CN116874431A - 一种功能化脲基双子咪唑多库酯盐及其制备方法和应用 - Google Patents
一种功能化脲基双子咪唑多库酯盐及其制备方法和应用 Download PDFInfo
- Publication number
- CN116874431A CN116874431A CN202310843741.5A CN202310843741A CN116874431A CN 116874431 A CN116874431 A CN 116874431A CN 202310843741 A CN202310843741 A CN 202310843741A CN 116874431 A CN116874431 A CN 116874431A
- Authority
- CN
- China
- Prior art keywords
- ureido
- imidazole
- functionalized
- salt
- gemini
- 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.)
- Pending
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims abstract description 111
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 title claims abstract description 59
- -1 ester salt Chemical class 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000005260 corrosion Methods 0.000 claims abstract description 44
- 230000007797 corrosion Effects 0.000 claims abstract description 44
- 150000001450 anions Chemical class 0.000 claims abstract description 19
- 150000001768 cations Chemical class 0.000 claims abstract description 17
- 230000005764 inhibitory process Effects 0.000 claims abstract description 12
- 238000005461 lubrication Methods 0.000 claims description 29
- 150000002460 imidazoles Chemical class 0.000 claims description 28
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000003960 organic solvent Substances 0.000 claims description 15
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 claims description 11
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 10
- 238000005342 ion exchange Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 238000005956 quaternization reaction Methods 0.000 claims description 10
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 claims description 8
- 150000001350 alkyl halides Chemical class 0.000 claims description 8
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 claims description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003438 dodecyl group Chemical group [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])* 0.000 claims description 4
- 125000000913 palmityl 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])[H] 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002704 decyl group Chemical group [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])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001421 myristyl 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])[H] 0.000 claims description 3
