CN109503503A - A kind of multifunctional ion liquid and the preparation method and application thereof - Google Patents
A kind of multifunctional ion liquid and the preparation method and application thereof Download PDFInfo
- Publication number
- CN109503503A CN109503503A CN201811568453.9A CN201811568453A CN109503503A CN 109503503 A CN109503503 A CN 109503503A CN 201811568453 A CN201811568453 A CN 201811568453A CN 109503503 A CN109503503 A CN 109503503A
- Authority
- CN
- China
- Prior art keywords
- ionic liquid
- methyl
- octadecyl
- general formula
- hydrogen atom
- 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.)
- Granted
Links
- 239000007788 liquid Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title abstract description 13
- 239000002608 ionic liquid Substances 0.000 claims abstract description 85
- 238000005260 corrosion Methods 0.000 claims abstract description 32
- 230000007797 corrosion Effects 0.000 claims abstract description 32
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229910052802 copper Inorganic materials 0.000 claims abstract description 30
- 239000010949 copper Substances 0.000 claims abstract description 30
- 239000000654 additive Substances 0.000 claims abstract description 26
- 230000000996 additive effect Effects 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
- 239000003112 inhibitor Substances 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 12
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 11
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 11
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 11
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 11
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 239000002199 base oil Substances 0.000 claims description 18
- 235000019441 ethanol Nutrition 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003879 lubricant additive Substances 0.000 claims description 9
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 claims description 8
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 8
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 8
- 239000012964 benzotriazole Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 claims description 6
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 claims description 6
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 claims description 6
- 239000013067 intermediate product Substances 0.000 claims description 6
- 239000000314 lubricant Substances 0.000 claims description 6
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 claims description 6
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 5
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 4
- 150000002192 fatty aldehydes Chemical class 0.000 claims description 4
- 229920002866 paraformaldehyde Polymers 0.000 claims description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 3
- SNAMIIGIIUQQSP-UHFFFAOYSA-N bis(6-methylheptyl) hydrogen phosphate Chemical compound CC(C)CCCCCOP(O)(=O)OCCCCCC(C)C SNAMIIGIIUQQSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims 2
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 claims 1
- 239000010687 lubricating oil Substances 0.000 abstract description 3
- 150000002500 ions Chemical class 0.000 description 18
- 229910000831 Steel Inorganic materials 0.000 description 12
- 239000010959 steel Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 101150092791 PAO4 gene Proteins 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 8
- 235000010446 mineral oil Nutrition 0.000 description 8
- 229920013639 polyalphaolefin Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 7
- -1 isoamyl dioctyl ester sulfonate radical Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 231100000241 scar Toxicity 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000007866 anti-wear additive Substances 0.000 description 4
- 150000001565 benzotriazoles Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000001603 reducing effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 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 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 1
- RQINQJTUMGQYOB-UHFFFAOYSA-N 6-methylheptyl dihydrogen phosphate Chemical compound CC(C)CCCCCOP(O)(O)=O RQINQJTUMGQYOB-UHFFFAOYSA-N 0.000 description 1
- 101100407030 Arabidopsis thaliana PAO2 gene Proteins 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- MOFINMJRLYEONQ-UHFFFAOYSA-N [N].C=1C=CNC=1 Chemical class [N].C=1C=CNC=1 MOFINMJRLYEONQ-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- BULOCEWDRJUMEL-UHFFFAOYSA-N benzene formaldehyde Chemical group C=O.C1=CC=CC=C1.C=O BULOCEWDRJUMEL-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- PZZHMLOHNYWKIK-UHFFFAOYSA-N eddha Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNC(C(O)=O)C1=CC=CC=C1O PZZHMLOHNYWKIK-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000004519 grease Substances 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
- 238000005461 lubrication Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
-
- 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/043—Ammonium or amine salts thereof
-
- 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
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
Abstract
The present invention relates to a kind of multifunctional ion liquids and the preparation method and application thereof, the ionic liquid is indicated by the following general formula (1), in the general formula (1), R indicates any one in hydrogen atom or methyl, R1 indicates hydrogen atom, methyl, propyl, amyl, heptyl, nonyl, undecyl, any one in phenyl, R2 indicates any one in octadecyl or 9- alkene octadecyl, ionic liquid of the invention has excellent wear-resistant, antifriction performance as lube oil additive, as copper corrosion inhibitor, there is excellent copper corrosion rejection.
