C10N2030/08—Resistance to extreme temperature
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Definitions
- the present invention relates to the use of a lubricant composition containing an antioxidant that inhibits oxidative degradation of the composition.
- Lubricant manufacturers are under constant pressure to improve their products according to the needs of manufacturers and users.
- the chemical and thermal stability of the lubricants and the associated resistance to oxidation processes should be constantly improved.
- a high level of resistance to oxidation processes is of great importance, as these affect the physical and chemical properties of the lubricant and reduce its ability to protect the surfaces treated with it.
- oxidation processes can increase the acidity of the lubricant, thereby accelerating wear and corrosion of metal surfaces. Oxidation processes can also lead to the formation of oxidation products that impair lubricity.
- oxidation processes can occur increase the viscosity of the oil and thereby undesirably influence the distribution of the lubricant on the surfaces.
- metal-containing particles can also be deposited in the lubricant. These particles can act as an oxidation catalyst and accelerate the degradation of the lubricant. This is particularly true at high temperatures, such as those common in engines.
- an oil-soluble antioxidant is often added to lubricants.
- amines such as bis-(4-(1,1,3,3-tetramethylbutyl)phenyl)amine, styrenated phenylamine, sterically hindered phenols such as thio-diethylene-bis(2-(2,-di -tertbutyl-4-hydroxyphenyl) propionate and/or combinations of two or three of the substance groups mentioned are used as antioxidants.
- antioxidant additives there are numerous patents that describe antioxidant additives.
- GB-A-1 271 556 an antioxidant additive which is a mixture of (a) the reaction product of a boron compound with a long chain hydrocarbon carboxylic acid or an anhydride thereof with a primary or secondary amine and (b) a polycyclic phenolic compound.
- US-A-5,354,484 describes a lubricant additive that provides high temperature stability and contains a mixture of (i) an amine salt of a substituted phosphoric acid and (ii) an amine-substituted hydrocarbon succinic acid compound.
- the aforementioned additives generally show satisfactory antioxidant properties.
- the amount to be used is usually quite high, which is a disadvantage for cost reasons.
- at higher concentrations there is a risk that the properties of the lubricant will be changed in an undesirable way.
- the aforementioned additives usually have to be synthesized using complex processes.
- a lubricant composition which comprises a base lubricant consisting of a base oil and a thickener and an additive added to the base lubricant, the additive comprising at least one compound selected from plant-derived polyphenolic compounds and compounds formed by decomposition thereof.
- Preferred polyphenol compounds are gallic acid, ellagic acid, chlorogenic acid, caffeic acid, curcumin and quercetin.
- polyphenol compounds are natural products.
- the compounds mentioned have a rather low antioxidant effect.
- some of them are strongly colored (e.g. curcumin), which limits their possible uses.
- the invention was based on the object of providing a lubricant composition which has an antioxidant with which the above-mentioned disadvantages can be at least partially eliminated.
- a lubricant composition which contains a base oil and hydroxytyrosol and/or esters thereof for lubricating the surfaces of sliding partners in a tribological system.
- Hydroxytyrosol belongs to the family of natural polyphenols and has the following structural formula:
- Hydroxytyrosol is known to have antioxidant properties. However, it was surprising to the person skilled in the art that it has equivalent or, based on the concentration used, even better antioxidant properties than synthetic antioxidants commonly used in practice, and that it can be added to common base oils without impairing their functional properties.
- Esters of hydroxytyrosol can also be used according to the invention. Particular preference is given to esters which have a solubility in the respective base oil at 25° C. of at least 0.1 g/l, for example from 0.1 to 5 g/l.
- the hydroxytyrosol can also only be partially present in the lubricant composition as an ester.
- Esters that are particularly suitable according to the invention are carboxylic acid esters, as discussed in more detail below. Below should if useful, when referring to hydroxytyrosol, its esters should also be included.
- the lubricant composition contains solubilized hydroxytyrosol.
- solubilized hydroxytyrosol means hydroxytyrosol whose solubility has been increased in relation to the base oil used by adding a solubilizing agent.
- the type and amount of the solubilizing agent depends, among other things, on the base oil used, the desired dissolving properties of the hydroxytyrosol and the intended uses of the lubricant compositions.
- compounds that enter into a chemical bond with the hydroxytyrosol, for example to form esters should also be included in the term solubilizing agent.
- solubilizing agents for polyphenols are known and, for example, in the publications EP 2 359 702 B1 , WO 2007/051329 A1 , US 2014/0377435 A1 described, the disclosure of which is incorporated by reference.
- solubilizing agents which are particularly suitable according to the invention are C 2 -10 carboxylic acids, which can be branched and/or unbranched, can have one or more substituents, in particular hydroxyl groups and/or one or more carboxylic acid groups. Hydroxycarboxylic acids with at least 2, preferably 3 carboxylic acid groups are preferred.
- hydroxycarboxylic acids with at least 2, preferably 3 hydroxyl groups and/or hydroxycarboxylic acids with at least 2, preferably 3 hydroxyl groups and at least 2, preferably 3 carboxylic acid groups are selected from the group consisting of citric acid, malic acid, fumaric acid, gluconic acid, glycolic acid, lactic acid, oxalic acid, Tartaric acid, almond salicylic acid and/or mixtures thereof. Citric acid is particularly preferred.
- the lubricant composition comprises at least a portion of hydroxytyrosol carboxylic acid esters, in particular esters of hydroxytyrosol and C 2 - 10 carboxylic acids, where the C 2 - 10 carboxylic acids can be branched and / or unbranched, one or more substituents, in particular May have hydroxy groups and/or one or more carboxylic acid groups.
- the lubricant composition comprises at least a proportion of esters of hydroxytyrosol and hydroxycarboxylic acids with at least 2, preferably 3, carboxylic acid groups.
- the lubricant composition also preferably comprises at least a proportion of esters of hydroxytyrosol and hydroxycarboxylic acids with at least 2, preferably 3 hydroxyl groups and/or esters of hydroxytyrosol and hydroxycarboxylic acids with at least 2, preferably 3 hydroxyl groups and at least 2, preferably 3 carboxylic acid groups.
- the lubricant composition comprises at least a proportion of esters of hydroxytyrosol and carboxylic acids, selected from the group consisting of citric acid, malic, fumaric, gluconic, glycolic, lactic, oxalic, tartaric, mandelic salicylic acid and/or Mixtures thereof.
- the lubricant composition comprises at least a proportion of esters of hydroxytyrosol and citric acid.
- the lubricant composition expediently contains hydroxytyrosol and/or its esters in an oxidation-inhibiting amount.
- the proportion of hydroxytyrosol and/or its esters is from 0.01% by weight to 2% by weight and/or from 0.1% by weight to 2% by weight and/or from 0.1% by weight to 1.5% by weight, and/or from 0.01% by weight to 0.5% by weight, and/or from 0.05% by weight to 1% by weight, more preferably from 0.1% by weight to 1% by weight, more preferably from 0.1% by weight to 0.5% by weight and in particular from 0.25% by weight to 0.35% by weight, in each case based on that Total weight of the lubricant composition.
- the amount of solubilizing agent in the lubricant composition is advantageously 0.5 to 4% by weight, more preferably from 0.5 to 3.5% by weight, even more preferably from 0. 5 to 3% by weight, more preferably from 1 to 3% by weight, even more preferably from 1.5 to 3% by weight and in particular from 1.5 to 3% by weight.
- a base oil is understood to mean the usual base fluids used for the production of lubricants, in particular oils that can be assigned to groups I, II, III, IV or V according to the classification of the American Petroleum Institute (API).
- Particularly preferred base oils are selected from the group consisting of esters, in particular synthetic esters, polyglycols, naphthenic and/or aromatic mineral oils, synthetic hydrocarbons, phenyl ethers, polyalphaolefins, native base oils and derivatives of native oils and/or mixtures thereof.
- Particularly preferred according to the invention are esters, in particular synthetic esters, and/or mixtures of esters, in particular synthetic esters, native base oils and polyglycols with synthetic hydrocarbons and/or polyalphaolefins.
- the base oil is selected from the group consisting of an ester of an aromatic or aliphatic di-, tri- or tetracarboxylic acid with one or in a mixture of C 7 - to C 22 -alcohols, from a polyphenyl ether or alkylated diphenyl ether, from an ester of trimethylolpropane, pentaerythritol or dipentaerythritol with aliphatic C 7 - to C 22 - carboxylic acids, from C 18 -dimer acid esters, prepared from C 7 - to C 22 -alcohols, from complex esters, as individual components or in any mixture.