- 125000002347 octyl 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])[H] 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 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 description 3
- 150000004693 imidazolium salts Chemical class 0.000 claims description 2
- 239000000758 substrate Substances 0.000 abstract description 10
- 239000007769 metal material Substances 0.000 abstract description 9
- 230000001050 lubricating effect Effects 0.000 abstract description 8
- 239000010687 lubricating oil Substances 0.000 abstract description 8
- 239000003112 inhibitor Substances 0.000 abstract description 5
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical class CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 abstract description 2
- 230000002378 acidificating effect Effects 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000002199 base oil Substances 0.000 description 13
- 230000002401 inhibitory effect Effects 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 230000003449 preventive effect Effects 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 239000002608 ionic liquid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000013556 antirust agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 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
- 239000007864 aqueous solution Substances 0.000 description 1
- YSIQDTZQRDDQNF-UHFFFAOYSA-L barium(2+);2,3-di(nonyl)naphthalene-1-sulfonate Chemical compound [Ba+2].C1=CC=C2C(S([O-])(=O)=O)=C(CCCCCCCCC)C(CCCCCCCCC)=CC2=C1.C1=CC=C2C(S([O-])(=O)=O)=C(CCCCCCCCC)C(CCCCCCCCC)=CC2=C1 YSIQDTZQRDDQNF-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000000840 electrochemical analysis Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
- C10M133/46—Imidazoles
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
- C10M135/10—Sulfonic acids or derivatives 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
- 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
- C10M141/08—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 sulfur-, selenium- or tellurium-containing compound
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/04—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in markedly acid liquids
-
- 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
- C10M2215/224—Imidazoles
-
- 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