Description
Technical field
The present invention relates to lubriation material fields, and in particular to a kind of multifunctional ion liquid and the preparation method and application thereof,
Ionic liquid of the invention has excellent tribological property and good copper corrosion rejection.
Background technique
Ionic liquid refers to molten salt system being in a liquid state in room temperature or near room temperature, being made of completely negative ions, one
As be relatively small inorganic by the relatively large organic cation of specific, volume and volume or organic anion passes through coulomb
Power is bonded.Compared with other solids or fluent material, its liquidus behavior and ion existence form makes it show uniqueness
Physicochemical property and distinctive function, be a kind of up-and-coming novel medium or " soft " functional material.Due to ionic liquid
One or more functions group is introduced on the cation or anion of ionic liquid by " designability ", i.e., by ionic liquid
Functionalization becomes new research hotspot, significant to designing and developing novel ion liquid lubricant.
However, but there is many cannot be neglected to ask while with excellent tribology performance for ion liquid lubricant
Topic.For example, most of ionic liquids are soluble in the biggish base oil of polarity, and in the lesser mineral oil of polarity or poly alpha olefin
Middle dissolubility is very poor.In addition, general ionic liquid has stronger surface corrosion to act on the various metals such as copper, steel, aluminium, existing skill
Art generallys use the corrosion that the additives such as copper corrosion inhibitor or antirust agent are added to inhibit ionic liquid to metal material.Mesh
Before, the domestic research report in relation to oil-soluble ionic liquid is very few, and 105254667 A of patent CN discloses a kind of function carburetion
Insoluble ionic liquid and its preparation method and application, with the quaternary phosphonium or quaternary ammonium cation of different alkyl chain lengths, anion two
Isooctyl phosphoric acid root (EDHPA), isoamyl dioctyl ester sulfonate radical (DOSS), O, O- diethyldithioposphoric acid root (DDSSP) and the moon
Cinnamic acid root has good dissolubility and greasy property in 500N and PAO10, while having certain corrosion resistance.
Summary of the invention
The present invention discloses a kind of multifunctional ion liquid and the preparation method and application thereof, solves ionic liquid in the prior art
Body dissolubility in mineral oil or poly alpha olefin is very poor, has stronger corrosive technical problem to metal surface.
The present invention uses following scheme: the ionic liquid is indicated by the following general formula (1), and in the general formula (1), R is indicated
Any one in hydrogen atom or methyl, R1 indicate hydrogen atom, methyl, propyl, amyl, heptyl, nonyl, undecyl, phenyl
In any one, R2 indicates any one in octadecyl or 9- alkene octadecyl.
A method of multifunctional ion liquid is prepared, is included the following steps: benzotriazole analog derivative, fat
Aldehyde/aromatic aldehyde, high carbon chain fatty amine are added in flask according to molar ratio 1:1.1:1, and ethyl alcohol is solvent, and addition 1wt%~
The hydrochloric acid of 5wt% removes ethyl alcohol as catalyst, 50~80 DEG C of 8~12h of reaction, revolving, and extraction and separation obtain organic phase, removes acetic acid
Ethyl ester obtains intermediate product, and the intermediate product is mixed with di (isooctyl) phosphate with molar ratio 1:1, and 80~100 DEG C of reactions 2~
8h obtains the ionic liquid.
Embodiment as one preferred, the benzotriazole analog derivative are benzotriazole or 5- methyl benzo
One of triazole.
Embodiment as one preferred, the fatty aldehyde be formaldehyde, paraformaldehyde, acetaldehyde, butyraldehyde, hexanal, octanal,
Any one of capraldehyde, lauric aldehyde.
Embodiment as one preferred, the aromatic aldehyde are benzaldehydes.
Embodiment as one preferred, the high carbon chain fatty amine is one of oleyl amine or octadecylamine.
Application of the ionic liquid as lubricant additive, the lubricant additive is indicated by the following general formula (1), described
In general formula (1), R indicates any one in hydrogen atom or methyl, and R1 indicates hydrogen atom, methyl, propyl, amyl, heptyl, nonyl
Base, undecyl, any one in phenyl, R2 indicate any one in octadecyl or 9- alkene octadecyl.
Embodiment as one preferred, it is 0.2 wt% that the lubricant additive, which is added to the dosage in base oil,
~2wt%.
