US20140200169A1 - High Temperature Oil - Google Patents
High Temperature Oil Download PDFInfo
- Publication number
- US20140200169A1 US20140200169A1 US14/119,015 US201214119015A US2014200169A1 US 20140200169 A1 US20140200169 A1 US 20140200169A1 US 201214119015 A US201214119015 A US 201214119015A US 2014200169 A1 US2014200169 A1 US 2014200169A1
- Authority
- US
- United States
- Prior art keywords
- temperature oil
- weight
- oil
- phloroglucinol
- dialkyldithiophosphates
- 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.)
- Abandoned
Links
- 239000003921 oil Substances 0.000 claims abstract description 124
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- -1 ester compound Chemical class 0.000 claims description 26
- 229920006007 hydrogenated polyisobutylene Polymers 0.000 claims description 19
- 239000002608 ionic liquid Substances 0.000 claims description 19
- 239000003963 antioxidant agent Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 230000003078 antioxidant effect Effects 0.000 claims description 15
- 239000007983 Tris buffer Substances 0.000 claims description 10
- 238000005461 lubrication Methods 0.000 claims description 9
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- LREUQCJWYZEDHP-UHFFFAOYSA-N (3,5-dihydroxyphenyl) tridecanoate Chemical compound CCCCCCCCCCCCC(=O)OC1=CC(O)=CC(O)=C1 LREUQCJWYZEDHP-UHFFFAOYSA-N 0.000 claims description 4
- 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
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-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
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 239000011733 molybdenum Substances 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
- 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 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 239000010937 tungsten Substances 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- SXUXYEGAUJZGHC-UHFFFAOYSA-N [3,5-di(dodecanoyloxy)phenyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC1=CC(OC(=O)CCCCCCCCCCC)=CC(OC(=O)CCCCCCCCCCC)=C1 SXUXYEGAUJZGHC-UHFFFAOYSA-N 0.000 claims description 3
- XAOLKTLYWUBFCE-UHFFFAOYSA-N [3,5-di(octanoyloxy)phenyl] octanoate Chemical compound CCCCCCCC(=O)OC1=CC(OC(=O)CCCCCCC)=CC(OC(=O)CCCCCCC)=C1 XAOLKTLYWUBFCE-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 150000003000 phloroglucinols Chemical class 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 3
- 239000002023 wood Substances 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
- 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 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
- PVQQVQHVSQFXEV-UHFFFAOYSA-J C(N)([S-])=S.[W+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S Chemical class C(N)([S-])=S.[W+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S PVQQVQHVSQFXEV-UHFFFAOYSA-J 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
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 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
- 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
- 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 claims description 2
- CKJFPVNRRHVMKZ-UHFFFAOYSA-L calcium;naphthalene-1-sulfonate Chemical class [Ca+2].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1.C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 CKJFPVNRRHVMKZ-UHFFFAOYSA-L 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 239000011810 insulating material Substances 0.000 claims description 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 2
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical class C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000010422 painting Methods 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
- 238000003825 pressing Methods 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000005497 tetraalkylphosphonium group Chemical group 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
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 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
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical class [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 claims description 2
- 229920002367 Polyisobutene Polymers 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract 1
- 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
- 150000003639 trimesic acids Chemical class 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 41
- 238000009834 vaporization Methods 0.000 description 28
- 230000008016 vaporization Effects 0.000 description 28
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000002199 base oil Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 239000000314 lubricant Substances 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 230000008092 positive effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000008646 thermal stress Effects 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 0 *C(=O)OC1=CC(OC(*)=O)=CC(OC(*)=O)=C1 Chemical compound *C(=O)OC1=CC(OC(*)=O)=CC(OC(*)=O)=C1 0.000 description 2
- BTMRYSYEOPOPBR-UHFFFAOYSA-N CC.c1ccccc1 Chemical compound CC.c1ccccc1 BTMRYSYEOPOPBR-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229910018928 (FSO2)2N Inorganic materials 0.000 description 1
- 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
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 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
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000001035 drying 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 229920013639 polyalphaolefin Polymers 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
- 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
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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
-
- 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 esters or a mixture, or derivatives of phloroglucinol such as phloroglucinol trioctanoate, phloroglucinol tridecanoate and phloroglucinol tridodecanoate thereof, and a fully hydrogenated or a hydrogenated polyisobutylene or a mixture thereof.
- aromatic esters such as trimellitic esters, pyromellitic esters, trimesic esters or a mixture
- derivatives of phloroglucinol such as phloroglucinol trioctanoate, phloroglucinol tridecanoate and phloroglucinol tridodecanoate thereof, and a fully hydrogenated or a hydrogenated polyisobutylene or a mixture thereof.
- High-temperature oils which are used in the field of industrial chain lubrication, for example in conveying systems, painting lines, the textile industry, the insulating materials industry, the glass industry, etc., and belt lubrication in continuous wood pressing plants, typically consist of a three-component system.
- This three-component system generally consists of an aromatic ester, a synthetic hydrocarbon and a polymer based on polyisobutylene.
- the synthetic hydrocarbon is used as a solubilizer.
- Also added to this lubricant system are commercial additives.
- a disadvantage of these systems is that the use of the synthetic hydrocarbon limits the working temperature of the oil, since it vaporizes very rapidly at temperatures >200° C.
- a three-component system is described, for example, in EP 1 154 011 B1.
- a lubricant oil composition comprising an aromatic ester compound and, as a further base oil, an ⁇ -olefin oligomer, and also a polyisobutene, is provided.
- the loss of performance for a three-component lubricant composition is high as a result of the vaporization of the solubilizer.
- the vaporization results in formation of a deposit or a residue formed from the remaining constituents of the lubricant on the application surface or the application area, as a result of which full lubrication can no longer be ensured.
- This deposit then has to be dissolved again.
- operation has to be stopped and the residue has to be removed.
- Such a high-temperature oil is especially required for chain and belt lubrication of wood presses, as present, for example, in ContipressenTM continuous presses for the production of laminate floors.
- R1 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 equal to 3,
- a hydrogenated polyisobutylene a fully hydrogenated polyisobutylene or a mixture of a fully hydrogenated and a hydrogenated polyisobutylene.
- a fully hydrogenated polyisobutylene is included.
- the high-temperature oil comprises 40 to 91.9% by weight of the aromatic ester of the general formula (I) or of the compound of the general formula (II) and 50 to 5% by weight of the hydrogenated, fully hydrogenated polyisobutylene or of a mixture of hydrogenated and fully hydrogenated polyisobutylene.
- the high-temperature oil may comprise 0.1 to 6% by weight, especially 2 to 5% by weight, of an antioxidant.
- the high-temperature oil may also comprise 0 to 4% by weight, especially 0.3 to 3.5% by weight, of an antiwear agent, 0.1 to 1.0% by weight of an anticorrosive, and 0 to 2% by weight, especially 0.1 to 1.5% by weight, of an ionic liquid.
- the ester compound of 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 phloroglucinol trioctanoate, phloroglucinol tridecanoate and phloroglucinol tridodecanoate.
- 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 aminic antioxidants such as alkylated phenyl-alpha-naphthylamine, dialkyldiphenylamine, sterically hindered phenols such as butylhydroxytoluene (BHT), phenolic antioxidants having thioether groups, zinc dialkyldithiophosphates or molybdenum dialkyldithiophosphates or tungsten dialkyldithiophosphates, and phosphites.