- Particularly preferred base oils are esters, in particular synthetic esters, and mixtures thereof with synthetic hydrocarbons and/or polyalphaolefins. In practical tests it was found that these base oils have a particularly good absorption capacity for hydroxytyrosol, in particular for hydroxytyrosol that has been solubilized with citric acid.
- base oils are native triglyceride-based oils, preferably with a high oleic acid content, in particular selected from the group consisting of sunflower oil, rapeseed oil, castor oil, linseed oil, corn oil, safflower oil, soybean oil, linseed oil, peanut oil, "lesquerella” oil, palm oil and their derivatives .
- base oils are triglycerides with a content (based on the bound fatty acids) of at least 50% by weight of oleic acid and less than 10% by weight of polyunsaturated fatty acids and their derivatives.
- the base oils can be used individually or in combination (if mixable). Particularly preferred base oils have a viscosity in the range from 10 mm 2 /s to 1000 mm 2 /s, measured at 40 °C.
- the proportion of the base oil in the lubricant composition according to the invention from 99.99% by weight to 90% by weight, more preferably from 99.5% by weight to 94.5% by weight and in particular from 99.75% by weight to 94.75% by weight, each based on the total weight of the lubricant composition.
- the aforementioned values relate in particular to lubricant compositions that are present as lubricating oil, ie essentially without thickeners. If, on the other hand, the lubricant composition is in the form of a lubricating grease, ie with a thickener, the proportion of base oil in the lubricant composition according to the invention is preferably from 70% by weight to 97.00% by weight.
- Hydroxytyrosol and/or its esters can be present as the sole antioxidant or in combination with other antioxidants.
- Further antioxidants which are particularly suitable according to the invention are the following compounds: styrenated diphenylamines, diaromatic amines, phenolic resins, thiophenolic resins, phosphites, butylated hydroxytoluene, butylated hydroxyanisole, phenylalpha-naphthylamine, phenyl-beta-naphthylamine, octylated/butylated diphenylamine, di-alpha-tocopherol, di -tert-butyl-phenyl, benzenepropane acid, sulfur-containing phenolic compounds and mixtures of these components.
- the lubricant composition can contain corrosion protection additives, metal deactivators, wear protection additives and/or ion complexing agents. These include triazoles, imidazolines, N-methylglycine (sarcosine), benzotriazole derivatives, N,N-bis(2-ethylhexyl)-ar-methyl-1 H-benzotriazole-1-methanamine; n-Methyl-N(1-oxo-9-octadecenyl)glycine, mixtures of phosphoric acid and mono- and di-isooctyl esters, reacted with (C 11-14 )-alkylamines, mixtures of phosphoric acid and mono- and di-isooctyl esters, reacted with tert-alkylamine and primary (C 12-14 ) amines, dodecanoic acid, triphenylphosphorothionate and amine phosphates.
- corrosion protection additives include triazoles, imidazo
- IRGAMET ® 39 IRGACOR ® DSS G, Amin O; SARKOSYL ® O (Ciba), COBRATEC ® 122, CUVAN ® 303, VANLUBE ® 9123, CI-426, CI-426EP, CI-429 and CI-498.
- wear protection additives are amines, amine phosphates, phosphates, thiophosphates, phosphorothionates and mixtures of these components.
- Commercially available anti-wear additives include IRGALUBE ® TPPT, IRGALUBE ® 232, IRGALUBE ® 349, IRGALUBE ® 211 and ADDITIN ® RC3760 Liq 3960, FIRC-SHUN ® FG 1505 and FG 1506, NA-LUBE ® KR-015FG, LUBEBOND ® , FLU ORO ® FG, SYNALOX ® 40-D, ACHESON ® FGA 1820 and ACHESON ® FGA 1810.
- the lubricant composition can include solid lubricants such as PTFE, BN, pyrophosphate, Zn oxide, Mg oxide, pyrophosphates, thiosulfates, Mg carbonate, Ca carbonate, Ca stearate, Zn sulfide, Mo sulfide, W sulfide, Sn -Sulfide, graphite, graphene, nano-tubes, SiO 2 modifications or a mixture thereof.
- solid lubricants such as PTFE, BN, pyrophosphate, Zn oxide, Mg oxide, pyrophosphates, thiosulfates, Mg carbonate, Ca carbonate, Ca stearate, Zn sulfide, Mo sulfide, W sulfide, Sn -Sulfide, graphite, graphene, nano-tubes, SiO 2 modifications or a mixture thereof.
- the lubricant composition can also contain thickeners, in particular metal soaps, metal complex soaps, bentonites, ureas, silicates, sulfonates and/or polyimides.
- the proportion of thickener in the lubricant composition according to the invention is preferably from 1% by weight to 20% by weight, based on the total weight of the lubricant composition.
- the base oil is mixed with hydroxytyrosol and/or its esters in the presence of a solubilizing agent, in particular in the presence of a solubilizing agent, as discussed in the context of the present invention in relation to the lubricant composition according to the invention.
- the process can also include further process steps in which, for example, the further components described in relation to the lubricant composition according to the invention, such as further antioxidants, thickeners, corrosion protection additives, metal deactivators, ion complexing agents and/or solid lubricants, are introduced.
- the lubricant composition is suitable for lubricating a wide variety of surfaces.
- the present invention relates to the use of the lubricant composition for lubricating the surfaces of sliding partners in a tribological system.
- the lubricant composition is particularly preferably used as an intermediate to reduce friction and/or wear in a tribological system.
- the lubricant composition is used simultaneously for power transmission, vibration damping and/or as corrosion protection.
- the lubricant composition is particularly useful tribological and rheological systems that are exposed to high oxidative stress.
- a preferred embodiment of the invention therefore relates to the use of the lubricant composition for H1 high-temperature applications for lifetime and/or consumption lubrication in components such as, in particular, chains, gears, bearings or fittings and/or marine components.
- Example 1 Preparation of various lubricant compositions
- the hydroxytyrosol used is a hydroxytyrosol solubilized with citric acid (about 2% by weight, based on the total amount of hydroxytyrosol and citric acid).
- Example 2 Measurement of the evaporation behavior and the apparent dynamic viscosity of selected compositions from Example 1
- the evaporation behavior and the apparent dynamic viscosity of the composition 1 according to the invention and the comparative examples 1, 2, 3 and 4 are measured (covered dish tests, gas exchange takes place).
- the evaporation behavior and the change in the apparent dynamic viscosity [mPas] as a criterion for progressive oxidation under thermal loading 72 hours of storage at 230°C, circulating air oven) are determined as a comparative measurement using a multiple determination (min. 3-fold determination).
- the sample quantity per test is 5g (+/- 0.1 g).
- the evaporation behavior is determined in% by weight by weighing.
- the rheological determination of the apparent dynamic viscosity is also used to draw conclusions about thermal aging (e.g. polymerization) or protection against thermal aging. Covered aluminum evaporation dishes with a diameter of 50 mm are used. The 2 opposite holes in the lid have a diameter of 5 mm and are 10 mm from the edge (see Figures 1 and 2 ). The Using a punching template makes sense, but is not absolutely necessary. The two bowls are stapled together using two staples at the fold of the bowls.
- hydroxytyrosol has no noticeable influence on the evaporation behavior. Furthermore, it is shown that hydroxytyrosol, as a phenolic antioxidant, has a comparable performance in terms of preventing radical aging processes as the amines, which are considered to be more efficient in the prior art, and works significantly better than other phenols.
- compositions 5, 6, 7 and 8 according to the invention were additionally examined comparatively.
- the results are in the following Table 3 and in Figure 5 (apparently dynamic viscosity).
- Table 3 Closed dish tests Composition according to the invention 05 Composition according to the invention 06 Composition according to the invention 07 Composition according to the invention 08 72h/230°C wt.% 62.3 59.5 60.5 60.4 72h/230°C mPas >100000 37174 34631 32403
- Example 3 Determination of the start of oxidation and the threshold value (threshold) of the oxidation course of selected compositions from Example 1
- the start of oxidation and the threshold value (threshold) of the oxidation course of selected compositions from Example 1 are determined using dynamic DSC (heating rate 1 ° C/min).
- DSC heating rate 1 ° C/min.
- the reaction kinetics are comparatively monitored within a base oil.
- the chemical dynamics within a material system become visible, from which conclusions can be drawn about the oxidation behavior in relation to the thermal energy input.
- the value "Start of oxidation” describes a first significant change in potential to the thermal energy input and thus refers to the delay that a mixture of substances experiences in comparison to another mixture of substances.
- the “threshold” describes the progress of the aging/oxidation process within the mixture of substances. This refers indirectly on the reaction rate of the oxidation process. This connection is in Figure 6 illustrated.
- composition 1 according to the invention has a higher oxidation resistance than the comparative examples.