A kind of application of multifunctional ion liquid, the ionic liquid are made as copper corrosion inhibitor, the ionic liquid
Dosage for copper corrosion inhibitor is 0.1wt%~1wt%.
The copper corrosion inhibitor made of ionic liquid, the ionic liquid is by the following general formula (1) expression, the general formula
(1) in, R indicates any one in hydrogen atom or methyl, and R1 indicates hydrogen atom, methyl, propyl, amyl, heptyl, nonyl, ten
Any one in one alkyl, phenyl, R2 indicate any one of octadecyl or 9- alkene octadecyl, the ionic liquid
Dosage be 0.1wt%~1wt%.
Beneficial effects of the present invention: it is simpler compared to conventional ionic liquid (fluo anion) preparation step, product at
This is lower；Oil-soluble is good, good with traditional infrastructure oil compatibility, such as with poly alpha olefin (PAO), mineral oil, polyethers, synthetic ester base
Plinth oil all has good intermiscibility, applied widely as additive；Tribological property is excellent in a variety of base oils；It is simultaneous
Have copper corrosion rejection, remains to show fabulous copper corrosion rejection in the presence of sulfur-containing additive.
Specific embodiment
Technical solution of the present invention is clearly and completely described below in conjunction with specific embodiments of the present invention, is shown
So, described embodiment is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the implementation in the present invention
Example, every other embodiment obtained by those of ordinary skill in the art without making creative efforts belong to
The scope of protection of the invention.
A kind of multifunctional ion liquid, the ionic liquid are indicated by the following general formula (1), and in the general formula (1), R is indicated
Any one in hydrogen atom or methyl, R1 indicate hydrogen atom, methyl, propyl, amyl, heptyl, nonyl, undecyl, phenyl
In any one, R2 indicates any one in octadecyl or 9- alkene octadecyl.
A method of multifunctional ion liquid being prepared, steps are as follows: by benzotriazole analog derivative, fatty aldehyde/virtue
Fragrant aldehyde, high carbon chain fatty amine are added in flask according to molar ratio 1:1.1:1, and ethyl alcohol is solvent, are added 1wt%~5wt%'s
Hydrochloric acid removes ethyl alcohol as catalyst, 50~80 DEG C of 8~12h of reaction, revolving, and extraction and separation obtain organic phase, removes ethyl acetate and obtains
To intermediate product, the intermediate product reacts 2~8h at 80~100 DEG C with molar ratio 1:1 with di (isooctyl) phosphate, obtains described
Ionic liquid.The benzotriazole analog derivative is one of benzotriazole or 5- methyl benzotriazazole, the rouge
Fat aldehyde is any one of formaldehyde, paraformaldehyde, acetaldehyde, butyraldehyde, hexanal, octanal, capraldehyde, lauric aldehyde, and the aromatic aldehyde is benzene
Formaldehyde, the high carbon chain fatty amine is one of oleyl amine or octadecylamine.
Application of the ionic liquid as lubricant additive, the lubricant additive is indicated by the following general formula (1), described
In general formula (1), R indicates any one in hydrogen atom or methyl, and R1 indicates hydrogen atom, methyl, propyl, amyl, heptyl, nonyl
Base, undecyl, any one in phenyl, R2 indicate any one in octadecyl or 9- alkene octadecyl.The profit
It is 0.2wt%~2wt% that lubrication prescription additive, which is added to the dosage in base oil,.
The base oil refers to poly alpha olefin (PAO), mineral oil, polyethers, synthetic ester base oil etc., the poly alpha olefin
(PAO), PAO2, PAO4, PAO10, PAO40, PAO100, PAO150, PAO300 are primarily referred to as；The mineral oil refers to API I
Class, II class of API, III class mineral base oil of API, typically 150SN, 500N, 100N；The polyethers, be primarily referred to as OSP46,
OSP68；The synthetic ester refers to dibasic acid esters, trimellitate, polyol ester, typically Plexol 201, trimellitic acid
One of different monooctyl ester, tricarboxymethyl propane oleate.It can be seen that present invention also provides a kind of lubricants.
Further, a kind of application of multifunctional ion liquid, the ionic liquid as copper corrosion inhibitor, it is described from
Sub- liquid is 0.1wt%~1wt% as the dosage of copper corrosion inhibitor.
