CN108795538B - Fluoro-polyester type detergent, preparation method and lubricating oil composition prepared from fluoro-polyester type detergent - Google Patents
Fluoro-polyester type detergent, preparation method and lubricating oil composition prepared from fluoro-polyester type detergent Download PDFInfo
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- CN108795538B CN108795538B CN201810752088.0A CN201810752088A CN108795538B CN 108795538 B CN108795538 B CN 108795538B CN 201810752088 A CN201810752088 A CN 201810752088A CN 108795538 B CN108795538 B CN 108795538B
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- China
- Prior art keywords
- fluoro
- polyester
- detergent
- acid
- lubricating oil
- Prior art date
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- 239000003599 detergent Substances 0.000 title claims abstract description 61
- 229920000728 polyester Polymers 0.000 title claims abstract description 54
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 21
- 239000000203 mixture Substances 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 27
- 239000002199 base oil Substances 0.000 claims description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims description 22
- -1 12-phenylbutyryl stearic acid Chemical compound 0.000 claims description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- NCGQPNAQUYGWMI-UHFFFAOYSA-N [3-heptanoyloxy-2,2-bis(heptanoyloxymethyl)propyl] heptanoate Chemical compound CCCCCCC(=O)OCC(COC(=O)CCCCCC)(COC(=O)CCCCCC)COC(=O)CCCCCC NCGQPNAQUYGWMI-UHFFFAOYSA-N 0.000 claims description 11
- 229920001225 polyester resin Polymers 0.000 claims description 11
- 239000004645 polyester resin Substances 0.000 claims description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 9
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 8
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000001569 carbon dioxide Substances 0.000 claims description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 6
- 239000000920 calcium hydroxide Substances 0.000 claims description 6
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000000395 magnesium oxide Substances 0.000 claims description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 6
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- UTPYAGUAONTRBN-UHFFFAOYSA-N 1,2,2,3-tetrafluorobutane-1,1-diol Chemical compound CC(F)C(F)(F)C(O)(O)F UTPYAGUAONTRBN-UHFFFAOYSA-N 0.000 claims description 4
- 229940114072 12-hydroxystearic acid Drugs 0.000 claims description 4
- YUDUFRYTKFGQCL-UHFFFAOYSA-N 2,2,3,3-tetrafluorobutanedioic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(O)=O YUDUFRYTKFGQCL-UHFFFAOYSA-N 0.000 claims description 4
- PQDNJBQKAXAXBQ-UHFFFAOYSA-N 3-fluoropropane-1,2-diol Chemical compound OCC(O)CF PQDNJBQKAXAXBQ-UHFFFAOYSA-N 0.000 claims description 4
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 claims description 4
- 238000005273 aeration Methods 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- IQUCNXSZNHPPML-UHFFFAOYSA-N 2-chloro-n-[(4-chlorophenyl)-phenylmethyl]acetamide Chemical compound C=1C=C(Cl)C=CC=1C(NC(=O)CCl)C1=CC=CC=C1 IQUCNXSZNHPPML-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000004140 cleaning Methods 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 230000008021 deposition Effects 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 238000001179 sorption measurement Methods 0.000 abstract description 3
- 239000012467 final product Substances 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 8
- 150000007524 organic acids Chemical class 0.000 description 8
- 239000007789 gas Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical group [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical group CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- YFSUTJLHUFNCNZ-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-M 0.000 description 1
- UQJDVLPHTXQTRP-UHFFFAOYSA-N 2,2-bis(heptanoyloxymethyl)butyl heptanoate Chemical compound CCCCCCC(=O)OCC(CC)(COC(=O)CCCCCC)COC(=O)CCCCCC UQJDVLPHTXQTRP-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000004313 potentiometry Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M161/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
- C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/06—Metal compounds
- C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
-
- 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
-
- 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
- C10M2207/284—Esters of aromatic monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/06—Perfluoro polymers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
-
- 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
- C10N2030/04—Detergent property or dispersant property
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- 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
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polyesters Or Polycarbonates (AREA)
- Lubricants (AREA)
Abstract
The invention belongs to the technical field of synthesis of lubricating oil detergents, and particularly relates to a fluoro-polyester detergent, and further discloses a preparation method thereof and a lubricating oil composition prepared from the fluoro-polyester detergent. The fluorinated polyester type detergent adopts fluorinated compounds as main organic raw materials, so that the high temperature resistance and the carbon deposition resistance of a final product are ensured; meanwhile, the polyester has larger molecular weight, more carboxyl groups and strong dispersing capacity, so that a detergent product with high base number (380-420mgKOH/g), low pour point, excellent high-temperature resistance and more stable performance can be obtained, and the fluoro-polycarboxy polyester salt with larger molecular weight can better form an adsorption film on the metal surface of an engine, thereby providing excellent high-temperature cleaning performance and greatly improving the comprehensive application performance.