- Tab. 5 see Fig.9: start of oxidation, Fig.10: limit value
- Comparative example 05 Comparative example 06
- Comparative example 07 Composition according to the invention 02 DSC dyn. [Heating rate 1°C/min] Start of oxidation (x0) °C 167 222 231 234 Threshold °C 196 228 266 237
- composition 2 according to the invention has a higher oxidation resistance than the pure base oil (comparative example 5) and than comparative example 6 provided with the same amount of antioxidant.
- the for the composition according to the invention The specific start of oxidation is above and the limit value is only slightly below the limit value of Comparative Example 7 - although this has more than ten times the amount of antioxidant.
- Tab. 6 (see Fig. 11: start of oxidation, Fig. 12: limit value) Comparative example 10 Comparative example 11 Composition according to the invention 04 DSC dyn. [Heating rate 1°C/min] Start of oxidation (x0) °C 215 223 234 Threshold °C 224 230 240
- composition 4 according to the invention has a higher oxidation resistance than the comparative examples.
- Tab. 7 see Fig. 13: start of oxidation, Fig. 14: limit value
- Comparative example 08 Comparative example 09 Composition according to the invention 03 DSC dyn. [Heating rate 1°C/min] Start of oxidation (x0) °C 174 168 179 Threshold °C 177 174 185
- composition 3 according to the invention has a higher oxidation resistance than the comparative examples.
- Tab. 8 (see Fig. 15: start of oxidation, Fig. 16: limit value) Composition according to the invention 05 Composition according to the invention 06 Composition according to the invention 07 Composition according to the invention 08 DSC dyn. [Heating rate 1°C/min] Start of oxidation (x0) °C 208 222 226 226 Threshold °C 210 226 231 234
Description
Die vorliegende Erfindung betrifft die Verwendung einer Schmiermittelzusammensetzung, die ein Antioxidationsmittel enthält, das den oxidativen Abbau der Zusammensetzung hemmt.The present invention relates to the use of a lubricant composition containing an antioxidant that inhibits oxidative degradation of the composition.
Hersteller von Schmiermitteln stehen unter ständigem Druck, ihre Produkte entsprechend den Anforderungen von Herstellern und Anwendern zu verbessern. So sollen insbesondere chemische und thermische Stabilität der Schmiermittel und damit verbunden ihre Resistenz gegen Oxidationsprozesse ständig verbessert werden. Eine hohe Resistenz gegen Oxidationsprozesse ist dabei von großer Bedeutung, da diese die physikalischen und chemischen Eigenschaften des Schmiermittels beeinträchtigen und seine Fähigkeit, die mit ihm behandelten Oberflächen zu schützen, vermindern. So können Oxidationsprozesse beispielsweise die Azidität des Schmiermittels erhöhen, wodurch die Abnutzung und Korrosion von Metalloberflächen beschleunigt wird. Oxidationsprozesse können ferner zur Bildung von Oxidationsprodukten führen, die das Schmiervermögen beeinträchtigen. Des Weiteren können Oxidationsprozesse die Viskosität des Öls erhöhen und hierdurch die Verteilung des Schmiermittels auf den Oberflächen in unerwünschter Weise beeinflussen.Lubricant manufacturers are under constant pressure to improve their products according to the needs of manufacturers and users. In particular, the chemical and thermal stability of the lubricants and the associated resistance to oxidation processes should be constantly improved. A high level of resistance to oxidation processes is of great importance, as these affect the physical and chemical properties of the lubricant and reduce its ability to protect the surfaces treated with it. For example, oxidation processes can increase the acidity of the lubricant, thereby accelerating wear and corrosion of metal surfaces. Oxidation processes can also lead to the formation of oxidation products that impair lubricity. Furthermore, oxidation processes can occur increase the viscosity of the oil and thereby undesirably influence the distribution of the lubricant on the surfaces.
Bei der Schmierung von metallischen Oberflächen kommt noch hinzu, dass es zu einer Abscheidung metallhaltiger Teilchen im Schmiermittel kommen kann. Diese Teilchen können als Oxidationskatalysator fungieren und den Abbau des Schmiermittels beschleunigen. Dies gilt insbesondere bei hohen Temperaturen, wie sie beispielsweise in Motoren üblich sind.When lubricating metallic surfaces, metal-containing particles can also be deposited in the lubricant. These particles can act as an oxidation catalyst and accelerate the degradation of the lubricant. This is particularly true at high temperatures, such as those common in engines.
Um diese unerwünschten Effekte zu verhindern, wird Schmiermitteln häufig ein öllösliches Antioxidationsmittel zugesetzt. So werden in der Praxis oft Amine wie z.B. Bis-(4-(1,1,3,3-tetramethylbutyl)phenyl)amin, styrolisiertes Phenylamin, sterisch gehindert Phenole wie z.B. Thio-diethylen-bis(2-(2,-di-tertbutyl-4-hydroxyphenyl) propionat und/oder Kombinationen von zwei oder drei der genannten Stoffgruppen als Antioxidationsmittel verwendet.To prevent these undesirable effects, an oil-soluble antioxidant is often added to lubricants. In practice, amines such as bis-(4-(1,1,3,3-tetramethylbutyl)phenyl)amine, styrenated phenylamine, sterically hindered phenols such as thio-diethylene-bis(2-(2,-di -tertbutyl-4-hydroxyphenyl) propionate and/or combinations of two or three of the substance groups mentioned are used as antioxidants.
Es gibt zahlreiche Patentschriften, die antioxidativ wirkende Additive beschreiben. Beispielsweise offenbart die
Zudem geben mehrere Druckschriften des Standes der Technik die Verwendung einer Kombination aus einer Borverbindung und einem aromatischen Amin in Schmiermittelzusammensetzungen an. Beispiele für solche Druckschriften schließen
Aus der
Die vorgenannten Additive zeigen in der Regel zufriedenstellende antioxidative Eigenschaften. Jedoch ist die einzusetzende Menge meist recht hoch, was aus Kostengründen von Nachteil ist. Zudem besteht bei höheren Konzentrationen die Gefahr, dass die Eigenschaften des Schmiermittels in unerwünschter Weise verändert werden. Darüber hinaus müssen die vorgenannten Additive in der Regel in aufwändigen Verfahren synthetisiert werden.The aforementioned additives generally show satisfactory antioxidant properties. However, the amount to be used is usually quite high, which is a disadvantage for cost reasons. In addition, at higher concentrations there is a risk that the properties of the lubricant will be changed in an undesirable way. In addition, the aforementioned additives usually have to be synthesized using complex processes.
Aus der
Der Erfindung lag die Aufgabe zu Grunde, eine Schmiermittelzusammensetzung bereitzustellen, die ein Antioxidans aufweist, mit dem die oben genannten Nachteile zumindest teilweise ausgeräumt werden können.The invention was based on the object of providing a lubricant composition which has an antioxidant with which the above-mentioned disadvantages can be at least partially eliminated.
Diese Aufgabe wird gelöst durch die Verwendung einer Schmiermittelzusammensetzung, die ein Basisöl sowie Hydroxytyrosol und/oder Ester hiervon enthält zur Schmierung der Oberflächen von Gleitpartnern in einem tribologischen System.This problem is solved by using a lubricant composition which contains a base oil and hydroxytyrosol and/or esters thereof for lubricating the surfaces of sliding partners in a tribological system.
Hydroxytyrosol gehört zur Familie der natürlichen Polyphenole und weist die folgende Strukturformel auf:
Es ist bekannt, dass Hydroxytyrosol antioxidative Eigenschaften aufweist. Für den Fachmann war jedoch überraschend, dass es gleichwertige oder bezogen auf die Einsatzkonzentration sogar bessere antioxidative Eigenschaften als in der Praxis üblicherweise verwendete synthetische Antioxidantien aufweist, sowie dass seine Zugabe zu gängigen Basisölen möglich ist, ohne deren funktionelle Eigenschaften zu verschlechtern.Hydroxytyrosol is known to have antioxidant properties. However, it was surprising to the person skilled in the art that it has equivalent or, based on the concentration used, even better antioxidant properties than synthetic antioxidants commonly used in practice, and that it can be added to common base oils without impairing their functional properties.