The copper corrosion inhibitor made of ionic liquid, the ionic liquid is by the following general formula (1) expression, the general formula
(1) in, R indicates any one in hydrogen atom or methyl, and R1 indicates hydrogen atom, methyl, propyl, amyl, heptyl, nonyl, ten
Any one in one alkyl, phenyl, R2 indicate any one of octadecyl or 9- alkene octadecyl, the ionic liquid
Dosage be 0.1wt%~1wt%.
Embodiment 1
A kind of preparation method of multifunctional ion liquid, by benzotriazole 11.9g, formalin 8.9g, oleyl amine 26.7g
250ml single-necked flask is added, ethyl alcohol 100g and 0.475g hydrochloric acid, 50 degree of stirring 12h is added, reaction terminates.Revolving removes ethyl alcohol.
It is gradually added into the saturated sodium bicarbonate solution of hydrochloric acid equimolar amounts into flask, and is stirred continuously, adds 100ml ethyl acetate
Three times acquisition organic phases are washed in extraction, and revolving removes ethyl acetate, and obtaining weak yellow liquid product N-, (benzotriazole -1- is sub-
Methyl) oleyl amine.Take product 19.9g, dioctylphosphoric acid ester 16.1g that 100ml single-necked flask is added, 100 degree of stirring 2h obtain ion
Liquid.
The resulting ionic liquid of above-mentioned steps is added in base oil as antiwear additive, dosage is as lubricant
0.2wt%~2wt%.
For the resulting ionic liquid of above-mentioned steps as copper corrosion inhibitor, dosage is 0.1wt%~1wt%.
Embodiment 2
A kind of preparation method of multifunctional ion liquid, by benzotriazole 11.9g, paraformaldehyde 3.3g, octadecylamine
250ml single-necked flask is added in 26.9g, and ethyl alcohol 100g and hydrochloric acid 0.475g, 80 degree of stirring 6h is added, and reaction terminates.Revolving removes
Ethyl alcohol.It is gradually added into the saturated sodium bicarbonate solution of hydrochloric acid equimolar amounts into flask, and is stirred continuously, 100ml is added later
Ethyl acetate extraction, washes three times acquisition organic phases, and revolving removes ethyl acetate, obtains faint yellow solid product N- (benzo three
Nitrogen azoles -1- methylene) octadecylamine.Take product 20g, dioctylphosphoric acid ester 16.1g that 100ml single-necked flask, 100 degree of stirrings are added
4h obtains ionic liquid.
The resulting ionic liquid of above-mentioned steps is added in base oil as antiwear additive, dosage is as lubricant
0.2wt%~2wt%.
For the resulting ionic liquid of above-mentioned steps as copper corrosion inhibitor, dosage is 0.1wt%~1wt%.
Embodiment 3
A kind of preparation method of multifunctional ion liquid, by 5- methyl benzotriazazole 13.32g, 7.93 g of n-butanal, oil
250ml single-necked flask is added in amine 26.7g, and ethyl alcohol 100g and hydrochloric acid 0.916g, 70 degree of stirring 8h is added, and reaction terminates.Revolving is removed
Remove ethyl alcohol.It is gradually added into the saturated sodium bicarbonate solution of hydrochloric acid equimolar amounts into flask and is stirred continuously, acetic acid is added later
Ethyl ester 100ml extraction, washes three times acquisition organic phases, and revolving removes ethyl acetate and obtains weak yellow liquid product 1- (5- methyl
Benzotriazole -1- (propyl) methine) oleyl amine, it takes product 22.7g, dioctylphosphoric acid ester 16.1g that 100ml single port is added and burns
Bottle, 80 degree of stirring 8h obtain ionic liquid.
The resulting ionic liquid of above-mentioned steps is added in base oil as antiwear additive, dosage is as lubricant
0.2wt%~2wt%.
For the resulting ionic liquid of above-mentioned steps as copper corrosion inhibitor, dosage is 0.1wt%~1wt%.
