CN114058020A - Preparation method and application of quaternary phosphonium salt - Google Patents
Preparation method and application of quaternary phosphonium salt Download PDFInfo
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- CN114058020A CN114058020A CN202111381060.9A CN202111381060A CN114058020A CN 114058020 A CN114058020 A CN 114058020A CN 202111381060 A CN202111381060 A CN 202111381060A CN 114058020 A CN114058020 A CN 114058020A
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- 150000004714 phosphonium salts Chemical group 0.000 title claims abstract description 68
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 239000011259 mixed solution Substances 0.000 claims abstract description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000008367 deionised water Substances 0.000 claims abstract description 55
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 55
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000000243 solution Substances 0.000 claims abstract description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000000645 desinfectant Substances 0.000 claims abstract description 31
- 238000003756 stirring Methods 0.000 claims abstract description 30
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 238000009210 therapy by ultrasound Methods 0.000 claims abstract description 15
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229920001661 Chitosan Polymers 0.000 claims abstract description 12
- 229920002261 Corn starch Polymers 0.000 claims abstract description 12
- 239000008120 corn starch Substances 0.000 claims abstract description 12
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 239000012043 crude product Substances 0.000 claims abstract description 8
- 239000011261 inert gas Substances 0.000 claims abstract description 7
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 7
- AKUNSPZHHSNFFX-UHFFFAOYSA-M tributyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC AKUNSPZHHSNFFX-UHFFFAOYSA-M 0.000 claims abstract description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 48
- 239000000284 extract Substances 0.000 claims description 46
- 239000007788 liquid Substances 0.000 claims description 41
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 33
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 239000000843 powder Substances 0.000 claims description 24
- 239000006228 supernatant Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- 238000005406 washing Methods 0.000 claims description 16
- 108010059820 Polygalacturonase Proteins 0.000 claims description 13
- 108010093305 exopolygalacturonase Proteins 0.000 claims description 13
- 239000002994 raw material Substances 0.000 claims description 13
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 11
- 108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 claims description 11
- 102100022624 Glucoamylase Human genes 0.000 claims description 11
- 238000001179 sorption measurement Methods 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 8
- 239000003480 eluent Substances 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- MKAZOCQEUWHHEE-UHFFFAOYSA-N 14,14-dibutyloctadecylphosphanium;chloride Chemical compound [Cl-].CCCCC(CCCC)(CCCC)CCCCCCCCCCCCC[PH3+] MKAZOCQEUWHHEE-UHFFFAOYSA-N 0.000 claims description 7
- 241000132012 Atractylodes Species 0.000 claims description 7
- 230000002255 enzymatic effect Effects 0.000 claims description 4
- 239000000413 hydrolysate Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000004659 sterilization and disinfection Methods 0.000 abstract description 24
- 230000000694 effects Effects 0.000 abstract description 14
- 230000001954 sterilising effect Effects 0.000 abstract description 10
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 23
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- 230000003385 bacteriostatic effect Effects 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 3
- 108010059892 Cellulase Proteins 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 229940106157 cellulase Drugs 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003619 algicide Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- -1 rare earth ion Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/34—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-halogen bonds; Phosphonium salts
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- 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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
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- 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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/12—Asteraceae or Compositae [Aster or Sunflower family], e.g. daisy, pyrethrum, artichoke, lettuce, sunflower, wormwood or tarragon
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Abstract
The invention belongs to the technical field of chemical synthesis, and particularly discloses a preparation method and application of quaternary phosphonium salt, wherein the preparation method of the quaternary phosphonium salt comprises the following steps: (1) adding tricyclohexylphosphine, tri-n-butyltetradecyl phosphonium chloride and butanone into a reaction kettle, adding a catalyst, and uniformly stirring to obtain a first mixed solution; (2) adding corn starch into deionized water, uniformly dispersing, adding chitosan and gamma-aminopropyltriethoxysilane, and uniformly stirring to obtain a second mixed solution; (3) dripping the second mixed solution into the first mixed solution, adding an acetic acid solution, stirring uniformly under the protection of inert gas, and performing ultrasonic treatment to obtain a crude product; (4) and removing redundant butanone through rotary evaporation to obtain the quaternary phosphonium salt. The quaternary phosphonium salt has good disinfection and sterilization effects and can be used as an effective component of a disinfectant.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a preparation method and application of a quaternary phosphorus salt.
Background
As a new generation surfactant, the quaternary phosphonium salt has good sterilization and permeability, and is widely used as a sterilization algicide, an oilfield flooding bactericide, an agricultural insecticide, an anti-tumor active drug and the like in an industrial circulating water system.
CN103374033A discloses an organic phosphine functionalized quaternary phosphonium salt ionic liquid and a preparation method thereof, and specifically discloses the preparation steps as follows: mixing triphenylphosphine and bromoalkyldiphenylphosphine oxide, bromoalkylphenylphenylphosphonic acid ethyl ester or bromoalkylphosphonic acid diethyl ester according to the molar ratio of 1: 1-1.2, adding an organic solvent, placing the mixture in a microwave reaction device, stirring and reacting under the conditions that the microwave power is 350-500W, the reaction temperature is 80-110 ℃ and the reaction time is 60-150 min to obtain a crude product, and removing unreacted raw materials to obtain the triphenylphosphine ionic liquid. The specification specifically discloses that the compound can be used as a flame retardant, a plasticizer, a rare earth ion extractant and the like, and therefore, the effect of the compound on sterilization and disinfection is still to be improved.
Disclosure of Invention
The invention provides a preparation method and application of quaternary phosphonium salt, which has good disinfection and sterilization effects and can be used as an effective component of a disinfectant.
The invention adopts the following technical scheme for solving the technical problems:
a method for preparing quaternary phosphonium salt comprises the following steps:
(1) adding tricyclohexylphosphine, tri-n-butyltetradecyl phosphonium chloride and butanone into a reaction kettle, adding a catalyst, and stirring at the rotating speed of 100-1000 rpm for 2-6 hours at the temperature of 60-90 ℃ to obtain a first mixed solution;
(2) adding corn starch into deionized water, uniformly dispersing, adding chitosan and gamma-aminopropyltriethoxysilane, and stirring at the rotating speed of 200-600 rpm for 60-180 min at the temperature of 65-80 ℃ to obtain a second mixed solution;
(3) dripping the second mixed solution into the first mixed solution, adding an acetic acid solution, stirring at a rotating speed of 400-800 rpm for 1-4 hours under the protection of inert gas, and performing ultrasonic treatment at 200-600W for 15-30 min to obtain a crude product;
(4) and removing redundant butanone through rotary evaporation to obtain the quaternary phosphonium salt.
As a preferable scheme, the weight ratio of the tricyclohexylphosphine, tri-n-butyltetradecyl phosphonium chloride, butanone and catalyst in the step (1) is 1: 1-1.3: 3-8: 0.02-0.06.
Preferably, the catalyst is an organometallic catalyst.
As a preferable scheme, the weight ratio of the corn starch, the deionized water, the chitosan and the gamma-aminopropyltriethoxysilane in the step (2) is 1: 4-8: 0.5-1.2: 0.02 to 0.1.
As a preferable scheme, the weight ratio of the first mixed solution, the second mixed solution and the acetic acid solution in the step (3) is 1: 0.2-0.6: 0.05 to 0.15.
The invention also provides application of the prepared quaternary phosphonium salt as an active ingredient of a disinfectant in preparation of the disinfectant.
The invention also provides a disinfectant, which is prepared from the following raw materials in parts by weight: 0.5-1.2 parts of rhizoma atractylodis extract, 0.8-3 parts of citric acid, 1-5 parts of quaternary phosphonium salt, 6-15 parts of ethylene glycol and 70-90 parts of deionized water;
the quaternary phosphonium salt is the quaternary phosphonium salt prepared by the method.
As a preferable scheme, the disinfectant is prepared from the following raw materials in parts by weight: 1 part of rhizoma atractylodis extract, 2 parts of citric acid, 4 parts of quaternary phosphonium salt, 10 parts of ethylene glycol and 83 parts of deionized water.
As a preferred scheme, the preparation method of the rhizoma atractylodis extract comprises the following steps:
(11) crushing the rhizoma atractylodis decoction pieces to 20-100 meshes to obtain rhizoma atractylodis powder;
(12) adding rhizoma atractylodis powder into the enzymolysis liquid, stirring at the rotating speed of 100-400 rpm for 30-60 min at the temperature of 55-70 ℃, performing ultrasonic treatment at 300-800W for 25-40 min, adding glycerol, and dispersing uniformly to obtain a mixed liquid;
(13) centrifuging the mixed solution, taking supernatant, adding the supernatant into deionized water to prepare sample liquid, putting the sample liquid on HPD400 macroporous adsorption resin at the speed of 0.8-2 BV/h, eluting at the speed of 0.8-2 BV/h, washing 1-2 BV with deionized water, washing 1-3 BV with 50-80 wt% ethanol solution, collecting ethanol solution eluent, and drying to obtain the rhizoma atractylodis extract;
in the step (12), the weight ratio of the rhizoma atractylodis powder to the enzymolysis liquid to the glycerol is 1: 3-10: 0.05 to 0.2;
the enzymolysis liquid is prepared from 1 weight part of hexadecyl trimethyl ammonium bromide, 1 to 4 weight parts of glucoamylase, 2 to 8 weight parts of pectinase and 85 to 98 weight parts of deionized water.
Preferably, the enzymatic hydrolysate is prepared from 1 part by weight of hexadecyl trimethyl ammonium bromide, 3 parts by weight of glucoamylase, 6 parts by weight of pectinase and 90 parts by weight of deionized water.
The invention has the beneficial effects that: the invention obtains a first mixed solution by reacting tricyclohexylphosphine, tri-n-butyltetradecyl phosphine chloride and butanone under the action of a catalyst, then compounds corn starch, chitosan and a coupling agent to obtain a second mixed solution, and drops the second mixed solution into the first mixed solution, and then adds an acetic acid solution to prepare the quaternary phosphonium salt with good disinfection effect, which can be used as an effective component of a disinfectant. The quaternary ammonium salt prepared by the invention is used as an effective component of the disinfectant, and is combined with the rhizoma atractylodis extract, so that the quaternary ammonium salt and the rhizoma atractylodis extract have obvious synergistic effect in the aspects of disinfection and sterilization.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are a part of the embodiments of the present invention, but 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.
In the present invention, the parts are all parts by weight unless otherwise specified.
In a first aspect, in at least one embodiment, there is provided a method of making a quaternary phosphonium salt, comprising the steps of:
(1) adding tricyclohexylphosphine, tri-n-butyltetradecyl phosphonium chloride and butanone into a reaction kettle, adding a catalyst, and stirring at the rotating speed of 100-1000 rpm for 2-6 hours at the temperature of 60-90 ℃ to obtain a first mixed solution;
(2) adding corn starch into deionized water, uniformly dispersing, adding chitosan and gamma-aminopropyltriethoxysilane, and stirring at the rotating speed of 200-600 rpm for 60-180 min at the temperature of 65-80 ℃ to obtain a second mixed solution;
(3) dripping the second mixed solution into the first mixed solution, adding an acetic acid solution, stirring at a rotating speed of 400-800 rpm for 1-4 hours under the protection of inert gas, and performing ultrasonic treatment at 200-600W for 15-30 min to obtain a crude product;
(4) and removing redundant butanone through rotary evaporation to obtain the quaternary phosphonium salt.
The inventor of the invention finds that the quaternary phosphonium salt with good disinfection effect can be prepared by reacting tricyclohexylphosphine, tri-n-butyltetradecyl phosphine chloride and butanone under the action of a catalyst to obtain a first mixed solution, compounding corn starch, chitosan and a coupling agent to obtain a second mixed solution, dripping the second mixed solution into the first mixed solution, and adding an acetic acid solution, and the quaternary phosphonium salt can be used as an effective component of a disinfectant.
Compared with the prior art, the method has the improvement that the method selects tricyclohexylphosphine and tri-n-butyltetradecyl phosphine chloride as main reaction components, and obtains the quaternary phosphonium salt with good disinfection effect through modification treatment of the second mixed solution.
In a preferred embodiment, the weight ratio of tricyclohexylphosphine, tri-n-butyltetradecylphosphonium chloride, butanone and catalyst in the step (1) is 1: 1-1.3: 3-8: 0.02-0.06.
In a preferred embodiment, the catalyst is an organometallic catalyst.
In a preferred embodiment, the weight ratio of the corn starch, the deionized water, the chitosan and the gamma-aminopropyltriethoxysilane in the step (2) is 1: 4-8: 0.5-1.2: 0.02 to 0.1.
In a preferred embodiment, the weight ratio of the first mixed solution, the second mixed solution and the acetic acid solution in the step (3) is 1: 0.2-0.6: 0.05 to 0.15.
In a second aspect, there is provided in at least one embodiment the use of the quaternary phosphonium salts prepared as described above as disinfectant active ingredients in the preparation of disinfectants.
In a third aspect, in at least one embodiment, a disinfectant is provided, which is prepared from the following raw materials in parts by weight: 0.5-1.2 parts of rhizoma atractylodis extract, 2 parts of citric acid, 4 parts of quaternary phosphonium salt, 10 parts of ethylene glycol and 83 parts of deionized water;
the quaternary phosphonium salt is the quaternary phosphonium salt prepared by the method.
In a preferred embodiment, the disinfectant is prepared from the following raw materials in parts by weight: 1 part of rhizoma atractylodis extract, 2 parts of citric acid, 4 parts of quaternary phosphonium salt, 10 parts of ethylene glycol and 83 parts of deionized water
In a preferred embodiment, the method for preparing the atractylodes rhizome extract comprises the following steps:
(11) crushing the rhizoma atractylodis decoction pieces to 20-100 meshes to obtain rhizoma atractylodis powder;
(12) adding rhizoma atractylodis powder into the enzymolysis liquid, stirring at the rotating speed of 100-400 rpm for 30-60 min at the temperature of 55-70 ℃, performing ultrasonic treatment at 300-800W for 25-40 min, adding glycerol, and dispersing uniformly to obtain a mixed liquid;
(13) centrifuging the mixed solution, taking supernatant, adding the supernatant into deionized water to prepare sample liquid, putting the sample liquid on HPD400 macroporous adsorption resin at the speed of 0.8-2 BV/h, eluting at the speed of 0.8-2 BV/h, washing 1-2 BV with deionized water, washing 1-3 BV with 50-80 wt% ethanol solution, collecting ethanol solution eluent, and drying to obtain the rhizoma atractylodis extract;
in the step (12), the weight ratio of the rhizoma atractylodis powder to the enzymolysis liquid to the glycerol is 1: 3-10: 0.05 to 0.2;
the enzymolysis liquid is prepared from 1 weight part of hexadecyl trimethyl ammonium bromide, 1 to 4 weight parts of glucoamylase, 2 to 8 weight parts of pectinase and 85 to 98 weight parts of deionized water.
The inventor of the invention obtains the rhizoma atractylodis extract with good antibacterial effect by crushing, enzymolysis, centrifugation and macroporous adsorption treatment of rhizoma atractylodis.
According to the invention, the rhizoma atractylodis cells can be fully crushed by selecting the enzymolysis liquid consisting of cetyl trimethyl ammonium bromide, glucoamylase, pectinase and deionized water, substances in the rhizoma atractylodis can be better extracted, the substances with the disinfection and sterilization effects in the rhizoma atractylodis are dissolved out, and the components with the disinfection and sterilization effects are enriched through subsequent macroporous adsorption treatment, so that the rhizoma atractylodis extract capable of remarkably improving the bacteriostasis is obtained.
The inventor finds that the antibacterial effects of the rhizoma atractylodis extracts prepared by different preparation methods of the rhizoma atractylodis extract are different, and compared with other methods, the rhizoma atractylodis extract prepared by the preparation method of the rhizoma atractylodis extract can remarkably improve the antibacterial effect.
The rhizoma atractylodis extract and the quaternary phosphonium salt prepared by the invention have obvious synergistic effect in disinfection and sterilization.
In a preferred embodiment, the enzymatic hydrolysate is prepared from 1 part by weight of cetyltrimethylammonium bromide, 3 parts by weight of glucoamylase, 6 parts by weight of pectinase and 90 parts by weight of deionized water.
Example 1
A method for preparing quaternary phosphonium salt comprises the following steps:
(1) adding 10 parts by weight of tricyclohexylphosphine, 12 parts by weight of tri-n-butyltetradecyl phosphine chloride and 50 parts by weight of butanone into a reaction kettle, adding 0.5 part by weight of stannous octoate, and stirring at the rotating speed of 900rpm for 4 hours at 80 ℃ to obtain a first mixed solution;
(2) adding 10 parts by weight of corn starch into 70 parts by weight of deionized water, uniformly dispersing, adding 6 parts by weight of chitosan and 0.5 part by weight of gamma-aminopropyltriethoxysilane, and stirring at the rotating speed of 500rpm for 120min at 70 ℃ to obtain a second mixed solution;
(3) dripping 5 parts by weight of the second mixed solution into 10 parts by weight of the first mixed solution, then adding 1 part by weight of acetic acid solution, stirring for 3 hours at the rotating speed of 500rpm under the protection of inert gas, and then carrying out ultrasonic treatment for 20 minutes at 500W to obtain a crude product;
(4) and removing redundant butanone through rotary evaporation to obtain the quaternary phosphonium salt.
Example 2
A method for preparing quaternary phosphonium salt comprises the following steps:
(1) adding 10 parts by weight of tricyclohexylphosphine, 11 parts by weight of tri-n-butyltetradecyl phosphine chloride and 60 parts by weight of butanone into a reaction kettle, adding 0.4 part by weight of stannous octoate, and stirring at the rotating speed of 800rpm for 4 hours at 75 ℃ to obtain a first mixed solution;
(2) adding 10 parts by weight of corn starch into 50 parts by weight of deionized water, uniformly dispersing, adding 5 parts by weight of chitosan and 0.4 part by weight of gamma-aminopropyltriethoxysilane, and stirring at the rotating speed of 500rpm for 100min at 70 ℃ to obtain a second mixed solution;
(3) dripping 4 parts by weight of the second mixed solution into 10 parts by weight of the first mixed solution, then adding 0.8 part by weight of acetic acid solution, stirring for 2 hours at the rotating speed of 500rpm under the protection of inert gas, and then carrying out ultrasonic treatment for 20 minutes at 400W to obtain a crude product;
(4) and removing redundant butanone through rotary evaporation to obtain the quaternary phosphonium salt.
Example 3
A method for preparing quaternary phosphonium salt comprises the following steps:
(1) adding 10 parts by weight of tricyclohexylphosphine, 10 parts by weight of tri-n-butyltetradecyl phosphine chloride and 40 parts by weight of butanone into a reaction kettle, adding 0.5 part by weight of stannous octoate, and stirring at the rotating speed of 500rpm for 6 hours at 90 ℃ to obtain a first mixed solution;
(2) adding 10 parts by weight of corn starch into 70 parts by weight of deionized water, uniformly dispersing, adding 10 parts by weight of chitosan and 0.5 part by weight of gamma-aminopropyltriethoxysilane, and stirring at the rotating speed of 200rpm for 180min at 80 ℃ to obtain a second mixed solution;
(3) dropping 6 parts by weight of the second mixed solution into 10 parts by weight of the first mixed solution, adding 0.5 part by weight of acetic acid solution, stirring at a rotating speed of 600rpm for 3 hours under the protection of inert gas, and then carrying out ultrasonic treatment at 400W for 20 minutes to obtain a crude product;
(4) and removing redundant butanone through rotary evaporation to obtain the quaternary phosphonium salt.
Example 4
The disinfectant is prepared from the following raw materials in parts by weight: 1 part of rhizoma atractylodis extract, 2 parts of citric acid, 4 parts of quaternary phosphonium salt, 10 parts of ethylene glycol and 83 parts of deionized water.
Wherein the quaternary phosphonium salt is the quaternary phosphonium salt prepared in example 1.
The preparation method of the rhizoma atractylodis extract comprises the following steps:
(11) crushing the rhizoma atractylodis decoction pieces to 50 meshes to obtain rhizoma atractylodis powder;
(12) adding rhizoma Atractylodis powder into the enzymolysis solution, stirring at 65 deg.C and 200rpm for 50min, performing ultrasonic treatment at 400W for 30min, adding glycerol, and dispersing to obtain mixed solution;
(13) centrifuging the mixed solution at the rotating speed of 5000rpm for 8min, taking supernatant, adding the supernatant into deionized water to prepare sample liquid (the weight ratio of the supernatant to the deionized water is 1: 3), adding the sample liquid on HPD400 macroporous adsorption resin at the speed of 1BV/h, eluting at the speed of 1BV/h, washing 1.5BV with deionized water, then washing 2BV with 70 wt% ethanol solution, collecting ethanol solution eluent, and drying to obtain the rhizoma atractylodis extract.
In the step (12), the weight ratio of the rhizoma atractylodis powder to the enzymolysis liquid to the glycerol is 1: 9: 0.1.
the enzymolysis liquid is prepared from 1 weight part of hexadecyl trimethyl ammonium bromide, 3 weight parts of glucoamylase, 6 weight parts of pectinase and 90 weight parts of deionized water.
Example 5
The disinfectant is prepared from the following raw materials in parts by weight: 0.8 part of rhizoma atractylodis extract, 1.5 parts of citric acid, 3 parts of quaternary phosphonium salt, 8 parts of ethylene glycol and 86.7 parts of deionized water.
Wherein the quaternary phosphonium salt is the quaternary phosphonium salt prepared in example 2.
The preparation method of the rhizoma atractylodis extract comprises the following steps:
(11) crushing the rhizoma atractylodis decoction pieces to 80 meshes to obtain rhizoma atractylodis powder;
(12) adding rhizoma Atractylodis powder into the enzymolysis solution, stirring at 60 deg.C at 300rpm for 40min, performing ultrasonic treatment at 600W for 30min, adding glycerol, and dispersing to obtain mixed solution;
(13) centrifuging the mixed solution at the rotating speed of 5000rpm for 8min, taking supernatant, adding the supernatant into deionized water to prepare sample liquid (the weight ratio of the supernatant to the deionized water is 1: 3), adding the sample liquid on HPD400 macroporous adsorption resin at the speed of 1BV/h, eluting at the speed of 1BV/h, washing 1.5BV with deionized water, then washing 2BV with 60 wt% ethanol solution, collecting ethanol solution eluent, and drying to obtain the rhizoma atractylodis extract.
In the step (12), the weight ratio of the rhizoma atractylodis powder to the enzymolysis liquid to the glycerol is 1: 8: 0.15.
the enzymolysis liquid is prepared from 1 weight part of hexadecyl trimethyl ammonium bromide, 2.5 weight parts of glucoamylase, 7.5 weight parts of pectinase and 89 weight parts of deionized water.
Example 6
The disinfectant is prepared from the following raw materials in parts by weight: 0.9 part of rhizoma atractylodis extract, 0.8 part of citric acid, 2 parts of quaternary phosphonium salt, 15 parts of ethylene glycol and 81.3 parts of deionized water;
wherein the quaternary phosphonium salt is the quaternary phosphonium salt prepared in example 3.
The preparation method of the rhizoma atractylodis extract comprises the following steps:
(11) crushing the rhizoma atractylodis decoction pieces to 100 meshes to obtain rhizoma atractylodis powder;
(12) adding rhizoma Atractylodis powder into the enzymolysis solution, stirring at 70 deg.C at 400rpm for 30min, performing ultrasonic treatment at 800W for 25min, adding glycerol, and dispersing to obtain mixed solution;
(13) centrifuging the mixed solution at the rotating speed of 5000rpm for 8min, taking supernatant, adding the supernatant into deionized water to prepare sample liquid (the weight ratio of the supernatant to the deionized water is 1: 3), adding the sample liquid on HPD400 macroporous adsorption resin at the speed of 1BV/h, eluting at the speed of 1BV/h, washing 1.5BV with deionized water, then washing 2BV with 60 wt% ethanol solution, collecting ethanol solution eluent, and drying to obtain the rhizoma atractylodis extract.
In the step (12), the weight ratio of the rhizoma atractylodis powder to the enzymolysis liquid to the glycerol is 1: 7: 0.05.
the enzymolysis liquid is prepared from 1 part by weight of hexadecyl trimethyl ammonium bromide, 1 part by weight of glucoamylase, 8 parts by weight of pectinase and 90 parts by weight of deionized water.
Comparative example 1
Comparative example 1 differs from example 4 in that the disinfectant of comparative example 1 has the same amount of atractylodes rhizome extract instead of the quaternary phosphonium salt, i.e. the comparative example does not contain the quaternary phosphonium salt, all else being equal.
The disinfectant is prepared from the following raw materials in parts by weight: 5 parts of rhizoma atractylodis extract, 2 parts of citric acid, 10 parts of ethylene glycol and 83 parts of deionized water.
Comparative example 2
Comparative example 2 is different from example 4 in that the disinfectant of comparative example 2 has the same amount of quaternary phosphonium salt instead of the atractylodes rhizome extract, i.e., the atractylodes rhizome extract is not contained in this comparative example, and the rest is the same.
The disinfectant is prepared from the following raw materials in parts by weight: 2 parts of citric acid, 5 parts of quaternary phosphonium salt, 10 parts of ethylene glycol and 83 parts of deionized water.
Comparative example 3
Comparative example 3 is different from example 4 in that the preparation method of the atractylodes rhizome extract described in comparative example 3 is different from example 4, and the other steps are the same.
In this comparative example, the enzymatic hydrolysate was prepared from an equal amount of a single pectinase and deionized water.
The preparation method of the rhizoma atractylodis extract comprises the following steps:
(11) crushing the rhizoma atractylodis decoction pieces to 50 meshes to obtain rhizoma atractylodis powder;
(12) adding rhizoma Atractylodis powder into the enzymolysis solution, stirring at 65 deg.C and 200rpm for 50min, performing ultrasonic treatment at 400W for 30min, adding glycerol, and dispersing to obtain mixed solution;
(13) centrifuging the mixed solution at the rotating speed of 5000rpm for 8min, taking supernatant, adding the supernatant into deionized water to prepare sample liquid (the weight ratio of the supernatant to the deionized water is 1: 3), adding the sample liquid on HPD400 macroporous adsorption resin at the speed of 1BV/h, eluting at the speed of 1BV/h, washing 1.5BV with deionized water, then washing 2BV with 70 wt% ethanol solution, collecting ethanol solution eluent, and drying to obtain the rhizoma atractylodis extract.
In the step (12), the weight ratio of the rhizoma atractylodis powder to the enzymolysis liquid to the glycerol is 1: 9: 0.1.
the enzymolysis liquid is prepared from 10 parts by weight of pectinase and 90 parts by weight of deionized water.
Comparative example 4
Comparative example 4 is different from example 4 in that the preparation method of the atractylodes rhizome extract described in comparative example 4 is different from example 4, and the other steps are the same.
In the comparative example, the enzymolysis solution is prepared by replacing cetyl trimethyl ammonium bromide and glucoamylase with equal amount of cellulase.
The preparation method of the rhizoma atractylodis extract comprises the following steps:
(11) crushing the rhizoma atractylodis decoction pieces to 50 meshes to obtain rhizoma atractylodis powder;
(12) adding rhizoma Atractylodis powder into the enzymolysis solution, stirring at 65 deg.C and 200rpm for 50min, performing ultrasonic treatment at 400W for 30min, adding glycerol, and dispersing to obtain mixed solution;
(13) centrifuging the mixed solution at the rotating speed of 5000rpm for 8min, taking supernatant, adding the supernatant into deionized water to prepare sample liquid (the weight ratio of the supernatant to the deionized water is 1: 3), adding the sample liquid on HPD400 macroporous adsorption resin at the speed of 1BV/h, eluting at the speed of 1BV/h, washing 1.5BV with deionized water, then washing 2BV with 70 wt% ethanol solution, collecting ethanol solution eluent, and drying to obtain the rhizoma atractylodis extract.
In the step (12), the weight ratio of the rhizoma atractylodis powder to the enzymolysis liquid to the glycerol is 1: 9: 0.1.
the enzymolysis liquid is prepared from 4 parts by weight of cellulase, 6 parts by weight of pectinase and 90 parts by weight of deionized water.
To further demonstrate the effect of the present invention, the following test methods were provided:
1. quaternary phosphonium salt bacteriostatic effect experiment: will be provided withCulturing Escherichia coli to 10 deg.C8cfu/ml, 100. mu.L of the suspension was applied, after the suspension was absorbed by the medium, a hole (diameter 10mm) was made in the medium, 50. mu.L of a solution to be tested (each of the solutions to be tested was a 5% quaternary phosphonium salt aqueous solution, wherein the quaternary phosphonium salt was the quaternary phosphonium salt prepared in examples 1 to 3) was dropped into the hole, the suspension was cultured at 25 ℃ for 16 hours, and the diameter of the antibacterial ring was observed and measured, and the measurement results are shown in Table 1.
TABLE 1 quaternary phosphonium salt bacteriostatic effect test
| Diameter/mm of bacteriostatic ring | |
| Example 1 (5% aqueous solution of quaternary phosphonium salt) | 9.75 |
| Example 2 (5% aqueous solution of quaternary phosphonium salt) | 8.97 |
| Example 3 (5% aqueous Quaternary phosphorus salt solution) | 9.12 |
As can be seen from Table 1, the quaternary phosphonium salt prepared by the invention has good antibacterial effect and can be used as an effective component of a disinfectant, and the experiment provides a theoretical basis for the quaternary phosphonium salt serving as the effective component of the disinfectant.
2. Culturing the bacterial liquid to be tested to 108The method comprises the steps of uniformly mixing 1000 mu L of bacterial liquid with a to-be-tested bactericidal solution (the disinfector described in examples 4-6 and comparative examples 1-4) according to the volume ratio of 1:1 at cfu/ml concentration (respectively escherichia coli and staphylococcus aureus), and culturing for 24h in an incubator at 25 DEG CAnd detecting the number of colonies in the sample, calculating the bacteriostasis rate, and obtaining a test result shown in a table 5.
TABLE 2 results of the bacteriostatic test
| Inhibition of E.coli/%) | Inhibition of Staphylococcus aureus/%) | |
| Example 4 | 99.99 | 99.99 |
| Example 5 | 97.85 | 97.61 |
| Example 6 | 99.99 | 99.99 |
| Comparative example 1 | 65.78 | 64.21 |
| Comparative example 2 | 67.22 | 67.19 |
| Comparative example 3 | 80.24 | 80.59 |
| Comparative example 4 | 83.24 | 82.18 |
As can be seen from Table 2, the disinfectant of the present invention has good antibacterial and disinfectant effects,
as can be seen from comparison of examples 4-6, the proportions of the different raw materials affect the disinfection effect of the disinfectant.
As can be seen from the comparison of example 4 with comparative examples 1 and 2, the quaternary phosphonium salt prepared by the invention and the rhizoma atractylodis extract have obvious synergistic effect.
As can be seen from comparison of example 4 and comparative examples 3 and 4, the rhizoma atractylodis extract of the present invention can significantly improve the disinfection effect, wherein different rhizoma atractylodis extracts prepared by different rhizoma atractylodis extract preparation methods have different disinfection and sterilization effects, and the rhizoma atractylodis extract prepared by the rhizoma atractylodis extract preparation method of the present invention can significantly improve the disinfection and sterilization effects compared with other methods.
In light of the foregoing description of preferred embodiments according to the invention, it is clear that many changes and modifications can be made by the person skilled in the art without departing from the scope of the invention. The technical scope of the present invention is not limited to the contents of the specification, and must be determined according to the scope of the claims.
Claims (10)
1. The preparation method of the quaternary phosphonium salt is characterized by comprising the following steps:
(1) adding tricyclohexylphosphine, tri-n-butyltetradecyl phosphonium chloride and butanone into a reaction kettle, adding a catalyst, and stirring at the rotating speed of 100-1000 rpm for 2-6 hours at the temperature of 60-90 ℃ to obtain a first mixed solution;
(2) adding corn starch into deionized water, uniformly dispersing, adding chitosan and gamma-aminopropyltriethoxysilane, and stirring at the rotating speed of 200-600 rpm for 60-180 min at the temperature of 65-80 ℃ to obtain a second mixed solution;
(3) dripping the second mixed solution into the first mixed solution, adding an acetic acid solution, stirring at a rotating speed of 400-800 rpm for 1-4 hours under the protection of inert gas, and performing ultrasonic treatment at 200-600W for 15-30 min to obtain a crude product;
(4) and removing redundant butanone through rotary evaporation to obtain the quaternary phosphonium salt.
2. The method for preparing the quaternary phosphonium salt according to claim 1, wherein the weight ratio of tricyclohexylphosphine, tri-n-butyltetradecylphosphine chloride, methyl ethyl ketone, and the catalyst in the step (1) is 1: 1-1.3: 3-8: 0.02-0.06.
3. The method for producing a quaternary phosphonium salt according to claim 1, wherein the catalyst is an organometallic catalyst.
4. The method for preparing quaternary phosphonium salt according to claim 1, wherein the weight ratio of corn starch, deionized water, chitosan, gamma-aminopropyltriethoxysilane in step (2) is 1: 4-8: 0.5-1.2: 0.02 to 0.1.
5. The method for preparing a quaternary phosphonium salt according to claim 1, wherein the weight ratio of the first mixed solution, the second mixed solution and the acetic acid solution in the step (3) is 1: 0.2-0.6: 0.05 to 0.15.
6. The use of the quaternary phosphonium salt prepared by the method of any one of claims 1 to 5 as an active ingredient in disinfectant preparations.
7. The disinfectant is characterized by being prepared from the following raw materials in parts by weight: 0.5-1.2 parts of rhizoma atractylodis extract, 0.8-3 parts of citric acid, 1-5 parts of quaternary phosphonium salt, 6-15 parts of ethylene glycol and 70-90 parts of deionized water;
the quaternary phosphonium salt is prepared by the method for preparing the quaternary phosphonium salt according to any one of claims 1 to 5.
8. The disinfectant as recited in claim 7, wherein the disinfectant is prepared from the following raw materials in parts by weight: 1 part of rhizoma atractylodis extract, 2 parts of citric acid, 4 parts of quaternary phosphonium salt, 10 parts of ethylene glycol and 83 parts of deionized water.
9. The disinfectant according to claim 7, wherein the atractylodes rhizome extract is prepared by the following steps:
(11) crushing the rhizoma atractylodis decoction pieces to 20-100 meshes to obtain rhizoma atractylodis powder;
(12) adding rhizoma atractylodis powder into the enzymolysis liquid, stirring at the rotating speed of 100-400 rpm for 30-60 min at the temperature of 55-70 ℃, performing ultrasonic treatment at 300-800W for 25-40 min, adding glycerol, and dispersing uniformly to obtain a mixed liquid;
(13) centrifuging the mixed solution, taking supernatant, adding the supernatant into deionized water to prepare sample liquid, putting the sample liquid on HPD400 macroporous adsorption resin at the speed of 0.8-2 BV/h, eluting at the speed of 0.8-2 BV/h, washing 1-2 BV with deionized water, washing 1-3 BV with 50-80 wt% ethanol solution, collecting ethanol solution eluent, and drying to obtain the rhizoma atractylodis extract;
in the step (12), the weight ratio of the rhizoma atractylodis powder to the enzymolysis liquid to the glycerol is 1: 3-10: 0.05 to 0.2;
the enzymolysis liquid is prepared from 1 weight part of hexadecyl trimethyl ammonium bromide, 1 to 4 weight parts of glucoamylase, 2 to 8 weight parts of pectinase and 85 to 98 weight parts of deionized water.
10. The disinfectant according to claim 9, wherein the enzymatic hydrolysate is prepared from 1 part by weight of cetyltrimethylammonium bromide, 3 parts by weight of glucoamylase, 6 parts by weight of pectinase and 90 parts by weight of deionized water.
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