Erfindungsgemäß können auch Ester des Hydroxytyrosols eingesetzt werden. Besonders bevorzugt sind Ester, die eine Löslichkeit in dem jeweiligen Basisöl bei 25°C von mindestens 0,1 g/l, beispielsweise von 0,1 bis 5 g/l haben. Dabei kann das Hydroxytyrosol in der Schmiermittelzusammensetzung auch nur zum Teil als Ester vorliegen. Erfindungsgemäß besonders geeignete Ester sind Carbonsäureester, wie weiter unten näher diskutiert. Im Folgenden sollen, wenn sinnvoll, bei Bezugnahmen auf Hydroxytyrosol, auch dessen Ester umfasst sein.Esters of hydroxytyrosol can also be used according to the invention. Particular preference is given to esters which have a solubility in the respective base oil at 25° C. of at least 0.1 g/l, for example from 0.1 to 5 g/l. The hydroxytyrosol can also only be partially present in the lubricant composition as an ester. Esters that are particularly suitable according to the invention are carboxylic acid esters, as discussed in more detail below. Below should if useful, when referring to hydroxytyrosol, its esters should also be included.
Es ist grundsätzlich möglich, Hydroxytyrosol in reiner Form einzusetzen. Um die Löslichkeit von Hydroxytyrosol zu erhöhen, ist es in einer Ausführungsform der Erfindung bevorzugt, dass die Schmiermittelzusammensetzung solubilisiertes Hydroxytyrosol enthält. Dabei ist unter dem Begriff "solubilisiertes Hydroxytyrosol" Hydroxytyrosol zu verstehen, dessen Löslichkeit im Bezug auf das jeweils verwendete Basisöl durch Hinzufügen eines Solubilisierungsmittels erhöht worden ist. Art und Menge des Solubilisierungsmittels ist unter anderem abhängig von dem jeweils verwendeten Basisöl, den erwünschten Lösungseigenschaften des Hydroxytyrosols sowie den avisierten Verwendungen der Schmiermittelzusammensetzungen. Insbesondere sollen auch Verbindungen, die mit dem Hydroxytyrosol eine chemische Verbindung eingehen, beispielsweise unter Ausbildung von Estern mit dem Begriff Solubilisierungsmittel umfasst werden.In principle it is possible to use hydroxytyrosol in pure form. In order to increase the solubility of hydroxytyrosol, in one embodiment of the invention it is preferred that the lubricant composition contains solubilized hydroxytyrosol. The term “solubilized hydroxytyrosol” means hydroxytyrosol whose solubility has been increased in relation to the base oil used by adding a solubilizing agent. The type and amount of the solubilizing agent depends, among other things, on the base oil used, the desired dissolving properties of the hydroxytyrosol and the intended uses of the lubricant compositions. In particular, compounds that enter into a chemical bond with the hydroxytyrosol, for example to form esters, should also be included in the term solubilizing agent.
Geeignete Solubilisierungsmittel für Polyphenole sind bekannt und beispielsweise in den Druckschriften
Ohne sich erfindungsgemäß auf einen Mechanismus festzulegen, wird vermutet, dass das Hydroxytyrosol mit den Carbonsäuren Ester bildet, wodurch die Löslichkeit des Hydroxytyrosols erhöht wird.Without committing to a mechanism according to the invention, it is assumed that the hydroxytyrosol forms esters with the carboxylic acids, which increases the solubility of the hydroxytyrosol.
Mithin umfasst die Schmiermittelzusammensetzung in einer bevorzugten Ausführungsform der Erfindung zumindest anteilig Hydroxytyrosol-Carbonsäureester, insbesondere Ester aus Hydroxytyrosol und C2-10-Carbonsäuren, wobei die C2-10-Carbonsäuren verzweigt und/oder unverzweigt vorliegen können, einen oder mehrere Substitutenten, insbesondere Hydroxygruppen und/oder eine oder mehrere Carbonsäuregruppen aufweisen können. Besonders bevorzugt umfasst die Schmiermittelzusammensetzung zumindest anteilig Ester aus Hydroxytyrosol und Hydroxycarbonsäuren mit mindestens 2, vorzugsweise 3 Carbonsäuregruppen. Ebenfalls bevorzugt umfasst die Schmiermittelzusammensetzung zumindest anteilig Ester aus Hydroxytyrosol und Hydroxycarbonsäuren mit mindestens 2, vorzugsweise 3 Hydroxygruppen und/oder Ester aus Hydroxytyrosol und Hydroxycarbonsäuren mit mindestens 2, vorzugsweise 3 Hydroxygruppen und mindestens 2, vorzugsweise 3 Carbonsäuregruppen. Erfindungsgemäß ebenfalls besonders bevorzugt umfasst die Schmiermittelzusammensetzung zumindest anteilig Ester aus Hydroxytyrosol und Carbonsäuren, ausgewählt aus der Gruppe bestehend aus Zitronensäure, Apfel-, Fumar-, Glucon-, Glycol-, Milch-, Oxal-, Wein-, Mandel-Salicylsäure und/oder Gemischen hiervon. Ganz besonders bevorzugt umfasst die Schmiermittelzusammensetzung zumindest anteilig Ester aus Hydroxytyrosol und Zitronensäure.Therefore, in a preferred embodiment of the invention, the lubricant composition comprises at least a portion of hydroxytyrosol carboxylic acid esters, in particular esters of hydroxytyrosol and C 2 - 10 carboxylic acids, where the C 2 - 10 carboxylic acids can be branched and / or unbranched, one or more substituents, in particular May have hydroxy groups and/or one or more carboxylic acid groups. Particularly preferably, the lubricant composition comprises at least a proportion of esters of hydroxytyrosol and hydroxycarboxylic acids with at least 2, preferably 3, carboxylic acid groups. The lubricant composition also preferably comprises at least a proportion of esters of hydroxytyrosol and hydroxycarboxylic acids with at least 2, preferably 3 hydroxyl groups and/or esters of hydroxytyrosol and hydroxycarboxylic acids with at least 2, preferably 3 hydroxyl groups and at least 2, preferably 3 carboxylic acid groups. Also particularly preferred according to the invention, the lubricant composition comprises at least a proportion of esters of hydroxytyrosol and carboxylic acids, selected from the group consisting of citric acid, malic, fumaric, gluconic, glycolic, lactic, oxalic, tartaric, mandelic salicylic acid and/or Mixtures thereof. Very particularly preferably, the lubricant composition comprises at least a proportion of esters of hydroxytyrosol and citric acid.
Zweckmäßigerweise enthält die Schmiermittelzusammensetzung Hydroxytyrosol und/oder dessen Ester in einer oxidationshemmenden Menge. In einer bevorzugten Ausführungsform der Erfindung beträgt der Anteil an Hydroxytyrosol und/oder an dessen Estern von 0,01 Gew.% bis 2 Gew.% und/oder von von 0,1 Gew. % bis 2 Gew. % und/oder von von 0, 1 Gew.% bis 1,5 Gew.%, und/oder von 0,01 Gew.% bis 0,5 Gew.%, und/oder von 0, 05 Gew.% bis 1 Gew.%, noch bevorzugter von 0,1 Gew.% bis 1 Gew.%, noch bevorzugter von 0,1 Gew.% bis 0,5 Gew.% und insbesondere von 0,25 Gew.% bis 0,35 Gew.%, jeweils bezogen auf das Gesamtgewicht der Schmiermittelzusammensetzung.The lubricant composition expediently contains hydroxytyrosol and/or its esters in an oxidation-inhibiting amount. In a preferred embodiment of the invention, the proportion of hydroxytyrosol and/or its esters is from 0.01% by weight to 2% by weight and/or from 0.1% by weight to 2% by weight and/or from 0.1% by weight to 1.5% by weight, and/or from 0.01% by weight to 0.5% by weight, and/or from 0.05% by weight to 1% by weight, more preferably from 0.1% by weight to 1% by weight, more preferably from 0.1% by weight to 0.5% by weight and in particular from 0.25% by weight to 0.35% by weight, in each case based on that Total weight of the lubricant composition.
Weiter bevorzugt beträgt die Menge an Solubilisierungsmittel in der Schmiermittelzusammensetzung, bezogen auf die Gesamtmenge von Hydroxytyrosol und Solubilisierungsmittel, vorteilhafter Weise 0,5 bis 4 Gew.%, noch bevorzugter von 0,5 bis 3,5 Gew.%, noch bevorzugter von 0,5 bis 3 Gew.%, noch bevorzugter von 1 bis 3 Gew.%, noch bevorzugter von 1,5 bis 3 Gew.% und insbesondere von 1,5 bis 3 Gew.%.More preferably, the amount of solubilizing agent in the lubricant composition, based on the total amount of hydroxytyrosol and solubilizing agent, is advantageously 0.5 to 4% by weight, more preferably from 0.5 to 3.5% by weight, even more preferably from 0. 5 to 3% by weight, more preferably from 1 to 3% by weight, even more preferably from 1.5 to 3% by weight and in particular from 1.5 to 3% by weight.