Embodiment 4
A kind of preparation method of multifunctional ion liquid, by benzotriazole 5.95g, benzaldehyde 5.84g, oleyl amine 13.35g
It is added in 150ml single-necked flask, ethyl alcohol 50g and hydrochloric acid 1.23g, 80 degree of stirring 10h is added, reaction terminates.Revolving removes second
Alcohol is gradually added into the saturated sodium bicarbonate solution of hydrochloric acid equimolar amounts and is stirred continuously, and 100ml ethyl acetate extraction is added later
It takes, washes three times acquisition organic phases, revolving removes ethyl acetate, and obtaining faint yellow product N-, (benzotriazole -1- (phenyl) is secondary
Methyl) oleyl amine.Take product 11.85g, dioctylphosphoric acid ester 8.05g that 50ml single-necked flask is added, 90 degree of stirring 6h obtain ion
Liquid.
The resulting ionic liquid of above-mentioned steps is added in base oil as antiwear additive, dosage is as lubricant
0.2wt%~2wt%.
For the resulting ionic liquid of above-mentioned steps as copper corrosion inhibitor, dosage is 0.1wt%~1wt%.
The obtained ionic liquid of embodiment 1-4, as shown in general formula (1), in the general formula (1), R indicates hydrogen atom or first
Any one in base, R1 indicate hydrogen atom, methyl, propyl, amyl, heptyl, nonyl, undecyl, any one in phenyl
It plants, any one in R2 expression octadecyl or 9- alkene octadecyl.
Experimental example
In order to further illustrate the performance of prepared ionic liquid, from dissolubility, antiwear and antifriction, corrosion resistance three
Aspect is tested.
Solubility experiment
There is good dissolubility in base oil, the ionic liquid of embodiment 1-4 is in multiple types base oil
Dissolubility of 1 ionic liquid of table in different type base oil
Dissolubility be shown in Table 1.
From the results shown in Table 1,1 to 4 gained ionic liquid of embodiment shows in different types of base oil
Excellent solubility property out.
Apply the frictional wear experiment of the ionic liquid of example 1 and embodiment 2
Using Xiamen nature's mystery produce four-ball friction and wear test machine, to embodiment 1-2 preparation ionic liquid in poly- α-
Frictional behaviour in alkene and mineral oil is determined, steel ball material GCR15, and diameter is 12.7 mm, hardness HRC59-
61, experimental condition are as follows: load 392N, temperature is 25 DEG C, time 30min, revolving speed 1200r/min.
Using 1 ionic liquid of embodiment as the additive of PAO4 as experimental group, it is not added with ionic liquid
2 embodiment of table, 1 ionic liquid is used for the antiwear and antifriction effect of PAO4 additive
As a control group, two groups of average friction coefficients and wear scar diameter size under steel/steel-steel pair are shown in Table 2 to PAO4.
As can be seen from Table 2, the average friction coefficient for being not added with the PAO4 of ionic liquid is 0.075, wear scar diameter is
0.631mm.Compared with PAO4, it is added to not the PAO4 antifriction of 1 ionic liquid of same amount embodiment and anti-wear effect and significantly improves, from
When sub- liquid additive amount is 0.5wt%, average friction coefficient minimum 0.060, friction reducing effect is best, additive amount 0.2wt%
When, wear scar diameter minimum 0.326, anti-wear effect is best.
Using 2 ionic liquid of embodiment as the additive of mineral oil 500N as experimental group, it is not added with the mine of ionic liquid
Object oil 500N group as a comparison, two groups of average friction coefficients and wear scar diameter under steel/steel-steel pair
3 embodiment of table, 2 ionic liquid is used as the antiwear and antifriction effect of mineral oil 500N additive
Size is shown in Table 3.
Seen from table 3, the experimental results showed that, the 500N of 2 gained ionic liquid of embodiment is added, and is not added with ionic liquid
500N compare, antifriction and abrasion resistance have significant raising.When wherein 2 ionic liquid additive amount of embodiment is 2wt%,
Average friction coefficient minimum 0.066, friction reducing effect is best；When additive amount is 0.5wt%, wear scar diameter minimum 0.313 resists
It is best to grind effect.
The frictional wear experiment of the ionic liquid of embodiment 3 and embodiment 4
Embodiment 3-4 system is evaluated using the SRV-V micro-vibration friction wear testing machine of German optimol grease company production
Friction and wear behavior of the standby ionic liquid as lubricant additive.Wherein upper friction pair steel ball is diameter 10mm GCr15
(SAE52100) steel ball, secondary lower friction is bloom, and hardness is in HRC59-61.Experimental condition: load 200N, temperature 100
DEG C, time 30min, frequency 25Hz.