- aromatic aminic antioxidants such as alkylated phenyl-alpha-naphthylamine, dialkyldiphenylamine, sterically hindered phenols such as butylhydroxytoluene (BHT), phenolic antioxidants having thioether groups, zinc dialkyldithiophosphates or molybdenum dial
- the antiwear agent present in the high-temperature oil is selected from the group consisting of antiwear additives based on diphenyl cresyl phosphate, amine-neutralized phosphates, alkylated and nonalkylated triaryl phosphates, alkylated and nonalkylated triaryl thiophosphates, zinc dialkyldithiophosphates or molybdenum dialkyldithiophosphates or tungsten dialkyldithiophosphates, carbamates, thiocarbamates, zinc dithiocarbamates or molybdenum dithiocarbamates or tungsten dithiocarbamates, dimercaptothiadiazole, calcium sulfonates and benzotriazole derivatives.
- the anticorrosive present in the high-temperature oil is selected from the group consisting of additives based on “overbased” calcium sulfonates having a TBN of 100 to 300 mg KOH/g, amine-neutralized phosphates, alkylated calcium naphthalenesulfonates, oxazoline derivatives, imidazole derivatives, succinic monoesters, N-alkylated benzotriazoles.
- the ionic liquid (IL) used in the high-temperature oil comprises what are called salt melts which, by definition, are 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, which may be combined with an anion selected from the group consisting of [PF 6 ] ⁇ , [BF 4 ] ⁇ , [CF 3 CO 2 ] ⁇ , [CF 3 SO 3 ] ⁇ .
- R 4 and R 5 radicals are each independently selected from hydrogen; linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups having 1 to 20 carbon atoms; heteroaryl groups, heteroaryl-C 1 -C 6 -alkyl groups having 3 to 8 carbon atoms in the heteroaryl radical and at least one heteroatom from N, O and S which may be substituted by at
- R 7 here represents partly or fully fluorinated radicals such as pentafluoroethyl or perfluorobutyl.
- the ionic liquids In order to display positive action in oils, the ionic liquids should firstly show solubility in the oils, although complete miscibility is not absolutely necessary.
- the ionic liquids should be thermally stable and not promote corrosion, for example by forming reaction products which are noncorrosive or corrosive only in a very delayed manner in the presence of water.
- Particularly advantageous ionic liquids have been found to be those such as tetraalkylammonium bis(trifluoromethylsulfonyl)imides and tetraalkylphosphonium bis(trifluoromethylsulfonyl)imides, for example trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide (HPDimide) and methyltrioctylammonium bis(trifluoromethylsulfonyl)imide (Moimide).
- HPDimide trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide
- Moimide methyltrioctylammonium bis(trifluoromethylsulfonyl)imide
- Ionic liquids which have likewise been found to be particularly advantageous are those such as tetraalkylammonium tris(perfluoroethyl)trifluorophosphate and tetraalkylphosphonium tris(perfluoroethyl)trifluorophosphate, for example tetrabutylphosphonium tris(perfluoroethyl)trifluorophosphate (BuPPFET), trihexyl(tetradecyl) tris(perfluoroethyl)trifluorophosphate (HDPPFET). It has likewise been found that pyrrolidinium tris(perfluoroethyl)trifluorophosphates are particularly advantageous.
- tetraalkylammonium perfluorobutanesulfonates and tetraalkylphosphonium perfluorobutanesulfonates such as trihexyl(tetradecyl)phosphonium perfluorobutanesulfonate (HDPnonaflate).
- the inventive two-component system has a much higher performance in terms of thermal stability and residue formation or residue characteristics.
- the enormous rise in thermal stability is manifested particularly in a distinct increase in lubrication characteristics.
- the relubrication intervals were extended and an energy saving of up to a 30% power saving was achieved.
- FIG. 1 shows the friction values as a function of temperature at a load of 250 N for an inventive high-temperature oil based on two components from example 1 compared with a known oil based on three components from comparative example 1 at a kinematic viscosity at 40° C. of about 260 mm 2 /sec;
- FIG. 2 shows the vaporization losses for an inventive high-temperature oil based on two components from example 1 compared with a known oil based on three components from comparative example 1 at a kinematic base oil viscosity at 40° C. of about 260 mm 2 /sec;
- FIG. 3 shows the increase in the apparent dynamic viscosity of an inventive high-temperature oil based on two components from example 1 compared with a known oil based on three components from comparative example 1 at a kinematic base oil viscosity at 40° C. of about 260 mm 2 /sec;
- FIG. 4 shows the friction values as a function of temperature at a load of 250 N for an inventive high-temperature oil based on two components from example 2 compared with a known oil based on three components from comparative example 2;
- FIG. 5 shows the vaporization losses for an inventive high-temperature oil based on two components from example 2 compared with a known oil based on three components from comparative example 2 at a kinematic base oil viscosity at 40° C. of about 100 mm 2 /sec;
- FIG. 6 shows the increase in the apparent viscosity of an inventive high-temperature oil based on two components from example 2 compared with a known oil based on three components from comparative example 2 at a kinematic base oil viscosity at 40° C. of about 100 mm 2 /sec;
- FIG. 7 shows the friction values as a function of temperature at a load of 250 N for an inventive high-temperature oil based on two components from example 3 compared with a known oil based on three components from comparative example 3;
- FIG. 8 shows the vaporization losses for an inventive high-temperature oil based on two components from example 3 compared with a known oil based on three components from comparative example 3 at a kinematic base oil viscosity at 40° C. of about 680 mm 2 /sec;
- FIG. 9 shows the increase in the apparent dynamic viscosity of an inventive high-temperature oil based on two components from example 3 compared with a known oil based on three components from comparative example 3 at a kinematic base oil viscosity at 40° C. of about 680 mm 2 /sec;
- FIG. 10 shows the vaporization losses for an inventive high-temperature oil based on two components with an ionic liquid from example 4 compared with comparative example 4, which corresponds to example 1 at a kinematic base oil viscosity of about 260 mm 2 /sec;
- FIG. 11 shows the increase in the apparent dynamic viscosity of an inventive high-temperature oil based on two components with an ionic liquid from example 4 compared with comparative example 4, which corresponds to example 1 at a kinematic base oil viscosity of about 260 mm 2 /sec;
- FIG. 12 shows the experimental setup for the high-performance chain test bed.
- composition of the high-temperature oil is Composition of the high-temperature oil:
- trimellitic ester is initially charged in a stirred tank. At 100° C., the polyisobutylene is added while stirring. Subsequently, the mixture is stirred for one 1 hour in order to obtain a homogeneous mixture. The antiwear agent and the antioxidant are added to the tank at 60° C. while stirring. After about 1 hour, the finished oil can be dispensed into the containers provided.
- composition of the high-temperature oil is Composition of the high-temperature oil:
- trimellitic ester is initially charged in a stirred tank together with the poly- ⁇ -olefin as the synthetic hydrocarbon.
- the polyisobutylene is added while stirring.
- the mixture is stirred for 1 hour in order to obtain a homogeneous mixture.
- the antiwear agent and the antioxidant are added to the tank at 60° C. while stirring. After about 1 hour, the finished oil can be dispensed into the containers provided.
- oils according to example 1 and comparative example 1 were compared with one another.
- the oil to be tested is weighed to 5 g onto a steel sheet which has been bent to size and cleaned with solvent beforehand, and then vaporized off at 250° C. in an air circulation drying cabinet for min. 72 h.
- the square sheet is bent manually on all four sides, so as to give a dish shape.
- the inventive high-temperature oil forms a lower level of residue at 4.8% than the known oil, which has a residue of 6.0%.