Unter einem Basisöl sind die üblichen für die Herstellung von Schmierstoffen verwendeten Basisflüssigkeiten, insbesondere Öle, die den Gruppen I, II, III, IV oder V nach der Klassifizierung des American Petroleum Institute (API) zugeordnet werden können, zu verstehen. Besonders bevorzugte Basisöle sind ausgewählt aus der Gruppe bestehend aus Estern, insbesondere synthetischen Estern, Polyglykolen, naphtenischen und/oder aromatischen Mineralölen, synthetischen Kohlenwasserstoffen, Phenylethern, Polyalphaolefinen, nativen Basisölen und Derivaten von nativen Ölen und/oder Gemischen hiervon. Erfindungsgemäß besonders bevorzugt sind dabei Ester, insbesondere synthetische Ester, und/oder Gemische von Estern, insbesondere synthetischen Estern, nativen Basisölen und Polyglycolen mit synthetischen Kohlenwasserstoffen und/oder Polyalphaolefinen.A base oil is understood to mean the usual base fluids used for the production of lubricants, in particular oils that can be assigned to groups I, II, III, IV or V according to the classification of the American Petroleum Institute (API). Particularly preferred base oils are selected from the group consisting of esters, in particular synthetic esters, polyglycols, naphthenic and/or aromatic mineral oils, synthetic hydrocarbons, phenyl ethers, polyalphaolefins, native base oils and derivatives of native oils and/or mixtures thereof. Particularly preferred according to the invention are esters, in particular synthetic esters, and/or mixtures of esters, in particular synthetic esters, native base oils and polyglycols with synthetic hydrocarbons and/or polyalphaolefins.
In einer bevorzugten Ausführungsform der Erfindung ist das Basisöl ausgewählt aus der Gruppe bestehend aus einem Ester einer aromatischen oder aliphatischen Di-, Tri- oder Tetracarbonsäure mit einem oder in Mischung vorliegenden C7- bis C22-Alkoholen, aus einem Polyphenylether oder alkyliertem Diphenylether, aus einem Ester von Trimethylolpropan, Pentaerythrit oder Dipentaerythrit mit aliphatischen C7- bis C22- Carbonsäuren, aus C18-Dimer-säureestern, hergestellt aus C7- bis C22-Alkoholen, aus Komplexestern, als Einzelkomponenten oder in beliebiger Mischung.In a preferred embodiment of the invention, the base oil is selected from the group consisting of an ester of an aromatic or aliphatic di-, tri- or tetracarboxylic acid with one or in a mixture of C 7 - to C 22 -alcohols, from a polyphenyl ether or alkylated diphenyl ether, from an ester of trimethylolpropane, pentaerythritol or dipentaerythritol with aliphatic C 7 - to C 22 - carboxylic acids, from C 18 -dimer acid esters, prepared from C 7 - to C 22 -alcohols, from complex esters, as individual components or in any mixture.
Besonders bevorzugte Basisöle sind Ester, insbesondere synthetische Ester, sowie deren Gemische mit synthetischen Kohlenwasserstoffen und/oder Polyalphaolefinen. So wurde in praktischen Versuchen gefunden, dass diese Basisöle ein besonders gutes Aufnahmevermögen für Hydroxytyrosol, insbesondere für Hydroxytyrosol, das mit Zitronensäure solubilisiert wurde, zeigen.Particularly preferred base oils are esters, in particular synthetic esters, and mixtures thereof with synthetic hydrocarbons and/or polyalphaolefins. In practical tests it was found that these base oils have a particularly good absorption capacity for hydroxytyrosol, in particular for hydroxytyrosol that has been solubilized with citric acid.
Ebenfalls bevorzugte Basisöle sind native Öle auf Triglyceridbasis, vorzugsweise mit einem hohen Ölsäureanteil, insbesondere ausgewählt aus der Gruppe bestehend aus Sonnenblumenöl, Rapsöl, Rizinusöl, Leinöl, Maisöl, Safloröl, Sojabohnenöl, Leinsamenöl, Erdnußöl, "Lesquerella"-Öl, Palmöl und deren Derivaten.Also preferred base oils are native triglyceride-based oils, preferably with a high oleic acid content, in particular selected from the group consisting of sunflower oil, rapeseed oil, castor oil, linseed oil, corn oil, safflower oil, soybean oil, linseed oil, peanut oil, "lesquerella" oil, palm oil and their derivatives .
Ebenfalls bevorzugte Basisöle sind Triglyceride mit einem Gehalt (bezogen auf die gebundenen Fettsäuren) von mindestens 50 Gew.% Ölsäure und weniger als 10 Gew.% mehrfach ungesättigter Fettsäuren und deren Derivate.Also preferred base oils are triglycerides with a content (based on the bound fatty acids) of at least 50% by weight of oleic acid and less than 10% by weight of polyunsaturated fatty acids and their derivatives.
Die Basisöle können einzeln oder in Kombination (falls mischbar) verwendet werden. Besonders bevorzugte Basisöle weisen eine Viskosität im Bereich von 10 mm2/s bis 1000 mm2/s auf, gemessen bei 40 °C.The base oils can be used individually or in combination (if mixable). Particularly preferred base oils have a viscosity in the range from 10 mm 2 /s to 1000 mm 2 /s, measured at 40 °C.
In einer Ausführungsform der Erfindung beträgt der Anteil des Basisöls in der erfindungsgemäßen Schmiermittelzusammensetzung von 99,99 Gew.% bis 90 Gew.%, noch bevorzugter von 99,5 Gew.% bis 94,5 Gew.% und insbesondere von 99,75 Gew.% bis 94,75 Gew.%, jeweils bezogen auf das Gesamtgewicht der Schmiermittelzusammensetzung. Dabei beziehen sich die vorgenannten Werte insbesondere auf Schmiermittelzusammensetzungen, die als Schmieröl, d.h. im Wesentlichen ohne Verdicker vorliegen. Liegt die Schmiermittelzusammensetzung dagegen als Schmierfett, d.h. mit Verdicker vor, beträgt der Anteil des Basisöls in der erfindungsgemäßen Schmiermittelzusammensetzung vorzugsweise von 70 Gew % bis 97,00 Gew %.In one embodiment of the invention, the proportion of the base oil in the lubricant composition according to the invention from 99.99% by weight to 90% by weight, more preferably from 99.5% by weight to 94.5% by weight and in particular from 99.75% by weight to 94.75% by weight, each based on the total weight of the lubricant composition. The aforementioned values relate in particular to lubricant compositions that are present as lubricating oil, ie essentially without thickeners. If, on the other hand, the lubricant composition is in the form of a lubricating grease, ie with a thickener, the proportion of base oil in the lubricant composition according to the invention is preferably from 70% by weight to 97.00% by weight.
Hydroxytyrosol und/oder dessen Ester können als alleiniges Antioxidans oder in Kombination mit weiteren Antioxidantien vorliegen. Erfindungsgemäß besonders geeignete weitere Antioxidantien sind die folgenden Verbindungen: styrolisierte Diphenylamine, diaromatische Amine, Phenolharze, Thiophenolharze, Phosphite, butyliertes Hydroxytoluol, butyliertes Hydroxyanisol, Phenylalpha-naphthylamin, Phenyl-beta-naphthylamin, octyliertes/butyliertes Diphenylamin, di-alpha-Tocopherol, di-tert-butyl-Phenyl, Benzolpropansaure, schwefelhaltige Phenolverbindungen und Mischungen dieser Komponenten.Hydroxytyrosol and/or its esters can be present as the sole antioxidant or in combination with other antioxidants. Further antioxidants which are particularly suitable according to the invention are the following compounds: styrenated diphenylamines, diaromatic amines, phenolic resins, thiophenolic resins, phosphites, butylated hydroxytoluene, butylated hydroxyanisole, phenylalpha-naphthylamine, phenyl-beta-naphthylamine, octylated/butylated diphenylamine, di-alpha-tocopherol, di -tert-butyl-phenyl, benzenepropane acid, sulfur-containing phenolic compounds and mixtures of these components.