3 ionic liquid of embodiment is as OSP46 additive as experimental group, and experimental group is 4 groups, and every group of additive amount is different,
Group, the average friction coefficient and wear volume of experimental group and contrast groups under steel/steel-steel pair are shown in Table 4 to OSP46 as a comparison.
4 embodiment of table, 3 ionic liquid is used as the antiwear and antifriction effect of OSP46 additive
By table 4 as it can be seen that compared with base oil OSP46, it is added to the OSP46 antifriction and wear resistence of 3 ionic liquid of embodiment
It can all be greatly improved.When wherein additive amount is 2wt%, average friction coefficient is minimum, and friction reducing effect is best.Additive amount is
When 2wt%, wear volume is minimum, and anti-wear effect is best.
As Plexol 201 additive as experimental group, experimental group totally 4 groups add 4 ionic liquid of embodiment
Dosage is different, is not added with the Plexol 201 of ionic liquid group as a comparison, experimental condition are as follows: load 200N, temperature
It is 25 DEG C, time 30min, frequency 25Hz.The average friction coefficient and mill of experimental group and contrast groups under steel/steel-steel pair
Damage volume is shown in Table 5.
5 embodiment of table, 4 ionic liquid is used as the antiwear and antifriction effect of Plexol 201 additive
By table 5 as it can be seen that compared with Plexol 201, it is added to the Plexol 201 of 4 ionic liquid of embodiment
It all increases in terms of antifriction and abrasion resistance.Wherein additive amount is 0.5wt%, and average friction coefficient is minimum, friction reducing effect
Most preferably；Additive amount is 0.5wt%, and wear volume is minimum, and anti-wear effect is best.
Copper corrosion experiment
The ionic liquid of embodiment 1 to embodiment 4 preparation is resisted by copper strip test (GB/T 7326-87)
The evaluation of corrosive nature.Further to investigate prepared effect of the ionic liquid as copper corrosion inhibitor, by base oil points
It Jia Ru not sulfur-containing additive RC2540, RC2526, zinc dialkyl dithiophosphate, sulfide isobutene progress copper strip test.
RC2540, RC2526 are Rhein Chemie Corporation's additive trade mark, belong to active sulfur additives, wherein in addition RC25401wt%
PAO4 on the basis of, be not added with group 1 as a comparison of ionic liquid, addition 1 ionic liquid 1wt% of experimental example as experimental group 1,
Carry out corrosion resistance comparison；On the basis of adding the 500N of RC25261wt%, group 2 as a comparison of ionic liquid are not added with,
2 ionic liquid 0.8wt% of experimental example is added as experimental group 2, corrosion resistance performance is carried out and compares；In addition dialkyl dithio
On the basis of the OSP46 of trbasic zinc phosphate 1wt%, group 3 as a comparison of ionic liquid are not added with, add 3 ionic liquid of experimental example
0.5wt% is as experimental group 3；On the basis of adding the Plexol 201 of sulfide isobutene 1wt%, it is not added with ionic liquid
As a comparison 4, add the conduct experimental group 4 of 4 ionic liquid 0.1wt% of embodiment.Above-mentioned group of other copper strip test knot
Fruit is shown in Table 6.
6 copper strip test result of table
By table 6 as it can be seen that compared with contrast groups 1, the copper corrosion grade of experimental group 1 drops to 1b from 4b；With 2 phase of contrast groups
Than the copper corrosion grade of experimental group 2 is down to 1b from 4a；Compared with contrast groups 3, the copper corrosion grade of experimental group 3 is dropped from 3a
To 1b；Compared with contrast groups 4, the copper corrosion grade of experimental group 4 is down to 1a from 1b.Therefore, embodiment 1 to embodiment 4 is made
Standby ionic liquid has preferable corrosion resistance.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (10)
1. a kind of multifunctional ion liquid, which is characterized in that the ionic liquid is by the following general formula (1) expression, the general formula (1)
In, R indicates any one in hydrogen atom or methyl, and R1 indicates hydrogen atom, methyl, propyl, amyl, heptyl, nonyl, hendecane
Any one in base, phenyl, R2 indicate any one in octadecyl or 9- alkene octadecyl.