- the residue formed from the inventive high-temperature oil has very good surface dissolvability, which means that these residues are easy to dissolve with fresh oil.
- the residue of the known oil has much poorer surface redissolvability with fresh oil.
- FIG. 12 shows the high-performance chain test bed, which works under the following test conditions:
- the chain Before the test, the chain is immersed into the lubricant oil to be tested. After the immersion, the chain is suspended, such that the excess lubricant can drip off. Subsequently, the chain is installed into the chain test bed (see FIG. 10 ) and the test is started under the conditions defined. It is possible to vary the temperature, the speed and the load.
- the run time is fixed at a chain lengthening of 0.1%.
- the lengthening of the chain arises through wear at the chain members during the test run.
- composition of the inventive high-temperature oil is a composition of the inventive high-temperature oil
- composition of the three-component high-temperature oil is Composition of the three-component high-temperature oil:
- the production is effected as described in comparative example 1.
- oils according to example 2 and comparative example 2 were compared with one another.
- Both the inventive high-temperature oil and the known oil had a residue of 3.0%; the residue formed from the inventive high-temperature oil had very good surface dissolvability, which means that these residues can be dissolved easily with fresh oil. In contrast, the residue of the known oil has much poorer surface redissolvability with fresh oil.
- the test on the high-performance chain test bed was conducted at 220° C., a speed of 2.0 m/sec and a load of 2600 N.
- the run time after chain lengthening 0.1% is 19 h for example 2, and that for comparative example 2 is 17 h.
- oils according to example 3 and comparative example 3 were compared with one another.
- the inventive high-temperature oil forms a lower level of residues at 4.8% than the known oil, which has a residue of 11.8%.
- the residue formed from the inventive high-temperature oil has very good surface dissolvability, which means that these residues can be dissolved easily with fresh oil.
- the residue of the known oil has much poorer surface redissolvability with fresh oil.
- the test on the high-performance chain test bed was conducted at 220° C., a speed of 2.0 m/sec and a load of 2600 N.
- the run time after chain lengthening 0.1% was 17 h for example 3 and 15 h for comparative example 3.
- the test was conducted as described in example 1.
- composition of the inventive high-temperature oil is a composition of the inventive high-temperature oil
- Example 4 Corresponds to example 1 Vaporization loss 19% 46% after 72 h/250° C. Increase in 2300 mPas 27 000 mPas apparent dynamic viscosity after 72 h/250° C.
- the inventive two-component system has much higher performance with regard to thermal stability and residue formation or residue characteristics.
- the enormous rise in thermal stability is manifested particularly in a distinct rise in lubrication characteristics.
- the relubrication intervals were extended and an energy saving of up to a 30% power saving was achieved.
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Abstract
The invention relates to novel high temperature oils based on aromatic esters, such as trimellitic acid esters, pryomellitic acid esters, trimesic acid esters or a mixture thereof or derivatives of phloroglucinol and a fully hydrated or a hydrated polyisobutylene or a mixture thereof.
Description
- The invention relates to novel high-temperature oils based on aromatic esters such as trimellitic esters, pyromellitic esters, trimesic esters or a mixture, or derivatives of phloroglucinol such as phloroglucinol trioctanoate, phloroglucinol tridecanoate and phloroglucinol tridodecanoate thereof, and a fully hydrogenated or a hydrogenated polyisobutylene or a mixture thereof.
- High-temperature oils which are used in the field of industrial chain lubrication, for example in conveying systems, painting lines, the textile industry, the insulating materials industry, the glass industry, etc., and belt lubrication in continuous wood pressing plants, typically consist of a three-component system.
- This three-component system generally consists of an aromatic ester, a synthetic hydrocarbon and a polymer based on polyisobutylene. The synthetic hydrocarbon is used as a solubilizer. Also added to this lubricant system are commercial additives. However, a disadvantage of these systems is that the use of the synthetic hydrocarbon limits the working temperature of the oil, since it vaporizes very rapidly at temperatures >200° C.
- A three-component system is described, for example, in
EP 1 154 011 B1. Here, a lubricant oil composition comprising an aromatic ester compound and, as a further base oil, an α-olefin oligomer, and also a polyisobutene, is provided. - As already stated above, the loss of performance for a three-component lubricant composition is high as a result of the vaporization of the solubilizer. The vaporization results in formation of a deposit or a residue formed from the remaining constituents of the lubricant on the application surface or the application area, as a result of which full lubrication can no longer be ensured. This deposit then has to be dissolved again. In general, operation has to be stopped and the residue has to be removed. There is thus a need for a high-temperature oil in which the vaporization of individual constituents of the oil is greatly reduced and hence the lubricity is not lost at constantly high temperature over a long period.
- Such a high-temperature oil is especially required for chain and belt lubrication of wood presses, as present, for example, in Contipressen™ continuous presses for the production of laminate floors.
- It was an object of the present invention to provide a high-temperature oil with which good lubricity is achieved at constantly high temperature over a long period and which can be provided in different viscosities according to the application.
- This object is surprisingly achieved by the provision of a high-temperature oil which consists, as a two-component system an aromatic ester of the general formula (I)
- where R1 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)
- where R is a linear or branched alkyl group having a chain length of 8 to 16 carbon atoms and n is equal to 3,
- and
- a hydrogenated polyisobutylene, a fully hydrogenated polyisobutylene or a mixture of a fully hydrogenated and a hydrogenated polyisobutylene. Preferably, a fully hydrogenated polyisobutylene is included.
- In general, the high-temperature oil comprises 40 to 91.9% by weight of the aromatic ester of the general formula (I) or of the compound of the general formula (II) and 50 to 5% by weight of the hydrogenated, fully hydrogenated polyisobutylene or of a mixture of hydrogenated and fully hydrogenated polyisobutylene.
- In addition, the high-temperature oil may comprise 0.1 to 6% by weight, especially 2 to 5% by weight, of an antioxidant.
- The high-temperature oil may also comprise 0 to 4% by weight, especially 0.3 to 3.5% by weight, of an antiwear agent, 0.1 to 1.0% by weight of an anticorrosive, and 0 to 2% by weight, especially 0.1 to 1.5% by weight, of an ionic liquid.
- The ester compound of 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 phloroglucinol trioctanoate, phloroglucinol tridecanoate and phloroglucinol tridodecanoate.
- 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 aminic antioxidants such as alkylated phenyl-alpha-naphthylamine, dialkyldiphenylamine, sterically hindered phenols such as butylhydroxytoluene (BHT), phenolic antioxidants having thioether groups, zinc dialkyldithiophosphates or molybdenum dialkyldithiophosphates or tungsten dialkyldithiophosphates, and phosphites.
- The antiwear agent present in the high-temperature oil is selected from the group consisting of antiwear additives based on diphenyl cresyl phosphate, amine-neutralized phosphates, alkylated and nonalkylated triaryl phosphates, alkylated and nonalkylated triaryl thiophosphates, zinc dialkyldithiophosphates or molybdenum dialkyldithiophosphates or tungsten dialkyldithiophosphates, carbamates, thiocarbamates, zinc dithiocarbamates or molybdenum dithiocarbamates or tungsten dithiocarbamates, dimercaptothiadiazole, calcium sulfonates and benzotriazole derivatives.
- The anticorrosive present in the high-temperature oil is selected from the group consisting of additives based on “overbased” calcium sulfonates having a TBN of 100 to 300 mg KOH/g, amine-neutralized phosphates, alkylated calcium naphthalenesulfonates, oxazoline derivatives, imidazole derivatives, succinic monoesters, N-alkylated benzotriazoles.
