CN111072707A - Multifunctional bactericidal compound and preparation method and application thereof - Google Patents
Multifunctional bactericidal compound and preparation method and application thereof Download PDFInfo
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- CN111072707A CN111072707A CN201911377354.7A CN201911377354A CN111072707A CN 111072707 A CN111072707 A CN 111072707A CN 201911377354 A CN201911377354 A CN 201911377354A CN 111072707 A CN111072707 A CN 111072707A
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 67
- 150000001875 compounds Chemical class 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 20
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000004202 carbamide Substances 0.000 claims abstract description 15
- 150000003949 imides Chemical class 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910000077 silane Inorganic materials 0.000 claims abstract description 4
- 238000006467 substitution reaction Methods 0.000 claims abstract description 3
- 230000000855 fungicidal effect Effects 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 12
- 239000010703 silicon Substances 0.000 claims description 12
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical group O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- -1 sodium alkoxide Chemical class 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 230000002140 halogenating effect Effects 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 239000000417 fungicide Substances 0.000 claims description 6
- IODUDVQDMKBOJC-UHFFFAOYSA-N tert-butyl hypobromite Chemical compound CC(C)(C)OBr IODUDVQDMKBOJC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 230000001954 sterilising effect Effects 0.000 abstract description 34
- 238000004659 sterilization and disinfection Methods 0.000 abstract description 29
- 239000000463 material Substances 0.000 abstract description 19
- 230000015556 catabolic process Effects 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 238000005956 quaternization reaction Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
- 239000002904 solvent Substances 0.000 description 25
- 239000003899 bactericide agent Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 241000588724 Escherichia coli Species 0.000 description 8
- 125000002091 cationic group Chemical group 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 7
- 230000003301 hydrolyzing effect Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000191967 Staphylococcus aureus Species 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 244000052616 bacterial pathogen Species 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RPOGHLNIRUYQIM-UHFFFAOYSA-N 2-bromoethyl(triethoxy)silane Chemical compound CCO[Si](CCBr)(OCC)OCC RPOGHLNIRUYQIM-UHFFFAOYSA-N 0.000 description 2
- IKBFHCBHLOZDKH-UHFFFAOYSA-N 2-chloroethyl(triethoxy)silane Chemical compound CCO[Si](CCCl)(OCC)OCC IKBFHCBHLOZDKH-UHFFFAOYSA-N 0.000 description 2
- DUMYGDGARBEHBO-UHFFFAOYSA-N 4-bromobutyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCBr DUMYGDGARBEHBO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000005915 ammonolysis reaction Methods 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- DNZPLHRZXUJATK-UHFFFAOYSA-N 2-sulfanylidene-5-[[5-[2-(trifluoromethyl)phenyl]furan-2-yl]methyl]-1,3-diazinane-4,6-dione Chemical compound FC(F)(F)C1=CC=CC=C1C(O1)=CC=C1CC1C(=O)NC(=S)NC1=O DNZPLHRZXUJATK-UHFFFAOYSA-N 0.000 description 1
- GXDMUOPCQNLBCZ-UHFFFAOYSA-N 3-(3-triethoxysilylpropyl)oxolane-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCCC1CC(=O)OC1=O GXDMUOPCQNLBCZ-UHFFFAOYSA-N 0.000 description 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 230000019522 cellular metabolic process Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
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- 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
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
- D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
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- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
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- D—TEXTILES; PAPER
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- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
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- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Life Sciences & Earth Sciences (AREA)
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- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention relates to a multifunctional sterilization compound, which has a structure shown in a general formula (I), and has two imide type halamines, one quaternary ammonium salt and three hydroxyl groups bonded with a material; the invention also relates to a preparation method of the multifunctional sterilization compound, which comprises the following steps: diethyl malonate is used as a reactant, tertiary amine is bonded through substitution reaction, and then the tertiary amine reacts with urea to generate imide bonds. Further, a quaternary ammonium salt is produced by quaternization with triethoxysilane having a halogen atom, an imide bond is halogenated to produce a haloamine bond, and finally an ether bond of silane is hydrolyzed to obtain a hydroxyl group. The multifunctional bactericidal compound has the advantages of high bactericidal efficiency, degradation resistance, wide bactericidal range, strong bactericidal durability, low cost, reproducibility, capability of utilizing various key joint modes and firm combination of materials and the like.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a multifunctional bactericidal compound containing two haloamine bactericidal groups, one quaternary ammonium salt bactericidal group and three hydroxyl groups capable of being bonded with a material, and a preparation method and application thereof.
Background
Harmful microorganisms such as bacteria and fungi are easy to cause pathological changes of organisms, and seriously threaten the life health and safety of human beings. The synthetic high-efficiency broad-spectrum safe bactericide is used for forming a bactericidal surface on a common material, is an important means for expanding the application range of the material in the sanitary field and protecting the health of people, is a research hotspot in the fields of material science, biological science and organic synthesis, and has important scientific research value and social significance.
The bactericidal group which has been used includes halamine, cationic salt (quaternary ammonium salt, quaternary phosphonium salt, pyridinium salt), heavy metal such as silver and its oxide, antibiotic, etc. Heavy metals are expensive and not easy to bond with the surface of the material, and the heavy metals need to be blended with the whole material by a doping method, so that metal particles on the surface are easy to fall off, and the particles in the material cannot contact and kill germs, thereby causing waste. In contrast, the haloamine and the cationic salt are widely used due to the advantages of wide sources, low price, multiple sterilization types, easy modification and the like.
The mechanism of sterilization of haloamines and cationic salts is different: the halamine compound can hydrolyze to release oxidized positive halide ions, diffuse into pathogenic bacteria and destroy cell metabolism by oxidation to realize sterilization, and has the advantages of high sterilization speed, environmental friendliness, reproducibility, low cost and the like. The cationic salt compounds cut into the cell walls of the bacteria due to the positive and negative electrostatic affinity with the negatively charged bacteria, so that substances in the bacteria flow out to cause death. The cationic salt is not consumed during sterilization, has good stability, but has lower sterilization efficiency, is not sensitive to gram-negative bacteria, and can achieve the best effect under the alkaline condition. At present, the bactericide contains one bactericidal group or a plurality of bactericidal groups of the same type, and has no mechanism complementation, and the bactericidal capability is still deficient.
As the sterilization mechanism and sterilization objects of the halamine and the cationic salt are different, the halamine and the cationic salt are integrated on one sterilization unit to prepare the composite sterilization unit, and the sterilization efficiency is higher than that of the single sterilization group. This phenomenon is commonly referred to as synergy. The theoretical explanation is that the cation salt with positive electricity can attract the germs with negative electricity to reach the vicinity of the halamine with strong sterilizing capability, thereby being beneficial to the sterilization of the halamine; in addition, the cation salt has good hydrophilicity, so that the water solubility of the composite sterilization unit is increased, and the sterilization unit is favorably soaked and contacted by a germ solution, thereby accelerating the sterilization process. To achieve good synergistic enhancement, it is desirable to combine as many haloamines as possible with cationic salts.
The firmness degree of the sterilizing layer on the surface of the material is another standard for determining the application value of the sterilizing agent. For example, the small molecular bactericide has low binding force with the material, and can quickly fall off from the material under the conditions of washing, ultraviolet aging in sunlight, long-term storage, friction and the like, so that the material loses the sterilization capability. Therefore, the bonding strength of the bactericide and the material is improved, and the application value is very important.
Disclosure of Invention
In order to solve the problems, the invention provides a multifunctional sterilization compound which simultaneously contains two halamines, one quaternary ammonium salt and three hydroxyl groups which can be used for bonding with materials. The design reason and advantages are as follows:
(1) the multifunctional bactericidal compound has two halamines and one quaternary ammonium salt, and the total number of the three different types of bactericidal groups is three. Compared with the existing bactericide containing single bactericidal groups or double bactericidal groups, the trifunctional groups can obtain higher bactericidal capacity and bactericidal range, and have better bactericidal synergistic effect.
(2) The multifunctional bactericidal compound has three hydroxyl groups, can be chemically bonded with the surface of a material through various reactions such as formation of aliphatic bonds with carboxyl groups, dehydration into ether bonds, addition with silicon-hydrogen bonds and the like to form a firm bactericidal surface, solves the problem that the bactericide falls off from the surface of the material, and greatly improves the bactericidal durability.
The technical scheme of the invention is as follows: a multifunctional bactericidal compound has a structure shown in a general formula (I):
wherein R is1,R2Is CH3Or CH2CH3In (1)Any one of them;
x is any one of Br or Cl;
m and n are any integer between 2 and 6.
The invention also provides a preparation method of the multifunctional sterilization compound with the structure of the general formula (I), which comprises the following steps:
(1) introducing a tertiary amine structure on diethyl malonate through substitution reaction between diethyl malonate and halogenated tertiary amine under the action of an alkali catalyst;
(2) reacting the product of the step (1) with urea by using an alkali catalyst;
(3) adjusting the pH value of the product obtained in the step (2) to 1-2, and neutralizing the alkali catalyst;
(4) adjusting the pH value of the product obtained in the step (3) to 11-12 to obtain tertiary amine containing a barbituric acid ring;
(5) carrying out quaternary ammonium salinization reaction on triethoxysilane containing halogen atoms and the product obtained in the step (4);
(6) halogenating the product obtained in the step (5) to enable N-H on the barbituric acid ring to generate halamine N-Cl or N-Br.
(7) Performing hydrolysis reaction to generate three hydroxyl groups from three silicon ether bonds of the silane, and finally forming the bactericide with two halamines, one quaternary ammonium salt and three hydroxyl groups and a multi-functional group;
preferably, the tertiary amine in the above step (1) has the following general formula:
wherein R is1,R2Is CH3Or CH2CH3Any one of the above;
x is any one of Br or Cl;
n is any integer between 2 and 6.
Preferably, the base in the above step (2) is sodium hydride, sodium ethoxide or sodium methoxide:
preferably, the triethoxysilane having a halogen atom in the above step (5) has a structure represented by general formula (iii):
x is any one of Br or Cl;
n is any integer between 2 and 6.
Preferably, any one of sodium hypochlorite, sodium hypobromite, tert-butyl hypochloride or tert-butyl hypobromite is used as the halogenating agent in the step (6).
Preferably, the reaction temperature of the solution in the step (2) is 40-70 ℃; the reaction time is 6-30 hours.
The invention also provides an application of the multifunctional bactericidal compound in preparing bactericides.
The multifunctional bactericidal compound is applied to preparing a bactericidal coating.
The thickness of the sterilization coating is 5-200 nm.
The preparation principle of the multifunctional bactericidal compound with the structure of the general formula (I) in the invention is as follows:
introducing tertiary amine on diethyl malonate through nucleophilic substitution reaction, and then carrying out ammonolysis reaction on two ester bonds derived from diethyl malonate and urea to generate imide bonds to form the barbituric acid derivative containing a tertiary amine structure. And then, carrying out quaternary ammonium salinization treatment on the derivatives by using triethoxysilane containing halogen atoms to generate quaternary ammonium salts, halogenating imide bonds to generate haloamine bonds, and finally hydrolyzing silicon ether bonds to obtain hydroxyl groups, thereby preparing the bactericide simultaneously containing haloamine, quaternary ammonium salt bactericidal groups and hydroxyl bonding groups.
Further, the preparation method of the multifunctional sterilization compound with the structure of the general formula (I) comprises the following steps:
(1) introducing tertiary amine on diethyl malonate through nucleophilic substitution reaction between the diethyl malonate and halogenated tertiary amine:
wherein R is1,R2Is any one of methyl or ethyl;
x is any one of Br or Cl;
n is any integer between 2 and 6.
(2) Performing ammonolysis reaction between an ester bond of diethyl malonate and an amino group of urea to form a barbiturate derivative containing a tertiary amine structure:
(3) acidifying with hydrochloric acid, adjusting the pH value to 1-2, and converting nitrogen anions in the step (2) into imide:
(4) dropwise adding NaOH into the reaction solution in the step (3), adjusting the pH value to 11-12, and removing hydrochloride formed by the tertiary amine to obtain the tertiary amine:
(5) adding an ethanol solution of triethoxysilane containing halogen atoms into the product obtained in the step (4), and carrying out quaternary ammonium salination reaction to generate quaternary ammonium salt on tertiary amine:
wherein m is any integer between 2 and 6; and X is any one of Br or Cl.
(6) Halogenating the product obtained in step (5) with a halogenating agent to halogenate the N-H bond of the imide to a haloamine (N-X):
(7) hydrolyzing the product obtained in step (6) in 1% aqueous acetic acid to hydrolyze the silyl ether bond to a hydroxyl group to obtain a compound of general formula (I):
two haloamines in the multifunctional bactericidal compound have the advantages of high bactericidal speed, high efficiency, easy consumption, regeneration, low cost, wide sources and difficult drug resistance, and the haloamine structure is derived from a barbituric acid ring, so that the compound has particularly good stability. The halamine is generated by halogenating amine, amide or imide, and the invention belongs to imide type halamine, and compared with halogenating amine and amide, the imide halamine has the highest sterilization efficiency. The quaternary ammonium salt contained in the invention has the advantages of no consumption during sterilization and good stability, can improve the dissolving capacity of the bactericide, and can attract negatively charged germs to reach imide type halamine to accelerate the sterilization process. Due to the advantages, the bactericide prepared by the invention represents the highest level of the bactericide at the present stage, and the excellent performance of the bactericide is also shown in the following application examples.
And (3) in the step (2), the alkali catalyst is sodium alkoxide.
Besides the bactericidal group, the bactericide has three bonding groups, namely hydroxyl, and can be bonded to the surface of a material through different chemical reactions, so that the bonding is firmer, the problem that the bactericide is easy to fall off is solved, and the comprehensive performance of the bactericide is further improved.
The multifunctional bactericidal compound has two halamine groups, one quaternary ammonium salt group and three hydroxyl groups, and has the following characteristics:
1) realizes a multifunctional bactericide which has high sterilization efficiency, wide sterilization range, strong sterilization durability, low cost and reproducibility.
2) The haloamine and quaternary ammonium salt compound bactericidal group has strong killing effect on gram-positive bacteria and gram-negative bacteria and has wider action range.
3) The bactericide is chemically bonded with the material, has high bonding firmness, is resistant to washing, friction and ultraviolet aging, and has the effects of both a softener and a finishing agent when used for treating fibers.
4) The cyclic barbituric acid structure therein is particularly resistant to hydrolysis and other damaging factors.
5) Does not contain harmful bactericidal groups (such as copper salt) such as heavy metal, is environment-friendly and meets the requirement of clean production.
Detailed Description
The present invention will be described in detail with reference to examples.
Example 1
To a 100mL three-necked round-bottomed flask equipped with a stirring magneton and a condenser, 25 parts by weight of diethyl malonate, 30 parts by weight of sodium ethoxide, 1.25 parts by weight of KI, 100 parts by weight of ethanol, and 25 parts by weight of 3-chloro-1- (N, N-dimethyl) propylamine were added. The system is reacted for 4-10 hours at the temperature of 80 ℃, then ethanol is removed through reduced pressure distillation, after the ethyl ether-water system is used for extraction and liquid separation, ethyl ether is removed through reduced pressure distillation of an organic layer, 25 parts by weight of urea is added, 30 parts by weight of sodium ethoxide is used as a catalyst, acetone is used as a solvent, reflux is carried out for 6-10 hours at the temperature of 60 ℃, an ester bond derived from diethyl malonate reacts with an amino group in the urea to obtain a sodium salt of a nitrogen negative ion, the pH value is adjusted to 1-2 through hydrochloric acid, the pH value is adjusted to 10-11 through triethylamine, and the barbiturate derivative containing a tertiary amine structure is obtained. And then adding 30 parts by weight of 3-chloropropyltriethoxysilane into the mixture by using a dropping funnel at room temperature, and reacting for 6-12 hours to obtain the quaternary ammonium salt. The solvent and unreacted 3-chloropropyltriethoxysilane were distilled off under reduced pressure. Using absolute ethyl alcohol as a solvent, adding 30 parts by weight of tert-butyl hypochlorite to react for 2-3.5 hours, chlorinating an imide bond into a chloramine bond, removing small molecular compounds such as ethyl alcohol and excessive tert-butyl hypochlorite under reduced pressure, finally hydrolyzing a silicon ether bond by using a 1% acetic acid aqueous solution to obtain a hydroxyl group, and removing the solvent to obtain a white powdery compound of a general formula (I), wherein the structure of the compound is as follows:
1h NMR (in DMSO solvent) measured the chemical shifts (ppm) of each proton as follows:
example 2
In a 100mL three-necked round-bottomed flask equipped with a stirring magneton and a condenser, 35 parts by weight of sodium ethoxide, 1.6 parts by weight of KI, and 128 parts by weight of ethanol were added, stirred for 20 minutes, and then 32 parts by weight of diethyl malonate was added via a dropping funnel, followed by slow addition of 30 parts by weight of 3-chloro-1- (N, N-diethyl) propylamine. The system is reacted for 8 hours at the temperature of 80 ℃, then ethanol is removed by reduced pressure distillation, extraction and liquid separation are carried out for multiple times by using an ether-water system, ether is removed by reduced pressure distillation of an organic layer, 32 weight parts of urea and 35 weight parts of sodium ethoxide are added, 128 weight parts of absolute ethanol is used as a solvent, reflux is carried out for 10 hours at the temperature of 80 ℃, an ester bond derived from diethyl malonate reacts with an amino group in the urea to obtain a sodium salt of a nitrogen anion, the pH value of hydrochloric acid is adjusted to 5, and the pH value of sodium carbonate is adjusted to 12, so that the barbiturate derivative containing a tertiary amine structure is obtained. Then, 30 parts by weight of 2-chloroethyltriethoxysilane was added at room temperature using a dropping funnel, and reacted for 12 hours to produce a quaternary ammonium salt, after which the solvent and unreacted 2-chloroethyltriethoxysilane were distilled off under reduced pressure. Then, 32 parts by weight of tert-butyl hypochlorite was added to the mixture using ethanol as a solvent to react for 3 hours, thereby chlorinating imide bonds to chloramine bonds. Removing small molecular compounds such as ethanol and excessive tert-butyl hypochlorite under reduced pressure, hydrolyzing the silicon ether bond with 1% acetic acid aqueous solution to obtain hydroxyl, removing solvent, and obtaining white powdery compound with general formula (I), wherein the structure is shown as follows:
1h NMR (in DMSO solvent) measured the chemical shifts (ppm) of each proton as follows:
example 3
55 parts by weight of sodium ethoxide, 3.33 parts by weight of KI and 300 parts by weight of absolute ethanol were added to a 250mL three-necked round-bottomed flask equipped with a stirring magneton and a condenser tube, and stirred for 20 minutes, 50 parts by weight of diethyl malonate was added to the flask via a dropping funnel, and 48 parts by weight of 2-bromo-1- (N, N-dimethyl) ethylamine was slowly added thereto. The system is reacted for 8 hours at the temperature of 80 ℃, then reduced pressure distillation is carried out to remove ethanol, ether-water system extraction and liquid separation are carried out for multiple times, organic layer is reduced pressure distillation to remove ether, 50 weight parts of urea and 55 weight parts of sodium ethoxide are added, 300 weight parts of absolute ethanol is used as solvent, reflux is carried out for 10 hours at the temperature of 80 ℃, ester bond from diethyl malonate reacts with amino in urea to obtain sodium salt of nitrogen negative ion, hydrochloric acid is used for adjusting the pH value to 5, and sodium hydroxide is used for adjusting the pH value to 13, so that barbiturate derivative containing tertiary amine structure is obtained. Then, 50 parts by weight of 2-bromoethyltriethoxysilane was added at room temperature using a dropping funnel, and reacted for 12 hours to produce a quaternary ammonium salt, after which the solvent and unreacted 2-bromoethyltriethoxysilane were distilled off under reduced pressure. Then, ethanol was added as a solvent, and 50 parts by weight of tert-butyl hypochlorite was added to react for 3 hours to chlorinate imide bonds into chloramine bonds. Removing small molecular compounds such as ethanol and excessive tert-butyl hypochlorite under reduced pressure, hydrolyzing the silicon ether bond with 1% acetic acid aqueous solution to obtain hydroxyl, removing solvent, and obtaining white powdery compound with general formula (I), wherein the structure is shown as follows:
1h NMR (in DMSO solvent) measured the chemical shifts (ppm) of each proton as follows:
example 4
A250 mL three-neck round-bottom flask equipped with a stirring magneton and a condenser was charged with 72 parts by weight of sodium ethoxide, 4 parts by weight of KI, and 420 parts by weight of absolute ethanol, stirred for 20 minutes, and 60 parts by weight of diethyl malonate was added via a dropping funnel, followed by slow addition of 57 parts by weight of 3-bromo-1- (N, N-dimethyl) propylamine. The system is reacted for 8 hours at 83 ℃, then reduced pressure distillation is carried out to remove ethanol, then ethyl acetate-water system extraction and liquid separation are carried out for multiple times, organic layer is reduced pressure distillation to remove ethyl acetate, 60 weight parts of urea and 72 weight parts of sodium ethoxide are added, 420 weight parts of absolute ethyl alcohol is used as solvent, reflux is carried out for 10 hours at 80 ℃, ester bond from diethyl malonate reacts with amino in urea to obtain sodium salt of nitrogen negative ion, hydrochloric acid is used for adjusting pH to 5, and sodium hydroxide is used for adjusting pH to 13, thus obtaining the barbiturate derivative containing tertiary amine structure. Then 60 parts by weight of 4-bromobutyl triethoxysilane was added at room temperature using a dropping funnel and reacted for 12 hours to produce a quaternary ammonium salt, after which the solvent and unreacted 4-bromobutyl triethoxysilane were distilled off under reduced pressure. Using ethanol as a solvent, 60 parts by weight of t-butyl hypobromite was added to react for 3 hours, brominating the imide bonds to bromoamine bonds. Removing small molecular compounds such as ethanol and excessive tert-butyl hypobromite under reduced pressure, hydrolyzing the silicon ether bond with 1% acetic acid aqueous solution to obtain hydroxyl, and removing the solvent to obtain white powdery compound of general formula (I), which has the following structure:
1h NMR (in DMSO solvent) measured the chemical shifts (ppm) of each proton as follows:
example 5
A250 mL three-neck round-bottom flask equipped with a stirring magneton and a condenser was charged with 72 parts by weight of sodium ethoxide, 4 parts by weight of KI, and 420 parts by weight of absolute ethanol, stirred for 20 minutes, and 60 parts by weight of diethyl malonate was added via a dropping funnel, followed by slow addition of 57 parts by weight of 4-bromo-1- (N, N-diethyl) butylamine. The system is reacted for 8 hours at 83 ℃, then reduced pressure distillation is carried out to remove ethanol, then ethyl acetate-water system extraction and liquid separation are carried out for multiple times, organic layer is reduced pressure distillation to remove ethyl acetate, 60 weight parts of urea and 72 weight parts of sodium ethoxide are added, 420 weight parts of absolute ethyl alcohol is used as solvent, reflux is carried out for 10 hours at 80 ℃, ester bond from diethyl malonate reacts with amino in urea to obtain sodium salt of nitrogen negative ion, hydrochloric acid is used for adjusting pH to 5, and sodium hydroxide is used for adjusting pH to 13, thus obtaining the barbiturate derivative containing tertiary amine structure. Then 60 parts by weight of 3-chloropropyltriethoxysilane was added at room temperature using a dropping funnel, and reacted for 12 hours to produce a quaternary ammonium salt, after which the solvent and unreacted 3-chloropropyltriethoxysilane were distilled off under reduced pressure. Finally, ethanol is used as a solvent, 60 parts by weight of tert-butyl hypobromite is added to react for 3 hours, and imide bonds are brominated into bromamine bonds. Removing small molecular compounds such as ethanol and excessive tert-butyl hypobromite under reduced pressure, hydrolyzing the silicon ether bond with 1% acetic acid aqueous solution to obtain hydroxyl, and removing the solvent to obtain light yellow powdery compound of the general formula (I), wherein the structure is shown as follows:
1h NMR (in DMSO solvent) measured the chemical shifts (ppm) of each proton as follows:
the application example of the compound bactericide which is synthesized by the invention and has the functions of halamine, quaternary ammonium salt and hydroxyl is as follows:
application example 1:
50mL of absolute ethanol was added to a beaker, then 1g of the organic fungicide prepared in example 2 of the embodiment and 30g of silica microspheres having an average diameter of 10 μm were added, stirred for 40 minutes, then the ethanol was removed under reduced pressure, and the silica coated with the fungicide was heated at 80 ℃ for 2 hours to prepare the bactericidal silica microspheres having a fungicide thickness of 40 nm. Placing the microspheres into a glass tube with diameter of 0.5cm and height of 20cm to obtain a filter column, and filtering to obtain Staphylococcus aureus and Escherichia coli with concentration of 106～107CFU/mL in water killed 99.999% of the bacteria in the water at a flow rate of 3 mL/min. The structure of the bactericidal microsphere is as follows:
application example 2:
selecting an average area of 1cm2Silicon wafer using O with frequency of 12.6MHz, pressure of 75Pa and power of 45W2Plasma treatment was performed for 1min on both sides. The glass sheet was then placed in a desiccator having an open container with 3- (triethoxysilyl) propyl succinic anhydride at the bottom. The treated wafer was subjected to a vacuum of about 50mbar and evaporated by additional heat input using an externally placed infrared lamp to induce a silanization reaction on the wafer surface for 4 hours, the wafer was rinsed with isopropanol and dried under a nitrogen stream to remove surface unbound silane molecules. Then, the sheet was put into a beaker containing 60mL of absolute ethanol, and then 2g of the organic fungicide prepared in example 4 of the embodiment was added and reacted at 80 ℃ for 8 hours, and acid anhydride was bonded to hydroxyl group of the fungicide to form an ester bond. The thickness of the bactericide is 110 nm. Then 100 μ L of each of Staphylococcus aureus and Escherichia coli with concentration of 1.5 × 106CFU/mL solution, two silicon sheets bonded with the bactericide, were added and after 5min contact, the E.coli mortality was 100%. Using the uncoated silicon wafer as a control, the mortality rate of Escherichia coli was 5.4%, and that of Staphylococcus aureus was 8.5%, which were caused by natural death. The structure of the sterilizing silicon wafer is as follows:
application example 3:
a solution of the bactericide prepared in example 5 of the embodiment having a concentration of 0.2g/mL was prepared using absolute ethanol, and cotton cloth was soaked in the solution for 30 minutes. After soaking, the cotton cloth is taken out and dried, and the thickness of the bactericide is 100 nm. Collecting Staphylococcus aureus and Escherichia coli each 100 μ L at a concentration of 1.8 × 106CFU/mL solution was added dropwise to two 2cm blocks2The organic bactericide is coated on cotton cloth, and after contacting for 3min, the death rate of Escherichia coli is 99.9%, and Staphylococcus aureus is obtainedThe mortality rate of (a) was 99%. Using uncoated cotton cloth as a control group, the mortality rate of escherichia coli was 4.6%, and that of staphylococcus aureus was 7.4%, which were caused by natural death.
The sterilizing efficiency gradually decreases as the number of washing times increases, but the sterilizing power remains good. After 50 times of ordinary machine washing, 99.999 percent of escherichia coli and golden yellow staphylococcus can be killed after the bactericidal cotton cloth is contacted with the bacterial solution for 20 minutes, and the bacterial quantity of the pure cotton cloth of the control group is only reduced by about 8 percent due to natural death. The schematic of the sterilized cotton produced is as follows:
while the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to one skilled in the art that various changes and modifications can be made therein. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (9)
1. A multifunctional bactericidal compound characterized by: has a structure shown in a general formula (I):
wherein R is1,R2Is CH3Or CH2CH3Any one of the above;
x is any one of Br or Cl;
m and n are any integer between 2 and 6.
2. A method for preparing the multifunctional fungicidal compound according to claim 1, wherein: the method comprises the following steps:
(1) diethyl malonate and the structure shown in the general formula (II) are subjected to substitution reaction under the action of a catalyst to bond an aliphatic bond to the main chain of the substance shown in the general formula (II);
wherein R is1,R2Is CH3Or CH2CH3Any one of the above;
x is any one of Br or Cl;
n is any integer between 2 and 6.
(2) Dissolving the product obtained in the step (1), an alkali catalyst and urea in tetrahydrofuran to form a solution and reacting;
(3) adjusting the pH value of the product obtained in the step (2) to 1-2, and neutralizing the alkali catalyst;
(4) adjusting the pH value of the product obtained in the step (3) to 11-12 to obtain tertiary amine containing a barbituric acid ring;
(5) carrying out quaternary ammonium salinization treatment on triethoxysilane containing halogen atoms and the product obtained in the step (4) to generate quaternary ammonium salt;
(6) halogenating the product obtained in the step (5) to enable barbituric acid to contain imide type halamine on a ring.
(7) And (3) carrying out hydrolysis reaction on the product (6) to enable three silicon ether bonds of the silane to generate three hydroxyl groups, thereby obtaining the multifunctional bactericidal compound with the structure of the general formula (I).
3. The method for preparing a multifunctional fungicidal compound according to claim 2, wherein: and (3) in the step (2), the alkali catalyst is sodium alkoxide.
4. The method for preparing a multifunctional fungicidal compound according to claim 2, wherein: in the step (5), the halogen atom-containing triethoxysilane has a structure represented by general formula (III):
x is any one of Br or Cl;
n is any integer between 2 and 6.
5. The method for preparing a multifunctional fungicidal compound according to claim 2, wherein: in the step (6), any one of sodium hypochlorite, tert-butyl hypochlorite or tert-butyl hypobromite is used as a halogenating reagent.
6. The method for preparing a multifunctional fungicidal compound according to claim 2, wherein: the reaction temperature of the solution in the step (2) is 40-70 ℃.
7. The method for preparing a multifunctional fungicidal compound according to claim 2, wherein: the solution in the step (2) is reacted for 6-30 hours.
8. Use of the multifunctional fungicidal compound according to claim 1 for the preparation of fungicides.
9. Use according to claim 8, characterized in that: the multifunctional bactericidal compound is applied to preparing a bactericidal coating.
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Application publication date: 20200428 Assignee: QINGDAO YUTONG PIPELINE Co.,Ltd. Assignor: SHANDONG University OF SCIENCE AND TECHNOLOGY Contract record no.: X2023980041233 Denomination of invention: A multifunctional bactericidal compound and its preparation method and application Granted publication date: 20230425 License type: Exclusive License Record date: 20230906 |