2. a kind of method for preparing a kind of multifunctional ion liquid described in claim 1, which is characterized in that including walking as follows
Rapid: by benzotriazole analog derivative, fatty aldehyde/aromatic aldehyde, high carbon chain fatty amine is added to burning according to molar ratio 1:1.1:1
In bottle, ethyl alcohol is solvent, the hydrochloric acid of 1wt%~5wt% is added as catalyst, 50~80 DEG C of 8~12h of reaction, revolving is except second
Alcohol, extraction and separation obtain organic phase, remove ethyl acetate obtain intermediate product, the intermediate product and di (isooctyl) phosphate with mole
Than 1:1 in 80~100 DEG C of 2~8h of reaction, the ionic liquid is obtained.
3. a kind of method for preparing multifunctional ion liquid described in claim 1 according to claim 2, feature exist
In the benzotriazole analog derivative is one of benzotriazole or 5- methyl benzotriazazole.
4. a kind of method for preparing multifunctional ion liquid described in claim 1 according to claim 2, feature exist
In the fatty aldehyde is any one of formaldehyde, paraformaldehyde, acetaldehyde, butyraldehyde, hexanal, octanal, capraldehyde, lauric aldehyde.
5. a kind of method for preparing multifunctional ion liquid described in claim 1 according to claim 2, feature exist
In the aromatic aldehyde is benzaldehyde.
6. a kind of method for preparing multifunctional ion liquid described in claim 1 according to claim 2 or 3, special
Sign is that the high carbon chain fatty amine is one of oleyl amine or octadecylamine.
7. application of the ionic liquid as lubricant additive, which is characterized in that the lubricant additive is by the following general formula (1)
Indicate, in the general formula (1), R indicates any one in hydrogen atom or methyl, R1 indicate hydrogen atom, methyl, propyl, amyl,
Heptyl, nonyl, undecyl, any one in phenyl, R2 indicates any one of octadecyl or 9- alkene octadecyl.
8. application of the ionic liquid according to claim 7 as lubricant additive, which is characterized in that the lubricant
It is 0.2wt%~2wt% that additive, which is added to the dosage in base oil,.
9. a kind of application of multifunctional ion liquid as described in claim 1, which is characterized in that the ionic liquid is as copper
Corrosion inhibitor, the ionic liquid are 0.1wt%~1wt% as the dosage of copper corrosion inhibitor.
10. with copper corrosion inhibitor made of ionic liquid, which is characterized in that the ionic liquid indicates by the following general formula (1),
In the general formula (1), R indicates any one in hydrogen atom or methyl, R1 indicate hydrogen atom, methyl, propyl, amyl, heptyl,
Nonyl, undecyl, any one in phenyl, R2 indicate any one of octadecyl or 9- alkene octadecyl, it is described from
The dosage of sub- liquid is 0.1wt%~1wt%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811568453.9A CN109503503B (en) | 2018-12-24 | 2018-12-24 | Multifunctional ionic liquid and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811568453.9A CN109503503B (en) | 2018-12-24 | 2018-12-24 | Multifunctional ionic liquid and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109503503A true CN109503503A (en) | 2019-03-22 |
| CN109503503B CN109503503B (en) | 2021-07-23 |
Family
ID=65754050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811568453.9A Active CN109503503B (en) | 2018-12-24 | 2018-12-24 | Multifunctional ionic liquid and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109503503B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110862356A (en) * | 2019-12-04 | 2020-03-06 | 中国科学院兰州化学物理研究所 | Benzotriazole functionalized quaternary ammonium salt ionic liquid and preparation method and application thereof |
| CN111004669A (en) * | 2019-12-11 | 2020-04-14 | 中国科学院兰州化学物理研究所 | Ionic liquid lignin lubricating composition and preparation method and application thereof |
| CN114763337A (en) * | 2021-01-14 | 2022-07-19 | 中国石油天然气股份有限公司 | Lubricating oil additive and preparation method and application thereof |
| CN115010751A (en) * | 2022-07-18 | 2022-09-06 | 新乡市瑞丰新材料股份有限公司 | Phosphorus-nitrogen type multifunctional additive and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106432333A (en) * | 2016-09-12 | 2017-02-22 | 中国科学院兰州化学物理研究所 | Sulfur-containing phosphate ionic liquid and preparation method and application thereof |