- The ionic liquid (IL) used in the high-temperature oil comprises what are called salt melts which, by definition, are 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, which may be combined with an anion selected from the group consisting of [PF6]−, [BF4]−, [CF3CO2]−, [CF3SO3]−. [(CF3SO2)2N]−, [(R4SO2) (R5SO2)N]−, [(CF3SO2) (CF3COO)N]−, [R4—SO3]−, [R4—O—SO3]−, [R4—COO]−, Cl−, Br−, [NO3]−, [N(CN)2]−, [HSO4]−, or [R4R5PO4]−, and the R4 and R5 radicals are each independently selected from hydrogen; linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups having 1 to 20 carbon atoms; heteroaryl groups, heteroaryl-C1-C6-alkyl groups having 3 to 8 carbon atoms in the heteroaryl radical and at least one heteroatom from N, O and S which may be substituted by at least one group selected from C1-C6-alkyl groups and/or halogen atoms; aryl groups, aryl-C1-C6-alkyl groups having 5 to 12 carbon atoms in the aryl radical, which may be substituted by at least one C1-C6-alkyl group, partly and fully fluorinated alkyl radicals. However, further combinations are also possible. Anions of [PF(6-x)R7 x], [R7—SO3]− type are also known. R7 here represents partly or fully fluorinated radicals such as pentafluoroethyl or perfluorobutyl.
- The following anion type is likewise quite thermally stable: (FSO2)2N.
- In order to display positive action in oils, the ionic liquids should firstly show solubility in the oils, although complete miscibility is not absolutely necessary. The ionic liquids should be thermally stable and not promote corrosion, for example by forming reaction products which are noncorrosive or corrosive only in a very delayed manner in the presence of water.
- Particularly advantageous ionic liquids have been found to be those such as tetraalkylammonium bis(trifluoromethylsulfonyl)imides and tetraalkylphosphonium bis(trifluoromethylsulfonyl)imides, for example trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide (HPDimide) and methyltrioctylammonium bis(trifluoromethylsulfonyl)imide (Moimide). Ionic liquids which have likewise been found to be particularly advantageous are those such as tetraalkylammonium tris(perfluoroethyl)trifluorophosphate and tetraalkylphosphonium tris(perfluoroethyl)trifluorophosphate, for example tetrabutylphosphonium tris(perfluoroethyl)trifluorophosphate (BuPPFET), trihexyl(tetradecyl) tris(perfluoroethyl)trifluorophosphate (HDPPFET). It has likewise been found that pyrrolidinium tris(perfluoroethyl)trifluorophosphates are particularly advantageous. Also particularly advantageous are tetraalkylammonium perfluorobutanesulfonates and tetraalkylphosphonium perfluorobutanesulfonates such as trihexyl(tetradecyl)phosphonium perfluorobutanesulfonate (HDPnonaflate).
- It is also possible to use any desired mixtures of the ionic liquids.
- The inventive two-component system has a much higher performance in terms of thermal stability and residue formation or residue characteristics. The enormous rise in thermal stability is manifested particularly in a distinct increase in lubrication characteristics. The relubrication intervals were extended and an energy saving of up to a 30% power saving was achieved.
- As already mentioned, the formation of residues is distinctly reduced. As a result, the formation of cracking residues is also reduced and the residues formed can be very easily dissolved with fresh oil.
- The appended figures show the advantages of the inventive high-temperature oil based on two components.
-
FIG. 1 shows the friction values as a function of temperature at a load of 250 N for an inventive high-temperature oil based on two components from example 1 compared with a known oil based on three components from comparative example 1 at a kinematic viscosity at 40° C. of about 260 mm2/sec; -
FIG. 2 shows the vaporization losses for an inventive high-temperature oil based on two components from example 1 compared with a known oil based on three components from comparative example 1 at a kinematic base oil viscosity at 40° C. of about 260 mm2/sec; -
FIG. 3 shows the increase in the apparent dynamic viscosity of an inventive high-temperature oil based on two components from example 1 compared with a known oil based on three components from comparative example 1 at a kinematic base oil viscosity at 40° C. of about 260 mm2/sec; -
FIG. 4 shows the friction values as a function of temperature at a load of 250 N for an inventive high-temperature oil based on two components from example 2 compared with a known oil based on three components from comparative example 2; -
FIG. 5 shows the vaporization losses for an inventive high-temperature oil based on two components from example 2 compared with a known oil based on three components from comparative example 2 at a kinematic base oil viscosity at 40° C. of about 100 mm2/sec; -
FIG. 6 shows the increase in the apparent viscosity of an inventive high-temperature oil based on two components from example 2 compared with a known oil based on three components from comparative example 2 at a kinematic base oil viscosity at 40° C. of about 100 mm2/sec; -
FIG. 7 shows the friction values as a function of temperature at a load of 250 N for an inventive high-temperature oil based on two components from example 3 compared with a known oil based on three components from comparative example 3; -
FIG. 8 shows the vaporization losses for an inventive high-temperature oil based on two components from example 3 compared with a known oil based on three components from comparative example 3 at a kinematic base oil viscosity at 40° C. of about 680 mm2/sec; -
FIG. 9 shows the increase in the apparent dynamic viscosity of an inventive high-temperature oil based on two components from example 3 compared with a known oil based on three components from comparative example 3 at a kinematic base oil viscosity at 40° C. of about 680 mm2/sec; -
FIG. 10 shows the vaporization losses for an inventive high-temperature oil based on two components with an ionic liquid from example 4 compared with comparative example 4, which corresponds to example 1 at a kinematic base oil viscosity of about 260 mm2/sec; -
FIG. 11 shows the increase in the apparent dynamic viscosity of an inventive high-temperature oil based on two components with an ionic liquid from example 4 compared with comparative example 4, which corresponds to example 1 at a kinematic base oil viscosity of about 260 mm2/sec; -
FIG. 12 shows the experimental setup for the high-performance chain test bed. - The invention is now illustrated in detail by the examples which follow.
- Production of an inventive two-component high-temperature oil
- Composition of the high-temperature oil:
- 63.4% by weight of aromatic trimellitic ester
- 30.0% by weight of fully hydrogenated polyisobutylene
- 3.5% by weight of antiwear agent
- 3.0% by weight of antioxidant
- 0.1% by weight of anticorrosive
- As the aromatic ester, trimellitic ester is initially charged in a stirred tank. At 100° C., the polyisobutylene is added while stirring. Subsequently, the mixture is stirred for one 1 hour in order to obtain a homogeneous mixture. The antiwear agent and the antioxidant are added to the tank at 60° C. while stirring. After about 1 hour, the finished oil can be dispensed into the containers provided.
- Production of a known three-component high-temperature oil
- Composition of the high-temperature oil:
- 47.4% by weight of aromatic trimellitic ester
- 16.0% by weight of polyisobutylene
- 30.0% by weight of synthetic hydrocarbon
- 3.5% by weight of antiwear agent
- 3.0% by weight of antioxidant
- 0.1% by weight of anticorrosive
- As the aromatic ester, trimellitic ester is initially charged in a stirred tank together with the poly-α-olefin as the synthetic hydrocarbon. At 100° C., the polyisobutylene is added while stirring. Subsequently, the mixture is stirred for 1 hour in order to obtain a homogeneous mixture. The antiwear agent and the antioxidant are added to the tank at 60° C. while stirring. After about 1 hour, the finished oil can be dispensed into the containers provided.
- The advantages of the inventive high-temperature oil are shown hereinafter.
- The base data for the oil according to example 1 and comparative example 1 are shown in table 1.
-
TABLE 1 Comparative Example 1 example 1 Appearance clear clear Kinematic viscosity 271 mm2/sec 275 mm2/ sec 40° C. Kinematic viscosity 24 mm2/sec 25 mm2/ sec 100° C. Flashpoint >250° C. >250° C. Pour point −30° C. −30° C. - 1.1. Thermal Stability Studies
- Studies were conducted with regard to vaporization and viscosity under thermal stress on a starting weight of 5 g in an aluminum pan at 230° C. For this purpose, the oils according to example 1 and comparative example 1 were compared with one another.
-
TABLE 2 Comparative Example 1 example 1 Vaporization loss 16% 30% after 24 h/230° C. Vaporization loss 25% 49% after 48 h/230° C. Vaporization loss 35% 62% after 72 h/230° C. Increase in 970 mPas 1300 mPas apparent dynamic viscosity after 24 h/230° C. Increase in 1400 mPas 4400 mPas apparent dynamic viscosity after 48 h/230° C. Increase in 3200 mPas 41 000 mPas apparent dynamic viscosity after 72 h/230° C. - The above results show that the use of fully hydrogenated polyisobutylene in a two-component high-temperature oil can distinctly reduce the rise in viscosity and in the vaporization loss compared to the known three-component oil. These results are also shown in the form of graphs in
FIGS. 2 and 3 . - 1.2. Comparison of the Friction Values
- The oils produced in example 1 and comparative example 1 were used for determination of the friction values. For this purpose, an oscillating frictional wear test (SRV) was conducted based on DIN 51834, ball/disk test condition, load 250 N, 50° C. to 250° C.,
stroke 1 mm, 50 Hz, 165 min. The results are shown in table 3. -
TABLE 3 Comparative Example 1 example 1 SRV TST 250N point Friction number Friction number 50 to 120° C. 0.104 0.109 to 140° C. 0.105 0.109 to 160° C. 0.102 0.118 to 180° C. 0.096 0.128 to 200° C. 0.090 0.138 to 210° C. 0.087 0.145 to 220° C. 0.087 0.151 to 230° C. 0.091 0.159 to 240° C. 0.102 0.166 to 250° C. 0.110 0.169 - These results, which are also shown in
FIG. 1 , show the positive effect of the high-temperature oil based on two components on the friction number compared to the three-component system. - 1.3. Residue Characteristics After Complete Vaporization of the Oil at 250° C.
- The formation of residues and the behavior of the residues with regard to solubility were studied.
- The oil to be tested is weighed to 5 g onto a steel sheet which has been bent to size and cleaned with solvent beforehand, and then vaporized off at 250° C. in an air circulation drying cabinet for min. 72 h. The square sheet is bent manually on all four sides, so as to give a dish shape.
- After cooling, the results of the re-weighing are documented.
- Important features for this test are the determination of the dissolvability of the residue surface with fresh oil and the amount of residue formed. For this purpose, a drop of the fresh oil is applied to the residue and rubbed in gently by means of a rounded glass rod with circular movements.
- The results show that the inventive high-temperature oil forms a lower level of residue at 4.8% than the known oil, which has a residue of 6.0%. The residue formed from the inventive high-temperature oil has very good surface dissolvability, which means that these residues are easy to dissolve with fresh oil. In contrast, the residue of the known oil has much poorer surface redissolvability with fresh oil.
- 1.4. High-Performance Chain Test Bed
-
FIG. 12 shows the high-performance chain test bed, which works under the following test conditions: - Temperature: 220° C.
- Speed: 2 m/sec
- Load: 2600 N
- Run time after 0.1% chain lengthening 22 hours for example 1, and 17 hours for comparative example 1.
- Before the test, the chain is immersed into the lubricant oil to be tested. After the immersion, the chain is suspended, such that the excess lubricant can drip off. Subsequently, the chain is installed into the chain test bed (see
FIG. 10 ) and the test is started under the conditions defined. It is possible to vary the temperature, the speed and the load. - The run time is fixed at a chain lengthening of 0.1%. The lengthening of the chain arises through wear at the chain members during the test run.
- Composition of the inventive high-temperature oil:
- 82% by weight of aromatic trimellitic ester
- 12.7% by weight of fully hydrogenated polyisobutylene
- 0.3% by weight of antiwear agent
- 4.5% by weight of antioxidant
- 0.5% by weight of anticorrosive
- The production is effected as described in example 1.
- Composition of the three-component high-temperature oil:
- 55.7% by weight of aromatic trimellitic ester
- 7% by weight of polyisobutylene
- 33.20% by weight of synthetic hydrocarbon
- 0.30% by weight of antiwear agent
- 3.7% by weight of antioxidant
- 0.10% by weight of anticorrosive
- The production is effected as described in comparative example 1.
- The advantages of the inventive high-temperature oil are shown hereinafter.
- The base data for the oil according to example 2 and comparative example 2 are shown in table 4.
-
TABLE 4 Viscosity at 40° C., Comparative 100 mm2/sec Example 2 example 2 Appearance clear clear Kinematic viscosity 120.0 mm2/sec 107.0 mm2/ sec 40° C. Kinematic viscosity 14 mm2/sec 13.5 mm2/ sec 100° C. Flashpoint >250° C. >250° C. Pour point −20° C. −30° C. - 2.1. Thermal Stability Studies
- Studies were conducted with regard to the vaporization and viscosity under thermal stress on a starting weight of 5 g in an aluminum pan at 230° C. For this purpose, the oils according to example 2 and comparative example 2 were compared with one another.
-
TABLE 5 Comparative Example 2 example 2 Vaporization loss 18% 36% after 24 h/230° C. Vaporization loss 37% 57% after 48 h/230° C. Vaporization loss 52% 71% after 72 h/230° C. Increase in 340 mPas 430 mPas apparent dynamic viscosity after 24 h/230° C. Increase in 1250 mPas 200 mPas apparent dynamic viscosity after 48 h/230° C. Increase in 4700 mPas 23 000 mPas apparent dynamic viscosity after 72 h/230° C. - The above results show that the use of fully hydrogenated polyisobutylene in a two-component high-temperature oil can distinctly reduce the rise in viscosity and in the vaporization loss compared to the known three-component oil. These results are also shown as graphs in
FIGS. 5 and 6 . - 2.2. Comparison of the Friction Values
- The oils produced in example 2 and comparative example 2 were used to determine the friction values. For this purpose, an oscillating frictional wear test (SRV) was conducted based on DIN 51834, ball/disk test condition, load 250 N, 50° C. to 250° C.,
stroke 1 mm, 50 Hz, 165 min. - The results are shown in table 6.
-
TABLE 6 Comparative Example 2 example 2 SRV TST 250N point Friction number Friction number 50 to 120° C. 0.097 0.105 to 140° C. 0.093 0.112 to 160° C. 0.122 0.129 to 180° C. 0.133 0.136 to 200° C. 0.138 0.143 to 210° C. 0.139 0.157 to 220° C. 0.136 0.175 to 230° C. 0.138 0.186 to 240° C. 0.136 0.196 to 250° C. 0.136 0.205 - These results, which are also shown in
FIG. 4 , show the positive effect of the high-temperature oil based on two components on the friction number compared to the three-component system. - 2.3. Residue Characteristics after Complete Vaporization of the Oil at 250° C.
- The formation of residues and the behavior of the residues in terms of solubility were studied. The method is described in example 1.
- Both the inventive high-temperature oil and the known oil had a residue of 3.0%; the residue formed from the inventive high-temperature oil had very good surface dissolvability, which means that these residues can be dissolved easily with fresh oil. In contrast, the residue of the known oil has much poorer surface redissolvability with fresh oil.
- 2.4. High-Performance Chain Test Bed
- The test on the high-performance chain test bed was conducted at 220° C., a speed of 2.0 m/sec and a load of 2600 N. The run time after chain lengthening 0.1% is 19 h for example 2, and that for comparative example 2 is 17 h.
- The test was conducted as described in example 1.
- Composition of the Inventive High-Temperature Oil:
- 45.4% by weight of aromatic trimellitic ester
- 48.00% by weight of fully hydrogenated polyisobutylene
- 2.5% by weight of antiwear agent
- 3.0% by weight of antioxidant
- 0.1% by weight of anticorrosive
- The production was effected as described in example 1.
- Composition of the Three-Component High-Temperature Oil:
- 47.0% by weight of aromatic trimellitic ester
- 17.4% by weight of polyisobutylene
- 29.0% by weight of synthetic hydrocarbon
- 3.5% by weight of antiwear agent
- 3.0% by weight of antioxidant
- 0.10% by weight of anticorrosive
- The production was effected as described in comparative example 1.
- The advantages of the inventive high-temperature oil are shown hereinafter.
- The base data for the oil according to example 3 and comparative example 3 are shown in table 7.
-
TABLE 7 Viscosity at 40° C., Comparative 680 mm2/sec Example 3 example 3 Appearance clear clear Kinematic viscosity 690 mm2/sec 690 mm2/ sec 40° C. Kinematic viscosity 24 mm2/sec 47 mm2/ sec 100° C. Flashpoint >250° C. >250° C. Pour point −30° C. −30° C. - 3.1. Thermal Stability Studies
- Studies were conducted with regard to vaporization and viscosity under thermal stress on a starting weight of 5 g in an aluminum pan at 230° C. For this purpose, the oils according to example 3 and comparative example 3 were compared with one another.
-
TABLE 8 Comparative Example 3 example 3 Vaporization loss 18% 20% after 24 h/230° C. Vaporization loss 28% 38% after 48 h/230° C. Vaporization loss 37% 53% after 72 h/230° C. Increase in 3400 mPas 2800 mPas apparent dynamic viscosity after 24 h/230° C. Increase in 6000 mPas 13 250 mPas apparent dynamic viscosity after 48 h/230° C. Increase in 12 700 mPas 47 000 mPas apparent dynamic viscosity after 72 h/230° C. - The above results show that the use of fully hydrogenated polyisobutylene in a two-component high-temperature oil can reduce the rise in viscosity and in the vaporization loss compared to the known three-component oil. These results are also shown as graphs in
FIGS. 8 and 9 . - 3.2. Comparison of the Friction Values
- The oils produced in example 3 and comparative example 3 were used to determine the friction values. For this purpose, an oscillating frictional wear test (SRV) was conducted based on DIN 51834, ball/disk test condition, load 250 N, 50° C. to 250° C.,
stroke 1 mm, 50 Hz, 165 min. - The results are shown in table 9.
-
TABLE 9 Comparative Example 3 example 3 SRV TST 250N point Friction number Friction number 50 to 120° C. 0.119 0.118 to 140° C. 0.116 0.115 to 160° C. 0.119 0.114 to 180° C. 0.115 0.110 to 200° C. 0.105 0.108 to 210° C. 0.098 0.105 to 220° C. 0.096 0.102 to 230° C. 0.099 0.102 to 240° C. 0.112 0.089 to 250° C. 0.126 0.086 - These results, which are also shown in
FIG. 7 , show the positive effect of the high-temperature oil based on two components on the friction number compared to the three-component system. - 3.3. Residue Characteristics After Complete Vaporization of the Oil at 250° C.
- The formation of residues and the behavior of the residues in terms of solubility were studied. The test was conducted as described in example 1.
- The results show that the inventive high-temperature oil forms a lower level of residues at 4.8% than the known oil, which has a residue of 11.8%. The residue formed from the inventive high-temperature oil has very good surface dissolvability, which means that these residues can be dissolved easily with fresh oil. In contrast, the residue of the known oil has much poorer surface redissolvability with fresh oil.
- 3.4. High-Performance Chain Test Bed
- The test on the high-performance chain test bed was conducted at 220° C., a speed of 2.0 m/sec and a load of 2600 N. The run time after chain lengthening 0.1% was 17 h for example 3 and 15 h for comparative example 3. The test was conducted as described in example 1.
- Composition of the Inventive High-Temperature Oil:
- 62.90% by weight of aromatic trimellitic ester
- 30.00% by weight of fully hydrogenated polyisobutylene
- 3.5% by weight of antiwear agent
- 3.0% by weight of antioxidant
- 0.1% by weight of anticorrosive
- 0.50% by weight of ionic liquid
- The production was effected as described in example 1.
- The ionic liquid used was HDP imide (=trihexyl(tetradey-phosphonium bis(trifluoromethylsulfonyl)imide).
- Composition of the inventive high-temperature oil:
- 63.40% by weight of aromatic trimellitic ester
- 30.00% by weight of fully hydrogenated polyisobutylene
- 3.5% by weight of antiwear agent
- 3.0% by weight of antioxidant
- 0.1% by weight of anticorrosive
- The production was effected as described in example 1.
- The base data for the oil according to example 4 and comparative example 4 are shown in table 10.
-
TABLE 10 Viscosity at 40° C., Comparative example 4 200 mm2/sec Example 4 (corresponds to ex. 1) Appearance clear clear Kinematic viscosity 270.0 mm2/sec 271.0 mm2/ sec 40° C. Kinematic viscosity 24 mm2/sec 25 mm2/ sec 100° C. Flashpoint >250° C. >250° C. Pour point −30° C. −30° C. - 4.1. Thermal Stability Studies
- Studies were conducted with regard to the vaporization and viscosity under thermal stress on a starting weight of 5 g in a closed aluminum pan at 250° C. The vaporization loss after 72 h/250° C. was 19%. The increase in apparent dynamic viscosity in mPas after 72 h/250° C. was 2300 mPas.
-
TABLE 11 Comparative example 4 Example 4 Corresponds to example 1 Vaporization loss 19% 46% after 72 h/250° C. Increase in 2300 mPas 27 000 mPas apparent dynamic viscosity after 72 h/250° C. - The above results show that the use of HDP imide can once again significantly improve the thermal stability of a two-component system. These results are also shown as graphs in
FIGS. 10 and 11 . - Composition of the Inventive High-Temperature Oil:
- 63.5% phloroglucinol tridecanoate
- 30.0% fully hydrogenated polyisobutylene
- 3.5% antiwear agent
- 3.0% antioxidant
- 0.1% by weight of anticorrosive
- The production was effected as described in example 1.
- It was also possible to obtain the results described in detail above with the high-temperature oil based on a derivative of phloroglucinol.
- The above experimental results show that the inventive high-temperature oil in all studies conducted gave much better values than in the case of the known high-temperature oils.
- In summary, it can be stated that the inventive two-component system has much higher performance with regard to thermal stability and residue formation or residue characteristics. The enormous rise in thermal stability is manifested particularly in a distinct rise in lubrication characteristics. The relubrication intervals were extended and an energy saving of up to a 30% power saving was achieved.
Claims (19)
1. A high-temperature oil for lubrication of chains, chain rollers and belts of continuous presses, comprising
40 to 91.9% by weight of an aromatic ester of the general formula (I)
where R1 is a linear or branched alkyl group having 6 to 16 carbon atoms and n is an integer of 3 to 4,
or 40 to 91.9% by weight of a compound of the general formula (II)
2. The high-temperature oil as claimed in claim 1 , further comprising 0.1 to 6% by weight of an antioxidant.
3. The high-temperature oil as claimed in claim 1 , further comprising 1 to 4% by weight of an antiwear agent.
4. The high-temperature oil as claimed in claim 1 , further comprising 0.1 to 0.5% by weight of an anticorrosive.
5. The high-temperature oil as claimed in claim 1 , further comprising 0 to 2% by weight of an ionic liquid.
6. The high-temperature oil as claimed in claim 1 , wherein the ester compound of the general formula (I) is selected from the group consisting of esters of trimellitic acid, pyromellitic acid, trimesic acid or of a mixture thereof.
7. The high-temperature oil as claimed claim 1 , wherein the compound of the general formula (II) is a derivative of phloroglucinol (benzene-1,3,5-triol).
8. The high-temperature oil as claimed in claim 7 , in which the derivative of phloroglucinol is phloroglucinol trioctanoate, phloroglucinol tridecanoate or phloroglucinol tridodecanoate.
9. The high-temperature oil as claimed in claim 2 , wherein the antioxidant bears sulfur and/or nitrogen and/or phosphorus in the molecule, and is selected from the group consisting of aromatic aminic antioxidants such as alkylated phenyl-alpha-naphthylamine, dialkyldiphenylamine, sterically hindered phenols such as butylhydroxytoluene (BHT), phenolic antioxidants having thioether groups, zinc dialkyldithiophosphates or molybdenum dialkyldithiophosphates or tungsten dialkyldithiophosphates, and phosphites.
10. The high-temperature oil as claimed in claim 3 , wherein the antiwear agent is selected from the group consisting of antiwear additives based on diphenyl cresyl phosphate, amine-neutralized phosphates, alkylated and nonalkylated triaryl phosphates, alkylated and nonalkylated triaryl thiophosphates, zinc dialkyldithiophosphates or molybdenum dialkyldithiophosphates or tungsten dialkyldithiophosphates, carbamates, thiocarbamates, zinc dithiocarbamates or molybdenum dithiocarbamates or tungsten dithiocarbamates, dimercaptothiadiazole, calcium sulfonates and benzotriazole derivatives.
11. The high-temperature oil as claimed in claim 4 , wherein the anticorrosive is selected from the group consisting of additives based on overbased calcium sulfonates, amine-neutralized phosphates, alkylated calcium naphthalenesulfonates, oxazoline derivatives, imidazole derivatives, succinic monoesters, N-alkylated benzotriazoles.
12. The high-temperature oil as claimed in claim 5 , wherein the ionic liquid is selected from the group consisting of tetraalkylammonium bis(trifluoromethylsulfonyl)imides and tetraalkylphosphonium bis(trifluoromethylsulfonyl)imides, for example trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide (HPDimide) and methyltrioctylammonium bis(trifluoromethylsulfonyl)imide (Moimide), and tetraalkylammonium tris(perfluoroethyl)trifluorophosphate and tetraalkylphosphonium tris(perfluoroethyl)trifluorophosphate, especially tetrabutylphosphonium tris(perfluoroethyl)trifluorophosphate (BuPPFET), trihexyl(tetradecyl) tris(perfluoroethyl)trifluorophosphate (HDPPFET), pyrrolidinium tris(perfluoroethyl)trifluorophosphates, tetraalkylammonium, tetraalkylphosphonium perfluorobutanesulfonates, trihexyl(tetradecyl)phosphonium perfluorobutanesulfonate (HDPnonaflate).
13. The use of the high-temperature oil as claimed in any of claim 1 for industrial chain lubrication in conveying systems, painting lines, the textile industry, the insulating materials industry, the glass industry, or for belt lubrication in continuous wood pressing plants.
14. The high-temperature oil as claimed in claim 2 , further comprising 1 to 4% by weight of an antiwear agent.
15. The high-temperature oil as claimed in claim 2 , further comprising 0.1 to 0.5% by weight of an anticorrosive.
16. The high-temperature oil as claimed in claim 3 , further comprising 0.1 to 0.5% by weight of an anticorrosive.
17. The high-temperature oil as claimed in claim 2 , further comprising 0 to 2% by weight of an ionic liquid.
18. The high-temperature oil as claimed in claim 3 , further comprising 0 to 2% by weight of an ionic liquid.
19. The high-temperature oil as claimed in claim 4 , further comprising 0 to 2% by weight of an ionic liquid.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102011102540A DE102011102540B4 (en) | 2011-05-26 | 2011-05-26 | High temperature oil |
| DE102011102540.9 | 2011-05-26 | ||
| PCT/EP2012/002172 WO2012159738A1 (en) | 2011-05-26 | 2012-05-22 | High temperature oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20140200169A1 true US20140200169A1 (en) | 2014-07-17 |
Family
ID=46317322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14/119,015 Abandoned US20140200169A1 (en) | 2011-05-26 | 2012-05-22 | High Temperature Oil |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20140200169A1 (en) |
| EP (1) | EP2714872B1 (en) |
| JP (1) | JP5752321B2 (en) |
| KR (1) | KR101539218B1 (en) |
| CN (1) | CN103764808A (en) |
| AU (1) | AU2012261221B2 (en) |
| BR (1) | BR112013030286B1 (en) |
| CL (1) | CL2013003397A1 (en) |
| DE (1) | DE102011102540B4 (en) |
| EA (1) | EA026445B1 (en) |
| ES (1) | ES2601401T3 (en) |
| HU (1) | HUE029149T2 (en) |
| LT (1) | LT2714872T (en) |
| MY (1) | MY164068A (en) |
| PL (1) | PL2714872T3 (en) |
| SI (1) | SI2714872T1 (en) |
| WO (1) | WO2012159738A1 (en) |
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| US10590225B2 (en) | 2015-09-25 | 2020-03-17 | Compagnie Generale Des Etablissements Michelin | Use of a silylated aromatic polyphenol derivative for the production of a phenol-aldehyde resin for reinforcement of a rubber composition |
| US10711132B2 (en) | 2015-09-25 | 2020-07-14 | Compagnie Generale Des Etablissements Michelin | Use of an esterified aromatic polyphenol derivative for the production of a phenol-aldehyde resin for reinforcement of a rubber composition |
| US10711131B2 (en) | 2015-09-25 | 2020-07-14 | Compagnie Generale Des Etablissements Michelin | High-strength rubber composition comprising an aromatic polyphenol derivative |
| WO2024187330A1 (en) | 2023-03-13 | 2024-09-19 | 克鲁勃润滑产品(上海)有限公司 | Lubricant and application thereof, and preparation method |