Description
Technical Field
The invention belongs to the technical field of synthesis of lubricating oil detergents, and particularly relates to a fluoro-polyester detergent, and further discloses a preparation method thereof and a lubricating oil composition prepared from the fluoro-polyester detergent.
Background
The lubricating oil is a liquid or semisolid lubricating agent used on various types of automobiles and mechanical equipment to reduce friction and protect machines and workpieces, and mainly plays roles in lubrication, cooling, rust prevention, cleaning, sealing, buffering and the like. However, in the use process of the engine lubricating oil, due to harsh working conditions and high-temperature oxidation, and the absorption of acid gases of nitrogen oxides and sulfur dioxide from the outside, the lubricating oil is prone to oxidative degradation, and a certain amount of acid corrosive substances, such as sulfuric acid, nitric acid, acid sludge and the like, are generated, so that the lubricating effect of the lubricating oil is reduced and the corrosion to equipment is aggravated. Therefore, it is necessary to add a lubricating oil detergent to continuously neutralize acidic substances generated during the use of the lubricating oil and prevent the acidic substances from corroding the engine, so that the purposes of prolonging the service life of the lubricating oil and protecting the engine are achieved.
The traditional lubricating oil detergent basically uses common carbon chain small molecular organic acid, such as dodecyl benzene sulfonic acid, alkyl salicylic acid, oleic acid and the like as raw materials, alkaline components are dispersed in diluent oil through reaction, and the adopted diluent oil is mainly common mineral oil lubricating oil base oil, such as 150SN, 250SN, 350SN and other types of mineral oil. On one hand, the mineral base oils belong to products of petroleum refining, have poor degradation capability, contain certain wax, and are not suitable for the high-end lubricating oil field with high requirements on environmental protection and pour point; on the other hand, the linear organic acid raw materials selected have poor dispersion performance due to small molecules and single carboxyl contained in the linear organic acid raw materials, the base number of the prepared detergent product is about 300mgKOH/g, and the detergent product with the required high base number (380-420mgKOH/g) cannot be stably obtained; moreover, the adopted organic acid raw material is in a straight chain structure, so that the dispersing performance of alkaline components such as colloidal calcium carbonate and magnesium carbonate is unstable, colloidal carbonate is easy to precipitate under the working condition of high-temperature use, and the cleaning dispersing capacity of the colloidal carbonate is reduced; moreover, because the molecules of the formed organic acid salt are too small, a stable adsorption film cannot be formed on the surface of the metal, and the detergency and protection capability of the engine are insufficient; especially, organic acid and diluent oil in the raw materials are compounds with common carbon chains, and the compounds have poor high temperature resistance, are easy to degrade under the action of high temperature, are easy to generate carbon deposition and influence the service performance of the compounds. Therefore, the development of new detergent products has been imperative.
Disclosure of Invention
Therefore, the technical problem to be solved by the invention is to provide a fluoro polyester type detergent, and further disclose a preparation method thereof and a lubricating oil composition prepared by the same.
In order to solve the technical problems, the fluoro polyester detergent provided by the invention is prepared from the following raw materials in molar weight:
preferably, the fluoro polyester type detergent is prepared by raw materials comprising the following raw material components in molar quantity:
the fluoro-polycarboxyl polyester resin is prepared by taking tetrafluorosuccinic acid, tetrafluorobutanediol, 3-fluoro-1, 2-propanediol and citric acid as raw materials and carrying out polymerization reaction at 220 ℃ in the presence of a catalyst.
The molar ratio of tetrafluorosuccinic acid, tetrafluorobutanediol, 3-fluoro-1, 2-propanediol and citric acid is 0.2-0.8: 0.5-1.5: 0.2-0.8: 1-2, and preferably 0.5: 1: 0.5: 1.5; the catalyst is preferably dibutyltin oxide, and the addition amount accounts for 0.5 wt% of the total amount of the materials.
The 12-phenylbutyryl stearic acid is prepared by taking phenylbutyric acid and 12-hydroxystearic acid as raw materials, and reacting the raw materials at the temperature of 120-160 ℃ by taking dimethylbenzene as a water-carrying agent under the catalytic action.
The molar ratio of the phenylbutyric acid to the 12-hydroxystearic acid is preferably 1: preferably, the catalyst is tetrabutyl titanate.
The dispersion stabilizer comprises triglycerol monostearate;
the solvent comprises toluene or xylene;
the promoter comprises trimethylamine or methanol.
The invention also discloses a method for preparing the fluoro polyester type detergent, which comprises the following steps:
(1) according to the selected molar weight, fully mixing the fluorinated polycarboxy polyester, 12-phenylbutyryl stearic acid, perfluorooctane sulfonic acid, pentaerythritol tetra-n-heptanoate, calcium hydroxide, active magnesium oxide, a solvent, an accelerant and a dispersion stabilizer, and carrying out neutralization reaction at 35-60 ℃;
(2) and then adding water with a selected molar weight, heating the reaction system to 65-80 ℃, introducing carbon dioxide gas with a selected molar weight for reaction, removing residues from the reaction product, and distilling under reduced pressure to remove the solvent to obtain the catalyst.
The aeration rate of the carbon dioxide gas is 60-300 mL/min.
The invention also discloses a lubricating oil composition which comprises the fluoro polyester type detergent.
Specifically, the addition amount of the fluoro polyester type detergent is 1-3% of the mass of the base oil.
The base oil includes synthetic ester base oils such as pentaerythritol tetraheptanoate, trimethylolpropane triheptanoate, and the like.
According to the fluorinated polyester type detergent, fluorinated carboxyl polyester resin with a large molecular weight is used as a main carboxyl raw material, organic acid 12-phenylbutyryl stearic acid with a phenyl branched chain and better compatibility with base oil and a proper amount of perfluorooctane sulfonate are matched as main organic acid raw materials, pentaerythritol tetra-n-heptanoate with good solubility on the fluorinated carboxyl polyester resin is used as base oil, and calcium hydroxide and magnesium oxide are used as basic raw materials, so that the polyester type detergent mixed with calcium and magnesium salts is obtained. The main organic raw materials of the polyester detergent adopt fluoro compounds, so that the high temperature resistance and the carbon deposition resistance of a final product are ensured; meanwhile, the polyester has larger molecular weight, more carboxyl groups and strong dispersing capacity, so that a detergent product with high base number (380-420mgKOH/g), low pour point, excellent high-temperature resistance and more stable performance can be obtained, and the fluoro-polycarboxy polyester salt with larger molecular weight can better form an adsorption film on the metal surface of an engine, thereby providing excellent high-temperature cleaning performance. Compared with the main detergent products of the conventional common carbon chain structure diluent oil such as 150SN base oil, 250SN base oil, 350SN base oil and the like in the market, the detergent has better self oxidation resistance, reduced pour point, improved high temperature resistance, obviously improved precipitation condition of colloid, can be used in areas with the temperature lower than minus 30 ℃, and greatly improved comprehensive application performance.
Detailed Description
EXAMPLE 1 Synthesis of Fluoropolycarboxy polyester resin
According to a molar ratio of 0.5: 1: 0.5: 1.5 adding tetrafluorosuccinic acid, tetrafluorobutanediol, 3-fluoro-1, 2-propanediol and citric acid into a reactor, adding dibutyltin oxide accounting for 0.5 wt% of the total amount of the materials as a catalyst, and heating the reaction system to 180-220 ℃ for carrying out polymerization reaction for 8-12h to obtain the fluorocarboxyl polyester resin. The acid value of the obtained polyester resin is detected to be 200-240 mgKOH/g.
Example 212 Synthesis of phenylbutyryl stearic acid
According to a molar ratio of 1: 1, adding phenylbutyric acid and 12-hydroxystearic acid into a reactor, adding dimethylbenzene serving as a water-carrying agent under the catalytic action of tetrabutyl titanate, reacting at the temperature of 120-160 ℃ for 2-6h, and removing a dimethylbenzene solvent under reduced pressure after the reaction is finished to obtain the 12-phenylbutyryl stearic acid.
The specific synthetic process and molecular structure are as follows:
example 3
The fluoro polyester type detergent is prepared by the following raw material components in molar quantity:
the preparation method of the fluoro polyester detergent comprises the following steps:
(1) according to the selected molar weight, fully mixing the fluorinated polycarboxy polyester, 12-phenylbutyryl stearic acid, perfluorooctane sulfonic acid, pentaerythritol tetra-n-heptanoate, calcium hydroxide, active magnesium oxide, a solvent, an accelerator and a dispersion stabilizer, and carrying out neutralization reaction at 35 ℃;
(2) and then adding a selected amount of water, heating the reaction system to 65 ℃, introducing carbon dioxide gas with a selected molar amount at an aeration rate of 60mL/min for reaction, removing residues from the reaction product, and distilling under reduced pressure to remove the solvent to obtain light yellow transparent liquid.
Example 4
The fluoro polyester type detergent is prepared by the following raw material components in molar quantity:
the preparation method of the fluoro polyester detergent comprises the following steps:
(1) according to the selected molar weight, fully mixing the fluorinated polycarboxy polyester, 12-phenylbutyryl stearic acid, perfluorooctane sulfonic acid, pentaerythritol tetra-n-heptanoate, calcium hydroxide, active magnesium oxide, a solvent, an accelerator and a dispersion stabilizer, and carrying out neutralization reaction at 60 ℃;
(2) and then adding water with a selected molar weight, heating the reaction system to 80 ℃, introducing a selected amount of carbon dioxide gas at the aeration rate of 300mL/min for reaction, removing residues from the reaction product, and distilling under reduced pressure to remove the solvent to obtain light yellow transparent liquid.
Example 5
The fluoro polyester type detergent is prepared by the following raw material components in molar quantity:
the preparation method of the fluoro polyester detergent comprises the following steps:
(1) according to the selected molar weight, fully mixing the fluorinated polycarboxy polyester, 12-phenylbutyryl stearic acid, perfluorooctane sulfonic acid, pentaerythritol tetra-n-heptanoate, calcium hydroxide, active magnesium oxide, a solvent, an accelerator and a dispersion stabilizer, and carrying out neutralization reaction at 45 ℃;
(2) and then adding water with a selected molar weight, heating the reaction system to 70 ℃, introducing a selected amount of carbon dioxide gas at the ventilation rate of 180mL/min for reaction, removing residues from the reaction product, and distilling under reduced pressure to remove the solvent to obtain light yellow transparent liquid.
Example 6
The fluoro polyester type detergent is prepared by the following raw material components in molar quantity:
the fluorinated polyester detergent described in this example was prepared in the same manner as in example 5.
Example 7
The fluoro polyester type detergent is prepared by the following raw material components in molar quantity:
the fluorinated polyester detergent described in this example was prepared in the same manner as in example 5.
Comparative example 1
The starting components of the fluoro-polyester detergent described in this example were the same as in example 5 except that the fluoro-polycarboxy polyester resin was not included.
Comparative example 2
The starting components of the fluoro-polyester type detergent described in this example were the same as in example 5 except that the fluoro-polycarboxy polyester resin was changed to a commercially available ordinary polyester resin, type: YL9050A, Industrial products, Huangshan Yongli New Material science and technology Co., Ltd.
Comparative example 3
The starting components of the fluoro polyester detergent described in this example were the same as in example 5 except that 12-phenylbutyryl stearic acid was simply replaced with commercially available stearic acid.
Comparative example 4
The base composition of the fluoro polyester detergent described in this example was the same as in example 5 except that perfluorooctanesulfonic acid was not contained.
Comparative example 5
The starting components of the fluoro polyester detergent described in this example were the same as in example 5 except that only perfluorooctane sulfonic acid was replaced with commercially available dodecylbenzene sulfonic acid.
Comparative example 6
The starting components of the fluoro-polyester type detergent described in this example were the same as those of example 5 except that only the pentaerythritol tetra-n-heptanoate base oil was replaced with a common commercially available diluent oil (150SN base oil) which was purchased from oil products, Inc. of Saussuren Seisakusho.
Comparative example 7
The starting components of the fluoro-polyester detergent described in this example were the same as in example 5 except that only the pentaerythritol tetra-n-heptanoate base oil was replaced with a common commercially available diluent oil (250SN base oil) which was purchased from oil products, Inc. of Saussuren Seisattva.
Comparative example 8
The starting components of the fluoro-polyester type detergent described in this example were the same as those of example 5 except that only the pentaerythritol tetra-n-heptanoate base oil was replaced with a common commercially available diluent oil (350SN base oil) which was purchased from oil products, Inc. of Saussuren Seisakusho.
Examples of the experiments
The detergents prepared in the above examples 3 to 7 and comparative examples 1 to 8 were tested for their properties, and the test indexes included base number, viscosity, thermal stability, colloidal precipitation and pour point. Wherein, the base number is determined according to SH/T0251-1993 petroleum product base number determination method (perchloric acid potentiometry titration method); the viscosity measurement is based on GB/T265-88 petroleum product kinematic viscosity measurement method and dynamic viscometer algorithm; thermal stability and colloidal precipitation are determined by SH/T0300-92 crankcase simulation test method (QZX method); the pour point is determined according to GB/T3535-. Specific assay data are shown in table 1 below.
TABLE 1 detergent product data
As can be seen from the data in the table, in the detergent of the invention, the product of the polyester mixed calcium and magnesium salt detergent with high base number (380-420mgKOH/g), low pour point and excellent high temperature resistance is prepared by using the fluoro-polycarboxy polyester resin, matching with the branched 12-phenylbutyryl stearic acid and perfluorooctane sulfonic acid as the raw materials of the organic acid, and using pentaerythritol tetra-n-heptanoate as the base oil; compared with main detergent products of conventional common carbon chain structure diluent oil such as 150SN base oil, 250SN base oil, 350SN base oil and the like in the market, the detergent has better oxidation resistance, lower pour point, higher high-temperature resistance and obviously improved precipitation condition of colloid, can be used in areas with the temperature lower than minus 30 ℃, and has greatly improved application performance.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (9)
1. The fluoro polyester type detergent is characterized in that the preparation raw materials comprise the following raw material components in molar quantity:
the fluoro-polycarboxyl polyester resin is prepared by taking tetrafluorosuccinic acid, tetrafluorobutanediol, 3-fluoro-1, 2-propanediol and citric acid as raw materials and carrying out polymerization reaction at 220 ℃ in the presence of a catalyst.
2. A fluoro-polyester detergent as claimed in claim 1, characterised in that its raw materials for preparation comprise the following raw components in molar amounts:
3. the fluoro-polyester detergent as claimed in claim 1 or 2, wherein the 12-phenylbutyryl stearic acid is prepared by using phenylbutyric acid and 12-hydroxystearic acid as raw materials, and xylene as a water-carrying agent under the catalysis, and reacting at the temperature of 120-160 ℃.
4. A fluoro polyester detergent as claimed in claim 3, characterised in that:
the dispersion stabilizer comprises triglycerol monostearate;
the solvent comprises toluene or xylene;
the promoter comprises trimethylamine or methanol.
5. A method of making a fluoro-polyester detergent as claimed in any one of claims 1 to 4, comprising the steps of:
(1) according to the selected molar weight, fully mixing the fluorinated polycarboxy polyester, 12-phenylbutyryl stearic acid, perfluorooctane sulfonic acid, pentaerythritol tetra-n-heptanoate, calcium hydroxide, active magnesium oxide, a solvent, an accelerant and a dispersion stabilizer, and carrying out neutralization reaction at 35-60 ℃;
(2) and then adding water with a selected molar weight, heating the reaction system to 65-80 ℃, introducing carbon dioxide gas with a selected molar weight for reaction, removing residues from the reaction product, and distilling under reduced pressure to remove the solvent to obtain the catalyst.
6. The method of manufacturing the fluoro polyester detergent as claimed in claim 5, wherein the aeration rate of the carbon dioxide gas is 60 to 300 mL/min.
7. A lubricating oil composition comprising the fluoro polyester type detergent as claimed in any one of claims 1 to 4.
8. Lubricating oil composition according to claim 7, characterized in that the fluoro-polyester detergent is added in an amount of 1 to 3% by mass of the base oil.
9. The lubricating oil composition of claim 8, wherein the base oil comprises a synthetic ester base oil.
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| CN115505449A (en) * | 2022-09-20 | 2022-12-23 | 广州诺拜因化工有限公司 | Polyester type high-temperature steel belt oil for high-temperature-resistant and wear-resistant artificial board continuous press |
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