-
2018
- 2018-12-24 CN CN201811568453.9A patent/CN109503503B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106432333A (en) * | 2016-09-12 | 2017-02-22 | 中国科学院兰州化学物理研究所 | Sulfur-containing phosphate ionic liquid and preparation method and application thereof |
Non-Patent Citations (5)
| Title |
|---|
| ALAN R. KATRITZKY等: "The N-Substitution of Aliphatic Primary Amines via 1-[ (Alky1amino)methyll benzotriazoles: Preparation of Secondary Amines", 《CHERN. BER.》 * |
| EL-S.H. EL-ASHRY等: "Synthesis of benzotriazole derivatives as antioxidants for industrial lubricating oils", 《LUBRICATION SCIENCE》 * |
| GUOWEI HUANGA等: "Probing the lubricating mechanism of oil-soluble ionic liquids additives", 《TRIBOLOGY INTERNATIONAL》 * |
| WILLIAM C. BARNHILL等: "Tertiary and Quaternary Ammonium-Phosphate Ionic Liquids as Lubricant Additives", 《TRIBOL LETT》 * |
| 高冬梅等: "新型苯并三氮唑离子液体的合成及其对铜缓蚀性能的研究", 《化学与黏合》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110862356A (en) * | 2019-12-04 | 2020-03-06 | 中国科学院兰州化学物理研究所 | Benzotriazole functionalized quaternary ammonium salt ionic liquid and preparation method and application thereof |
| CN111004669A (en) * | 2019-12-11 | 2020-04-14 | 中国科学院兰州化学物理研究所 | Ionic liquid lignin lubricating composition and preparation method and application thereof |
| CN114763337A (en) * | 2021-01-14 | 2022-07-19 | 中国石油天然气股份有限公司 | Lubricating oil additive and preparation method and application thereof |
| CN114763337B (en) * | 2021-01-14 | 2024-04-30 | 中国石油天然气股份有限公司 | Lubricating oil additive and preparation method and application thereof |
| CN115010751A (en) * | 2022-07-18 | 2022-09-06 | 新乡市瑞丰新材料股份有限公司 | Phosphorus-nitrogen type multifunctional additive and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109503503B (en) | 2021-07-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109503503A (en) | A kind of multifunctional ion liquid and the preparation method and application thereof | |
| Li et al. | Tribological studies on a novel borate ester containing benzothiazol-2-yl and disulfide groups as multifunctional additive | |
| CN103205301B (en) | Gear oil composition and preparation method thereof | |
| CN101113383B (en) | Ester flame-proof hydraulic-oil containing nano abrasion-resistant additive and production method thereof | |
| CN103289797B (en) | Worm and gear oil composition and preparation method thereof | |
| JP7084794B2 (en) | Ionic liquids and lubricant compositions | |
| CN1993452B (en) | Lubricating oil additive, fuel oil additive, lubricating oil composition, and fuel oil composition | |
| BR112017005274B1 (en) | Industrial lubricating compositions based on polyalkylene glycol | |
| CN103571591B (en) | Lubricating oil composition and uses thereof | |
| CN102131906B (en) | Lubricant oil composition in contact with a silver-containing material | |
| CN104342252A (en) | Antirust oil composition, and preparation method and application thereof | |
| CN103725365A (en) | Water-based hydraulic fluid composition | |
| CN102329680A (en) | Lubrication additive suitable for various kinds of lubricating oil | |
| CN106947571B (en) | Preparation of ionic liquid modified zinc sulfide nano extreme pressure antiwear agent and energy-saving antiwear hydraulic oil containing same | |
| TW200413285A (en) | Succinic acid semi-amides as anti-corrosive agents | |
| CN108048174A (en) | The wear-resistant antirust chain grease of environment-friendly type | |
| CN106133124B (en) | Lubricant oil composite | |
| CN102888262B (en) | Industrial gear oil composition | |
| Panja | Tribological Properties of Ionic Liquids | |
| JP2005330328A (en) | Method of improving oil performance | |
| JP2020059835A (en) | Environmentally friendly, low viscosity, highly flammable, non-water soluble processing oil | |
| WO2020131603A1 (en) | Lubricating composition comprising a sulfur-containing carboxylic acid or ester additive | |
| CN108192703A (en) | A kind of textile machinery lubricating oil | |
| CN102839036B (en) | Water base extreme pressure wear resistance multifunctional additive and preparation method thereof, and water base lubricating liquid composition | |
| CA2968265C (en) | Hydrophilic ether carboxylic acids as lubricant for salt based drilling systems |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |