EP2242823B1 - Method for preparing a grease composition - Google Patents
Method for preparing a grease composition Download PDFInfo
- Publication number
- EP2242823B1 EP2242823B1 EP09701564A EP09701564A EP2242823B1 EP 2242823 B1 EP2242823 B1 EP 2242823B1 EP 09701564 A EP09701564 A EP 09701564A EP 09701564 A EP09701564 A EP 09701564A EP 2242823 B1 EP2242823 B1 EP 2242823B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- grease
- substituted
- solution
- 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
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- 239000004519 grease Substances 0.000 title claims description 43
- 239000000203 mixture Substances 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 18
- 239000002199 base oil Substances 0.000 claims description 29
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 24
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 12
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical class C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 239000002480 mineral oil Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 150000003248 quinolines Chemical class 0.000 claims 3
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 29
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 20
- 230000001050 lubricating effect Effects 0.000 description 18
- 239000003921 oil Substances 0.000 description 10
- -1 C-H acidic compounds Chemical class 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000005248 alkyl aryloxy group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000007812 deficiency Effects 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 238000011179 visual inspection Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- XXMBEHIWODXDTR-UHFFFAOYSA-N 1,2-diaminoethanol Chemical class NCC(N)O XXMBEHIWODXDTR-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical class NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- HHMKYMUNEQYWND-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1.C1=CC=C2C(C)=CC(C)(C)NC2=C1 HHMKYMUNEQYWND-UHFFFAOYSA-N 0.000 description 1
- WRGWVXRANTWQOG-UHFFFAOYSA-N 2,4-diethyl-2-methyl-1h-quinoline Chemical compound C1=CC=C2C(CC)=CC(C)(CC)NC2=C1 WRGWVXRANTWQOG-UHFFFAOYSA-N 0.000 description 1
- JNODDICFTDYODH-UHFFFAOYSA-N 2-hydroxytetrahydrofuran Chemical compound OC1CCCO1 JNODDICFTDYODH-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- VIQSRHWJEKERKR-UHFFFAOYSA-L disodium;terephthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 VIQSRHWJEKERKR-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical class OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- 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
- C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
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- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/40—Six-membered ring containing nitrogen and carbon only
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- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/06—Mixtures of thickeners and additives
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
- C10M2203/1025—Aliphatic fractions used as base material
-
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- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
- C10M2203/1085—Residual fractions, e.g. bright stocks used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/126—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/126—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic
- C10M2207/1265—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic used as thickening agent
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/127—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids polycarboxylic
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/127—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids polycarboxylic
- C10M2207/1276—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids polycarboxylic used as thickening agent
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
- C10M2207/1415—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic used as thickening agent
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/16—Naphthenic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/26—Waterproofing or water resistance
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/70—Soluble oils
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Definitions
- the present invention relates to a method for preparing a lubricating composition, in particular a grease.
- Alkyl-substituted quinolines and polymerized derivatives thereof are known as very effective, low cost antioxidants for several uses, including the use in lubricating compositions.
- WO 94/24235 discloses the use of alkyl-substituted 1,2-dihydroquinolines (including monomers, dimers, trimers and tetramers thereof) in motor oils, transmission oils, gear oils, metal working fluids, hydraulic fluids, greases and the like.
- alkyl-substituted 1,2-dihydroquinolines are 2,2,4-trimethyl-1,2-dihydroquinoline, 2-methyl-2,4-diethyl-1,2-dihydroquinoline, 2,2,4,6-tetramethyl-1,2,-dihydroquinoline, 2,2,4,7-tetramethyl-1,2,-dihydroquinoline, 6,6'-bis(2,2,4-trimethyl-1,2,-dihydroquinoline) and the like.
- US 5 246 606 discloses that dimeric, trimeric and tetrameric tetrahydroquinoline derivatives are suitable for stabilising organic materials against light-induced, thermal and/or oxidative degradation. US 5 246 606 suggests to use these compounds amongst others in functional fluids such as lubricants and hydraulic fluids.
- US 2 908 646 relates to lubricating greases containing polymerized dihydroquinoline derivatives. This document teaches that the polymerized dihydroquinoline derivatives may be added directly to the grease mixture or may be added in the form of a solution. In the example of US 2 908 646 , a polymerized 2,2,4-trimethyl-1,2-dihydroquinoline is added during the oil addition at a temperature of 240°F.
- alkyl-substituted quinolines such as 2,2,4-trimethyl-1,2-dihydroquinoline (also referred to as “TMQ”, “TMDQ” and “TMHQ”) and oligomeric (i.e. dimeric, trimeric and tetrameric) derivatives thereof, are widely used as antioxidants, they have a number of disadvantages.
- TMQ is in the form of a brittle solid at room temperature and, being usually in the form of a mixture of monomer and oligomers, it has no well-defined melting point. Although it softens as the temperature increases, it is still a very viscous and stringy material at typical additive addition temperatures of around 80 to 100°C.
