CN109553637A - A kind of anti-space radiation POSS base ionic liquid and its preparation method and application - Google Patents
A kind of anti-space radiation POSS base ionic liquid and its preparation method and application Download PDFInfo
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- CN109553637A CN109553637A CN201811443800.5A CN201811443800A CN109553637A CN 109553637 A CN109553637 A CN 109553637A CN 201811443800 A CN201811443800 A CN 201811443800A CN 109553637 A CN109553637 A CN 109553637A
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 87
- 230000005855 radiation Effects 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000007788 liquid Substances 0.000 claims abstract description 23
- 150000001450 anions Chemical class 0.000 claims abstract description 19
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001768 cations Chemical class 0.000 claims abstract description 12
- 238000007306 functionalization reaction Methods 0.000 claims abstract description 12
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 7
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 60
- 239000002904 solvent Substances 0.000 claims description 60
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 52
- 239000000314 lubricant Substances 0.000 claims description 30
- 239000004519 grease Substances 0.000 claims description 24
- -1 aminopropyl Chemical group 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000000706 filtrate Substances 0.000 claims description 20
- 239000012074 organic phase Substances 0.000 claims description 20
- 239000000843 powder Substances 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 16
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- 229910000831 Steel Inorganic materials 0.000 claims description 11
- 239000010959 steel Substances 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 10
- 239000011261 inert gas Substances 0.000 claims description 10
- 238000001556 precipitation Methods 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 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 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
- KYALJNOKIYRMTG-UHFFFAOYSA-N C(CCCCC(C)C)OS(=O)(=O)CCCCCC(C)C.C(CCC(=O)O)(=O)O Chemical compound C(CCCCC(C)C)OS(=O)(=O)CCCCCC(C)C.C(CCC(=O)O)(=O)O KYALJNOKIYRMTG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract description 12
- 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 abstract description 7
- 239000001384 succinic acid Substances 0.000 abstract description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 48
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 19
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 15
- 238000001819 mass spectrum Methods 0.000 description 14
- 150000002500 ions Chemical class 0.000 description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 125000002091 cationic group Chemical group 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 230000003292 diminished effect Effects 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 230000001050 lubricating effect Effects 0.000 description 7
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 5
- 238000005461 lubrication Methods 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- 239000002199 base oil Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- KMWHQYDMBYABKL-UHFFFAOYSA-N 1-iodohexadecane Chemical compound CCCCCCCCCCCCCCCCI KMWHQYDMBYABKL-UHFFFAOYSA-N 0.000 description 2
- UWLHSHAHTBJTBA-UHFFFAOYSA-N 1-iodooctane Chemical compound CCCCCCCCI UWLHSHAHTBJTBA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 230000003746 surface roughness Effects 0.000 description 2
- JTCWXISSLCZBQV-UHFFFAOYSA-N tribol Natural products CC(CO)CCC1OC2(O)CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C2C1C)OC6OC(CO)C(OC7OC(C)C(O)C(O)C7O)C(O)C6OC8OC(C)C(O)C(O)C8O JTCWXISSLCZBQV-UHFFFAOYSA-N 0.000 description 2
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 235000015842 Hesperis Nutrition 0.000 description 1
- 235000012633 Iberis amara Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011825 aerospace material Substances 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- NJGCRMAPOWGWMW-UHFFFAOYSA-N octylphosphonic acid Chemical compound CCCCCCCCP(O)(O)=O NJGCRMAPOWGWMW-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- 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
- 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
- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
- C10M139/04—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00 having a silicon-to-carbon bond, e.g. silanes
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of anti-space radiation POSS base ionic liquids, the ionic liquid is functionalization quaternary ammonium ion liquid, its cation is the POSS quaternary ammonium salt with different chain length, and anion is diisooctyl phosphoric acid root (EDHPA) or succinic acid di-isooctyl sulfonate radical (DOSS).The invention also discloses the preparation method and applications of the ionic liquid.Ionic liquid of the present invention has excellent anti-wear and wear-resistant performance and high bearing capacity.
Description
Technical field
The present invention relates to space lubricants technical field more particularly to a kind of anti-space radiation POSS base ionic liquid and its
Preparation method and application.
Background technique
Aerospace cause (all kinds of aerospace equipments such as satellite, space station, manned spaceship) are greatly developed, are had very
Profound significance.However, harsh space environment, especially high vacuum environment, charged particle, neutral particle, electromagnetic radiation etc.
Service life and stability to space mechanism cause serious destruction (Chen, J.; Ding, N.W.; Li, Z.F.;
Wang, W. Prog. Aerosp. Sci., 2016, 83, 37-56. Shen Zicai;Jiang Haifu;Xu Kunbo;Ding Yigang;
Liu Yuming aerospace material technique, 2016,2, 1-8.), traditional lubricant grease is difficult to meet lubricating component such as
Lubrication and requirement of shelter under this harsh conditions, for this purpose, the design efficient lubricant of synthesizing new is more and more by people
Concern.
At present report in the world the space lubricants applied mainly include multi-alkyl cyclopentane (MACs), silicon hydrocarbon oil,
Perfluoro polyether oil, the silicone oil of fluorine-containing chlorphenyl, ionic liquid and its corresponding lubricating grease (Quan, X.; Hu, M.; Gao,
X. M.; Fu, Y. L.; Weng, L.J.; Wang, D. S.; Jiang, D.; Sun, J. Y. Tribol. Int., 2016, 99, 1186-1194. Guo, R. S.; Hua, H. Y.; Liu, Z. L.; Wang, X. L.;
Zhou, F. RSC Adv., 2014, 4, 28780-28785. Lv, M.; Yang, L. J.; Wang, Q. H.;
Wang, T. M.; Liang, Y. M. Tribol. Lett., 2015, 59:20. Yu, Q. L.; Wu, Y.; Li,
D. M.; Cai, M. R.; Zhou, F.; Liu, W. M. J. Colloid. Interf. Sci., 2017, 487,
130-140. journey Asia;Hu Xianguo;Xu Yufu;Sun Xiaojun Spacecraft Environment Engineering, 2013,30, 14-19.
