WO2012159738A1 - Hochtemperaturöl - Google Patents
Hochtemperaturöl Download PDFInfo
- Publication number
- WO2012159738A1 WO2012159738A1 PCT/EP2012/002172 EP2012002172W WO2012159738A1 WO 2012159738 A1 WO2012159738 A1 WO 2012159738A1 EP 2012002172 W EP2012002172 W EP 2012002172W WO 2012159738 A1 WO2012159738 A1 WO 2012159738A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- temperature oil
- oil according
- high temperature
- oil
- alkylated
- Prior art date
Links
- 239000003921 oil Substances 0.000 claims abstract description 115
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 4
- -1 ester compound Chemical class 0.000 claims description 28
- 229920006007 hydrogenated polyisobutylene Polymers 0.000 claims description 19
- 239000003963 antioxidant agent Substances 0.000 claims description 17
- 239000002608 ionic liquid Substances 0.000 claims description 16
- 230000003078 antioxidant effect Effects 0.000 claims description 14
- 238000005260 corrosion Methods 0.000 claims description 14
- 230000007797 corrosion Effects 0.000 claims description 14
- 239000003112 inhibitor Substances 0.000 claims description 13
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 13
- 239000011814 protection agent Substances 0.000 claims description 11
- 239000007983 Tris buffer Substances 0.000 claims description 8
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000005461 lubrication Methods 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims description 6
- 235000021317 phosphate Nutrition 0.000 claims description 6
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 6
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 6
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 230000001050 lubricating effect Effects 0.000 claims description 5
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims description 4
- 150000003949 imides Chemical class 0.000 claims description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 4
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 claims description 3
- XMNDMAQKWSQVOV-UHFFFAOYSA-N (2-methylphenyl) diphenyl phosphate Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 XMNDMAQKWSQVOV-UHFFFAOYSA-N 0.000 claims description 2
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 claims description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical class C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 2
- 239000007866 anti-wear additive Substances 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- UIFJOXOHICDFDO-UHFFFAOYSA-N benzene-1,3,5-triol Chemical class OC1=CC(O)=CC(O)=C1.OC1=CC(O)=CC(O)=C1 UIFJOXOHICDFDO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
- 239000012990 dithiocarbamate Substances 0.000 claims description 2
- 150000004659 dithiocarbamates Chemical class 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 238000009413 insulation Methods 0.000 claims description 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000002530 phenolic antioxidant Substances 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- FFUQCRZBKUBHQT-UHFFFAOYSA-N phosphoryl fluoride Chemical class FP(F)(F)=O FFUQCRZBKUBHQT-UHFFFAOYSA-N 0.000 claims description 2
- 150000003871 sulfonates Chemical class 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims description 2
- LAGQNGWYNLUQRI-UHFFFAOYSA-N trioctylmethylammonium bis(trifluoromethylsulfonyl)imide Chemical compound FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC LAGQNGWYNLUQRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 238000010422 painting Methods 0.000 claims 1
- 229920002367 Polyisobutene Polymers 0.000 abstract description 8
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 150000003639 trimesic acids Chemical class 0.000 abstract description 2
- 125000002444 phloroglucinyl group Chemical class [H]OC1=C([H])C(O[H])=C(*)C(O[H])=C1[H] 0.000 abstract 1
- 125000005590 trimellitic acid group Chemical class 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 33
- 238000001704 evaporation Methods 0.000 description 24
- 230000008020 evaporation Effects 0.000 description 24
- 239000002199 base oil Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 238000011835 investigation Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000008092 positive effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical class OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 3
- 229960001553 phloroglucinol Drugs 0.000 description 3
- 230000005611 electricity Effects 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
- 0 CC*C(Oc1cc(OC(*(CC)=C)=O)cc(OC(*CC)=O)c1)=O Chemical compound CC*C(Oc1cc(OC(*(CC)=C)=O)cc(OC(*CC)=O)c1)=O 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- HYNYWFRJHNNLJA-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;trihexyl(tetradecyl)phosphanium Chemical compound FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC HYNYWFRJHNNLJA-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- SZHOJFHSIKHZHA-UHFFFAOYSA-N n-Tridecanoic acid Natural products CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000004711 α-olefin Substances 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
- C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
- C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
-
- 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
- C10M169/04—Mixtures of base-materials and additives
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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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
- C10M143/06—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing butene
-
- 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
- C10M169/04—Mixtures of base-materials and additives
- C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
-
- 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
- C10M169/04—Mixtures of base-materials and additives
- C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
- C10M2205/0265—Butene 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
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds 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
- C10M2207/28—Esters
- C10M2207/285—Esters of aromatic polycarboxylic acids
- C10M2207/2855—Esters of aromatic polycarboxylic acids 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
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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
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/079—Liquid crystals
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- 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
- C10N2030/02—Pour-point; Viscosity index
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
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- 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
- C10N2030/08—Resistance to extreme temperature
-
- 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
- C10N2030/74—Noack Volatility
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/38—Conveyors or chain belts
Definitions
- the invention relates to novel high-temperature oils based on aromatic esters, such as trimellitic esters, pyromellitic esters, trimesic acid esters or a mixture or derivatives of phloroglucin, such as Phloroglucentr trioctylklareester, Phloroglucin tridecylklareester and Phloroglucin- tridodecylklareester thereof and a fully hydrogenated or a hydrogenated polyisobutylene or a mixture thereof ,
- aromatic esters such as trimellitic esters, pyromellitic esters, trimesic acid esters or a mixture or derivatives of phloroglucin, such as Phloroglucentr trioctylklareester, Phloroglucin tridecylklareester and Phloroglucin- tridodecylklareester thereof and a fully hydrogenated or a hydrogenated polyisobutylene or
- High temperature oils used in industrial chain lubrication e.g. in conveyor systems, paint lines, textile industry, insulation industry, glass industry, etc., and belt lubrication are used in continuous Holzpreßanlagen, usually consist of a three-component system.
- This three-component system usually consists of an aromatic ester, a synthetic hydrocarbon and a polymer based on polyisobutylene.
- the synthetic hydrocarbon is used as a solubilizer.
- commercial additives are added to this lubrication system.
- a disadvantage of these systems, however, is that by the use of the synthetic hydrocarbon the Working temperature of the oil is limited because it evaporates very quickly at temperatures> 200 ° C.
- a three-component system is described for example in EP 1 154 011 B1.
- a lubricating oil composition containing an aromatic ester compound and, as another base oil, an ⁇ -olefin oligomer and a polyisobutene.
- Such a high-temperature oil is particularly required for the chain and belt lubrication of wood presses, as they are present for example in Contipressen TM for the production of laminate flooring.
- the object of the present invention was to provide a high-temperature oil, with which a good lubricating effect is achieved at a constant high temperature over a long period of time and which can be provided in different viscosities depending on the application.
- This object is achieved, surprisingly, by the provision of a high-temperature oil which, as a two-component system, comprises an aromatic ester of the general formula (I) wherein R 1 is a linear or branched alkyl group having 6 to 16 carbon atoms and n is 3 or 4 or a compound of the general formula (II)
- R is a linear or branched alkyl group having a chain length of 8 to 16 carbon atoms and n is 3
- a hydrogenated polyisobutylene a fully hydrogenated polyisobutylene or a mixture of a fully hydrogenated and a hydrogenated polyisobutylene.
- a fully hydrogenated polyisobutylene a fully hydrogenated polyisobutylene
- the high temperature oil comprises from 40 to 91, 9% by weight of the aromatic ester of general formula (I) or the compound of general formula (II) and from 50 to 5% by weight of hydrogenated, fully hydrogenated polyisobutylene or a mixture of hydrogenated and fully hydrogenated polyisobutylene.
- the high-temperature oil may comprise from 0.1 to 6% by weight, in particular from 2 to 5% by weight, of an antioxidant.
- the high-temperature oil 0 to 4 wt .-%, in particular 0.3 to 3.5 wt .-% of a wear protection agent, 0.1 to 1, 0 wt .-% of a corrosion inhibitor and 0 to 2 wt .-%, in particular 0.1 to 1, 5% by weight of an ionic liquid.
- the ester compound of the formula (I) present in the high-temperature oil is preferably selected from the group consisting of esters of trimellitic acid, pyromellitic acid, trimesic acid or mixtures thereof.
- the compound of the general formula (II) is a derivative of phloroglucinol (benzene-1,3,5-triol), preferably phloroglucinotrioctylic acid ester, phloroglucin tridecylic acid ester and phloroglucinetridodecylic acid ester.
- the antioxidant present in the high temperature oil which may contain sulfur and / or nitrogen and / or phosphorus in the molecule, is selected from the group consisting of aromatic amine antioxidants, such as alkylated phenyl-alpha-naphthylamine, dialkyldiphenylamine, hindered phenols, such as butylhydroxytoluene ( BHT), phenolic antioxidants with thioether groups, Zn or Mo or W dialkyldithiophosphates and phosphites.
- aromatic amine antioxidants such as alkylated phenyl-alpha-naphthylamine, dialkyldiphenylamine, hindered phenols, such as butylhydroxytoluene ( BHT), phenolic antioxidants with thioether groups, Zn or Mo or W dialkyldithiophosphates and phosphites.
- the anti-wear agent present in the high-temperature oil is selected from the group consisting of diphenyl cresyl phosphate-based anti-wear additives, amine-neutralized phosphates, alkylated and non-alkylated triaryl phosphates, alkylated and non-alkylated triaryl thiophosphates, zinc or Mo or dialkyldithiophosphates, carbamates, thiocarbamates , Zinc or Mo or W dithiocarbamates, dimercapto thiadiazole, calcium sulfonates and benzothazole derivatives.
- the corrosion inhibitor present in the high-temperature oil is selected from the group consisting of additives based on overbased Ca sulfonates having a TBN of 100 to 300 mg KOH / g, amine-neutralized phosphates, alkylated Ca naphthalenesulfonates, oxazoline derivatives, imidazole Derivatives, succinic acid half esters, N-alkylated benzotriazoles.
- the ionic liquid (IL) used in the high-temperature oil is so-called molten salt, which by definition is liquid at temperatures below 100 ° C. Many ionic liquids are also liquid at room temperature or at lower temperatures.
- Suitable cations for ionic liquids have been found to be a quaternary ammonium cation, a phosphonium cation, an imidazolium cation, a pyridinium cation, a pyrazolium cation, an oxazolium cation, a pyrrolidinium cation, a guanidinium cation, a morpholinium cation or a triazolium cation selected from the group consisting of [PF 6 r, [BF 4 V, [CF 3 CO 2 ] " , [CF 3 SO 3 ] " , [(CF 3 SO 2 ) 2 N] ' , [(R 4 S0 2 ) (R 5 S0 2 ) N] - , [(CF 3 SO 2 ) (CF 3 COO) N] ⁇ [R -SO 3 ] " , [R 4 -O-S0 3 ] " , [R-COO] -, Cl
- R 7 represent here or completely fluorinated radicals such as pentafluoroethyl or perfluorobutyl.
- the following anionic type is also quite stable thermally : (FS0 2 ) 2 N ⁇
- the ionic liquids should firstly show a solubility in the oils, but complete miscibility is not absolutely necessary.
- the ionic liquids should be thermally stable and not promote corrosion, for example by not forming corrosive reaction products in the presence of water or only with a very long delay.
- Ionic liquids such as tetraalkylammonium and tetraalkylphosphonium bis (trifluoromethylsulfonyl) imides such as, for example, trihexyl (tetradecyl) phosphonium bis (trifluoromethylsulfonyl) imide (HPDimide) and methyltrioctylammonium bis (trifluoromethylsulfonyl) imide have proved to be particularly advantageous (moimide).
- ionic liquids such as tetraalkylammonium and tetraalkylphosphonium tris (perfluoroethyl) trifluorophosphate such as tetrabutylphosphonium tris (perfluoroethyl) trifluorophosphate (BuPPFET), trihexyl (tetradecyl) tris (perfluoroethyl) trifluorophosphate (HDPPFET). Also particularly advantageous pyrrolidium tris (perfluoroethyl) trifluorophosphates have shown.
- tetraalkylammonium and tetraalkylphosphonium perfluorobutanesulfonates such as trihexyl (tetradecyl) phosphonium perfluorobutanesulfonate (HDPnonaflat).
- the two-component system according to the invention has a significantly higher performance in terms of thermal stability and residue formation or residue behavior.
- the enormous increase in thermal stability is particularly noticeable in a significant increase in the lubricating behavior.
- the relubrication intervals could be extended and an energy saving of up to 30% electricity savings could be achieved.
- the attached figures show the advantages of the high temperature oil based on two components according to the invention. shows the friction values in dependence on the temperature and a load of 250 N of a high temperature oil of the invention on two-component base of Example 1 compared to a known oil on three-component basis of Comparative Example 1 at a kinematic viscosity at 40 ° C of about 260 mm 2 / sec;
- Example 1 shows the evaporation losses of a two-component-based high-temperature oil according to the invention of Example 1 compared to a known three-component oil of Comparative Example 1 with a kinematic base oil viscosity at 40 ° C of about 260 mm 2 / sec;
- Fig. 12 shows an increase in the apparent dynamic viscosity of a two-component-based high-temperature oil of Example 1 compared with a known three-component-based oil of Comparative Example 1 at a kinematic base oil viscosity at 40 ° C of about 260 mm 2 / sec;
- Fig. 12 shows the friction values versus temperature and a load of 250 N of a two-component-based high-temperature oil of Example 2 of the present invention as compared with a known three-component-based oil of Comparative Example 2;
- Example 2 shows the evaporation losses of a two-component high-temperature oil according to the invention of Example 2 compared to a known three-component oil of Comparative Example 2 at a kinematic base oil viscosity at 40 ° C of about 100 mm 2 / sec;
- Fig. 10 shows an increase in apparent viscosity of a two-component-based high-temperature oil of Example 2 compared with a known three-component-based oil of Comparative Example 2 at a kinematic base oil viscosity at 40 ° C of about 100 mm 2 / sec; shows the friction values as a function of the temperature and a load of 250 N of an inventive Two component high temperature high temperature oil of Example 3 compared with a known three component based oil of Comparative Example 3;
- Figure 8 shows the evaporation losses of an inventive
- FIG. 9 shows an increase in the apparent dynamic viscosity of a two-component-based high-temperature oil of Example 3 compared with a known three-component-based oil of Comparative Example 3 at a kinematic base oil viscosity at 40 ° C. of approximately 680 mm 2 / sec;
- FIG. 10 shows the evaporation losses of a device according to the invention
- FIG. 11 shows the increase in the apparent dynamic viscosity of a high-temperature oil according to the invention on a two-component basis with an ionic liquid of Example 4 compared with Comparative Example 4, which corresponds to Example 1, with a kinematic base oil viscosity of approximately 260 mm 2 / sec.
- FIG. 12 shows the experimental setup for the power chain test bench.
- composition of high-temperature oil is Composition of high-temperature oil
- trimellitic acid ester As the aromatic ester, trimellitic acid ester is placed in a stirred tank. At 100 ° C, the polyisobutylene is added with stirring. Subsequently, the mixture is stirred for 1 hour to obtain a homogeneous mixture. The anti-wear agents and the antioxidant are added to the kettle at 60 ° C with stirring. After about 1 hour, the finished oil can be filled into the containers provided.
- Example 1 The oils prepared in Example 1 and Comparative Example 1 were used to determine the friction values.
- a vibration friction wear test (SRV) based on DIN 51834, test condition ball / disc, 250 N load, 50 ° C to 250 ° C, 1 mm stroke 50 Hz, 165 min was performed. The results are shown in Table 3.
- the oil to be tested is weighed on a previously bent and solvent-cleaned steel sheet with 5 g and then evaporated at 250 ° C in a convection oven min 72h.
- the square sheet is bent manually on all four sides to create a shell shape.
- Essential for this test is the determination of the solubility of the residue with fresh oil and the amount of residue formed.
- FIG. 12 shows the performance chain test bench which operates under the following test conditions
- Chain test stand installed (see Figure 10) and started the test under the specified conditions. It can change the temperature, the
- the maturity is fixed with a chain elongation of 0.1%.
- Chain is created by wear on the chain links throughout the
- composition of the high-temperature oil according to the invention is composition of the high-temperature oil according to the invention:
- composition of the three-component high-temperature oil is Composition of the three-component high-temperature oil:
- Example 2 The oils prepared in Example 2 and Comparative Example 2 were used to determine the friction values.
- a vibration friction wear test (SRV) based on DIN 51834, test condition ball / disc, 250 N load, 50 ° C to 250 ° C, 1 mm stroke 50 Hz, 165 min was performed. The results are shown in Table 6.
- Table 6 The results are shown in Table 6.
- the performance chain test was carried out at 220 ° C, a speed of 2.0 m / sec and a load of 2600 N.
- the run time after 0.1% chain elongation for example 2 is 19 h, that of comparative example 2 is 17 h.
- composition of the high-temperature oil according to the invention is composition of the high-temperature oil according to the invention:
- composition of the three-component high-temperature oil is Composition of the three-component high-temperature oil:
- Example 3 The oils prepared in Example 3 and Comparative Example 3 were used to determine the friction values.
- a vibration friction wear test (SRV) based on DIN 51834, test condition ball / disc, 250 N load, 50 ° C to 250 ° C, 1 mm stroke 50 Hz, 165 min was performed. The results are shown in Table 9.
- the performance chain test was carried out at 220 ° C, a speed of 2.0 m / sec and a load of 2600 N.
- the transit time after 0.1% chain elongation was 17 h for Example 3 and 15 h for Comparative Example 3.
- the test was carried out as described in Example 1.
- composition of the high-temperature oil according to the invention is composition of the high-temperature oil according to the invention:
- ionic liquid 0.50% by weight ionic liquid
- the preparation was carried out as described in Example 1.
- composition of high-temperature oil according to the invention 63.5% Phloroglucin tridecylklareester
- the two-component system according to the invention has a significantly higher performance in terms of thermal stability and residue formation or residue behavior.
- the enormous increase in thermal stability is particularly noticeable in a significant increase in the lubricating behavior.
- the relubrication intervals could be extended and an energy saving of up to 30% electricity savings could be achieved.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
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Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR112013030286-0A BR112013030286B1 (pt) | 2011-05-26 | 2012-05-22 | óleo de alta temperatura e uso do dito óleo |
CN201280024232.XA CN103764808A (zh) | 2011-05-26 | 2012-05-22 | 高温油 |
ES12727785.3T ES2601401T3 (es) | 2011-05-26 | 2012-05-22 | Aceite para altas temperaturas |
EP12727785.3A EP2714872B1 (de) | 2011-05-26 | 2012-05-22 | Hochtemperaturöl |
AU2012261221A AU2012261221B2 (en) | 2011-05-26 | 2012-05-22 | High temperature oil |
LTEP12727785.3T LT2714872T (lt) | 2011-05-26 | 2012-05-22 | Aukštatemperatūrinė tepalinė alyva |
SI201230680A SI2714872T1 (sl) | 2011-05-26 | 2012-05-22 | Visokotemperaturno olje |
KR1020137030344A KR101539218B1 (ko) | 2011-05-26 | 2012-05-22 | 고온용 윤활 오일 |
US14/119,015 US20140200169A1 (en) | 2011-05-26 | 2012-05-22 | High Temperature Oil |
EA201301331A EA026445B1 (ru) | 2011-05-26 | 2012-05-22 | Высокотемпературное масло и его применение |
JP2014511763A JP5752321B2 (ja) | 2011-05-26 | 2012-05-22 | 高温用オイル |
Applications Claiming Priority (2)
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DE102011102540A DE102011102540B4 (de) | 2011-05-26 | 2011-05-26 | Hochtemperaturöl |
DE102011102540.9 | 2011-05-26 |
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WO2012159738A1 true WO2012159738A1 (de) | 2012-11-29 |
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PCT/EP2012/002172 WO2012159738A1 (de) | 2011-05-26 | 2012-05-22 | Hochtemperaturöl |
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US (1) | US20140200169A1 (ja) |
EP (1) | EP2714872B1 (ja) |
JP (1) | JP5752321B2 (ja) |
KR (1) | KR101539218B1 (ja) |
CN (1) | CN103764808A (ja) |
AU (1) | AU2012261221B2 (ja) |
BR (1) | BR112013030286B1 (ja) |
CL (1) | CL2013003397A1 (ja) |
DE (1) | DE102011102540B4 (ja) |
EA (1) | EA026445B1 (ja) |
ES (1) | ES2601401T3 (ja) |
HU (1) | HUE029149T2 (ja) |
LT (1) | LT2714872T (ja) |
MY (1) | MY164068A (ja) |
PL (1) | PL2714872T3 (ja) |
SI (1) | SI2714872T1 (ja) |
WO (1) | WO2012159738A1 (ja) |
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JP2017538840A (ja) * | 2014-12-17 | 2017-12-28 | クリューバー リュブリケーション ミュンヘン ソシエタス ヨーロピア ウント コンパニー コマンディートゲゼルシャフトKlueber Lubrication Muenchen SE & Co.KG | 食品産業のための高温用潤滑剤 |
JP2017538838A (ja) * | 2014-12-17 | 2017-12-28 | クリューバー リュブリケーション ミュンヘン ソシエタス ヨーロピア ウント コンパニー コマンディートゲゼルシャフトKlueber Lubrication Muenchen SE & Co.KG | 高温用潤滑剤 |
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FR3041647B1 (fr) * | 2015-09-25 | 2017-10-27 | Michelin & Cie | Composition de caoutchouc a haute rigidite a base d'un derive de polyphenol aromatique |
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- 2012-05-22 PL PL12727785T patent/PL2714872T3/pl unknown
- 2012-05-22 HU HUE12727785A patent/HUE029149T2/hu unknown
- 2012-05-22 US US14/119,015 patent/US20140200169A1/en not_active Abandoned
- 2012-05-22 CN CN201280024232.XA patent/CN103764808A/zh active Pending
- 2012-05-22 KR KR1020137030344A patent/KR101539218B1/ko active IP Right Grant
- 2012-05-22 AU AU2012261221A patent/AU2012261221B2/en active Active
- 2012-05-22 LT LTEP12727785.3T patent/LT2714872T/lt unknown
- 2012-05-22 BR BR112013030286-0A patent/BR112013030286B1/pt active IP Right Grant
- 2012-05-22 MY MYPI2013003925A patent/MY164068A/en unknown
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JP2017538840A (ja) * | 2014-12-17 | 2017-12-28 | クリューバー リュブリケーション ミュンヘン ソシエタス ヨーロピア ウント コンパニー コマンディートゲゼルシャフトKlueber Lubrication Muenchen SE & Co.KG | 食品産業のための高温用潤滑剤 |
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WO2023016908A1 (de) | 2021-08-12 | 2023-02-16 | Klueber Lubrication Muenchen Se & Co. Kg | Verwendung von hemimellitsäureester als basisöl für schmierstoffzusammensetzungen |
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Publication number | Publication date |
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EP2714872A1 (de) | 2014-04-09 |
CN103764808A (zh) | 2014-04-30 |
PL2714872T3 (pl) | 2017-01-31 |
KR20140009499A (ko) | 2014-01-22 |
MY164068A (en) | 2017-11-15 |
DE102011102540B4 (de) | 2013-12-12 |
KR101539218B1 (ko) | 2015-07-29 |
CL2013003397A1 (es) | 2014-07-11 |
ES2601401T3 (es) | 2017-02-15 |
BR112013030286A2 (pt) | 2016-11-29 |
EA201301331A1 (ru) | 2014-05-30 |
JP2014515412A (ja) | 2014-06-30 |
EP2714872B1 (de) | 2016-08-03 |
SI2714872T1 (sl) | 2016-11-30 |
AU2012261221B2 (en) | 2016-05-12 |
AU2012261221A1 (en) | 2013-12-12 |
US20140200169A1 (en) | 2014-07-17 |
HUE029149T2 (hu) | 2017-02-28 |
JP5752321B2 (ja) | 2015-07-22 |
LT2714872T (lt) | 2016-09-26 |
DE102011102540A1 (de) | 2012-11-29 |
BR112013030286B1 (pt) | 2020-11-10 |
EA026445B1 (ru) | 2017-04-28 |
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