- C10N2030/06—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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Lubricants (AREA)
Abstract
本发明提供了一种功能化脲基双子咪唑多库酯盐及其制备方法和应用,涉及润滑材料技术领域。本发明提供的功能化脲基双子咪唑多库酯盐,包括阳离子和阴离子;所述阳离子和阴离子的摩尔比为1:2;所述阳离子为功能化脲基双子化咪唑,阴离子为多库酯盐。本发明提供的功能化脲基双子咪唑多库酯盐具有优异的减摩抗磨性能,可以作为润滑因子,在润滑油中形成均匀稳定的润滑体系,所述润滑材料的热稳定性好且摩擦学性能优异。同时,所述功能化脲基双子咪唑多库酯盐还具有优异的缓蚀性能,可以作为缓蚀剂有效阻隔酸性介质对金属材料基底的侵蚀。
Description
技术领域
本发明涉及润滑材料技术领域,具体涉及一种功能化脲基双子咪唑多库酯盐及其制备方法和应用。
背景技术
随着工业的快速发展,越来越多的机械设备工作于高温、极压等苛刻环境中。每年,摩擦引起的设备损失造成了大量的经济损失和资源浪费。在润滑领域,随着机械设备的精度要求不断提高,应用场景愈加复杂,研发更加高效的润滑剂成为有利的选择。润滑油是解决摩擦磨损问题的有效方案,具有成本低、使用寿命长、耐高温等优点,是所有润滑剂中应用最广泛的一种。通过添加剂改善润滑油性能,使其适应各类极端环境,是长期以来的热门研究内容。
咪唑类离子液体是常见的润滑添加剂,其中往往存在丰富的N、O、S等活性元素,易在摩擦过程中与金属反应,生成抗磨化合物。然而,传统咪唑类离子液体往往具有在基础油中溶解性不佳、在空气中有吸湿性、阴离子含卤素会对金属表面造成腐蚀等缺点。
发明内容
本发明的目的在于提供一种功能化脲基双子咪唑多库酯盐及其制备方法和应用,本发明提供的功能化脲基双子咪唑多库酯盐具有优异的减摩抗磨性能,可以作为润滑因子,在润滑油中形成均匀稳定的润滑体系,所述润滑材料的热稳定性好且摩擦学性能优异。同时,所述功能化脲基双子咪唑多库酯盐还具有优异的缓蚀性能,可以作为缓蚀剂有效阻隔酸性介质对金属材料基底的侵蚀。
为了实现上述发明目的,本发明提供以下技术方案:
本发明提供了一种功能化脲基双子咪唑多库酯盐,包括阳离子和阴离子;所述阳离子和阴离子的摩尔比为1:2;
所述阳离子具有式I所示结构:
所述式I中R为C1~C18的烷基;
所述阴离子具有式II所示结构:
优选地,所述R为甲基、乙基、丙基、丁基、异丁基、戊基、异戊基、辛基、异辛基、癸基、异癸基、十二烷基、十四烷基、十六烷基或十八烷基。
本发明提供了上述技术方案所述功能化脲基双子咪唑多库酯盐的制备方法,包括以下步骤:
将1,6-己二异氰酸酯、1-(3-氨基丙基)咪唑和第一有机溶剂混合,进行脲基化反应,得到脲基功能化的咪唑盐;
将所述脲基功能化的咪唑盐和卤代烷混合,进行季铵化反应,得到具备长烷基链结构的脲基功能化咪唑盐;
将所述具备长烷基链结构的脲基功能化咪唑盐、磺化琥珀酸二辛酯钠盐和第二有机溶剂混合,进行离子交换反应,得到所述功能化脲基双子咪唑多库酯盐;
所述脲基功能化的咪唑盐具有式III所示结构:
优选地,所述1,6-己二异氰酸酯和1-(3-氨基丙基)咪唑的摩尔比为1:2。
优选地,所述脲基化反应的温度为75~85℃,时间为3~5h。
优选地,所述脲基功能化的咪唑盐和卤代烷的摩尔比为1:2~2.2。
优选地,所述季铵化反应的温度为75~85℃,时间为8~48h。
优选地,所述具备长烷基链结构的脲基功能化咪唑盐和磺化琥珀酸二辛酯钠盐的摩尔比为1:2~2.2。
优选地,所述离子交换反应的温度为75~85℃,时间为8~48h。
本发明提供了上述技术方案所述功能化脲基双子咪唑多库酯盐或上述技术方案所述制备方法制备得到的功能化脲基双子咪唑多库酯盐在润滑、防锈或缓蚀领域的应用。
本发明提供了一种功能化脲基双子咪唑多库酯盐,包括阳离子和阴离子;所述阳离子和阴离子的摩尔比为1:2;所述阳离子为功能化脲基双子化咪唑,阴离子为多库酯盐。本发明在咪唑结构中引入烷基链及脲基官能团,所得功能化脲基双子咪唑多库酯盐具有优异的油溶解性能,可以作为润滑油添加剂,在润滑油中热稳定性良好且摩擦学性能优异;所述功能化脲基双子咪唑多库酯盐还具有优异的缓蚀性能,可以作为缓蚀剂有效阻隔腐蚀介质对金属材料基底的侵蚀。具体的,本发明在咪唑环2号位上引入长烷基链结构,同时增强了功能化脲基双子咪唑多库酯盐的抗氧化性;所引入的脲基官能团可以通过形成配位键的方式结合在金属表面,提高功能化脲基双子咪唑多库酯盐的吸附性能,以抑制腐蚀;相比于传统的六氟磷酸盐或四氟硼酸盐,本发明在阴离子上引入的多库酯基团具备优秀防腐性能,还拥有一定的清洁性(可以有效的抑制界面积碳的沉积,保持摩擦副的清洁),改善耐蚀性能。同时,阴离子中包含的活性元素S也有利于参与摩擦化学反应,生成抗磨化合物。
本发明提供的功能化脲基双子咪唑多库酯盐还具有优异的缓蚀性能,可以作为金属材料基底在酸性介质中的缓蚀剂,具体的,所述功能化脲基双子咪唑多库酯盐能够有效的吸附在金属材料基底表面,通过脲基中的N原子与金属材料基底中金属形成稳定的配位键进而形成致密的吸附膜,此外,功能化脲基双子咪唑多库酯盐中疏水链能够反向伸入水中且相互缠绕而形成致密的疏水膜,能够有效的阻隔酸性介质对金属材料基底的侵蚀,从而起到防腐作用。
附图说明
图1为2M16-DOSS的Tafel极化曲线;
图2为2M16-DOSS的盐雾实验图。
具体实施方式
本发明提供了一种功能化脲基双子咪唑多库酯盐,包括阳离子和阴离子;所述阳离子和阴离子的摩尔比为1:2;
所述阳离子具有式I所示结构:
所述式I中R为C1~C18的烷基;
所述阴离子具有式II所示结构:
在本发明中,所述R为甲基、乙基、丙基、丁基、异丁基、戊基、异戊基、辛基、异辛基、癸基、异癸基、十二烷基、十四烷基、十六烷基或十八烷基,更优选为十二烷基或十六烷基。
本发明提供了上述技术方案所述功能化脲基双子咪唑多库酯盐的制备方法,包括以下步骤:
将1,6-己二异氰酸酯、1-(3-氨基丙基)咪唑和第一有机溶剂混合,进行脲基化反应,得到脲基功能化的咪唑盐;
将所述脲基功能化的咪唑盐和卤代烷混合,进行季铵化反应,得到具备长烷基链结构的脲基功能化咪唑盐;
将所述具备长烷基链结构的脲基功能化咪唑盐、磺化琥珀酸二辛酯钠盐和第二有机溶剂混合,进行离子交换反应,得到所述功能化脲基双子咪唑多库酯盐;
所述脲基功能化的咪唑盐具有式III所示结构:
本发明将1,6-己二异氰酸酯、1-(3-氨基丙基)咪唑和第一有机溶剂混合,进行脲基化反应,得到脲基功能化的咪唑盐。在本发明中,所述1,6-己二异氰酸酯和1-(3-氨基丙基)咪唑的摩尔比优选为1:2。在本发明中,所述第一有机溶剂优选包括乙腈、甲醇或异丙醇,更优选为乙腈。在本发明中,所述1-(3-氨基丙基)咪唑和第一有机溶剂的用量比优选为0.1mol:140~160mL。
在本发明中,所述1,6-己二异氰酸酯、1-(3-氨基丙基)咪唑和第一有机溶剂混合优选包括:将1-(3-氨基丙基)咪唑滴加至1,6-己二异氰酸酯中,再加入第一有机溶剂。在本发明中,所述滴加的速率优选为5~20滴/min,更优选为10滴/min。本发明采用滴加的方式能够控制反应速率。
在本发明中,所述脲基化反应的温度优选为75~85℃,更优选为80℃;时间优选为3~5h,更优选为4h。在本发明中,所述脲基化反应的气氛优选为空气气氛。
得到脲基功能化的咪唑盐后,本发明将所述脲基功能化的咪唑盐和卤代烷混合,进行季铵化反应,得到具备长烷基链结构的脲基功能化咪唑盐。在本发明中,所述脲基功能化的咪唑盐和卤代烷的摩尔比优选为1:2~2.2。在本发明中,所述卤代烷优选包括溴代烷、氯代烷和碘代烷中的一种或几种;所述溴代烷优选包括溴代十二烷或溴代十六烷。
在本发明中,所述季铵化反应的温度优选为75~85℃,更优选为80℃;时间优选为8~48h,更优选为20~30h,进一步优选为24h。在本发明中,所述季铵化反应的气氛优选为空气气氛。
本发明优选在所述季铵化反应后,将所得固体产物用石油醚洗涤,得到具备长烷基链结构的脲基功能化咪唑盐。
得到具备长烷基链结构的脲基功能化咪唑盐后,本发明将所述具备长烷基链结构的脲基功能化咪唑盐、磺化琥珀酸二辛酯钠盐和第二有机溶剂混合,进行离子交换反应,得到所述功能化脲基双子咪唑多库酯盐。在本发明中,所述具备长烷基链结构的脲基功能化咪唑盐和磺化琥珀酸二辛酯钠盐的摩尔比优选为1:2~2.2。在本发明中,所述第二有机溶剂优选包括乙腈、甲醇或异丙醇,更优选为乙腈。在本发明中,所述具备长烷基链结构的脲基功能化咪唑盐和第二有机溶剂的用量比优选为0.1mol:140~160mL。
在本发明中,所述离子交换反应的温度优选为75~85℃,更优选为80℃;时间优选为8~48h,更优选为20~30h,进一步优选为24h。在本发明中,所述离子交换反应的气氛优选为空气气氛。
在本发明中,所述离子交换反应后,优选还包括:将所得体系进行减压蒸馏除去有机溶剂,剩余物用二氯甲烷进行萃取,得到有机相;将所述有机相进行干燥,得到所述功能化脲基双子咪唑多库酯盐。本发明对所述减压蒸馏以及二氯甲烷萃取的具体操作没有特殊限定,采用本领域技术人员熟知的方法即可。
本发明提供了上述技术方案所述功能化脲基双子咪唑多库酯盐或上述技术方案所述制备方法制备得到的功能化脲基双子咪唑多库酯盐在润滑、防锈或缓蚀领域的应用。在本发明中,所述应用优选包括:将所述功能化脲基双子咪唑多库酯盐作为润滑油添加剂或防锈油添加剂;或者,将所述功能化脲基双子咪唑多库酯盐作为润滑剂、缓蚀剂和防锈剂中的一种或几种单独使用。
在本发明中,所述应用优选应用于金属材料基底的防护;所述金属材料基底的元素优选包括铁、铜和铝中的至少一种。在本发明的具体实施例中,所述金属材料基底为碳钢。
下面将结合本发明中的实施例,对本发明中的技术方案进行清楚、完整地描述。显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
将0.1mol的1-(3-氨基丙基)咪唑以10滴/min的速率滴加至0.05mol的1,6-己二异氰酸酯中,加入150mL乙腈,在80℃条件下进行脲基化反应4h;加入0.1mol的溴代十六烷,在80℃条件下进行季铵化反应24h,所得固体产物用石油醚洗涤,得到具备长烷基链结构的脲基功能化咪唑盐;将0.1mol磺化琥珀酸二辛酯钠盐(CAS:577-11-7)添加到所述具备长烷基链结构的脲基功能化咪唑盐中,加入150mL乙腈,在80℃条件下进行离子交换反应24h;所得产物减压蒸馏除去溶剂,二氯甲烷萃取有机相后,将所得有机相进行干燥,得到功能化脲基双子咪唑多库酯盐(2M16-DOSS)。
本实施例制备的2M16-DOSS的阳离子为阴离子为所述阳离子和阴离子的摩尔比为1:2。
本实施例制备的2M16-DOSS为淡黄色的液态熔融盐,表征结果为:
氢谱数据为:1H NMR(400MHz,CDCl3)δ:9.47(s,2H),7.80(s,2H),7.20(s,2H),6.28(s,2H),5.91(s,2H),5.29(s,2H),4.37(t,J=8.0Hz,8H),4.23-4.15(m,8H),4.07-3.91(m,8H),3.26-3.08(m,18H),2.02(t,J=8.0Hz,6H),1.87(s,6H),1.63-1.25(m,86H),0.88-0.83(m,30H).