Fan, X. Q.; Wang, L. P. ACS Appl. Mater. Interfaces, 2014, 6, 14660-14671.).
Although these space lubricants are highly stable in atmospheric environment, it is difficult to keep stable molecule in harsh space environment
Structure.
It is well known that the operation many places of spacecraft are transported in the Low Earth Orbit of 200 ~ 700 km altitude ranges in the track
In row environment, spacecraft is more elemental oxygen (AO) other than by serious space ultraviolet radioactive, charged particle bombardment
Destroy (Gonzalez, R. I.; Phillips, S. H.; Hoflund, G. B.J Spacecraft Rockets,
2000, 37, 463-467).Both at home and abroad research it was demonstrated that AO have extremely strong reactivity, by chemical bond rupture, decomposition,
The diversified forms such as oxidation and polymerization cause serious erosion damage to act on space lubricants, lead to the physico of space lubricants
It learns performance to occur to degenerate and fail, serious threat (Wang, H. Z. is caused to the operational safety of spacecraft; Wang, X.
L.; Qiao, D.; Sun, X. J.; Feng, D. P.; Liu, W. M. Chem. Lett., 2014, 43,1578-
1580.).The existing space lubricants used in China, itself does not have anti-AO irradiation behaviour, and long service is in space environment
Easily cause lubrication failure.Therefore, the anti-space radiation lubricant of Development of Novel is to improve the Flouride-resistani acid phesphatase of space lubricant grease
Can, it prolongs its service life and greasy property, great influence not only is played to the development of China's aerospace cause, but also to me
The leading edge developments of state's lubricating area have very important significance.
In recent years, polyhedral oligomeric silsesquioxane (Polyhedral Oligomerie Silsesquioxane, abbreviation
POSS) and its derivative is because having high thermal stability, anti-oxidant, high tenacity, resistance to combustion, not generating volatile materials, odorlessness
And many advantages, such as environmental-friendly, it is widely used in the additive of spatial clustering object composite material, to mitigate irradiation to the damage of material
Hurt (Lei, X. F.; Qiao, M. T.; Tian, L. D.; Yao, P.; Ma, Y.; Zhang, H. P.;
Zhang, Q. Y. Corros. Sci., 2015, 90, 223-238. Minton, T. K.; Wright, M. E.;
Tomczak, S. J.; Marquez, S. A.; Shen, L. H.; Brunsvold, A.L.; Cooper, R.;
Zhang, J. M.; Vij, V.; Guenthner, A. J.; Petteys, B. J. ACS Appl. Mater. Interfaces, 2012, 4, 492-502.).And research have shown that by POSS group introduce polymeric matrix or with
After polymer monomer is copolymerized, can significantly improve polymer material mechanical performance (intensity, modulus, rigidity) and anti-AO
Irradiation behaviour (Zhou, H.; Ye, Q.; Xu, J. W.Mater. Chem. Front. 2017, 1, 212-230.),
Meanwhile it introducing being aggregated in after elemental oxygen bombards after POSS system and showing better stability of material (Verker, R.;
Grossman, E.; Eliaz, N. Acta Mater., 2009, 57, 1112-1119.).
Summary of the invention
Technical problem to be solved by the invention is to provide a kind of with excellent anti-wear and wear-resistant performance and high carrying
The anti-space radiation POSS base ionic liquid of ability.
Another technical problem to be solved by this invention is to provide the preparation of the anti-space radiation POSS base ionic liquid
Method.
Third technical problem to be solved by this invention is to provide the application of the anti-space radiation POSS base ionic liquid.
To solve the above problems, a kind of anti-space radiation POSS base ionic liquid of the present invention, it is characterised in that: should
Ionic liquid is functionalization quaternary ammonium ion liquid, and cation is the POSS quaternary ammonium salt with different chain length, and anion is two different
Octylphosphonic acid root (EDHPA) or succinic acid di-isooctyl sulfonate radical (DOSS), general formula is as follows: its general formula is as follows:
,
In formula: R1=isobutyl group, R2To be independently selected from C1~C16Alkyl.
The R2It is respectively and independently selected from methyl, butyl, octyl, any one in cetyl.
A kind of preparation method of anti-space radiation POSS base ionic liquid as described above, comprising the following steps:
(1) aminopropyl POSS, idoalkane, solid K are added in solvent acetonitrile2CO3, in inert gas and it is protected from light the lower room temperature of protection
24 ~ 72 h are reacted, are cooled to room temperature precipitation white powder, and solvent is evaporated off；The aminopropyl POSS rubs with the idoalkane
You are than being 1:4；The aminopropyl POSS and solid K2CO3Molar ratio be 1:4 ~ 10；
(2) the white powder is dissolved with methylene chloride, filter K2CO3, respectively obtain filter residue and filtrate；The filter residue washes away residual
The K stayed2CO3, the filtrate is evaporated off solvent after being then dried overnight and obtains POSS-n-I；
(3) the EDHPANa or DOSSNa of equimolar amounts, acetonitrile as solvents, at 60 ~ 85 DEG C are added in the POSS-n-I
8 ~ 36 h are stirred to react, solvent is evaporated off after reaction, obtain grease；
(4) after the grease is completely dissolved with methylene chloride, repeatedly washing remove unreacted EDHPANa or DOSSNa to get
Organic phase, the organic phase through drying, solvent is evaporated off to get ionic liquid.
Reaction equation equation is as follows:
In formula, diisooctyl phosphoric acid ester sodium salt (EDHPANa) is according to document (D. Jiang, L. T. Hu, D. P. Feng.
Tribol Lett (2011) 41:417-424) and the synthesis of patent ZL 201510789114.3.
A kind of application of the anti-space radiation POSS base ionic liquid as described above in terms of lubricant, it is characterised in that:
Lubricant or space lubricants of the ionic liquid as steel-steel frictional pair.
A kind of application of the anti-space radiation POSS base ionic liquid as described above in terms of additive, it is characterised in that:
The ionic liquid is as anti-atomic oxygen additive.
Compared with the prior art, the present invention has the following advantages:
1, through to commercially available synthetic space lubricating base oil multi-alkyl cyclopentane (MACs) lubricant compositions and POSS of the present invention from
The contrast test of the thermal stability of sub- fluid lubricant, kinematic viscosity and viscosity index (VI), it can be found that the resulting ion of the present invention
Liquid viscosity-temperature characteristic with higher (referring to table 1).
Kinematic viscosity, viscosity index (VI), the decomposition temperature of 1 MACs and POSS ion liquid lubricant of table
Note: using the SVM3000 oil product kinematic viscosity instrument measurement kinematic viscosity and viscosity of Austrian Anton Paar company production
Index.449 F3TGA-DSC(NETZSCH of STA for using German Nai Chi company to produce) synchronous solving is steady to their heat
It is qualitative to be analyzed, experimental condition are as follows: nitrogen atmosphere, 50 ml/min of nitrogen flow rate；10 DEG C/minute of heating rate, heating
25 ~ 600 DEG C of section.
2, through to commercially available synthetic space lubricating base oil multi-alkyl cyclopentane (MACs) lubricant compositions and the present invention
The contrast test of the anti-wear and wear-resistant performance of POSS ion liquid lubricant it can be found that compared with MACs the resulting ion of the present invention
The anti-wear and wear-resistant performance of liquid is all very excellent (referring to table 2).
2 MACs and POSS ionic liquid of table is as 25 DEG C of steel-steel frictional pair lubricant of average friction coefficient and average abrasion
Volume
Note: friction and abrasion is evaluated using the SRV-IV micro-vibration friction wear testing machine of Optimol grease company, Germany production
Energy.
The friction pair way of contact of SRV-IV micro-vibration friction wear testing machine is that ball-is made an inventory contact, test condition are as follows: warm
25 DEG C, 25 hertz of frequency, 1 millimeter of amplitude, experimental period 30 minutes of degree；It is tried in test as 10 millimeters of diameter of AISI
52100 steel balls.Lower sample is 24 millimeters of diameter, 7.9 millimeters of thickness, and hardness is 52100 bloom of AISI of 59-61 HRC, test
Used load is 200 Ns, and the wear volume of lower sample is measured by BRUKER-NPFLEX three-dimensional optical contourgraph.
3, lubricant of the ionic liquid of the present invention as steel-steel frictional pair has excellent anti-wear and wear-resistant performance and height
Bearing capacity.
Table 3, to the coefficient of friction and wear volume data of steel, selects load as MACs and POSS ion liquid addictive
200 Ns, 25 hertz of frequency, 1 millimeter of amplitude, experimental period 30 minutes, 25 DEG C of temperature, experimentally trying as diameter was 10 millimeters
Steel ball, lower sample are bloom.The experimental results showed that the anti-wear and wear-resistant performance of POSS ion liquid addictive is all non-compared with MACs
Chang Youyi.
3 MACs and POSS ion liquid addictive of table is as 25 DEG C of steel-steel frictional pair lubricant of average friction coefficient
With average wear volume
4, to commercially available synthetic space lubricating base oil multi-alkyl cyclopentane (MACs) lubricant compositions and POSS ion of the present invention
Fluid lubricant carries out the experiment of anti-atomic oxygen space radiation:
MACs and POSS ion liquid lubricant is respectively placed in progress elemental oxygen irradiation on the bloom of 25 mm of diameter, control profit
The thickness of lubrication prescription is no more than 4 mm；Atomic oxygen beam from top to bottom vertical incidence MACs or POSS ionic liquid surface, line
Flux density 5.6 × 1015 atoms/( cm2S), mean kinetic energy is 5 eV, and the vacuum degree of radiation environment is 3.0 × 10-2
Pa, elemental oxygen irradiation time are respectively 4h.Bloom will be uniformly applied to by MACs the and POSS ionic liquid of elemental oxygen irradiation
Surface carries out friction test, tests the variation of its coefficient of friction at any time.It is tested on vacuum sphere-disk-type friction testing machine to rub
Coefficient is wiped, using GCr15 stainless steel round block as lower sample, surface roughness Ra is 0. 02 μm, and hardness is 800 ~ 900HV,
Upper sample is the 9Cr18 steel ball of 3 mm of diameter.Friction test condition: normal load 2.0 N, 300 r of disk rotating speed/min, friction
30 min of time, the radius of friction track are 5.0 mm, and vacuum degree is better than 4 × 10-4 Pa。
The result shows that: MACs has excessively poor anti-atomic oxygen irradiation behaviour, the lubrication of the MACs oil after elemental oxygen irradiation
Performance is completed to lose, and coefficient of friction fluctuation is quite obvious.In contrast, POSS ionic liquid shows excellent anti-atomic oxygen
Irradiation behaviour, after elemental oxygen irradiates nearly 240 minutes, sample still has highly stable, and low-down coefficient of friction is (referring to table
4, Fig. 1), this also further demonstrates that this kind of ionic liquid is expected to as new spatial lubricant.
The average friction coefficient of room temperature after 4 MACs and POSS-16-DOSS ionic liquid elemental oxygen predose of table
5, to commercially available synthetic space lubricating base oil multi-alkyl cyclopentane (MACs) lubricant compositions and addition POSS-16-
DOSS ionic liquid carries out the experiment of anti-atomic oxygen space radiation:
The MACs for adding 1% POSS-16-DOSS is placed in progress elemental oxygen irradiation on the bloom of 25 mm of diameter, controls lubricant
Thickness be no more than 4 mm；The atomic oxygen beam from top to bottom original position vertical incidence POSS ion liquid lubicating additive surface, beam
The flux density 5.6 × 10 of stream15 atoms/( cm2S), mean kinetic energy is 5 eV, the vacuum degree of radiation environment is 3.0 ×
10-2 Pa, elemental oxygen irradiation time are respectively 4 h.By the 1% POSS-16-DOSS ion liquid lubicating by elemental oxygen irradiation
Additive is uniformly applied to bloom surface and carries out friction test, tests the variation of its coefficient of friction at any time.In vacuum sphere-disc type
Its coefficient of friction is tested on frictional testing machine, using GCr15 stainless steel round block as lower sample, surface roughness Ra is 0. 02
μm, hardness is 800 ~ 900 HV, and upper sample is the 9Cr18 steel ball of 3 mm of diameter.Friction test condition: 2.0 N of normal load, disk
300 r of revolving speed/min, 30 min of fraction time, the radius of friction track are 5.0 mm, and vacuum degree is better than 4 × 10-4 Pa。
The result shows that: after elemental oxygen irradiates nearly 240 minutes, 1% POSS-16-DOSS ionic liquid of addition compares
MACs shows excellent anti-atomic oxygen irradiation behaviour, and sample still has lower coefficient of friction (referring to table 5, Fig. 2),
This also further demonstrates that this kind of POSS-16-DOSS ionic liquid is expected to apply as space lubrication and anti-atomic oxygen additive.
5 MACs of table and the average friction coefficient for adding room temperature after POSS-16-DOSS ionic liquid elemental oxygen predose
Detailed description of the invention
Specific embodiments of the present invention will be described in further detail with reference to the accompanying drawing.
Fig. 1 is influence of the elemental oxygen irradiation to MACs and POSS ionic liquid POSS-16-DOSS coefficient of friction.
Fig. 2 is the influence that elemental oxygen irradiated to MACs and added 1% POSS-16-DOSS ionic liquid coefficient of friction.
Specific embodiment
A kind of anti-space radiation POSS base ionic liquid, the ionic liquid are functionalization quaternary ammonium ion liquid, cation
For the POSS quaternary ammonium salt with different chain length, anion is diisooctyl phosphoric acid root (EDHPA) or succinic acid di-isooctyl sulfonic acid
Root (DOSS), general formula is as follows:
,
In formula: R1=isobutyl group, R2To be independently selected from C1~C16Alkyl.
A kind of anti-space radiation POSS base ionic liquid POSS-1-EDHPA of embodiment 1, the ionic liquid are functionalization season
Ammonium ion liquid, cation are the POSS quaternary ammonium salt with different chain length, and anion is diisooctyl phosphoric acid root (EDHPA),
Its structural formula is as follows:
,
In formula: R1=isobutyl group, R2=CH3。
The preparation method of the anti-space radiation POSS base ionic liquid, comprising the following steps:
(1) 0.02 mole of aminopropyl POSS, 0.08 mole of iodomethane, 0.16 mole of solid K are added in solvent acetonitrile2CO3,
In inert gas and lower 48 h(of room temperature reaction of protection are protected from light because of iodomethane low boiling point, but activity is high, therefore at room temperature
Reaction), it is cooled to room temperature precipitation white powder, and solvent is evaporated off with Rotary Evaporators.
(2) white powder is dissolved with methylene chloride, be filtered under diminished pressure K with water pump and Bush's funnel2CO3, respectively obtain filter residue and
Filtrate；Remaining K is washed with deionized water in filter residue2CO3, after filtrate is then dried overnight with anhydrous sodium sulfate, steamed with Rotary Evaporators
Except solvent obtains POSS-1-I.
(3) the EDHPANa of equimolar amounts is added in POSS-1-I, acetonitrile as solvents is stirred to react 24 h at 80 DEG C,
After reaction, solvent is evaporated off with Rotary Evaporators, obtains grease.
(4) after grease is completely dissolved with methylene chloride, repeatedly washing removes unreacted EDHPANa to get organic phase,
The organic phase is dried over anhydrous sodium sulfate, solvent is evaporated off with Rotary Evaporators to get ionic liquid.
The ionic liquid is faint yellow solid,1H NMR (400 MHz, CDCl3) δ: 4.46 (s, 4H), 3.71-
3.65 (m, 8H), 3.59 (t, J = 8.0 Hz 4H), 3.33 (s, 12H), 1.81-1.69 (m, 4H),
1.49-1.24 (m, 80H), 0.88-0.83 (m, 30H). 13C NMR (100 MHz, CDCl3) δ: 69.22,
68.05, 67.99, 53.41, 40.51, 40.43, 30.22, 28.19, 25.80, 24.05, 23.96, 23.46,
23.25, 22.57, 22.55, 17.10, 14.24, 11.11, 8.94. 29 Si NMR (80 MHz, CDCl3) δ:-
67.62 (s), -69.59 (s).The mass spectrum calculated value of cationic portion: 916.3566, measured value: 915.3565, anion
Partial mass spectrum calculated value: 321.2200, measured value: 321.2190.
A kind of anti-space radiation POSS base ionic liquid POSS-1-DOSS of embodiment 2, the ionic liquid are functionalization season
Ammonium ion liquid, cation are the POSS quaternary ammonium salt with different chain length, and anion is succinic acid di-isooctyl sulfonate radical
(DOSS), structural formula is as follows:
,
In formula: R1=isobutyl group, R2=CH3。
The preparation method of the anti-space radiation POSS base ionic liquid, comprising the following steps:
(1) 0.02 mole of aminopropyl POSS, 0.08 mole of iodomethane, 0.16 mole of solid K are added in solvent acetonitrile2CO3,
In inert gas and protection 48 h of lower room temperature reaction are protected from light, are cooled to room temperature precipitation white powder, and be evaporated off with Rotary Evaporators
Solvent.
(2) white powder is dissolved with methylene chloride, be filtered under diminished pressure K with water pump and Bush's funnel2CO3, respectively obtain filter residue and
Filtrate；Remaining K is washed with deionized water in filter residue2CO3, after filtrate is then dried overnight with anhydrous sodium sulfate, steamed with Rotary Evaporators
Except solvent obtains POSS-1-I.
(3) the DOSSNa of equimolar amounts is added in POSS-1-I, acetonitrile as solvents is stirred to react 24 h at 80 DEG C,
After reaction, solvent is evaporated off with Rotary Evaporators, obtains grease.
(4) after grease is completely dissolved with methylene chloride, repeatedly washing removes unreacted DOSSNa to get organic phase, is somebody's turn to do
Organic phase is dried over anhydrous sodium sulfate, solvent is evaporated off with Rotary Evaporators to get ionic liquid.
The ionic liquid is white solid,1H NMR (400 MHz, CDCl3) δ: 4.24 – 3.60 (m, 13H),
3.56 – 3.03 (m, 6H), 1.30 – 1.19 (m, 80H), 0.87 (dt, J = 7.5, 5.2 Hz, 27H).13C NMR (100 MHz, CDCl3) δ: 171.62, 169.51, 69.02, 68.14, 67.34, 61.93, 53.16,
38.80, 38.72, 38.64, 34.00, 30.43, 30.19, 29.04, 29.01, 25.80, 24.04, 23.96,
23.77, 23.55, 23.08, 22.56, 17.11, 14.19, 14.15, 11.05, 11.02, 10.94, 8.82.29Si NMR (80 MHz, CDCl3) δ:-67.63 (s), -69.46 (s).The mass spectrum calculated value of cationic portion:
916.3566, measured value: 915.3565, the mass spectrum calculated value of anion part: 421.2266, measured value 421.2265.
A kind of anti-space radiation POSS base ionic liquid POSS-4-EDHPA of embodiment 3, the ionic liquid are functionalization season
Ammonium ion liquid, cation are the POSS quaternary ammonium salt with different chain length, and anion is diisooctyl phosphoric acid root (EDHPA),
Its structural formula is as follows:
,
In formula: R1=isobutyl group, R2=C4H9。
The preparation method of the anti-space radiation POSS base ionic liquid, comprising the following steps:
(1) 0.02 mole of aminopropyl POSS, 0.08 mole of iodobutane, 0.16 mole of solid K are added in solvent acetonitrile2CO3,
In inert gas and it is protected from light lower 48 h of back flow reaction of protection, is cooled to room temperature precipitation white powder, and be evaporated off with Rotary Evaporators
Solvent.
(2) white powder is dissolved with methylene chloride, be filtered under diminished pressure K with water pump and Bush's funnel2CO3, respectively obtain filter residue and
Filtrate；Remaining K is washed with deionized water in filter residue2CO3, after filtrate is then dried overnight with anhydrous sodium sulfate, steamed with Rotary Evaporators
Except solvent obtains POSS-4-I.
(3) the EDHPANa of equimolar amounts is added in POSS-4-I, acetonitrile as solvents is stirred to react 24 h at 80 DEG C,
After reaction, solvent is evaporated off with Rotary Evaporators, obtains grease.
(4) after grease is completely dissolved with methylene chloride, repeatedly washing removes unreacted EDHPANa to get organic phase,
The organic phase is dried over anhydrous sodium sulfate, solvent is evaporated off with Rotary Evaporators to get ionic liquid.
The ionic liquid is faint yellow solid,1H NMR (400 MHz, CDCl3) δ: 4.42 (s, 4 H), 3.81-
3.77 (m, 8 H), 3.57 (t, J = 8.0 Hz, 4 H), 3.30 (s, 12H), 1.79-1.69 (m, 4 H),
1.53-1.19 (m, 88 H), 0.89-0.85 (m, 30 H). 13C NMR (100 MHz, CDCl3)δ: 67.84,
67.78, 58.38, 40.56, 40.48, 30.23, 29.22, 25.80, 23.97, 23.44, 23.28, 22.56,
19.92, 18.60, 14.25, 13.86, 11.10. 29 Si NMR (80 MHz, CDCl3) δ:-67.41 (s), -
68.86 (s).The mass spectrum calculated value of cationic portion: 1042.5061, measured value: 1042.5081, the matter of anion part
Spectrum calculated value: 321.2200, measured value 321.2208.
A kind of anti-space radiation POSS base ionic liquid POSS-4-DOSS of embodiment 4, the ionic liquid are functionalization season
Ammonium ion liquid, cation are the POSS quaternary ammonium salt with different chain length, and anion is succinic acid di-isooctyl sulfonate radical
(DOSS), structural formula is as follows:
,
In formula: R1=isobutyl group, R2=C4H9。
The preparation method of the anti-space radiation POSS base ionic liquid, comprising the following steps:
(1) 0.02 mole of aminopropyl POSS, 0.08 mole of iodobutane, 0.16 mole of solid K are added in solvent acetonitrile2CO3,
In inert gas and it is protected from light lower 48 h of back flow reaction of protection, is cooled to room temperature precipitation white powder, and be evaporated off with Rotary Evaporators
Solvent.
(2) white powder is dissolved with methylene chloride, be filtered under diminished pressure K with water pump and Bush's funnel2CO3, respectively obtain filter residue and
Filtrate；Remaining K is washed with deionized water in filter residue2CO3, after filtrate is then dried overnight with anhydrous sodium sulfate, steamed with Rotary Evaporators
Except solvent obtains POSS-4-I.
(3) the DOSSNa of equimolar amounts is added in POSS-4-I, acetonitrile as solvents is stirred to react 24 h at 80 DEG C,
After reaction, solvent is evaporated off with Rotary Evaporators, obtains grease.
(4) after grease is completely dissolved with methylene chloride, repeatedly washing removes unreacted DOSSNa to get organic phase, is somebody's turn to do
Organic phase is dried over anhydrous sodium sulfate, solvent is evaporated off with Rotary Evaporators to get ionic liquid.
The ionic liquid is faint yellow solid,1H NMR (400 MHz, CDCl3) δ: 4.24 – 3.60 (m,
13H), 3.56 – 3.03 (m, 6H), 1.30 – 1.19 (m, 80H), 0.87 (dt, J = 7.5, 5.2 Hz,
27H). 13C NMR (100 MHz, CDCl3) δ: 171.77, 169.70, 68.02, 67.14, 61.91, 38.80,
38.69, 38.63, 30.45, 30.42, 29.02, 25.81, 24.05, 23.79, 23.57, 23.11, 23.09,
14.20, 14.17, 13.82, 11.07, 11.03, 10.99, 10.93. 29 Si NMR (80 MHz, CDCl3) δ:-
67.74 (s), -68.82 (s).The mass spectrum calculated value of cationic portion: 1042.5061, measured value: 1042.5081, yin
The mass spectrum calculated value of ionic portions: 421.2266, measured value 421.2265.
A kind of anti-space radiation POSS base ionic liquid POSS-8-EDHPA of embodiment 5, the ionic liquid are functionalization season
Ammonium ion liquid, cation are the POSS quaternary ammonium salt with different chain length, and anion is diisooctyl phosphoric acid root (EDHPA),
Its structural formula is as follows:
,
In formula: R1=isobutyl group, R2=C8H17。
The preparation method of the anti-space radiation POSS base ionic liquid, comprising the following steps:
(1) 0.02 mole of aminopropyl POSS, 0.08 mole of iodo-octane, 0.16 mole of solid K are added in solvent acetonitrile2CO3,
In inert gas and it is protected from light lower 48 h of back flow reaction of protection, is cooled to room temperature precipitation white powder, and be evaporated off with Rotary Evaporators
Solvent.
(2) white powder is dissolved with methylene chloride, be filtered under diminished pressure K with water pump and Bush's funnel2CO3, respectively obtain filter residue and
Filtrate；Remaining K is washed with deionized water in filter residue2CO3, after filtrate is then dried overnight with anhydrous sodium sulfate, steamed with Rotary Evaporators
Except solvent obtains POSS-8-I.
(3) the EDHPANa of equimolar amounts is added in POSS-8-I, acetonitrile as solvents is stirred to react 24 h at 80 DEG C,
After reaction, solvent is evaporated off with Rotary Evaporators, obtains grease.
(4) after grease is completely dissolved with methylene chloride, repeatedly washing removes unreacted EDHPANa to get organic phase,
The organic phase is dried over anhydrous sodium sulfate, solvent is evaporated off with Rotary Evaporators to get ionic liquid.
The ionic liquid is weak yellow liquid,1H NMR (400 MHz, CDCl3)δ: 4.49 (s,4H), 3.72-
3.69 (m, 8H), 3.59 (t, J = 8.0 Hz, 4H), 3.31 (s, 12H), 1.81-1.65 (m, 4H),
1.48-1.11 (m, 96H), 0.84 (t, J = 8.0 Hz, 30H). 13C NMR (100 MHz, CDCl3) δ:
68.10, 68.05, 65.92, 57.27, 50.69, 40.47, 40.39, 32.04, 30.16, 29.82, 29.77,
29.71, 29.62, 29.55, 29.47, 29.15, 26.31, 23.38, 23.24, 22.80, 14.23, 11.18,
11.04.29 Si NMR (80 MHz, CDCl3) δ:-67.62 (s), -69.59 (s).The mass spectrum of cationic portion calculates
Value 1210.6904, measured value 1210.6959, the mass spectrum calculated value of anion part: 321.2200, measured value 321.2204.
A kind of anti-space radiation POSS base ionic liquid POSS-8-DOSS of embodiment 6, the ionic liquid are functionalization season
Ammonium ion liquid, cation are the POSS quaternary ammonium salt with different chain length, and anion is succinic acid di-isooctyl sulfonate radical
(DOSS), structural formula is as follows:
,
In formula: R1=isobutyl group, R2=C8H17。
The preparation method of the anti-space radiation POSS base ionic liquid, comprising the following steps:
(1) 0.02 mole of aminopropyl POSS, 0.08 mole of iodo-octane, 0.16 mole of solid K are added in solvent acetonitrile2CO3,
In inert gas and it is protected from light lower 48 h of back flow reaction of protection, is cooled to room temperature precipitation white powder, and be evaporated off with Rotary Evaporators
Solvent.
(2) white powder is dissolved with methylene chloride, be filtered under diminished pressure K with water pump and Bush's funnel2CO3, respectively obtain filter residue and
Filtrate；Remaining K is washed with deionized water in filter residue2CO3, after filtrate is then dried overnight with anhydrous sodium sulfate, steamed with Rotary Evaporators
Except solvent obtains POSS-8-I.
(3) the DOSSNa of equimolar amounts is added in POSS-8-I, acetonitrile as solvents is stirred to react 24 h at 80 DEG C,
After reaction, solvent is evaporated off with Rotary Evaporators, obtains grease.
(4) after grease is completely dissolved with methylene chloride, repeatedly washing removes unreacted DOSSNa to get organic phase, is somebody's turn to do
Organic phase is dried over anhydrous sodium sulfate, solvent is evaporated off with Rotary Evaporators to get ionic liquid.
The ionic liquid is yellow liquid,1H NMR (400 MHz, CDCl3) δ: 4.24 – 3.60 (m, 13H),
3.56 – 3.03 (m, 6H), 1.30 – 1.19 (m, 80H), 0.87 (dt, J = 7.5, 5.2 Hz, 27H).13C NMR (100 MHz, CDCl3) δ: 171.51, 169.18, 67.16, 62.08, 61.73, 59.10, 58.32,
53.21, 38.65, 33.90, 31.90, 30.30, 30.10, 29.6229.54,29.40, 29.14, 28.89,
27.15, 26.37, 25.14, 23.64, 23.44, 22.96, 22.37, 22.06,18.41, 16.44, 14.09,
14.02,10.92, 10.85,10.78. 29 Si NMR (80 MHz, CDCl3) δ:-67.63 (s), -69.46 (s)。
The mass spectrum calculated value of cationic portion: 1210.6904, measured value 1210.6959, the mass spectrum calculated value of anion part:
421.2266 measured value 421.2265.
A kind of anti-space radiation POSS base ionic liquid POSS-16-EDHPA of embodiment 7, the ionic liquid are functionalization
Quaternary ammonium ion liquid, cation are the POSS quaternary ammonium salt with different chain length, and anion is diisooctyl phosphoric acid root
(EDHPA), structural formula is as follows:
,
In formula: R1=isobutyl group, R2=C16H33。
The preparation method of the anti-space radiation POSS base ionic liquid, comprising the following steps:
(1) 0.02 mole of aminopropyl POSS, 0.08 mole of iodohexadecane, 0.20 mole of solid are added in solvent acetonitrile
K2CO3, in inert gas and it is protected from light lower 72 h of back flow reaction of protection, is cooled to room temperature precipitation white powder, and use Rotary Evaporators
Solvent is evaporated off.
(2) white powder is dissolved with methylene chloride, be filtered under diminished pressure K with water pump and Bush's funnel2CO3, respectively obtain filter residue and
Filtrate；Remaining K is washed with deionized water in filter residue2CO3, after filtrate is then dried overnight with anhydrous sodium sulfate, steamed with Rotary Evaporators
Except solvent obtains POSS-16-I.
(3) the EDHPANa of equimolar amounts is added in POSS-16-I, acetonitrile as solvents is stirred to react 8 h at 85 DEG C,
After reaction, solvent is evaporated off with Rotary Evaporators, obtains grease.
(4) after grease is completely dissolved with methylene chloride, repeatedly washing removes unreacted EDHPANa to get organic phase,
The organic phase is dried over anhydrous sodium sulfate, solvent is evaporated off with Rotary Evaporators to get ionic liquid.
The ionic liquid is weak yellow liquid,1H NMR (400 MHz, CDCl3) δ: 3.70-3.65 (m, 8H),
3.15 (s, 4H), 2.41 (s, 12H), 1.62-1.17 (m, 108H), 0.86-0.82 (m,42H). 13C NMR
(100 MHz, CDCl3) δ:70.35, 68.13, 58.12, 40.45, 40.37, 40.13, 40.05, 31.88,
31.84, 30.93, 30.11, 29.15, 23.33, 23.22, 22.71, 22.06, 14.19, 14.13, 11.16,
10.99, 10.92.29 Si NMR (80 MHz, CDCl3) δ:-67.41 (s), -68.86 (s).The matter of cationic portion
Spectrum calculated value: 1547.0640, measured value: 1547.0715, the mass spectrum calculated value of anion part: 321.2200, actual measurement
Value 321.2208.
A kind of anti-space radiation POSS base ionic liquid POSS-16-DOSS of embodiment 8, the ionic liquid are functionalization season
Ammonium ion liquid, cation are the POSS quaternary ammonium salt with different chain length, and anion is succinic acid di-isooctyl sulfonate radical
(DOSS), structural formula is as follows:
,
In formula: R1=isobutyl group, R2=C16H33。
The preparation method of the anti-space radiation POSS base ionic liquid, comprising the following steps:
(1) 0.02 mole of aminopropyl POSS, 0.08 mole of iodohexadecane, 0.08 mole of solid are added in solvent acetonitrile
K2CO3, in inert gas and it is protected from light lower 24 h of back flow reaction of protection, is cooled to room temperature precipitation white powder, and use Rotary Evaporators
Solvent is evaporated off.
(2) white powder is dissolved with methylene chloride, be filtered under diminished pressure K with water pump and Bush's funnel2CO3, respectively obtain filter residue and
Filtrate；Remaining K is washed with deionized water in filter residue2CO3, after filtrate is then dried overnight with anhydrous sodium sulfate, steamed with Rotary Evaporators
Except solvent obtains POSS-16-I.
(3) the DOSSNa of equimolar amounts is added in POSS-16-I, acetonitrile as solvents is stirred to react 36 h at 60 DEG C,
After reaction, solvent is evaporated off with Rotary Evaporators, obtains grease.
(4) after grease is completely dissolved with methylene chloride, repeatedly washing removes unreacted DOSSNa to get organic phase, is somebody's turn to do
Organic phase is dried over anhydrous sodium sulfate, solvent is evaporated off with Rotary Evaporators to get ionic liquid.
The ionic liquid is yellow liquid,1H NMR (400 MHz, CDCl3) δ: 4.24 – 3.60 (m, 13H),
3.56 – 3.03 (m, 6H), 1.30 – 1.19 (m, 80H), 0.87 (dt, J = 7.5, 5.2 Hz, 27H).13C
NMR (100 MHz, CDCl3) δ: 171.51, 169.18, 67.16, 62.08, 61.73, 59.10, 58.32,
53.21, 38.65, 33.90, 31.90, 30.30, 30.10, 29.62, 29.54,29.40, 29.14, 28.89,
27.15, 26.37, 25.14, 23.64, 23.44, 22.96, 22.37 22.06, 18.41, 16.44, 14.09,
14.02,10.92, 10.85,10.78. 29 Si NMR (80 MHz, CDCl3) δ:-67.74 (s), -68.82 (s)。
The mass spectrum calculated value of cationic portion: 1547.0640, measured value: 1547.0715, the mass spectrum calculated value of anion part:
421.2266 measured value 421.2265.
Application of the ionic liquid in terms of lubricant in above-described embodiment 1 ~ 8 refers to: the ionic liquid rubs as steel-steel
Wipe secondary lubricant or space lubricants.
Application of the ionic liquid in terms of additive in above-described embodiment 1 ~ 8 refers to: the ionic liquid is as antigen
Oxygen additive.
It should be understood that embodiment discussed here and embodiment simply to illustrate that, can be with to person skilled in the art
It is proposed various modifications and variations, such modifications and variations are included within spirit herein spirit and scope and appended right
In claimed range.
Claims (5)
1. a kind of anti-space radiation POSS base ionic liquid, it is characterised in that: the ionic liquid is functionalization quaternary ammonium ion liquid,
Its cation is the POSS quaternary ammonium salt with different chain length, and anion is diisooctyl phosphoric acid root or succinic acid di-isooctyl sulfonic acid
Root, general formula are as follows:
,
In formula: R1=isobutyl group, R2To be independently selected from C1~C16Alkyl.
2. a kind of anti-space radiation POSS base ionic liquid as described in claim 1, it is characterised in that: the R2Independently
Any one in methyl, butyl, octyl, cetyl.
3. a kind of preparation method of anti-space radiation POSS base ionic liquid as claimed in claim 1 or 2, including following step
It is rapid:
(1) aminopropyl POSS, idoalkane, solid K are added in solvent acetonitrile2CO3, in inert gas, room temperature is anti-down with protection is protected from light
24 ~ 72 h are answered, are cooled to room temperature precipitation white powder, and solvent is evaporated off；Mole of the aminopropyl POSS and the idoalkane
Than for 1:4；The aminopropyl POSS and solid K2CO3Molar ratio be 1:4 ~ 10；
(2) the white powder is dissolved with methylene chloride, filter K2CO3, respectively obtain filter residue and filtrate；The filter residue washes away residual
K2CO3, the filtrate is evaporated off solvent after being then dried overnight and obtains POSS-n-I；
(3) the EDHPANa or DOSSNa of equimolar amounts, acetonitrile as solvents, at 60 ~ 85 DEG C are added in the POSS-n-I
8 ~ 36 h are stirred to react, solvent is evaporated off after reaction, obtain grease；
(4) after the grease is completely dissolved with methylene chloride, repeatedly washing remove unreacted EDHPANa or DOSSNa to get
Organic phase, the organic phase through drying, solvent is evaporated off to get ionic liquid.
4. a kind of application of the anti-space radiation POSS base ionic liquid as claimed in claim 1 or 2 in terms of lubricant, special
Sign is: lubricant or space lubricants of the ionic liquid as steel-steel frictional pair.
5. a kind of application of the anti-space radiation POSS base ionic liquid as claimed in claim 1 or 2 in terms of additive, special
Sign is: the ionic liquid is as anti-atomic oxygen additive.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013032340A (en) * | 2011-07-01 | 2013-02-14 | Jnc Corp | Quaternary ammonium salt, oxidation catalyst obtained from the same, and method for producing epoxy derivative using the catalyst |
| CN105254667A (en) * | 2015-11-17 | 2016-01-20 | 中国科学院兰州化学物理研究所 | Functionalized oil-soluble ionic liquid and preparing method and application thereof |
| CN107828056A (en) * | 2017-11-23 | 2018-03-23 | 上海大学 | POSS based quaternary ammonium salt class ionic liquids and preparation method thereof |
-
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013032340A (en) * | 2011-07-01 | 2013-02-14 | Jnc Corp | Quaternary ammonium salt, oxidation catalyst obtained from the same, and method for producing epoxy derivative using the catalyst |
| CN105254667A (en) * | 2015-11-17 | 2016-01-20 | 中国科学院兰州化学物理研究所 | Functionalized oil-soluble ionic liquid and preparing method and application thereof |
| CN107828056A (en) * | 2017-11-23 | 2018-03-23 | 上海大学 | POSS based quaternary ammonium salt class ionic liquids and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| PAOLA CARDIANO等: "POSS-Tetraalkylammonium Salts: A New Class of Ionic Liquids", 《EUR. J. INORG. CHEM》 * |
| 俞传永等: "多面体低聚倍半硅氧烷在涂料领域的研究进展", 《涂料工业》 * |
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