Weiterhin kann die Schmiermittelzusammensetzung Korrosionsschutzadditive, Metalldesaktivatoren, Verschleißschutzadditive und/oder lonen-Komplexbildner enthalten. Hierzu zählen Triazole, Imidazoline, N-Methylglycin (Sarcosin), Benzotriazolderivate, N,N-Bis(2-ethylhexyl)-ar-methyl-1 H-benzotriazol-1-methanamin; n-Methyl-N(1-oxo-9-octadecenyl)glycin, Gemische aus Phosphorsäure und Mono-und Diisooctylester, umgesetzt mit (C11-14)-Alkylaminen, Gemische aus Phosphorsäure und Mono-und Diisooctylester, umgesetzt mit tert-Alkylamin und primären (C12-14)-Aminen, Dodekansäure, Triphenylphosphorthionat und Aminphosphate. Kommerziell erhältliche Additive sind die folgenden: IRGAMET® 39, IRGACOR® DSS G, Amin O; SARKOSYL® O (Ciba), COBRATEC® 122, CUVAN® 303, VANLUBE®9123, CI-426, CI-426EP, CI-429 und CI-498.Furthermore, the lubricant composition can contain corrosion protection additives, metal deactivators, wear protection additives and/or ion complexing agents. These include triazoles, imidazolines, N-methylglycine (sarcosine), benzotriazole derivatives, N,N-bis(2-ethylhexyl)-ar-methyl-1 H-benzotriazole-1-methanamine; n-Methyl-N(1-oxo-9-octadecenyl)glycine, mixtures of phosphoric acid and mono- and di-isooctyl esters, reacted with (C 11-14 )-alkylamines, mixtures of phosphoric acid and mono- and di-isooctyl esters, reacted with tert-alkylamine and primary (C 12-14 ) amines, dodecanoic acid, triphenylphosphorothionate and amine phosphates. Commercially available additives are the following: IRGAMET ® 39, IRGACOR ® DSS G, Amin O; SARKOSYL ® O (Ciba), COBRATEC ® 122, CUVAN ® 303, VANLUBE ® 9123, CI-426, CI-426EP, CI-429 and CI-498.
Weitere denkbare Verschleißschutzadditive sind Amine, Aminphosphate, Phosphate, Thiophosphate, Phosphorthionate und Mischungen dieser Komponenten. Zu den kommerziell erhältlichen Verschleißschutzadditiven gehören IRGALUBE®TPPT, IRGALUBE® 232, IRGALUBE® 349, IRGALUBE®211 und ADDITIN® RC3760 Liq 3960, FIRC-SHUN® FG 1505 und FG 1506, NA-LUBE® KR-015FG, LUBEBOND®, FLUORO®FG, SYNALOX® 40-D, ACHESON® FGA 1820 und ACHESON®FGA 1810.Other conceivable wear protection additives are amines, amine phosphates, phosphates, thiophosphates, phosphorothionates and mixtures of these components. Commercially available anti-wear additives include IRGALUBE ® TPPT, IRGALUBE ® 232, IRGALUBE ® 349,
Des Weiteren kann die Schmiermittelzusammensetzung Festschmierstoffe wie PTFE, BN, Pyrophosphat, Zn-Oxid, Mg-Oxid, Pyrophosphate, Thiosulfate, Mg-Carbonat, Ca-Carbonat, Ca-Stearat, Zn-Sulfid, Mo-Sulfid, W-Sulfid, Sn-Sulfid, Graphite, Graphen, Nano-Tubes, SiO2-Modifikationen oder eine Mischung daraus enthalten.Furthermore, the lubricant composition can include solid lubricants such as PTFE, BN, pyrophosphate, Zn oxide, Mg oxide, pyrophosphates, thiosulfates, Mg carbonate, Ca carbonate, Ca stearate, Zn sulfide, Mo sulfide, W sulfide, Sn -Sulfide, graphite, graphene, nano-tubes, SiO 2 modifications or a mixture thereof.
Die Schmiermittelzusammensetzung kann darüber hinaus Verdicker, insbesondere Metallseifen, Metallkomplexseifen, Bentonite, Harnstoffe, Silikate, Sulfonate und/oder Polyimide enthalten. Dabei beträgt der Anteil des Verdickers in der erfindungsgemäßen Schmiermittelzusammensetzung vorzugsweise von 1 Gew.% bis 20 Gew.%, jeweils bezogen auf das Gesamtgewicht der Schmiermittelzusammensetzung.The lubricant composition can also contain thickeners, in particular metal soaps, metal complex soaps, bentonites, ureas, silicates, sulfonates and/or polyimides. The proportion of thickener in the lubricant composition according to the invention is preferably from 1% by weight to 20% by weight, based on the total weight of the lubricant composition.
Beschrieben wird ferner ein Verfahren zur Herstellung einer Schmiermittelzusammensetzung, vorzugsweise einer Schmiermittelzusammensetzung gemäß einer oder mehrerer der erfindungsgemäßen Ausführungsformen, umfassend folgende Schritte:
- Bereitstellung eines Basisöls,
- Vermischen des Basisöls mit Hydroxytyrosol und/oder dessen Estern, wodurch die Schmiermittelzusammensetzung erhalten wird.
- Providing a base oil,
- Mixing the base oil with hydroxytyrosol and/or its esters, thereby obtaining the lubricant composition.
Besonders geeignete Ausführungsformen für Basisöle, Ester des Hydroxytyrosols, sowie Solubilisierungsmittel und/oder Additive sind die im Rahmen der vorliegenden Erfindung im Bezug auf die erfindungsgemäße Schmiermittelzusammensetzung diskutierten.Particularly suitable embodiments for base oils, esters of hydroxytyrosol, as well as solubilizing agents and/or additives are those discussed in the context of the present invention in relation to the lubricant composition according to the invention.
In einer besonders bevorzugten Ausführungsform der Erfindung findet das Vermischen des Basisöls mit Hydroxytyrosol und/oder dessen Estern in Gegenwart eines Solubilisierungsmittels, insbesondere in Gegenwart eines Solubilisierungsmittels, wie im Rahmen der vorliegenden Erfindung im Bezug auf die erfindungsgemäße Schmiermittelzusammensetzung diskutiert, statt.In a particularly preferred embodiment of the invention, the base oil is mixed with hydroxytyrosol and/or its esters in the presence of a solubilizing agent, in particular in the presence of a solubilizing agent, as discussed in the context of the present invention in relation to the lubricant composition according to the invention.
Das Verfahren kann noch weitere Verfahrensschritte umfassen, in denen beispielsweise die im Bezug auf die erfindungsgemäße Schmiermittelzusammensetzung beschriebenen weiteren Komponenten, wie weitere Antioxidantien, Verdicker, Korrosionsschutzadditive, Metalldesaktivatoren, lonen-Komplexbildner und/oder Festschmierstoffe, eingebracht werden.The process can also include further process steps in which, for example, the further components described in relation to the lubricant composition according to the invention, such as further antioxidants, thickeners, corrosion protection additives, metal deactivators, ion complexing agents and/or solid lubricants, are introduced.
Die Schmiermittelzusammensetzung eignet sich zur Schmierung der verschiedensten Oberflächen. Insofern betrifft die vorliegende Erfindung die Verwendung der Schmiermittelzusammensetzung zur Schmierung der Oberflächen von Gleitpartnern in einem tribologischen System. Besonders bevorzugt wird die Schmiermittelzusammensetzung als Zwischenstoff zur Verringerung von Reibung und/oder Verschleiß in einem tribologischen System eingesetzt. In einer weiteren bevorzugten Ausführungsform wird die Schmiermittelzusammensetzung gleichzeitig zur Kraftübertragung, Schwingungsdämpfung und/oder als Korrosionsschutz eingesetzt. Besonders großen Nutzen hat die Schmiermittelzusammensetzung naturgemäß bei tribologischen und rheologischen Systemen, die großen oxidativen Belastungen ausgesetzt sind. Eine bevorzugte Ausführungsform der Erfindung betrifft mithin die Verwendung der Schmiermittelzusammensetzung für H1-Hochtemperaturanwendungen für Lebensdauer- und/oder Verbrauchsschmierung in Bauteilen wie insbesondere Ketten, Getrieben, Lagern oder Armaturen und/oder Marinebauteilen.The lubricant composition is suitable for lubricating a wide variety of surfaces. In this respect, the present invention relates to the use of the lubricant composition for lubricating the surfaces of sliding partners in a tribological system. The lubricant composition is particularly preferably used as an intermediate to reduce friction and/or wear in a tribological system. In a further preferred embodiment, the lubricant composition is used simultaneously for power transmission, vibration damping and/or as corrosion protection. Naturally, the lubricant composition is particularly useful tribological and rheological systems that are exposed to high oxidative stress. A preferred embodiment of the invention therefore relates to the use of the lubricant composition for H1 high-temperature applications for lifetime and/or consumption lubrication in components such as, in particular, chains, gears, bearings or fittings and/or marine components.
Im Folgenden wird die Erfindung anhand verschiedener Beispiele näher erläutert.The invention is explained in more detail below using various examples.
- Figur 1:Figure 1:
- Gedeckelte Verdampfungsschalen in der Seitenansicht.Lidded evaporation dishes in side view.
- Figur 2:Figure 2:
- Gedeckelte Verdampfungsschalen in der Aufsicht.Top view of covered evaporation dishes.
- Figur 3:Figure 3:
- Abdampfverhalten verschiedener Schmiermittelzusammensetzungen.Evaporation behavior of various lubricant compositions.
- Figur 4:Figure 4:
- Scheinbar dynamische Viskosität verschiedener Schmiermittelzusammensetzungen.Apparently dynamic viscosity of various lubricant compositions.
- Figur 5:Figure 5:
- Scheinbar dynamische Viskosität verschiedener Schmiermittelzusammensetzungen.Apparently dynamic viscosity of various lubricant compositions.
- Figur 6:Figure 6:
- Illustration der Messung von Oxidationsbeginn und Grenzwert (Treshhold).Illustration of the measurement of oxidation start and threshold value (threshold).
- Figur 7:Figure 7:
- Oxidationsbeginn ausgewählter Zusammensetzungen.Start of oxidation of selected compositions.
- Figur 8:Figure 8:
- Grenzwert (Treshhold) des Oxidationsverlaufs ausgewählter Zusammensetzungen.Limit value (threshold) of the oxidation process of selected compositions.
- Figur 9:Figure 9:
- Oxidationsbeginn ausgewählter Zusammensetzungen.Start of oxidation of selected compositions.
- Figur 10:Figure 10:
- Grenzwert (Treshhold) des Oxidationsverlaufs ausgewählter Zusammensetzungen.Limit value (threshold) of the oxidation process of selected compositions.
- Figur 11:Figure 11:
- Oxidationsbeginn ausgewählter Zusammensetzungen.Start of oxidation of selected compositions.
- Figur 12:Figure 12:
- Grenzwert (Treshhold) des Oxidationsverlaufs ausgewählter Zusammensetzungen.Limit value (threshold) of the oxidation process of selected compositions.
- Figur 13:Figure 13:
- Oxidationsbeginn ausgewählter Zusammensetzungen.Start of oxidation of selected compositions.
- Figur 14:Figure 14:
- Grenzwert (Treshhold) des Oxidationsverlaufs ausgewählter Zusammensetzungen.Limit value (threshold) of the oxidation process of selected compositions.
- Figur 15:Figure 15:
- Oxidationsbeginn ausgewählter Zusammensetzungen.Start of oxidation of selected compositions.
- Figur 16:Figure 16:
- Grenzwert (Treshhold) des Oxidationsverlaufs ausgewählter Zusammensetzungen.Limit value (threshold) of the oxidation process of selected compositions.
Es werden verschiedene mit Antioxidationsmitteln versehene Schmiermittelzusammensetzungen hergestellt: Bei dem eingesetzten Hydroxytyrosol handelt es sich um ein mit Zitronensäure (etwa 2 Gew.%, bezogen auf die Gesamtmenge von Hydroxytyrosol und Zitronensäure) solubilisiertes Hydroxytyrosol.
2.1 Das Abdampfverhalten und die scheinbar dynamische Viskosität der erfindungsgemäßen Zusammensetzung 1 und der Vergleichsbeispiele 1, 2, 3 und 4 werden gemessen (Gedeckelte Schälchentests, Gasaustausch findet statt). Hierzu wird über eine Mehrfachbestimmung (min. 3-fach-Bestimmung) das Abdampfverhalten und die Veränderung der scheinbar dynamischen Viskosität [mPas] als Kriterium fortschreitender Oxidation unter thermischer Belatung (jeweils 72h Lagerung bei 230°C, Umluftofen) als vergleichende Messung bestimmt. Pro Prüfung beträgt die Probenmenge 5g (+/- 0,1 g). Durch Rückwaage wird das Abdampfverhalten in Gew.% bestimmt. Ebenfalls vergleichend wird durch die rheologische Bestimmung der scheinbar dynamischen Viskosität (Anton Paar-Rheometer rotierend, Scherrate 300-1) Rückschluss auf die thermische Alterung (z.B. Polymerisation) bzw. dem Schutz vor thermischer Alterung getroffen. Es werden gedeckelte Verdampfungsschalen aus Aluminium, Durchmesser 50 mm eingesetzt. Die 2 im Deckel befindlichen gegenüberliegenden Löcher haben einen Durchmesser von 5 mm und sind 10 mm vom Rand entfernt (siehe
Die Ergebnisse sind in der nachfolgenden Tab. 2 und in den
Es zeigt sich, dass Hydroxytyrosol keinen merklichen Einfluss auf das Abdampfverhalten hat. Ferner zeigt sich, dass Hydroxytyrosol als phenolischer Antioxidant hinsichtlich der Unterbindung radikalischer Alterungsprozesse eine vergleichbare Leistungsfähigkeit zeigt wie die im Stand der Technik als effizienter eingeschätzten Amine und deutlich besser wirkt als andere Phenole.It turns out that hydroxytyrosol has no noticeable influence on the evaporation behavior. Furthermore, it is shown that hydroxytyrosol, as a phenolic antioxidant, has a comparable performance in terms of preventing radical aging processes as the amines, which are considered to be more efficient in the prior art, and works significantly better than other phenols.
2.2 Um den Einfluss der Konzentration von Hydroxytyrosol bestimmen zu können, wurden zusätzlich die erfindungsgemäßen Zusammensetzungen 5, 6, 7 und 8 vergleichend untersucht. Die Ergebnisse sind in der nachfolgenden Tab. 3 und in
Es zeigt sich, dass Hydroxytyrosol bereits in sehr geringer Konzentration eine hohe Wirksamkeit hat.It turns out that hydroxytyrosol is highly effective even in very low concentrations.
Der Oxidationsbeginn und der Grenzwert (Treshhold) des Oxidationsverlaufs ausgewählter Zusammensetzungen aus Beispiel 1 wird mittels dynamischer DSC (Heizrate 1°C/min) bestimmt. Bei der DSC-Messung wird vergleichend innerhalb eines Basisöles die Reaktionskinetik überwacht. Sichtbar wird dabei die chemische Dynamik innerhalb eines Stoffsystems, aus welcher wiederum auf das Oxidationsverhalten in Bezug auf den thermischen Energieeintrag geschlossen wird.The start of oxidation and the threshold value (threshold) of the oxidation course of selected compositions from Example 1 are determined using dynamic DSC (heating rate 1 ° C/min). During DSC measurement, the reaction kinetics are comparatively monitored within a base oil. The chemical dynamics within a material system become visible, from which conclusions can be drawn about the oxidation behavior in relation to the thermal energy input.
Der Wert "Oxidationsbeginn" beschreibt eine erste signifikate Potentialänderung zum thermischen Energieeintrag und verweist somit auf die Verzögerung, welche eine Stoffmischung im Vergleich zu einer anderen Stoffmischung erfährt. Der "Grenzwert" (Treshhold) beschreibt den Fortschritt des Alterungs/Oxidationprozesses innerhalb des Stoffgemisches. Dies verweist indirekt auf die Reaktionsgeschwindigkeit des Oxidationsvorganges. Dieser Zusammenhang ist in
Figuren dargestellten Ergebnisse erzielt.
Es zeigt sich, dass die erfindungsgemäße Zusammensetzung 1 eine höhere Oxidationsresistenz als die Vergleichsbeispiele hat.
Es zeigt sich, dass die erfindungsgemäße Zusammensetzung 2 eine höhere Oxidationsresistenz als das reine Basisöl (Vergleichsbeispiel 5) und als das mit der gleichen Menge an Antioxidationsmittel versehene Vergleichsbeispiel 6 hat. Darüber hinaus liegt der für die erfindungsgemäße Zusammensetzung bestimmte Oxidationsbeginn über und der Grenzwert nur geringfügig unterhalb des Grenzwerts des Vergleichsbeispiels 7 - obwohl dieses mehr als die zehnfache Menge an Antioxidationsmittel aufweist.
Es zeigt sich, dass die erfindungsgemäße Zusammensetzung 4 eine höhere Oxidationsresistenz als die Vergleichsbeispiele hat.
Es zeigt sich, dass die erfindungsgemäße Zusammensetzung 3 eine höhere Oxidationsresistenz als die Vergleichsbeispiele hat.
Es zeigt sich, dass Hydroxytyrosol bereits bei sehr geringen Einsatzkonzentrationen eine hohe antioxidative Wirkung hat.It turns out that hydroxytyrosol has a high antioxidant effect even at very low concentrations.
Claims (11)
- Use of a lubricant composition comprising a base oil and hydroxytyrosol and/or esters thereof for lubrication of the surfaces of lubrication partners in a tribological system.
- Use according to Claim 1, characterized in that the esters have a solubility in the base oil at 25°C of at least 0.1 g/l, for example of 0.1 to 5.0 g/l.
- Use according to Claim 1 or 2, characterized in that the esters are at least partly carboxylic esters, especially esters of hydroxytyrosol and C2-10 carboxylic acids that may be branched and/or unbranched, and may have one or more substituents, especially hydroxyl groups and/or one or more carboxylic acid groups.
- Use according to one or more of the preceding claims, characterized in that the esters are at least partly esters of hydroxytyrosol and citric acid.
- Use according to one or more of the preceding claims, characterized in that the hydroxytyrosol is solubilized hydroxytyrosol.
- Use according to one or more of the preceding claims, characterized in that the solubility of the hydroxytyrosol has been increased by adding, as solubilizing agent, C2-10 carboxylic acids that may be branched and/or unbranched, and may have one or more substituents, especially hydroxyl groups and/or one or more carboxylic acid groups.
- Use according to one or more of the preceding claims, characterized in that the proportion of hydroxytyrosol and/or esters thereof is from 0.01% by weight to 2% by weight, based on the total weight of the lubricant composition.
- Use according to one or more of the preceding claims, characterized in that the base oil is selected from the group consisting of esters, polyglycols, naphthenic and/or aromatic mineral oils, synthetic hydrocarbons, phenyl ethers, polyalphaolefins, native base oils and derivatives of native oils and/or mixtures thereof.
- Use according to one or more of the preceding claims, characterized in that the base oil has a viscosity, measured at 40°C, in the range from 10 mm2/s to 1000 mm2/s.
- Use according to one or more of the preceding claims, characterized in that the base oil is selected from the group consisting of an ester of an aromatic or aliphatic di-, tri- or tetracarboxylic acid with one or a mixture of C7 to C22 alcohol(s), of a polyphenyl ether or alkylated diphenyl ether, of an ester of trimethylolpropane, pentaerythritol or dipentaerythritol with aliphatic C7 to C22 carboxylic acids, of C18 dimer acid esters, prepared from C7 to C22 alcohols, or of complex esters, as individual components or in any mixture.
- Use according to one or more of the preceding claims for H1 high-temperature applications for lifetime lubrication and/or on-demand lubrication in components such as, in particular, chains, gears, bearings, fittings and/or marine components.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102018006661.5A DE102018006661A1 (en) | 2018-08-23 | 2018-08-23 | lubricant composition |
| PCT/EP2019/071417 WO2020038737A1 (en) | 2018-08-23 | 2019-08-09 | Lubricant composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP3841190A1 EP3841190A1 (en) | 2021-06-30 |
| EP3841190B1 true EP3841190B1 (en) | 2023-09-27 |
Family
ID=67614578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19752696.5A Active EP3841190B1 (en) | 2018-08-23 | 2019-08-09 | Use of a lubricant composition |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US11248188B2 (en) |
| EP (1) | EP3841190B1 (en) |
| CN (1) | CN112424320B (en) |
| DE (1) | DE102018006661A1 (en) |
| WO (1) | WO2020038737A1 (en) |
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| GB1271556A (en) | 1969-11-12 | 1972-04-19 | Exxon Research Engineering Co | Oil and fuel compositions |
| US4657686A (en) | 1980-06-12 | 1987-04-14 | Union Oil Company Of California | Lubricating compositions |
| JPS5915477A (en) * | 1982-07-16 | 1984-01-26 | Tanabe Seiyaku Co Ltd | Antioxidant |
| DE3568577D1 (en) | 1984-10-12 | 1989-04-13 | Ciba Geigy Ag | Boron containing thioethers as additives |
| WO1987007637A2 (en) | 1986-06-13 | 1987-12-17 | The Lubrizol Corporation | Phosphorus-containing lubricant and functional fluid compositions |
| JP2617807B2 (en) | 1990-03-16 | 1997-06-04 | 日本石油株式会社 | Engine oil composition |
| JP2859077B2 (en) | 1993-04-09 | 1999-02-17 | 出光興産株式会社 | Lubricating oil composition |
| JP3650629B2 (en) | 1993-10-29 | 2005-05-25 | 東燃ゼネラル石油株式会社 | Lubricating oil composition |
| JPH07258671A (en) | 1994-03-24 | 1995-10-09 | Lubrizol Corp:The | Ash-free low-phosphorus lubricant |
| AU706587B2 (en) | 1994-04-19 | 1999-06-17 | Lubrizol Corporation, The | Lubricating compositions with improved oxidation resistance containing a dispersant and an antioxidant |
| IT1286564B1 (en) | 1996-03-05 | 1998-07-15 | Comiter Trading & Services S R | A PRODUCT BASED ON EXTRA VIRGIN OLIVE OIL, VIRGIN OLIVE OIL OR ENRICHED AND INTEGRATED OLIVE OIL, AND A PROCEDURE FOR |
| CA2420893C (en) * | 2000-09-01 | 2011-11-22 | Creagri, Inc. | Method of obtaining a hydroxytyrosol-rich composition from vegetation water |
| ES2246603B1 (en) * | 2002-07-03 | 2007-06-16 | Consejo Sup. De Investig. Cientificas | PROCEDURE FOR THE PREPARATION OF HYDROXYTIROSOL ESTERS, ESTERS OBTAINED AND USE. |
| WO2007051329A1 (en) | 2005-11-02 | 2007-05-10 | Laboswiss Ag | Method for extracting and solubilizing active substances from organic material, active substance products produced by the method, and the use thereof |
| WO2007074490A1 (en) * | 2005-12-29 | 2007-07-05 | Universita' Degli Studi Di Napoli Federico Ii | Process for producing triacξtylhydroxytyrosol from olive oil mill waste waters for use as stabilized antioxidant |
| EP1897530A1 (en) * | 2006-09-08 | 2008-03-12 | DSMIP Assets B.V. | Skin care composition |
| WO2009013596A2 (en) * | 2007-07-23 | 2009-01-29 | Probelte Pharma, S.A. | Fortification of nutritional products with olive extracts containing hydroxytyrosol and hydroxytyrosol fortified nutritional products |
| EP2070421B1 (en) | 2007-12-13 | 2016-09-14 | Cognis IP Management GmbH | A lipophilic antioxidant |
| DE102009022593A1 (en) * | 2008-06-13 | 2009-12-17 | KLüBER LUBRICATION MüNCHEN KG | Lubricant composition based on natural and renewable raw materials |
| WO2010098337A1 (en) | 2009-02-27 | 2010-09-02 | Ntn株式会社 | Grease composition, grease-packed bearing, universal joint for propeller shaft, lubricating oil composition, and oil-impregnated sintered bearing |
| EP2359702B1 (en) | 2010-01-22 | 2014-06-04 | Symrise AG | Solubilization agent for solubilizing polyphenols, flavonoids and/or diterpenoid glucosides |
| US8895490B2 (en) * | 2010-04-12 | 2014-11-25 | The Lubrizol Corporation | Food grade compressor lubricant |
| ES2387590B1 (en) * | 2010-09-27 | 2013-10-31 | Consejo Superior De Investigaciones Científicas (Csic) | PROCEDURE FOR OBTAINING OILS OR FATS WITH HIGH ANTIOXIDANT CONTENT. |
| US9963656B2 (en) * | 2012-04-12 | 2018-05-08 | Infineum International Limited | Lubricating oil compositions |
| CN104544463A (en) * | 2013-10-16 | 2015-04-29 | 戴留庆 | Efficient and safe antioxidant |
| US9334229B2 (en) * | 2013-11-04 | 2016-05-10 | Eastman Chemical Company | Hydroxytyrosol derivatives, their method of preparation and use in personal care |
| WO2015086516A1 (en) * | 2013-12-09 | 2015-06-18 | Mattias GRAHN | An aqueous lubricant composition, a method for making the same and uses thereof |
| ES2760539T3 (en) * | 2014-10-01 | 2020-05-14 | Cargill Inc | Stabilized oil and procedure for its elaboration |
| DE102014018718A1 (en) * | 2014-12-17 | 2016-06-23 | Klüber Lubrication München Se & Co. Kg | High temperature lubricants |
-
2018
- 2018-08-23 DE DE102018006661.5A patent/DE102018006661A1/en active Pending
-
2019
- 2019-08-09 CN CN201980046512.2A patent/CN112424320B/en active Active
- 2019-08-09 WO PCT/EP2019/071417 patent/WO2020038737A1/en unknown
- 2019-08-09 EP EP19752696.5A patent/EP3841190B1/en active Active
- 2019-08-09 US US17/059,519 patent/US11248188B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| DE102018006661A1 (en) | 2020-02-27 |
| EP3841190A1 (en) | 2021-06-30 |
| US11248188B2 (en) | 2022-02-15 |
| CN112424320B (en) | 2022-11-01 |
| CN112424320A (en) | 2021-02-26 |
| US20210207053A1 (en) | 2021-07-08 |
| WO2020038737A1 (en) | 2020-02-27 |
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