| CN119685074A (en) * | 2024-12-11 | 2025-03-25 | 广东电网有限责任公司 | Compound additive and application thereof in removal of corrosive sulfur products in mineral insulating oil |
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| CN104087392A (en) * | 2014-07-28 | 2014-10-08 | 中国石油化工股份有限公司 | Special high-temperature lubricating oil for steel belt of continuous press for plate processing industry and preparation method of high-temperature lubricating oil |
| DE102014018719A1 (en) * | 2014-12-17 | 2016-06-23 | Klüber Lubrication München Se & Co. Kg | High temperature lubricant for the food industry |
| DE102014018718A1 (en) * | 2014-12-17 | 2016-06-23 | Klüber Lubrication München Se & Co. Kg | High temperature lubricants |
| DE102016105758B4 (en) | 2015-04-10 | 2024-10-24 | Minebea Mitsumi Inc. | Use of a lubricant composition in fluid dynamic bearing systems |
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| KR102295397B1 (en) * | 2015-06-18 | 2021-08-30 | 에스케이이노베이션 주식회사 | Ionic liquid and lubricant composition comprising thereof |
| US10550349B2 (en) * | 2015-07-16 | 2020-02-04 | Afton Chemical Corporation | Lubricants with titanium and/or tungsten and their use for improving low speed pre-ignition |
| FR3041633A1 (en) * | 2015-09-25 | 2017-03-31 | Michelin & Cie | ESTERIFIED COMPOUND TO PREVENT EARLY RETICULATION OF A PHENOL ALDEHYDE RESIN |
| FR3041647B1 (en) * | 2015-09-25 | 2017-10-27 | Michelin & Cie | HIGH RIGIDITY RUBBER COMPOSITION BASED ON AROMATIC POLYPHENOL DERIVATIVE |
| JP6822635B2 (en) * | 2016-03-25 | 2021-01-27 | 出光興産株式会社 | Lubricating oil composition and how to use the lubricating oil composition |
| JP2019172729A (en) * | 2018-03-27 | 2019-10-10 | Emgルブリカンツ合同会社 | Lubricant composition |
| CN109181811B (en) * | 2018-09-05 | 2021-04-06 | 安徽泰达新材料股份有限公司 | High-viscosity high-temperature-resistant trimesic acid synthetic ester base oil and preparation method thereof |
| KR102097232B1 (en) * | 2019-02-28 | 2020-04-06 | 대림산업 주식회사 | Lubricant composition for gear oil |
| CN117940537A (en) | 2021-08-12 | 2024-04-26 | 克鲁勃润滑剂慕尼黑两合欧洲公司 | Use of trimellitates as base oils for lubricant compositions |
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-
2011
- 2011-05-26 DE DE102011102540A patent/DE102011102540B4/en not_active Expired - Fee Related
-
2012
- 2012-05-22 BR BR112013030286-0A patent/BR112013030286B1/en active IP Right Grant
- 2012-05-22 EP EP12727785.3A patent/EP2714872B1/en active Active
- 2012-05-22 LT LTEP12727785.3T patent/LT2714872T/en unknown
- 2012-05-22 HU HUE12727785A patent/HUE029149T2/en unknown
- 2012-05-22 ES ES12727785.3T patent/ES2601401T3/en active Active
- 2012-05-22 WO PCT/EP2012/002172 patent/WO2012159738A1/en not_active Ceased
- 2012-05-22 JP JP2014511763A patent/JP5752321B2/en not_active Expired - Fee Related
- 2012-05-22 KR KR1020137030344A patent/KR101539218B1/en active Active
- 2012-05-22 AU AU2012261221A patent/AU2012261221B2/en active Active
- 2012-05-22 US US14/119,015 patent/US20140200169A1/en not_active Abandoned
- 2012-05-22 MY MYPI2013003925A patent/MY164068A/en unknown
- 2012-05-22 CN CN201280024232.XA patent/CN103764808A/en active Pending
- 2012-05-22 SI SI201230680A patent/SI2714872T1/en unknown
- 2012-05-22 PL PL12727785T patent/PL2714872T3/en unknown
- 2012-05-22 EA EA201301331A patent/EA026445B1/en not_active IP Right Cessation
-
2013
- 2013-11-26 CL CL2013003397A patent/CL2013003397A1/en unknown
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| US3336349A (en) * | 1964-09-17 | 1967-08-15 | Koppers Co Inc | Alkanoyl esters of the trihydroxy benzenes |
| EP0351906A1 (en) * | 1988-07-22 | 1990-01-24 | Akzo N.V. | Synthetic lubricant composition |
| US6465400B1 (en) * | 1998-12-25 | 2002-10-15 | Idemitsu Kosan Co., Ltd. | Lubricating oil composition for high-temperature use |
| WO2008154998A1 (en) * | 2007-06-20 | 2008-12-24 | KLüBER LUBRICATION MüNCHEN KG | Use of ionic liquids for improving the properties of lubricating compositions |
| US20100187481A1 (en) * | 2007-06-20 | 2010-07-29 | Bodesheim Guenther | Use of ionic liquids to improve the properties of lubricating compositons |
| US8697618B2 (en) * | 2007-06-20 | 2014-04-15 | KLüBER LUBRICATION MüNCHEN KG | Method of using ionic liquids to improve the lubrication of chains, steel belts, wheel bearings, roller bearings, and electric motors |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10590225B2 (en) | 2015-09-25 | 2020-03-17 | Compagnie Generale Des Etablissements Michelin | Use of a silylated aromatic polyphenol derivative for the production of a phenol-aldehyde resin for reinforcement of a rubber composition |
| US10711132B2 (en) | 2015-09-25 | 2020-07-14 | Compagnie Generale Des Etablissements Michelin | Use of an esterified aromatic polyphenol derivative for the production of a phenol-aldehyde resin for reinforcement of a rubber composition |
| US10711131B2 (en) | 2015-09-25 | 2020-07-14 | Compagnie Generale Des Etablissements Michelin | High-strength rubber composition comprising an aromatic polyphenol derivative |
| WO2024187330A1 (en) | 2023-03-13 | 2024-09-19 | 克鲁勃润滑产品(上海)有限公司 | Lubricant and application thereof, and preparation method |
| EP4682229A1 (en) | 2023-03-13 | 2026-01-21 | Klueber Lubrication München GmbH & Co. KG | Lubricant and application thereof, and preparation method |
| CN119685074A (en) * | 2024-12-11 | 2025-03-25 | 广东电网有限责任公司 | Compound additive and application thereof in removal of corrosive sulfur products in mineral insulating oil |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012159738A1 (en) | 2012-11-29 |
| KR101539218B1 (en) | 2015-07-29 |
| AU2012261221A1 (en) | 2013-12-12 |
| SI2714872T1 (en) | 2016-11-30 |
| BR112013030286B1 (en) | 2020-11-10 |
| DE102011102540B4 (en) | 2013-12-12 |
| AU2012261221B2 (en) | 2016-05-12 |
| KR20140009499A (en) | 2014-01-22 |
| JP2014515412A (en) | 2014-06-30 |
| EA201301331A1 (en) | 2014-05-30 |
| CN103764808A (en) | 2014-04-30 |
| ES2601401T3 (en) | 2017-02-15 |
| EP2714872A1 (en) | 2014-04-09 |
| EA026445B1 (en) | 2017-04-28 |
| EP2714872B1 (en) | 2016-08-03 |
| DE102011102540A1 (en) | 2012-11-29 |
| BR112013030286A2 (en) | 2016-11-29 |
| MY164068A (en) | 2017-11-15 |
| PL2714872T3 (en) | 2017-01-31 |
| CL2013003397A1 (en) | 2014-07-11 |
| LT2714872T (en) | 2016-09-26 |
| JP5752321B2 (en) | 2015-07-22 |
| HUE029149T2 (en) | 2017-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: KLUBER LUBRICATION MUNCHEN SE & CO. KG, GERMANY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KILTHAU, THOMAS, DR.;EGERSDORFER, KARL;SCHMIDT-AMELUNXEN, MARTIN, DR.;SIGNING DATES FROM 20131104 TO 20131105;REEL/FRAME:031645/0951 |
|
| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |