CN115197163A - Ionic liquid compound and preparation method and application thereof - Google Patents
Ionic liquid compound and preparation method and application thereof Download PDFInfo
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- CN115197163A CN115197163A CN202210831213.3A CN202210831213A CN115197163A CN 115197163 A CN115197163 A CN 115197163A CN 202210831213 A CN202210831213 A CN 202210831213A CN 115197163 A CN115197163 A CN 115197163A
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- ionic liquid
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- thiazole
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 47
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000011248 coating agent Substances 0.000 claims abstract description 20
- 238000000576 coating method Methods 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- MIKMKQZBTHHMGR-UHFFFAOYSA-N CCC[S+]1C=NC=C1 Chemical compound CCC[S+]1C=NC=C1 MIKMKQZBTHHMGR-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 4
- 230000000845 anti-microbial effect Effects 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 238000010517 secondary reaction Methods 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 35
- 230000000694 effects Effects 0.000 abstract description 7
- 230000032683 aging Effects 0.000 abstract description 4
- 239000003242 anti bacterial agent Substances 0.000 abstract description 4
- 239000006185 dispersion Substances 0.000 abstract description 4
- 239000013067 intermediate product Substances 0.000 abstract description 4
- 229910021645 metal ion Inorganic materials 0.000 abstract description 4
- 239000003899 bactericide agent Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 8
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 6
- 229910001431 copper ion Inorganic materials 0.000 description 6
- -1 4-chlorphenyl Chemical group 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 239000005823 Propineb Substances 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 238000007034 nitrosation reaction Methods 0.000 description 3
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 3
- 239000004308 thiabendazole Substances 0.000 description 3
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 3
- 229960004546 thiabendazole Drugs 0.000 description 3
- 235000010296 thiabendazole Nutrition 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241000195628 Chlorophyta Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000227166 Harrimanella hypnoides Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000003405 preventing effect Effects 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000031068 symbiosis, encompassing mutualism through parasitism Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses an ionic liquid compound and a preparation method and application thereof. An ionic liquid compound having a structural formula shown in formula I:
the invention also discloses a preparation method of the ionic liquid compound. The ionic liquid compound has good antibacterial performance, and the antibacterial coating obtained by being doped into the coating is used on the surface of insulating equipment, so that a good antibacterial and moss-preventing effect can be achieved, and the insulating performance of the coating cannot be damaged; meanwhile, the ionic liquid compound has good dispersion effect, is not easy to migrate when dispersed in the coating, and has longer antibacterial aging time compared with a metal ion antibacterial agent. In addition, the ionic liquid compound of the present invention does not produce an intermediate product harmful to the environment during the preparation process.
Description
Technical Field
The invention relates to the technical field of ionic liquid compounds, in particular to an ionic liquid compound and a preparation method and application thereof.
Background
Lichen is a low-grade plant formed by symbiosis of green algae and some fungi, and can be propagated through spores. When spores of fungi such as mold fall on the surface of the insulation equipment, the spores greatly breed in a humid environment, so that the surface of the insulation equipment is covered by moss. And as the moss plants easily absorb moisture and inorganic salt in the air, a conductive layer is formed on the surface of the insulating equipment, flashover is easily generated under the action of an electric field, and the insulating strength of the external insulating equipment is greatly reduced.
Chinese patent CN 104222108A-a compound bactericide containing thiabendazole copper discloses a compound bactericide containing thiabendazole copper, the active ingredients include thiabendazole copper a and bactericidal active compound B, bactericidal active compound B is any one of triazole bactericide, amide bactericide, imidazole bactericide, dicarboximide bactericide, carbamate bactericide, antibiotic bactericide, oxazole bactericide, pyrimidine bactericide, quinoline bactericide, dithiocarbamate bactericide, morpholine bactericide or bactericidal active compound of other selected bactericide; chinese patent CN 107540584B-a method for synthesizing propineb discloses a method for preparing propineb by using 1, 2-propane diamine and carbon disulfide as raw materials, reacting with an ammonium weak alkaline aqueous solution to generate propineb, and then reacting with zinc salt under the catalysis of quaternary ammonium salt; chinese patent CN 112341392A-method for preparing 1- (4-chlorphenyl) -pyrazolidin-3-ketone discloses a method for preparing 1- (4-chlorphenyl) -pyrazolidin-3-ketone, which comprises the following steps: 1) Reacting parachloroaniline with acrylic acid to obtain an addition reaction product; 2) Purifying the addition reaction product and then carrying out a nitrosation reaction with nitrite, or directly carrying out a nitrosation reaction on the addition reaction product and nitrite to obtain a nitrosation reaction product; 3) Reducing by using palladium carbon as a catalyst and hydrogen as a reducing agent to obtain a reduction product; 4) And (3) removing the catalyst from the reduction product, and then carrying out heat treatment to obtain the 1- (4-chlorphenyl) -pyrazolidin-3-ketone.
In the technologies disclosed in the above patents, some copper ions are grafted on the surface to achieve the moss preventing effect, but the copper ions have conductivity, and the insulating property of the insulating equipment is damaged when the copper ions are coated on the surface of the insulating equipment; meanwhile, the bactericidal activity of the copper preparation depends on the concentration of copper ions, the release speed of the copper ions is easily influenced by the environment, the copper ions are easily migrated and lost in a severe environment, and the antibacterial aging is influenced to a certain extent; some easily generate toxic intermediate products in the preparation process, which affects the environment.
Aiming at the defects of the surface grafting metal ion antibacterial agent, the invention prepares the ionic liquid compound with antibacterial property from another angle, and does not generate an intermediate product harmful to the environment in the preparation process; the antibacterial coating obtained by doping the compound into the coating is used on the surface of insulating equipment, can achieve good antibacterial and moss-preventing effects, and does not damage the insulating property of the coating; meanwhile, the ionic liquid compound has good dispersion effect and is not easy to migrate when dispersed in the coating, so that the antibacterial aging time is longer than that of a metal ion antibacterial agent.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide an ionic liquid compound.
Another object of the present invention is to provide a method for preparing the above ionic liquid compound.
It is a further object of the present invention to provide the use of the above ionic liquid compounds.
The purpose of the invention is realized by the following technical scheme: an ionic liquid compound having a structural formula shown in formula I:
the preparation method of the ionic liquid compound comprises the following steps:
(1) Mixing thiazole and potassium hydroxide solution with an organic solvent, reacting, adding 1, 3-dibromopropane, reacting again, removing potassium bromide precipitate, standing the filtrate in water, washing the obtained solid, and drying to obtain a 1, 4-di (1H-thiazole-1-yl) propane monomer;
(2) Adding the 1, 4-di (1H-thiazole-1-yl) propane monomer and 1, 4-dibromopropane in the step (1) into an alcohol solvent, reacting, removing ethanol, adding acetone, and drying the generated liquid to obtain the ionic liquid compound.
Preferably, the organic solvent in the step (1) is acetone and ethyl acetate, and the amount is a proper amount; more preferably, the volume ratio of acetone to ethyl acetate is 1.5-2:1.5-2.
Preferably, the concentration of the potassium hydroxide solution in the step (1) is 50%.
Preferably, the mass ratio of the thiazole, the potassium hydroxide and the 1, 3-dibromopropane in the step (1) is (4.45-5.56): (12 to 16): (5-8).
Preferably, the reaction in the step (1) is carried out at 65-70 ℃ for 1.5-2 hours.
Preferably, the re-reaction in the step (1) is carried out at 60-75 ℃ for 2-2.5 hours.
Preferably, the mass ratio of the 1, 4-bis (1H-thiazol-1-yl) propane monomer and the 1, 4-dibromopropane in the step (2) is (4.8-5.2): (5.32-6.34 g).
Preferably, the alcohol solvent in the step (2) is ethanol and isopropanol, and the amount is proper; more preferably, the volume ratio of ethanol to isopropanol is 9-10:3-4.
Preferably, the reaction in the step (2) is an oil bath reaction at 100 ℃ for 80-100h.
Preferably, the ethanol removal in the step (2) adopts a reduced pressure distillation mode.
The ionic liquid compound is applied to preparing the antibacterial coating.
Compared with the prior art, the invention has the following beneficial effects:
the ionic liquid compound has good antibacterial performance, and the antibacterial coating obtained by being doped into the coating is used on the surface of insulating equipment, so that a good antibacterial and moss-preventing effect can be achieved, and the insulating performance of the coating cannot be damaged; meanwhile, the ionic liquid compound has good dispersion effect, is not easy to migrate when dispersed in the coating, and has longer antibacterial aging time compared with a metal ion antibacterial agent. In addition, the ionic liquid compound of the present invention does not produce an intermediate product harmful to the environment during the preparation process.
Drawings
FIG. 1 is a graph showing the effect of the ionic liquid compound in the antibacterial test in example 2.
FIG. 2 shows the insulation performance test results of the coating material of example 3 with the ionic liquid compound added.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
An ionic liquid compound with bactericidal effect is prepared by the following steps:
(1) Synthesis of monomer (1, 4-bis (1H-thiazol-1-yl) propane):
5g of thiazole was weighed, prepared as a 50% (v/v) KOH solution, and the solution was charged into a 100mL single-neck flask together with 20mL of acetone and 20mL of ethyl acetate, and reacted at 70 ℃ for 2 hours on a rotary evaporator. Then, the mixed reaction solution was transferred to a three-necked flask, 6mL of 1, 3-dibromopropane was added thereto, and the reaction was stirred at 70 ℃ for 2 hours. And filtering the solid-liquid mixture obtained after the reaction is finished to remove white potassium bromide precipitate, adding the filtrate into 150mL of deionized water, standing to obtain white needle-shaped solid, washing with ultrapure water for three times, and placing in a vacuum drying oven for one week. Drying gave a yield of 90% of white needle-like solid.
(2) Synthesis of ionic liquid compound:
in a three-necked flask, 5g of 1, 4-bis (1H-thiazol-1-yl) propane monomer and 6g of 1, 4-dibromopropane were placed in 50mL of ethanol and 20mL of isopropanol as solvents, and reacted in an oil bath at 100 ℃ for 100 hours. After the reaction, ethanol was distilled off under reduced pressure. 50mL of acetone was added to give a pale yellow oily liquid, which was stored in a vacuum oven for 24h with a final yield of 60%.
Example 2
Inoculating moss spores onto a BBM culture medium plate under an aseptic condition, performing illumination culture at 25 ℃ for 14d to obtain spores and protonema, adding 10mL of BBM culture solution, fully grinding by using a tissue grinder, diluting by 10 times by using the BBM culture solution, and immediately inoculating the mycelia to the surface of the culture medium as an inoculation solution; the medium was modified MS + BA 1.0mg/L +2, 4-D0.2 mg/L + IAA 0.3mg/L + agar 7g/L + white sugar 20g/L, pH 6.0, and 1mL of the ionic liquid compound prepared in example 1 was added. At the same time, a control was set in which no ionic liquid compound was added to the medium.
Placing the inoculated culture dish into a constant-temperature constant-humidity illumination incubator (the temperature is 25 ℃, the relative humidity h is 85%, and the illumination intensity is 2000 lux), illuminating for 14h every day, keeping the sample surface moist (spraying BBM culture solution for moisture preservation), observing the growth condition of moss in the culture dish, continuously culturing for 21 days, and recording the test result.
As can be seen from fig. 1, no colony growth occurred in the petri dish containing the ionic liquid compound, demonstrating that the ionic liquid compound of example 1 has better antibacterial properties.
Example 3
Adding 100 parts by mass of hydroxyl-terminated polydimethylsiloxane (viscosity 3000 cSt), 3 parts by mass of white carbon black and 3 parts by mass of methyl silicone oil into a powerful dispersion machine for dispersing for 30 minutes, heating to 120 ℃, dehydrating for 2 hours under vacuum pumping, and cooling to room temperature. Then, 10 parts of gamma-aminopropyltriethoxysilane (KH 550), 5 parts of dibutyltin dilaurate, 3 parts of the ionic liquid compound prepared in example 1 and 100 parts of 1,3, 5-trimethylbenzene as a solvent were added thereto, and after uniform mixing, vacuum was applied for 10 minutes to obtain a coating material.
The coating was applied to the surface of a glass substrate, and the surface resistivity of the coating was measured using a high resistance meter, and as a result, as shown in FIG. 2, the surface resistivity of the coating decreased with increasing applied voltage and was 0.54X 10 at 800V 13 Omega/m, the insulating property of the coating is proved to be good.
While the foregoing is directed to the preferred embodiment of the present invention, it will be understood by those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention.
Claims (9)
1. An ionic liquid compound having a structural formula represented by formula I:
2. a process for the preparation of the ionic liquid compound of claim 1, comprising the steps of:
(1) Mixing thiazole and potassium hydroxide solution with an organic solvent, reacting, adding 1, 3-dibromopropane, reacting again, removing potassium bromide precipitate, standing the filtrate in water, washing the obtained solid, and drying to obtain a 1, 4-di (1H-thiazole-1-yl) propane monomer;
(2) Adding the 1, 4-di (1H-thiazole-1-yl) propane monomer and 1, 4-dibromopropane in the step (1) into an alcohol solvent, reacting, removing ethanol, adding acetone, and drying the generated liquid to obtain the ionic liquid compound.
3. The method for producing an ionic liquid compound according to claim 2, characterized by comprising at least one of the following A) and B):
a) The mass ratio of the thiazole, the potassium hydroxide and the 1, 3-dibromopropane in the step (1) is (4.45-5.56): (12 to 16): (5-8);
b) The mass ratio of the 1, 4-di (1H-thiazole-1-yl) propane monomer to the 1, 4-dibromopropane in the step (2) is (4.8-5.2): (5.32-6.34 g).
4. The method for producing an ionic liquid compound according to claim 2, characterized by comprising at least one of the following A) and B):
a) The organic solvent in the step (1) is acetone and ethyl acetate, and the dosage is proper;
b) The alcohol solvent in the step (2) is ethanol and isopropanol, and the dosage is proper.
5. The method for producing an ionic liquid compound according to claim 4, comprising at least one of the following A) and B):
a) The volume ratio of the acetone to the ethyl acetate is 1.5-2:1.5-2;
b) The volume ratio of the ethanol to the isopropanol is 9-10:3-4.
6. The method for preparing an ionic liquid compound according to claim 2, wherein the concentration of the potassium hydroxide solution in the step (1) is 50%.
7. The method for producing an ionic liquid compound according to claim 2, characterized by comprising at least one of the following A) and B):
a) The reaction in the step (1) is carried out for 1.5 to 2 hours at a temperature of between 65 and 70 ℃;
b) The secondary reaction in the step (1) is carried out for 2 to 2.5 hours at the temperature of between 60 and 75 ℃.
8. The process for producing an ionic liquid compound as claimed in claim 2, wherein the reaction in the step (2) is carried out in an oil bath at 100 ℃ for 80 to 100 hours.
9. Use of the ionic liquid compound according to claim 1 for the preparation of an antimicrobial coating.
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| CN101341872A (en) * | 2008-08-22 | 2009-01-14 | 集美大学 | Ion liquid anti-virus activities bactericide, synthesis and application thereof |
| CN102870781A (en) * | 2012-09-18 | 2013-01-16 | 浙江大学 | Imidazolium macromolecular antimicrobial agent and preparation method thereof |
| CN112493246A (en) * | 2020-11-23 | 2021-03-16 | 广东电网有限责任公司电力科学研究院 | Molecular sieve grafted with ionic liquid, preparation method of molecular sieve, moss-preventing coating and preparation method of moss-preventing coating |
| CN113185463A (en) * | 2021-05-11 | 2021-07-30 | 苏州科技大学 | Ionic liquid compound, preparation method thereof and application of ionic liquid compound as extracting agent |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101341872A (en) * | 2008-08-22 | 2009-01-14 | 集美大学 | Ion liquid anti-virus activities bactericide, synthesis and application thereof |
| CN102870781A (en) * | 2012-09-18 | 2013-01-16 | 浙江大学 | Imidazolium macromolecular antimicrobial agent and preparation method thereof |
| CN112493246A (en) * | 2020-11-23 | 2021-03-16 | 广东电网有限责任公司电力科学研究院 | Molecular sieve grafted with ionic liquid, preparation method of molecular sieve, moss-preventing coating and preparation method of moss-preventing coating |
| CN113185463A (en) * | 2021-05-11 | 2021-07-30 | 苏州科技大学 | Ionic liquid compound, preparation method thereof and application of ionic liquid compound as extracting agent |
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Application publication date: 20221018 |