- TMQ TMQ is added to lubricating compositions such as greases at this typical temperature range of from 80 to 100°C, it will not be suitably dispersed into the grease and will result in e.g. filter blockages in grease delivery systems. Even if the filter loading of these grease delivery systems is not enough for the filter to block immediately, some of the antioxidant will have been taken out of the grease, which would then suffer from reduced life as a result.
- alkyl-substituted quinolines are usually added to greases at temperatures above 150°C, usually between 150-160°C after the grease has completed its critical cooling phase after establishing the thickener system in the base oil.
- an associated problem of the known method is that the window of opportunity for adding the alkyl-substituted quinolines is usually narrow, if they are to be dispersed properly in the grease. If the alkyl-substituted quinolines are added e.g. ten minutes later, this may be too late as the grease may have been cooled too much.
- a further problem of the known method of adding the alkyl-substituted quinolines to the grease at relatively high temperatures is that more severe health and safety issues need to be taken into account, relating e.g. to the dangers of grease at high temperature and the danger of fumes when the manufacturing vessel has to be opened.
- One or more of the above or other objects are obtained by the present invention by providing a method for preparing a lubricating composition, in particular a grease, the method at least comprising the steps of:
- the alkyl-substituted quinolines or oligomeric derivatives thereof
- they can be added at a lower temperature, whilst still obtaining a proper dispersing thereof in the base oil composition.
- an important advantage of the present invention is that the alkyl-substituted quinolines (or oligomeric derivatives thereof) can be added at a lower temperature, resulting in less severe safety requirements. Also, there is more flexibility in the moment of adding the alkyl-substituted quinolines (or oligomeric derivatives thereof), as the specific temperature for adding thereof is less critical than in the case where no solvent is used.
- step c) the solution of step b) is added at a temperature below 120°C, preferably in the range of from 10 to 110°C, more preferably from 15 to 100°C.
- the one or more alkyl-substituted quinolines are alkyl-substituted 1,2-dihydroquinolines having the general formula (I) wherein R 1 -R 8 are independently selected from hydrogen or an alkyl group having 1-8 carbon atoms.
- R 1 -R 8 are independently selected from hydrogen or an alkyl group having 1-4 carbon atoms, preferably having 1-2 carbon atoms.
- R 4 is H. It is even more preferred that R 4 -R 8 are all H. Also it is preferred that R 1 -R 3 are all a methyl group.
- one or more alkyl substituted 1,2-dihydroquinolines have an average value for n of from 1.0 to 2.0, preferably from 1.3 to 1.6.
- the one or more alkyl substituted quinolines provided in the solution have a solubility of below 0.1% as determined using ASTM D893.
- alkyl substituted quinoline compounds as used in the present invention are either commercially available or can be prepared by various reactions that are known in the art. Examples of preparation methods have been given in the above-mentioned WO 94/24235 and US 5 246 606 and references cited therein. Other examples are given in US 4 692 258 and US 3 910 918 and references cited therein.
- the solvent comprises a polyalkylene glycol.
- Polyglycols are well known in the art and are not further discussed here in detail.
- the polyalkylene glycols exhibit alkylene oxide units with 1 to 6 carbon atoms (-R-O-) as monomer units.
- the polyalkylene glycols may exhibit hydrogen end groups, alkyl, aryl, alkylaryl, aryloxy, alkoxy, alkylaryloxy and/or hydroxy end groups.
- Alkylaryloxy groups should also be understood to mean arylalkyl (ene)oxy groups and alkylaryl groups to mean arylalkyl(ene) groups (e.g. aryl CH 2 CH 2 -).
- the end groups of the alkyl type, including the alkoxy type, or of the aryl types, including the alkylaryl type, aryloxy type and alkylaryloxy type preferably exhibit 6 to 24 carbon atoms, particularly preferably 6 to 18 carbon atoms, based on the aryl types, and preferably 1 to 12 carbon atoms, based on the alkyl types.
- the polyalkylene glycols according to the invention may be either homopolymers, namely polypropylene glycol (and/or polypropylene oxide) or copolymers, terpolymers etc.
- the monomer units may exhibit a random distribution or a block structure. If the polyalkylene glycols are not homopolymers, preferably at least 20%, preferably at least 40% of all monomer units are producible from polypropylene oxide (PO), and also preferably, at least 20% of all monomer units of these polyalkylene glycols are producible by using ethylene oxide (EO) (PO/EO copolymers).
- PO polypropylene oxide
- EO ethylene oxide
- preferably at least 20%, preferably at least 40% of all monomer units are obtainable from butylene oxide (BO) and, moreover, preferably at least 20% of all monomer units of these polyalkylene glycols are obtainable by using ethylene oxide (BO/EO copolymers).
- BO butylene oxide
- BO/EO copolymers ethylene oxide
- the starting compound is incorporated into the polymer and, according to the meaning of the invention, also referred to as end group of the polymer chain.
- Suitable starting groups consist of compounds comprising active hydrogen such as e.g. n-butanol, propylene glycol, ethylene glycol, neopentyl glycols such as pentaerythritol, ethylene diamine, phenol, cresol or other (C1 to C16 (mono, di or tri)alkyl) aromatics, (hydroxyalkyl) aromatics, hydroquinone, aminoethanolamines, triethylenetetramines, polyamines, sorbitol or other sugars.
- Other C-H acidic compounds such as carboxylic acids or carboxylic anhydrides can also be used as starting compounds.
- the polyalkylene glycols comprise aryl groups or corresponding heteroaromatic groups, e.g. inserted into the polymer chain, as side groups or end groups; the groups may, if necessary, be substituted with linear or branched alkyl groups or alkylene groups, the alkyl groups or alkylene groups overall exhibiting preferably 1 to 18 carbon atoms.
- Cyclic ether alcohols such as hydroxyfurfuryl or hydroxytetrahydrofuran, nitrogen heterocyclics or sulphur heterocyclics can also be used as starting groups.
- Such polyalkylene glycols are disclosed in WO 01/57164 , the teaching of which is herewith incorporated by reference.
- the polyalkylene glycols according to the invention have an average molecular weight (number average) of 200 to 3000 g/mole, more preferably 400 to 2000 g/mole.
- the kinematic viscosity of the polyalkylene glycols is 10 to 400 mm 2 /s (cSt) measured at 40°C according to DIN 51562.
- the polyalkylene glycols used according to the invention can be produced by reacting alcohols, including polyalcohols, as starting compounds with oxiranes such as ethylene oxide, propylene oxide and/or butylene oxide. Following the reaction, these possess only one free hydroxy group as end group. Polyalkylene glycols with only one hydroxy group are preferred over those with two free hydroxy groups. Polyalkylene glycols which, e.g. after a further etherification step, comprise no free hydroxy groups any longer are particularly preferred regarding the stability, hygroscopicity and compatibility. The alkylation of terminal hydroxyl groups leads to an increase in the thermal stability.
- the PAG base oil comprises end-capped PAG, i.e. where no free hydroxyl groups are present.
- base oil in the method according to the present invention various conventional mineral oils and synthetic oils may be conveniently used.
- base oil is meant to also include a grease base stock.
- the base oil composition used in the present invention may conveniently comprise mixtures of one or more mineral oils and/or one or more synthetic oils.
- Mineral oils include liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oil of the paraffinic, naphthenic, or mixed paraffinic/naphthenic type which may be further refined by hydrofinishing processes and/or dewaxing.
- Suitable base oils for use in the lubricating oil composition of the present invention are Group I, Group II or Group III base oils, polyalphaolefins, Fischer-Tropsch derived base oils and mixtures thereof.
- Group I base oil By “Group I” base oil, “Group II” base oil and “Group III” base oil in the present invention are meant lubricating oil base oils according to the definitions of American Petroleum Institute (API) categories I, II and III. Such API categories are defined in API Publication 1509, 15th Edition, Appendix E, April 2002.
- API American Petroleum Institute
- Suitable Fischer-Tropsch derived base oils that may be conveniently used in the base oil in the lubricating oil composition of the present invention are those as for example disclosed in EP 0 776 959 , EP 0 668 342 , WO 97/21788 , WO 00/15736 , WO 00/14188 , WO 00/14187 , WO 00/14183 , WO 00/14179 , WO 00/08115 , WO 99/41332 , EP 1 029 029 , WO 01/18156 and WO 01/57166 .
- Synthetic oils include hydrocarbon oils such as olefin oligomers (PAOs), dibasic acid esters, polyol esters, and dewaxed waxy raffinate. Synthetic hydrocarbon base oils sold by the Shell Group under the designation "XHVI” (trade mark) may be conveniently used.
- PAOs olefin oligomers
- XHVI XHVI
- the total amount of base oil incorporated in the lubricating composition of the present invention is preferably present in an amount in the range of from 60 to 92 wt.%, more preferably in an amount in the range of from 75 to 90 wt.% and most preferably in an amount in the range of from 75 to 88 wt.%, with respect to the total weight of the lubricating composition.
- the final lubricating composition may further comprise one or more additives such as antioxidants, anti-wear agents, dispersants, detergents, friction modifiers, viscosity index improvers, pour point depressants, tackifying agents, corrosion inhibitors, demulsifiers, defoaming agents and seal fix or seal compatibility agents, etc.
- additives such as antioxidants, anti-wear agents, dispersants, detergents, friction modifiers, viscosity index improvers, pour point depressants, tackifying agents, corrosion inhibitors, demulsifiers, defoaming agents and seal fix or seal compatibility agents, etc.
- the additives may be added to the base oil composition before or after the one or more alkyl-substituted quinolines are added in step c). Also, if appropriate, the additives may also be added at the same time with the one or more alkyl-substituted quinolines.
- Said additives are typically present in an amount in the range of from 0.01 to 12.5 wt.%, based on the total weight of the lubricating composition, preferably in an amount in the range of from 0.05 to 10.0 wt.%, more preferably from 1.0 to 9.0 wt.% and most preferably in the range of from 2.0 to 5.0 wt.%, based on the total weight of the lubricating composition.
- the base oil as contained in the lubricating composition may contain or be compounded with one or more thickeners such as metallic soaps, organic substances or inorganic substances, for example, lithium soaps, lithium complex soaps, sodium terephthalate, urea/urethane compounds and clays.
- thickeners such as metallic soaps, organic substances or inorganic substances, for example, lithium soaps, lithium complex soaps, sodium terephthalate, urea/urethane compounds and clays.
- the lubricating composition has a kinematic viscosity in the range of from 2 to 80 mm 2 /s at 100 °C, more preferably in the range of from 3 to 70 mm 2 /s, most preferably in the range of from 4 to 50 mm 2 /s.
- the lubricating compositions of the present invention may be conveniently prepared by admixing the one or more base oils and, optionally, one or more additives that are usually present in lubricating compositions, for example as herein before described, with mineral and/or synthetic base oil.
- the one or more alkyl-substituted quinoline compounds (or oligomeric derivatives thereof) have a sufficiently small particle size (e.g. below 50 ⁇ m, preferably below 20 ⁇ m) to allow easy dispersion thereof in the lubricating composition.
- the present invention provides a lubricating composition, in particular a grease, obtained by the method according to the present invention.
- a 500 ml 50 % m/m solution of oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline (solid; available from Rhein Chemie Rheinau GmbH under the trade designation "Additin RC7010”) in polyalkylene glycol (available from The Dow Chemical Company, USA under the trade designation "Oxilube 504") was prepared by heating the polyalkylene glycol to 100°C before adding the oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline. The oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline was added slowly over about two minutes, allowing it to disperse throughout the fluid before adding more. The mixture thus obtained was stirred for a further 30 minutes at 100°C. A stable, homogeneous solution was formed.
- a grease was prepared using the above mentioned Solution A (50 ml) and a conventional grease base stock (4950 g).
- the conventional grease base stock contained about 10% m/m lithium complex thickener and about 90% m/m paraffinic mineral base oil blended from SN 500 and bright stock (viscosity at 40°C of 180 mm 2 /s according to ASTM D445).
- the conventional grease base stock also contained an antiwear additive (a zinc dialkyl dithiophosphate), an extreme pressure additive (a sulphurised ester) and a rust inhibitor (a zinc naphthenate).
- the grease base stock and Solution A were simply mixed during 30 minutes using a laboratory paddle mixer, after both had been previously heated to 80°C before mixing.
- Table I Test Method / Conditions Value Penetration (worked) ASTM D217 25°C 260 Penetration (long term worked) ASTM D217 100,000 strokes 280 Oil separation IP 121 7 days at 40°C 3.5% Oxidation stability ASTM D942 100h at 99°C 30 kPa Copper corrosion ASTM D4048 24h at 100°C 1b Water washout ASTM D1264 1h at 79°C 0.5%
- a grease was prepared using the same amount of oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline (without the solvent) and the same grease base stock of Examples 1 and 2.
- the grease base stock was heated to about 160°C. Then, a part of the solid oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline was added to the heated grease base stock and left at this temperature for about 10 minutes. Mixing took place using a laboratory paddle mixer until the mixture had reached the temperature of about 60°C.
- the present invention allows adding the alkyl-substituted quinolines or oligomeric derivatives thereof at a significant lower temperature, whilst still obtaining a stable grease having desired properties. It goes without saying that this is highly desired from a health and safety perspective as well as from a practical manufacturing perspective.
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Description
- The present invention relates to a method for preparing a lubricating composition, in particular a grease.
- Alkyl-substituted quinolines and polymerized derivatives thereof are known as very effective, low cost antioxidants for several uses, including the use in lubricating compositions.
- As an example,
WO 94/24235 - Further,
US 5 246 606 discloses that dimeric, trimeric and tetrameric tetrahydroquinoline derivatives are suitable for stabilising organic materials against light-induced, thermal and/or oxidative degradation.US 5 246 606 suggests to use these compounds amongst others in functional fluids such as lubricants and hydraulic fluids. -
US 2 908 646 relates to lubricating greases containing polymerized dihydroquinoline derivatives. This document teaches that the polymerized dihydroquinoline derivatives may be added directly to the grease mixture or may be added in the form of a solution. In the example ofUS 2 908 646 , a polymerized 2,2,4-trimethyl-1,2-dihydroquinoline is added during the oil addition at a temperature of 240°F. - Although alkyl-substituted quinolines such as 2,2,4-trimethyl-1,2-dihydroquinoline (also referred to as "TMQ", "TMDQ" and "TMHQ") and oligomeric (i.e. dimeric, trimeric and tetrameric) derivatives thereof, are widely used as antioxidants, they have a number of disadvantages.
- As an example, TMQ is in the form of a brittle solid at room temperature and, being usually in the form of a mixture of monomer and oligomers, it has no well-defined melting point. Although it softens as the temperature increases, it is still a very viscous and stringy material at typical additive addition temperatures of around 80 to 100°C.
- If TMQ is added to lubricating compositions such as greases at this typical temperature range of from 80 to 100°C, it will not be suitably dispersed into the grease and will result in e.g. filter blockages in grease delivery systems. Even if the filter loading of these grease delivery systems is not enough for the filter to block immediately, some of the antioxidant will have been taken out of the grease, which would then suffer from reduced life as a result.
- In view of the above, alkyl-substituted quinolines are usually added to greases at temperatures above 150°C, usually between 150-160°C after the grease has completed its critical cooling phase after establishing the thickener system in the base oil.
- However, an associated problem of the known method is that the window of opportunity for adding the alkyl-substituted quinolines is usually narrow, if they are to be dispersed properly in the grease. If the alkyl-substituted quinolines are added e.g. ten minutes later, this may be too late as the grease may have been cooled too much.
- A further problem of the known method of adding the alkyl-substituted quinolines to the grease at relatively high temperatures, is that more severe health and safety issues need to be taken into account, relating e.g. to the dangers of grease at high temperature and the danger of fumes when the manufacturing vessel has to be opened.
- It is an object of the present invention to avoid the above problems.
- It is another object to provide an alternative method for preparing a lubricating composition, in particular a grease.
- One or more of the above or other objects are obtained by the present invention by providing a method for preparing a lubricating composition, in particular a grease, the method at least comprising the steps of:
- a) providing a base oil composition containing one or more additives, wherein the base oil composition comprises mineral oil;
- b) providing a solution of one or more alkyl-substituted quinolines in a solvent, wherein the one or more alkyl-substituted quinolines are alkyl-substituted 1,2-dihydroquinolines having the general formula (I)
- c) adding the solution of step b) to the base oil composition of step a) at a temperature below 150°C.
- Surprisingly, it has been found according to the present invention that if the alkyl-substituted quinolines (or oligomeric derivatives thereof) are added in a solvent to the base oil composition, they can be added at a lower temperature, whilst still obtaining a proper dispersing thereof in the base oil composition.
- An important advantage of the present invention is that the alkyl-substituted quinolines (or oligomeric derivatives thereof) can be added at a lower temperature, resulting in less severe safety requirements. Also, there is more flexibility in the moment of adding the alkyl-substituted quinolines (or oligomeric derivatives thereof), as the specific temperature for adding thereof is less critical than in the case where no solvent is used.
- Preferably in step c) the solution of step b) is added at a temperature below 120°C, preferably in the range of from 10 to 110°C, more preferably from 15 to 100°C.
-
- Preferably, R1-R8 are independently selected from hydrogen or an alkyl group having 1-4 carbon atoms, preferably having 1-2 carbon atoms. Preferably R4 is H. It is even more preferred that R4-R8 are all H. Also it is preferred that R1-R3 are all a methyl group.
- Further the one or more alkyl substituted 1,2-dihydroquinolines have an average value for n of from 1.0 to 2.0, preferably from 1.3 to 1.6.
- Also it is preferred that the one or more alkyl substituted quinolines provided in the solution have a solubility of below 0.1% as determined using ASTM D893.
- The alkyl substituted quinoline compounds as used in the present invention are either commercially available or can be prepared by various reactions that are known in the art. Examples of preparation methods have been given in the above-mentioned
WO 94/24235 US 5 246 606 and references cited therein. Other examples are given inUS 4 692 258 andUS 3 910 918 and references cited therein. - One specific example for preparing TMQ (2,2,4-trimethyl-1,2-dihydroquinoline) has been given in W.R. Vaughan, "Organic synthesis", Collective Volume III, pp 329-30, (1955).
- The solvent comprises a polyalkylene glycol. Polyglycols are well known in the art and are not further discussed here in detail.
- The polyalkylene glycols (PAG) exhibit alkylene oxide units with 1 to 6 carbon atoms (-R-O-) as monomer units.
- The polyalkylene glycols may exhibit hydrogen end groups, alkyl, aryl, alkylaryl, aryloxy, alkoxy, alkylaryloxy and/or hydroxy end groups. Alkylaryloxy groups should also be understood to mean arylalkyl (ene)oxy groups and alkylaryl groups to mean arylalkyl(ene) groups (e.g. aryl CH2CH2-). The end groups of the alkyl type, including the alkoxy type, or of the aryl types, including the alkylaryl type, aryloxy type and alkylaryloxy type preferably exhibit 6 to 24 carbon atoms, particularly preferably 6 to 18 carbon atoms, based on the aryl types, and preferably 1 to 12 carbon atoms, based on the alkyl types.
- The polyalkylene glycols according to the invention may be either homopolymers, namely polypropylene glycol (and/or polypropylene oxide) or copolymers, terpolymers etc. For the latter cases, the monomer units may exhibit a random distribution or a block structure. If the polyalkylene glycols are not homopolymers, preferably at least 20%, preferably at least 40% of all monomer units are producible from polypropylene oxide (PO), and also preferably, at least 20% of all monomer units of these polyalkylene glycols are producible by using ethylene oxide (EO) (PO/EO copolymers). According to a further embodiment, preferably at least 20%, preferably at least 40% of all monomer units are obtainable from butylene oxide (BO) and, moreover, preferably at least 20% of all monomer units of these polyalkylene glycols are obtainable by using ethylene oxide (BO/EO copolymers).
- When (poly)alcohols are used, the starting compound is incorporated into the polymer and, according to the meaning of the invention, also referred to as end group of the polymer chain. Suitable starting groups consist of compounds comprising active hydrogen such as e.g. n-butanol, propylene glycol, ethylene glycol, neopentyl glycols such as pentaerythritol, ethylene diamine, phenol, cresol or other (C1 to C16 (mono, di or tri)alkyl) aromatics, (hydroxyalkyl) aromatics, hydroquinone, aminoethanolamines, triethylenetetramines, polyamines, sorbitol or other sugars. Other C-H acidic compounds such as carboxylic acids or carboxylic anhydrides can also be used as starting compounds.
- Preferably, the polyalkylene glycols comprise aryl groups or corresponding heteroaromatic groups, e.g. inserted into the polymer chain, as side groups or end groups; the groups may, if necessary, be substituted with linear or branched alkyl groups or alkylene groups, the alkyl groups or alkylene groups overall exhibiting preferably 1 to 18 carbon atoms.
- Cyclic ether alcohols such as hydroxyfurfuryl or hydroxytetrahydrofuran, nitrogen heterocyclics or sulphur heterocyclics can also be used as starting groups. Such polyalkylene glycols are disclosed in
WO 01/57164 - Preferably, the polyalkylene glycols according to the invention have an average molecular weight (number average) of 200 to 3000 g/mole, more preferably 400 to 2000 g/mole. The kinematic viscosity of the polyalkylene glycols is 10 to 400 mm2/s (cSt) measured at 40°C according to DIN 51562.
- The polyalkylene glycols used according to the invention can be produced by reacting alcohols, including polyalcohols, as starting compounds with oxiranes such as ethylene oxide, propylene oxide and/or butylene oxide. Following the reaction, these possess only one free hydroxy group as end group. Polyalkylene glycols with only one hydroxy group are preferred over those with two free hydroxy groups. Polyalkylene glycols which, e.g. after a further etherification step, comprise no free hydroxy groups any longer are particularly preferred regarding the stability, hygroscopicity and compatibility. The alkylation of terminal hydroxyl groups leads to an increase in the thermal stability. Thus, in an especially preferred embodiment according to the present invention, the PAG base oil comprises end-capped PAG, i.e. where no free hydroxyl groups are present.
- In the base oil composition used in the method according to the present invention various conventional mineral oils and synthetic oils may be conveniently used. For the purpose of this description, the term "base oil" is meant to also include a grease base stock.
- The base oil composition used in the present invention may conveniently comprise mixtures of one or more mineral oils and/or one or more synthetic oils.
- Mineral oils include liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oil of the paraffinic, naphthenic, or mixed paraffinic/naphthenic type which may be further refined by hydrofinishing processes and/or dewaxing.
- Suitable base oils for use in the lubricating oil composition of the present invention are Group I, Group II or Group III base oils, polyalphaolefins, Fischer-Tropsch derived base oils and mixtures thereof.
- By "Group I" base oil, "Group II" base oil and "Group III" base oil in the present invention are meant lubricating oil base oils according to the definitions of American Petroleum Institute (API) categories I, II and III. Such API categories are defined in API Publication 1509, 15th Edition, Appendix E, April 2002.
- Suitable Fischer-Tropsch derived base oils that may be conveniently used in the base oil in the lubricating oil composition of the present invention are those as for example disclosed in
EP 0 776 959 ,EP 0 668 342 ,WO 97/21788 WO 00/15736 WO 00/14188 WO 00/14187 WO 00/14183 WO 00/14179 WO 00/08115 WO 99/41332 EP 1 029 029 ,WO 01/18156 WO 01/57166 - Synthetic oils include hydrocarbon oils such as olefin oligomers (PAOs), dibasic acid esters, polyol esters, and dewaxed waxy raffinate. Synthetic hydrocarbon base oils sold by the Shell Group under the designation "XHVI" (trade mark) may be conveniently used.
- The total amount of base oil incorporated in the lubricating composition of the present invention is preferably present in an amount in the range of from 60 to 92 wt.%, more preferably in an amount in the range of from 75 to 90 wt.% and most preferably in an amount in the range of from 75 to 88 wt.%, with respect to the total weight of the lubricating composition.
- If desired, the final lubricating composition may further comprise one or more additives such as antioxidants, anti-wear agents, dispersants, detergents, friction modifiers, viscosity index improvers, pour point depressants, tackifying agents, corrosion inhibitors, demulsifiers, defoaming agents and seal fix or seal compatibility agents, etc.
- As the person skilled in the art is familiar with the above and other additives, these are not further discussed here. The additives may be added to the base oil composition before or after the one or more alkyl-substituted quinolines are added in step c). Also, if appropriate, the additives may also be added at the same time with the one or more alkyl-substituted quinolines.
- Said additives are typically present in an amount in the range of from 0.01 to 12.5 wt.%, based on the total weight of the lubricating composition, preferably in an amount in the range of from 0.05 to 10.0 wt.%, more preferably from 1.0 to 9.0 wt.% and most preferably in the range of from 2.0 to 5.0 wt.%, based on the total weight of the lubricating composition.
- As the lubricating composition may also be (and preferably is) in the form of a grease, the base oil as contained in the lubricating composition may contain or be compounded with one or more thickeners such as metallic soaps, organic substances or inorganic substances, for example, lithium soaps, lithium complex soaps, sodium terephthalate, urea/urethane compounds and clays.
- Preferably, the lubricating composition has a kinematic viscosity in the range of from 2 to 80 mm2/s at 100 °C, more preferably in the range of from 3 to 70 mm2/s, most preferably in the range of from 4 to 50 mm2/s.
- The lubricating compositions of the present invention may be conveniently prepared by admixing the one or more base oils and, optionally, one or more additives that are usually present in lubricating compositions, for example as herein before described, with mineral and/or synthetic base oil. Preferably, and as is customary in the art, the one or more alkyl-substituted quinoline compounds (or oligomeric derivatives thereof) have a sufficiently small particle size (e.g. below 50 µm, preferably below 20 µm) to allow easy dispersion thereof in the lubricating composition.
- In another aspect the present invention provides a lubricating composition, in particular a grease, obtained by the method according to the present invention.
- The present invention is described below with reference to the following Examples, which are not intended to limit the scope of the present invention in any way.
- A 500 ml 50 % m/m solution of oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline (solid; available from Rhein Chemie Rheinau GmbH under the trade designation "Additin RC7010") in polyalkylene glycol (available from The Dow Chemical Company, USA under the trade designation "Oxilube 504") was prepared by heating the polyalkylene glycol to 100°C before adding the oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline. The oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline was added slowly over about two minutes, allowing it to disperse throughout the fluid before adding more. The mixture thus obtained was stirred for a further 30 minutes at 100°C. A stable, homogeneous solution was formed.
- Similar to Solution A, a 500 ml 50% m/m solution of oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline in polyglycol (available from The Dow Chemical Company, USA under the trade designation "Synalox 50-50B") was prepared. A stable, homogeneous solution was formed.
- A grease was prepared using the above mentioned Solution A (50 ml) and a conventional grease base stock (4950 g).
- The conventional grease base stock contained about 10% m/m lithium complex thickener and about 90% m/m paraffinic mineral base oil blended from SN 500 and bright stock (viscosity at 40°C of 180 mm2/s according to ASTM D445). The conventional grease base stock also contained an antiwear additive (a zinc dialkyl dithiophosphate), an extreme pressure additive (a sulphurised ester) and a rust inhibitor (a zinc naphthenate).
- The grease base stock and Solution A were simply mixed during 30 minutes using a laboratory paddle mixer, after both had been previously heated to 80°C before mixing.
- After visual inspection no apparent deficiencies of the obtained grease were found. No lumps were formed. Also, no separating of the oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline out of the grease occurred after 12 months of storage.
- Other properties of the obtained grease are indicated in Table I below.
Table I Test Method / Conditions Value Penetration (worked) ASTM D217 25°C 260 Penetration (long term worked) ASTM D217 100,000 strokes 280 Oil separation IP 121 7 days at 40°C 3.5% Oxidation stability ASTM D942 100h at 99°C 30 kPa Copper corrosion ASTM D4048 24h at 100°C 1b Water washout ASTM D1264 1h at 79°C 0.5% - The results in Table I show that the desired properties for a grease such as mechanical stability, oil retention and surprisingly also the stability against water are still present in the grease of Example 1 and are not affected by the presence of the solvent (polyalkylene glycol) used to dissolve the oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline.
- Similar to Example 1, a grease was prepared using Solution B.
- After visual inspection no apparent deficiencies of the obtained grease were found. No lumps were formed.
- Also, no separating of the oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline 2,2,4-trimethyl-1,2-dihydroquinoline out of the grease occurred after 12 months of storage. Similar to Example 1, the grease of Example 2 showed desired properties of mechanical stability, oil retention and stability against water.
- A grease was prepared using the same amount of oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline (without the solvent) and the same grease base stock of Examples 1 and 2.
- The grease base stock was heated to about 160°C. Then, a part of the solid oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline was added to the heated grease base stock and left at this temperature for about 10 minutes. Mixing took place using a laboratory paddle mixer until the mixture had reached the temperature of about 60°C.
- Then the mixture was reheated to about 160°C and left at this temperature for about 30 minutes. Subsequently, the steps of adding and mixing was repeated until all oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline was added and mixed.
- After visual inspection no apparent deficiencies of the obtained grease were found. No lumps were formed.
- Similar to Comparative Example 1 a grease was prepared, although the heating was to about 60°C (instead of to about 160°C).
- It was not possible to disperse the solid oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline into the grease base stock, which would lead to severe filter blockages in case the grease of Comparative Example 2 was to be used in e.g. grease delivery systems.
- As can be seen from the Examples, the present invention allows adding the alkyl-substituted quinolines or oligomeric derivatives thereof at a significant lower temperature, whilst still obtaining a stable grease having desired properties. It goes without saying that this is highly desired from a health and safety perspective as well as from a practical manufacturing perspective.
- In this respect it is noted that if no solvent was used (see Comparative Example 2) whilst adding the alkyl-substituted quinolines or oligomeric derivatives thereof, no stable grease was obtained.
Claims (7)
- A method for preparing a grease, the method at least comprising the steps of:a) providing a base oil composition containing one or more additives, wherein the base oil composition comprises mineral oil;b) providing a solution of one or more alkyl-substituted quinolines in a solvent, wherein the one or more alkyl-substituted quinolines are alkyl-substituted 1,2-dihydroquinolines having the general formula (I)c) adding the solution of step b) to the base oil composition of step a) at a temperature in the range of from 10 to 110°C.
- The method according to claim 1, wherein in step c) the solution of step b) is added at a temperature in the range of from 15 to 100°C.
- The method according to claim 1 or 2, wherein R1-R8 are independently selected from hydrogen or an alkyl group having 1-4 carbon atoms.
- The method according to any of claims 1 to 3, wherein R1-R8 are independently selected from hydrogen or an alkyl group having having 1-2 carbon atoms.
- The method according to any of claims 1 to 4, wherein R4-R8 are hydrogen.
- The method according to any of claims 1 to 5, wherein the one or more alkyl-substituted 1,2-dihydroquinolines have an average value for n of from 1.3 to 1.6.
- The method according to any one of claims 1 to 6, wherein the one or more alkyl substituted quinolines provided in the solution have a solubility in the solvent of below 0.1% as determined using ASTM D893.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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EP09701564A EP2242823B1 (en) | 2008-01-16 | 2009-01-16 | Method for preparing a grease composition |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP08100550 | 2008-01-16 | ||
EP09701564A EP2242823B1 (en) | 2008-01-16 | 2009-01-16 | Method for preparing a grease composition |
PCT/EP2009/050483 WO2009090238A1 (en) | 2008-01-16 | 2009-01-16 | Method for preparing a lubricating composition |
Publications (2)
Publication Number | Publication Date |
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EP2242823A1 EP2242823A1 (en) | 2010-10-27 |
EP2242823B1 true EP2242823B1 (en) | 2013-03-13 |
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EP09701564A Active EP2242823B1 (en) | 2008-01-16 | 2009-01-16 | Method for preparing a grease composition |
Country Status (8)
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US (1) | US20110021392A1 (en) |
EP (1) | EP2242823B1 (en) |
JP (1) | JP5651018B2 (en) |
CN (1) | CN101910385B (en) |
AR (1) | AR070686A1 (en) |
BR (1) | BRPI0906868B1 (en) |
RU (1) | RU2492217C2 (en) |
WO (1) | WO2009090238A1 (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2012162020A1 (en) * | 2011-05-26 | 2012-11-29 | The Lubrizol Corporation | Stabilized blends containing antioxidants |
ES2660479T3 (en) | 2011-12-27 | 2018-03-22 | Arçelik Anonim Sirketi | Cooking device |
CA2955352C (en) * | 2014-09-19 | 2018-11-13 | Vanderbilt Chemicals, Llc | Polyalkylene glycol-based industrial lubricant compositions |
JP6646379B2 (en) * | 2015-08-10 | 2020-02-14 | Ntn株式会社 | Grease composition and grease-filled rolling bearing |
JP7108373B2 (en) * | 2016-10-21 | 2022-07-28 | Ntn株式会社 | ball bearing |
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JPS5649800A (en) * | 1979-09-29 | 1981-05-06 | Daihatsu Motor Co Ltd | Grease composition for brake or clutch |
JPS57115493A (en) * | 1981-01-05 | 1982-07-17 | Sumitomo Chem Co Ltd | Antioxidant for lubricating oil |
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- 2009-01-16 WO PCT/EP2009/050483 patent/WO2009090238A1/en active Application Filing
- 2009-01-16 JP JP2010542635A patent/JP5651018B2/en active Active
- 2009-01-16 BR BRPI0906868-6A patent/BRPI0906868B1/en active IP Right Grant
- 2009-01-16 EP EP09701564A patent/EP2242823B1/en active Active
- 2009-01-16 CN CN200980102363.3A patent/CN101910385B/en active Active
- 2009-01-16 US US12/812,820 patent/US20110021392A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
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CN101910385A (en) | 2010-12-08 |
WO2009090238A1 (en) | 2009-07-23 |
RU2492217C2 (en) | 2013-09-10 |
JP2011514912A (en) | 2011-05-12 |
US20110021392A1 (en) | 2011-01-27 |
CN101910385B (en) | 2014-03-05 |
BRPI0906868A2 (en) | 2015-07-07 |
AR070686A1 (en) | 2010-04-28 |
BRPI0906868B1 (en) | 2017-12-05 |
JP5651018B2 (en) | 2015-01-07 |
EP2242823A1 (en) | 2010-10-27 |
RU2010134003A (en) | 2012-02-27 |
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