碳谱数据为:13C NMR(100MHz,CDCl3)δ:171.37,169.04,159.64,67.93,67.86,67.28,62.07,38.68,38.58,31.92,30.29,30.15,30.08,29.70,29.65,29.56,29.42,29.35,29.04,28.89,26.34,23.67,23.47,22.95,22.68,14.09,14.06,14.03.
质谱数据如表1所示:
表1 2M16-DOSS的质谱数据
测试例
(1)样品配制
将实施例1制备的2M16-DOSS在常见的矿物油MVI 150中溶解,配制成均匀稳定的润滑体系。在MVI 150基础油中分别加入0.5wt%、1.0wt%和2.0wt%的2M16-DOSS,制备2M16-DOSS润滑体系。其中,2M16-DOSS和矿物油MVI 150的添加量以质量百分含量计,如1.0wt%的2M16-DOSS润滑体系的含义是指100g的2M16-DOSS润滑体系中,2M16-DOSS的质量分数是1%,矿物油MVI 150的质量分数为99%。
(2)热稳定性能
使用SYP1003-III粘度测试仪在40℃和100℃的温度下测量矿物油MVI 150和制备的2M16-DOSS润滑体系的运动粘度。热重分析(TGA)使用TA仪器公司的TGA-2950仪器,在氮气环境下以10℃/分钟的加热速度进行分析。
同步热分析仪(STA)对MVI 150、0.5wt%的2M16-DOSS润滑体系(0.5wt%2M16-DOSS)、1.0wt%的2M16-DOSS润滑体系(1.0wt%2M16-DOSS)和2.0wt%的2M16-DOSS润滑体系(2.0wt%2M16-DOSS)测量了从室温到600℃的温度范围。结合表2可以看出,MVI 150的初始降解温度较高,而所有润滑体系样品的初始分解温度均大于220℃。表明添加本发明2M16-DOSS所得润滑体系具有较高的热稳定性。
(3)粘温性能
表2中列出了MVI 150、0.5wt%的2M16-DOSS润滑体系、1.0wt%的2M16-DOSS润滑体系和2.0wt%的2M16-DOSS润滑体系的运动粘度、粘度指数以及它们在不同热失重比率下对应的分解温度。在粘度实验中可以看出,添加2M16-DOSS后,在0.5wt%和1.0wt%的添加量下,样品表现出一定程度的粘度降低。随着2M16-DOSS的浓度增大到2.0wt%,样品粘度超过MVI 150达到最大。这是由于2.0wt%的添加量下,2M16-DOSS在MVI 150中的分散达到了饱和。表明添加本发明2M16-DOSS所得润滑体系具有较好的粘温性能。
表2 MVI 150、2M16-DOSS润滑体系的粘度指数和热失重温度
(4)2M16-DOSS润滑体系的摩擦学性能
采用德国Optimol润滑脂公司生产的SRV-IV摩擦磨损测试仪,通过球盘接触的方式测评样品的摩擦学性能。摩擦试验在25℃下进行,试验频率为25Hz,载荷为200N,振幅为1mm,试验时间为30分钟,试验气氛为空气。试验使用了直径为10毫米的GCr15钢球和直径为24毫米、厚度为7.9毫米的GCr15钢盘。检测结果如表3所示。
如表3所示,2M16-DOSS润滑体系,在室温(25℃)与高温(100℃)下表现出较好的减摩抗磨性能。由表3可知,室温(25℃)下,三种浓度的2M16-DOSS润滑体系均有效降低了摩擦系数,加入2M16-DOSS的样品平均摩擦系数均在0.118,与MVI 150相比降低了42%。结合分析,随着加入2M16-DOSS浓度的增大,润滑体系的磨损体积逐渐降低,在1.0wt%浓度下达到极限,对应降低了约54%的磨损体积。表明室温下2M16-DOSS的加入能够有效地提升MVI150的减摩抗磨性能。
在高温100℃下,2M16-DOSS润滑体系的润滑效果依旧较好。高温下2M16-DOSS的减摩效果出现了部分恶化,但仍优于MVI 150基础油。与低温条件下相比,2.0wt%浓度样品的摩擦系数未出现明显升高(增幅约7.8%)。与基础油相比,2.0wt%浓度的2M16-DOSS样品的平均摩擦系数降低了34%。可以观察到在2.0wt%浓度下,2M16-DOSS有效降低了MVI 150的磨损体积,其降幅约为62.4%,与低浓度样品拉开明显差距。在更为苛刻的高温环境下,2M16-DOSS表现出更好的减摩抗磨效果,这是由于高温催化下摩擦化学反应进行得更快,导致更多2M16-DOSS参与到反应过程中,高含量的2M16-DOSS生产了更多具备减摩抗磨作用的化合物,在磨痕表面形成了摩擦化学反应保护膜。
表3 2M16-DOSS作为钢/钢摩擦副润滑剂的平均摩擦系数和磨损体积
(5)2M16-DOSS的缓蚀性能
使用电化学测试的方法评价2M16-DOSS的缓蚀性能:
使用1厘米×1厘米的铂电极作为对电极;采用环氧树脂包裹的,直径0.8厘米的铁盘电极(纯度>99.99%),留下直径0.5厘米的暴露的区域,作为工作电极;使用饱和甘汞作为参比电极,形成三电极系统。将三电极系统浸入乙醇:H2O=2:1(质量比)的溶液中。为了获得稳定的开路电位(OCP),记录60分钟。电位动态极化(Tafel)的参数为E=Eocp±200mV,扫描速率为0.333mV/s。
为了进一步验证2M16-DOSS的缓蚀性能,进行了Tafel极化电化学实验。由于2M16-DOSS无法在纯水中溶解,采用乙醇水溶液(乙醇:H2O=2:1(质量比))作为溶剂与腐蚀介质。图1显示了2M16-DOSS在乙醇水溶液中对铁的防腐性能,图1中的“0%”是乙醇水溶液,“0.5%”、“1%”和“2%”均为2M16-DOSS在乙醇水溶液中的质量浓度。与乙醇水溶液相比,2M16-DOSS的腐蚀电流密度普遍较小。一般来说,腐蚀电位越大表明其腐蚀趋势越低,腐蚀电流密度越大其腐蚀程度越大。实验中,随着2M16-DOSS在乙醇水溶液中浓度的增加,腐蚀电位正向转移,腐蚀电流密度显著降低,表现出了良好的耐蚀性。这表明2M16-DOSS有效地提高了铁的防腐性能。将耐蚀性的增强归因于2M16-DOSS通过脲基官能团与铁表面的配位作用吸附在基体表面形成了保护膜,2M16-DOSS特有的咪唑环长碳链结构能够有效隔绝腐蚀环境,从而阻止了铁的腐蚀。
(6)2M16-DOSS防锈油的润滑与缓蚀性能
为验证2M16-DOSS的润滑与缓蚀效果,配制了一系列2M16-DOSS不同添加量的防锈油,其配方如下:2M16-DOSS的添加量分别为0%、1wt%、2wt%、3wt%;中性二壬基萘磺酸钡(T705A)的添加量为7.0wt%;羊毛脂镁皂的添加量为2.0wt%;山梨醇酐单油酸酯(Span80)的添加量为2.5wt%;2,6-二叔丁基对甲基苯酚(T501)的添加量为0.5wt%;A51基础油的添加量为5.0wt%;MVI 150为余量。
1)润滑性能在四球摩擦试验机上进行,实验标准符合GB/T 3142-2019,结果如表4所示。表4中,防锈基础油指的是2M16-DOSS的添加量为0%的防锈油,防锈基础油+1wt%2M16-DOSS指的是2M16-DOSS的添加量为1wt%的防锈油,防锈基础油+2wt%2M16-DOSS指的是2M16-DOSS的添加量为2wt%的防锈油,防锈基础油+3wt%2M16-DOSS指的是2M16-DOSS的添加量为3wt%的防锈油。
表4 2M16-DOSS防锈油的平均摩擦系数与平均磨斑直径
由表4可知,未添加2M16-DOSS的防锈油样品(防锈基础油)减摩性能较差,平均摩擦系数约为0.106。添加1wt%2M16-DOSS后,防锈油的减摩性能得到改善,2M16-DOSS质量分数增大到2wt%以上时,防锈油减摩情况得到明显改善。2wt%2M16-DOSS润滑的平均摩擦系数约为0.09,3wt%2M16-DOSS润滑的平均摩擦系数约为0.08,与防锈基础油相比分别降低了5.1%与13.83%的摩擦系数。分析平均磨斑直径数据可知,随着2M16-DOSS添加量的增大,平均磨斑直径有所降低,说明所配制的防锈油具备一定的抗磨作用,有效降低了磨损体积。与防锈基础油相比,所有样品均有效降低了磨损体积。
2)耐蚀性能
采用盐雾挂板实验的方式对上述制备的2M16-DOSS防锈油的耐蚀性能进行了表征,将钢片垂直悬挂于防锈油样品中,拔出后静置3h使防锈油在钢片表面均匀分布,制备了四组2M16-DOSS浓度(0%、1wt%、2wt%、3wt%)不同的样片。在盐雾腐蚀试验中,添加2M16-DOSS(1wt%、2wt%、3wt%)的防锈油表现出较为优越的耐蚀性能。观察图2可知,盐雾试验进行50h后,四组样片表面均未出现明显的锈蚀痕迹。盐雾试验持续至100h后,未添加2M16-DOSS的样品表面出现明显的点蚀现象,而此时1wt%、2wt%、3wt%三种浓度的2M16-DOSS样品表面均保持完好,说明2M16-DOSS作为防锈剂发挥了较好的作用。当盐雾试验持续至150h后,所有样品的表面均出现锈蚀痕迹,防锈基础油样品表面被大片锈蚀,添加2M16-DOSS的样品表面仅出现点蚀痕迹。以上现象说明,2M16-DOSS作为防锈油添加剂具备杰出的防腐性能。
以上所述仅是本发明的优选实施方式,应当指出,对于本技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以做出若干改进和润饰,这些改进和润饰也应视为本发明的保护范围。
Claims (10)
1.一种功能化脲基双子咪唑多库酯盐,包括阳离子和阴离子;所述阳离子和阴离子的摩尔比为1:2;
所述阳离子具有式I所示结构:
所述式I中R为C1~C18的烷基;
所述阴离子具有式II所示结构:
2.根据权利要求1所述的功能化脲基双子咪唑多库酯盐,其特征在于,所述R为甲基、乙基、丙基、丁基、异丁基、戊基、异戊基、辛基、异辛基、癸基、异癸基、十二烷基、十四烷基、十六烷基或十八烷基。
3.权利要求1~2任一项所述功能化脲基双子咪唑多库酯盐的制备方法,包括以下步骤:
将1,6-己二异氰酸酯、1-(3-氨基丙基)咪唑和第一有机溶剂混合,进行脲基化反应,得到脲基功能化的咪唑盐;
将所述脲基功能化的咪唑盐和卤代烷混合,进行季铵化反应,得到具备长烷基链结构的脲基功能化咪唑盐;
将所述具备长烷基链结构的脲基功能化咪唑盐、磺化琥珀酸二辛酯钠盐和第二有机溶剂混合,进行离子交换反应,得到所述功能化脲基双子咪唑多库酯盐;
所述脲基功能化的咪唑盐具有式III所示结构:
4.根据权利要求3所述的制备方法,其特征在于,所述1,6-己二异氰酸酯和1-(3-氨基丙基)咪唑的摩尔比为1:2。
5.根据权利要求3或4所述的制备方法,其特征在于,所述脲基化反应的温度为75~85℃,时间为3~5h。
6.根据权利要求3所述的制备方法,其特征在于,所述脲基功能化的咪唑盐和卤代烷的摩尔比为1:2~2.2。
7.根据权利要求3或6所述的制备方法,其特征在于,所述季铵化反应的温度为75~85℃,时间为8~48h。
8.根据权利要求3所述的制备方法,其特征在于,所述具备长烷基链结构的脲基功能化咪唑盐和磺化琥珀酸二辛酯钠盐的摩尔比为1:2~2.2。
9.根据权利要求3或8所述的制备方法,其特征在于,所述离子交换反应的温度为75~85℃,时间为8~48h。
10.权利要求1~2任一项所述功能化脲基双子咪唑多库酯盐或权利要求3~9任一项所述制备方法制备得到的功能化脲基双子咪唑多库酯盐在润滑、防锈或缓蚀领域的应用。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202310843741.5A CN116874431A (zh) | 2023-07-11 | 2023-07-11 | 一种功能化脲基双子咪唑多库酯盐及其制备方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202310843741.5A CN116874431A (zh) | 2023-07-11 | 2023-07-11 | 一种功能化脲基双子咪唑多库酯盐及其制备方法和应用 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN116874431A true CN116874431A (zh) | 2023-10-13 |
Family
ID=88265663
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202310843741.5A Pending CN116874431A (zh) | 2023-07-11 | 2023-07-11 | 一种功能化脲基双子咪唑多库酯盐及其制备方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN116874431A (zh) |
-
2023
- 2023-07-11 CN CN202310843741.5A patent/CN116874431A/zh active Pending
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8455407B2 (en) | Lubricating grease composition based on ionic liquids | |
CN110862356B (zh) | 苯并三氮唑功能化的季铵盐离子液体及其制备方法和应用 | |
JP5920900B2 (ja) | イオンを含んでなるイオン液体をベースとする潤滑剤および潤滑添加剤 | |
TW200923071A (en) | Lubricating oil base oil and lubricating oil composition | |
US20170096614A1 (en) | Halogen free ionic liquids as lubricant or lubricant additives and a process for the preparation thereof | |
CN110845430B (zh) | 苯并三氮唑功能化的季铵盐及其制备方法和应用 | |
US8153569B2 (en) | Lubricant base oil | |
CN110845417A (zh) | 一种氨基酸离子液体水基添加剂及其制备方法和应用 | |
Ma et al. | Synthesis and evaluation of oil-soluble ionic liquids as multifunctional lubricant additives | |
EP3119859A1 (en) | Halogen free ionic liquids as lubricant or lubricant additives and a process for the preparation thereof | |
CN112062729B (zh) | 一种功能化季铵盐离子液体及其制备方法和应用 | |
Zhang et al. | Study on the synthesis and tribological properties of anti-corrosion benzotriazole ionic liquid | |
TW201211234A (en) | Lubricant base oil and lubricant composition | |
WO2016181726A1 (ja) | ケイ素含有イオン液体を含む潤滑剤 | |
Li et al. | Excellent lubrication performance and superior corrosion resistance of vinyl functionalized ionic liquid lubricants at elevated temperature | |
JP2022107707A (ja) | イオン液体、及び潤滑剤組成物 | |
CN109503503B (zh) | 一种多功能离子液体及其制备方法与应用 | |
Song et al. | In situ preparation of anti-corrosion ionic liquids as the lubricant additives in multiply-alkylated cyclopentanes | |
JP5902074B2 (ja) | 潤滑油組成物 | |
CN116874431A (zh) | 一种功能化脲基双子咪唑多库酯盐及其制备方法和应用 | |
CN112142778A (zh) | 一种兼具油溶性和水溶性的离子液体及其制备方法与应用 | |
CN111575084A (zh) | 一种合成抗水型长寿命真空泵油及其制备方法 | |
Li et al. | Tribological and corrosive properties of ionic liquids containing triazole functional groups | |
CN112391222B (zh) | 一种抗氧抗磨润滑油添加剂及其应用 | |
CN111662760B (zh) | 一种螺杆压缩机油及其制备方法 |
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 |