CN115039773A - Application of methyl substituent diallyl quaternary ammonium salt homopolymer in preparation of bactericide - Google Patents
Application of methyl substituent diallyl quaternary ammonium salt homopolymer in preparation of bactericide Download PDFInfo
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- diallyl
- ammonium salt
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 52
- 229920001519 homopolymer Polymers 0.000 title claims abstract description 48
- -1 methyl substituent diallyl quaternary ammonium salt Chemical class 0.000 title claims abstract description 24
- 239000003899 bactericide agent Substances 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 241000588724 Escherichia coli Species 0.000 claims abstract description 32
- 241000191967 Staphylococcus aureus Species 0.000 claims abstract description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000575 pesticide Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000008235 industrial water Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 230000001954 sterilising effect Effects 0.000 description 47
- 238000004659 sterilization and disinfection Methods 0.000 description 40
- 230000001580 bacterial effect Effects 0.000 description 35
- 239000007864 aqueous solution Substances 0.000 description 24
- 238000012258 culturing Methods 0.000 description 20
- 239000007788 liquid Substances 0.000 description 19
- 230000000694 effects Effects 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000000265 homogenisation Methods 0.000 description 6
- PZNOBXVHZYGUEX-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine;hydrochloride Chemical compound Cl.C=CCNCC=C PZNOBXVHZYGUEX-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 150000003863 ammonium salts Chemical group 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229920000289 Polyquaternium Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- WGESLFUSXZBFQF-UHFFFAOYSA-N n-methyl-n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCN(C)CC=C WGESLFUSXZBFQF-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Images
Classifications
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
-
- 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
Abstract
The invention discloses an application of methyl substituent diallyl quaternary ammonium salt homopolymer in preparation of a bactericide. The methyl substituent diallyl quaternary ammonium salt homopolymer is polymethyl propyl diallyl ammonium chloride, polymethyl amyl diallyl ammonium chloride or polymethyl heptyl diallyl ammonium chloride. The methyl substituent diallyl quaternary ammonium salt homopolymer disclosed by the invention is good in water solubility, shows an excellent bactericidal effect on escherichia coli and staphylococcus aureus, and can be applied to the fields of industrial water treatment, medicines, textiles, health care, pesticides and the like.
Description
Technical Field
The invention belongs to the field of antibacterial materials, and relates to an application of a methyl substituent diallyl quaternary ammonium salt homopolymer in preparation of a bactericide.
Background
The quaternary ammonium salt compound as an efficient antibacterial agent is widely applied to the fields of water treatment, medical treatment and health, packaging materials and the like. The polyquaternium as the polynitrogen cationic bactericide is a typical high-molecular organic antibacterial agent, has good antibacterial property and safety, and also has the advantages of difficult volatilization, good chemical stability, low toxicity, environmental friendliness and the like.
Poly dimethyl diallyl ammonium chloride (PDMDAAC) is a five-membered ring water-soluble polyquaternary ammonium salt, and the specific structure of the polyquaternary ammonium salt capable of inhibiting the growth of microorganisms endows the polyquaternary ammonium salt with bactericidal performance, so that the polyquaternary ammonium salt is suitable for various bactericidal treatment processes. However, PDMDAAC has limited applications in many lipophilic fields due to the poor lipophilicity of the monomer DMDAAC. The polymethyl substituent diallyl ammonium chloride is used as a functional group lipophilicity-improved diallyl polyquaternary ammonium salt, and has good lipophilicity on the premise of maintaining higher positive charge density of a polymer unit structure.
The product formed by homopolymerizing DMDAAC and the lipophilic modified monomer thereof through polymerization reaction has good water solubility and good bactericidal effect, and can be applied to a plurality of fields of water treatment, health care, pesticide and the like. However, the reports of methyl substituent diallyl ammonium chloride homopolymers and sterilization performance thereof at home and abroad are poor at present. The related documents available to date are reported below.
Document 1 (Zhao Xiao Lei, Zhang Jun, Zhu Ling. bactericidal performance of characteristic viscosity-series polydimethyldiallyl ammonium chloride [ J ] applied chemistry, 2009,26(01):27-31.) researches the bactericidal capacity of characteristic viscosity-series polydimethyldiallyl ammonium chloride (PDMDAAC), and finds that the higher the characteristic viscosity of PDMDAAC is, the better the bactericidal performance is, and lays a foundation for researching the bactericidal performance of a dimethyldiallyl ammonium chloride series polymer.
Document 2 (liulihua, xiaozirale, chenjinwen, zhao yanmin, liu feng.) synthesis and bactericidal properties [ J ] of poly (N, N-diallyl-N-butoxycarbonyl methyl ammonium chloride application chemistry 2010,27(08):887 jun 892.) poly (N, N-diallyl-N-butoxycarbonyl methyl ammonium chloride) (PDACBMAC) was synthesized by aqueous solution polymerization using N, N-diallyl-N-butoxycarbonyl methyl ammonium chloride (DACBMAC) as a monomer and ammonium persulfate as an initiator, and the bactericidal properties and antibacterial mechanisms of the poly (N, N-diallyl-N-butoxycarbonyl methyl ammonium chloride) on escherichia coli were studied. The result shows that the sterilizing capability of PDACBMAC to the escherichia coli is obviously higher than that of poly dimethyl diallyl ammonium chloride (PDMDAAC), and the sterilizing rate of the PDACBMAC to the escherichia coli is increased along with the increase of the intrinsic viscosity. Therefore, the diallyl polyquaternium with different substituent structures has different bactericidal effects.
Literature 3 (Synthesis of the diallyl methyl alkyl ammonium chloride series of Tao xian, Jia Xue, Zhang Jun, et al [ J ]]Chemical reagent 2019,41(8):779-783.) 7 kinds of diallyl methyl alkyl (n ═ 3, 4, 5, 6, 7, 8, 10) ammonium chloride are synthesized by using 1-bromoalkane and diallyl methylamine with different carbon chains as raw materials, and FT-IR, and, 1 HNMR and element analysis are used for characterizing the structure of the product, and simultaneously determining the water solubility, the surface activity and the flocculation performance of the polymer of the series of monomers.
Disclosure of Invention
The invention aims to provide application of methyl substituent diallyl quaternary ammonium salt homopolymer in preparation of bactericide.
The methyl substituent diallyl quaternary ammonium salt homopolymer is polymethylpropyl diallyl ammonium chloride (PMPDAAC), polymethylpentyl diallyl ammonium chloride (PMADAAC) or polymethylheptyl diallyl ammonium chloride (PMHDAAC).
The methyl substituent diallyl quaternary ammonium salt homopolymer disclosed by the invention has the characteristic viscosity of 0.5-5 dL/g. The characteristic viscosity of the invention refers to the characteristic viscosity measured by 0.1mol/L NaCl solution.
In a specific embodiment of the invention, PMPDAAC has an intrinsic viscosity of 1.09dL/g to 3.22 dL/g. The intrinsic viscosity of PMADAAC is 1.23dL/g, and the intrinsic viscosity of PMHDAAC is 1.03 dL/g.
In the bactericide of the present invention, the concentration of the methyl substituent diallyl quaternary ammonium salt homopolymer is 0.03mg/L to 0.25mg/L, and more preferably 0.15mg/L to 0.25 mg/L.
The bactericidal object of the bactericide in the invention is typical gram-positive bacteria and gram-negative bacteria, including but not limited to escherichia coli, staphylococcus aureus and the like.
The invention discovers for the first time that methyl alkyl substituent diallyl ammonium chloride homopolymers PMPDDAAC, PMADAAC and PMHDAAC have better hydrophilic and lipophilic properties compared with PDMDAAC, show more excellent sterilization performance on escherichia coli and staphylococcus aureus, and can realize effective sterilization in the related field of water treatment.
Drawings
FIG. 1 is a graph showing the bactericidal effect of PMPDDAAC, PMADAAC, PMHDAAC and PDMDAAC homopolymers on E.coli.
FIG. 2 is a graph showing the bactericidal effect of PMPDAAC on E.coli at different characteristic viscosities.
FIG. 3 is a graph of the bactericidal effect of PMPDDAAC, PMADAAC, PMHDAAC and PDMDAAC homopolymers on Staphylococcus aureus.
FIG. 4 is a graph of the bactericidal effect of PMPDAAC on Staphylococcus aureus at different characteristic viscosities.
Detailed Description
The present invention will be described in detail below with reference to specific embodiments and the accompanying drawings.
In the following examples, PMPDAAC, PMADAAC and PMHDAAC homopolymer references (preparation of Zhangjuan. Polyalkyldiallylammonium chloride and study of its structure-activity relationship [ D ]. Nanjing: university of Nanjing Physician, 2018) were used.
Example 1
Selecting the characteristic viscosity [ eta ]]PMPDAAC homopolymer at 1.09dL/g was prepared as an aqueous solution and tested for bactericidal performance: taking a certain volume of escherichia coli micro-polluted bacteria suspension (the bacterial cell content is 10) 4 CFU/mL) in the Erlenmeyer flask, PMPDAAC homopolymer aqueous solution is added, and all the Erlenmeyer flasks are placed in a shaker (140r/min, 20min) for homogenization. Culturing at room temperature for 24h, taking 1mL of bacterial liquid, culturing at 37 ℃ for 24h on a plate, and counting colonies. The bacterial liquid without PMPAAC is used as the airAnd (5) calculating the sterilization rate by using a white control group.
As can be seen from FIG. 1, when the addition amount is 0.10mg/L, the sterilization rate of PMPDAAC on Escherichia coli reaches 93.58%; when the adding amount is 0.25mg/L, the sterilization rate of PMPDAAC on the escherichia coli reaches 99.32%, which shows that PMPDAAC has obvious sterilization effect on the escherichia coli.
Example 2
Selecting the characteristic viscosity [ eta ]]An aqueous solution was prepared from 1.23dL/g of PMADAAC homopolymer and tested for bactericidal performance: taking a certain volume of escherichia coli micro-polluted bacteria suspension (the bacterial cell content is 10) 4 CFU/mL) in erlenmeyer flasks, the aqueous PMADAAC homopolymer solution was added and all erlenmeyers were homogenized by shaking (140r/min, 20min) in a shaker. Culturing at room temperature for 24h, taking 1mL of bacterial liquid, culturing at 37 ℃ for 24h on a plate, and counting colonies. And (4) calculating the sterilization rate by taking the bacterial liquid without PMADAAC as a blank control group.
As can be seen from FIG. 1, the bactericidal rate of PMADAAC on Escherichia coli reaches 97.12% when the addition amount is 0.10 mg/L; when the adding amount is 0.25mg/L, the sterilizing rate of the PMADAAC on the escherichia coli reaches 99.99 percent, which shows that the PMADAAC has obvious sterilizing effect on the escherichia coli.
Example 3
Selecting the characteristic viscosity [ eta ]]An aqueous solution was prepared from PMHDAAC homopolymer at 1.03dL/g, and its bactericidal performance was measured: taking a certain volume of escherichia coli micro-polluted bacteria suspension (the bacterial cell content is 10) 4 CFU/mL) in erlenmeyer flasks, the PMHDAAC homopolymer aqueous solution was added and all erlenmeyers were shaken (140r/min, 20min) uniformly in a shaker. Culturing at room temperature for 24h, taking 1mL of bacterial liquid, culturing at 37 ℃ for 24h on a plate, and then calculating the colony number. And (4) taking the bacterial liquid without PMHDAAC as a blank control group, and calculating the sterilization rate.
As can be seen from FIG. 1, the bactericidal rate of PMHDAAC on Escherichia coli reaches 85.41% when the addition amount is 0.10 mg/L; when the adding amount is 0.25mg/L, the sterilizing rate of the PMHDAAC on the escherichia coli reaches 99.68 percent, which shows that the PMHDAAC has obvious sterilizing effect on the escherichia coli.
Example 4
While selecting the characteristic viscosity [ eta ]]1.09, 2.17 and3.22dL/g PMPDAAC homopolymer, preparing an aqueous solution, and detecting the sterilization performance of the aqueous solution: taking a certain volume of escherichia coli micro-polluted bacteria suspension (the bacterial cell content is 10) 4 CFU/mL) in the Erlenmeyer flask, PMPDAAC homopolymer aqueous solution is added, and all the Erlenmeyer flasks are placed in a shaker (140r/min, 20min) for homogenization. Culturing at room temperature for 24h, taking 1mL of bacterial liquid, culturing at 37 ℃ for 24h on a plate, and counting colonies. And (4) taking the bacterial liquid without PMPDAAC as a blank control group, and calculating the sterilization rate.
As can be seen from fig. 2, when the amount of pmpadac added was 0.10mg/L, [ η ] ═ 1.09, 2.17, and 3.22dL/g, the escherichia coli-killing rates reached 93.58%, 95.72%, and 97.96%, respectively; when the addition amount is 0.25mg/L, the sterilization rate respectively reaches 99.32%, 99.63% and 99.78%, which indicates that PMPAAC has obvious sterilization effect on Escherichia coli.
Comparative example 1
Selecting the characteristic viscosity [ eta ]]PDMDAAC homopolymer, 1.12dL/g, was used to prepare an aqueous solution, which was tested for bactericidal performance: taking a certain volume of Escherichia coli micro-pollution bacterial suspension (the bacterial cell content is 10) 4 CFU/mL) in erlenmeyer flasks, the PDMDAAC homopolymer aqueous solution was added and all erlenmeyers were placed in a shaker (140r/min, 20min) for homogenization. Culturing at room temperature for 24h, taking 1mL of bacterial liquid, culturing at 37 ℃ for 24h on a plate, and counting colonies.
As can be seen from FIG. 1, the bactericidal rate of PDMDAAC against E.coli was only 79.27% at 0.10mg/L, which was lower than the bactericidal rates of PMPDDAAC, PMADAAC and PMHDAAC against E.coli at equivalent doses (93.58%, 97.12% and 85.41%, respectively); the sterilizing rate of PDMDAAC to Escherichia coli is only 99.10% when the adding amount is 0.25mg/L, and is lower than that of PMPDDAAC, PMADAAC and PMHDAAC to Escherichia coli (99.32%, 99.99% and 99.68% respectively) when the adding amount is equal. The above results indicate that PDMDAAC has a weaker bactericidal effect on escherichia coli than pmpadac, PMADAAC and PMHDAAC.
Comparative example 2
The homopolymers in examples 1-3 and comparative example 1 were selected to prepare aqueous solutions, and the aqueous solutions were subjected to the detection of the bactericidal performance of escherichia coli with a fixed bactericidal rate.
When the bactericidal rate of the Escherichia coli is fixed at 90%, the addition amounts of PMPAAC, PMADAC and PMHDAAC are respectively 0.09, 0.06 and 0.10mg/L, and the addition amount of PDMDAAC is 0.13mg/L and is higher than that of PMPAAC, PMADAC and PMHDAAC homopolymers, which indicates that the bactericidal effect is lower than that of PMPAAC, PMADAC and PMHDAAC homopolymers.
Example 5
Selecting the characteristic viscosity [ eta ]]PMPDAAC homopolymer at 1.09dL/g was prepared as an aqueous solution and tested for bactericidal performance: taking a certain volume of staphylococcus aureus micro-pollution bacterial suspension (the bacterial cell content is 10) 4 CFU/mL) in the Erlenmeyer flask, PMPDAAC homopolymer aqueous solution is added, and all the Erlenmeyer flasks are placed in a shaker (140r/min, 20min) for homogenization. Culturing at room temperature for 24h, taking 1mL of bacterial liquid, culturing at 37 ℃ for 24h on a plate, and counting colonies. And (4) taking the bacterial liquid without PMPDAAC as a blank control group, and calculating the sterilization rate.
As can be seen from FIG. 3, when the addition amount is 0.10mg/L, the sterilization rate of PMPDAAC on Staphylococcus aureus reaches 93.2%; when the adding amount is 0.25mg/L, the sterilization rate of PMPDAAC on staphylococcus aureus reaches 99.33%, which shows that PMPDAAC has obvious sterilization effect on staphylococcus aureus.
Example 6
Selecting the characteristic viscosity [ eta ]]An aqueous solution was prepared from 1.23dL/g of PMADAAC homopolymer and tested for bactericidal performance: taking a certain volume of staphylococcus aureus micro-pollution bacterial suspension (the bacterial cell content is 10) 4 CFU/mL) in erlenmeyer flasks, the aqueous PMADAAC homopolymer solution was added and all erlenmeyers were homogenized by shaking (140r/min, 20min) in a shaker. Culturing at room temperature for 24h, taking 1mL of bacterial liquid, culturing at 37 ℃ for 24h on a plate, and counting colonies. And (4) calculating the sterilization rate by taking the bacterial liquid without PMADAAC as a blank control group.
As can be seen from FIG. 3, when the addition amount is 0.10mg/L, the sterilization rate of the PMADACA on staphylococcus aureus reaches 98.63%; when the adding amount is 0.25mg/L, the sterilization rate of the PMADAAC on staphylococcus aureus reaches 99.99%, which shows that the PMADAAC has obvious sterilization effect on staphylococcus aureus.
Example 7
Selecting the characteristic viscosity [ eta ]]＝1.03dL/gPreparing an aqueous solution of the PMHDAAC homopolymer, and detecting the sterilization performance of the aqueous solution: taking a certain volume of staphylococcus aureus micro-pollution bacterial suspension (the bacterial cell content is 10) 4 CFU/mL) in erlenmeyer flasks, the PMHDAAC homopolymer aqueous solution was added and all erlenmeyers were shaken (140r/min, 20min) uniformly in a shaker. Culturing at room temperature for 24h, taking 1mL of bacterial liquid, culturing at 37 ℃ for 24h on a plate, and counting colonies. And (4) taking the bacterial liquid without PMHDAAC as a blank control group, and calculating the sterilization rate.
As can be seen from FIG. 3, when the adding amount is 0.10mg/L, the sterilization rate of the PMHDAAC on staphylococcus aureus reaches 91.63%; when the adding amount is 0.25mg/L, the sterilization rate of the PMHDAAC on staphylococcus aureus reaches 99.30%, which shows that the PMHDAAC has obvious sterilization effect on staphylococcus aureus.
Example 8
Selecting the characteristic viscosity [ eta ]]PMPDAAC homopolymer at 1.09, 2.17 and 3.22dL/g was prepared in aqueous solution and tested for bactericidal performance: taking a certain volume of staphylococcus aureus micro-pollution bacterial suspension (the bacterial cell content is 10) 4 CFU/mL) in the Erlenmeyer flask, PMPDAAC homopolymer aqueous solution is added, and all the Erlenmeyer flasks are placed in a shaker (140r/min, 20min) for homogenization. Culturing at room temperature for 24h, taking 1mL of bacterial liquid, culturing at 37 ℃ for 24h on a plate, and then calculating the colony number. And (4) taking the bacterial liquid without PMPDAAC as a blank control group, and calculating the sterilization rate.
As can be seen from fig. 4, the sterilization rates of staphylococcus aureus by PMPDAAC were 93.2%, 96.19% and 98.03%, respectively, at 0.10mg/L, [ η ] ═ 1.09, 2.17 and 3.22 dL/g; when the addition amount is 0.25mg/L, the sterilization rate respectively reaches 99.33%, 99.76% and 99.92%, which shows that PMPDAAC has obvious sterilization effect on staphylococcus aureus.
Comparative example 3
Selecting the characteristic viscosity [ eta ]]An aqueous solution was prepared from 1.12dL/g PDMDAAC homopolymer and tested for bactericidal performance: taking a certain volume of staphylococcus aureus micro-pollution bacterial suspension (the bacterial cell content is 10) 4 CFU/mL) in erlenmeyer flasks, the PDMDAAC homopolymer aqueous solution was added and all erlenmeyers were placed in a shaker (140r/min, 20min) for homogenization.Culturing at room temperature for 24h, taking 1mL of bacterial liquid, culturing at 37 ℃ for 24h on a plate, and counting colonies. And (4) taking the bacterial liquid without PDMDAAC as a blank control group, and calculating the sterilization rate.
As can be seen from FIG. 3, the bactericidal rate of PDMDAAC against Staphylococcus aureus was only 82.43% at 0.10mg/L, which is lower than the bactericidal rates of PMPDDAAC, PMADAAC and PMHDAAC against Staphylococcus aureus at the same dosage (93.22%, 95.83% and 91.73%, respectively); the sterilization rate of PDMDAAC to staphylococcus aureus is only 99.16% when the dosage is 0.25mg/L, which is lower than the sterilization rate of PMPDDAAC, PMADAAC and PMHDAAC to staphylococcus aureus (99.49%, 99.95% and 99.32% respectively) when the dosage is the same. The above results indicate that PDMDAAC has a weaker bactericidal effect on staphylococcus aureus than pmpadac, PMADAAC and PMHDAAC homopolymers.
Comparative example 4
The homopolymers in examples 4-6 and comparative example 3 are selected to prepare an aqueous solution, and then the sterilization performance of the staphylococcus aureus with fixed sterilization rate is detected.
When the sterilization rate of staphylococcus aureus is fixed at 90%, the dosage of PMPAAC, PMADAC and PMHDAAC is 0.09, 0.06 and 0.09mg/L respectively, and the dosage of PDMDAAC is 0.14mg/L and is higher than that of PMPAAC, PMADAC and PMHDAAC homopolymers, which indicates that the sterilization effect of the staphylococcus aureus is lower than that of PMPAAC, PMADAC and PMHDAAC homopolymers.
In conclusion, the methyl substituent diallyl quaternary ammonium salt homopolymer disclosed by the invention has a good sterilization effect on escherichia coli and staphylococcus aureus, and the sterilization effect is obviously superior to that of unmodified PDMDACC, so that the sterilization performance is improved after alkyl substitution.
The above description is only for the specific implementation method of the present invention, but the protection scope of the present invention is not limited thereto, and the changes or substitutions that can be easily obtained by those skilled in the art within the technical scope of the present invention are all covered within the protection scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (8)
1. The application of methyl substituent diallyl quaternary ammonium salt homopolymer in preparing bactericide is characterized in that the methyl substituent diallyl quaternary ammonium salt homopolymer is polymethyl propyl diallyl ammonium chloride, polymethyl pentyl diallyl ammonium chloride or polymethyl heptyl diallyl ammonium chloride.
2. The use according to claim 1, wherein the methyl-substituted diallyl quaternary ammonium salt homopolymer has an intrinsic viscosity of 0.5 to 5 dL/g.
3. The use according to claim 1, wherein the polymethylpropyldiallylammonium chloride has an intrinsic viscosity of 1.09dL/g to 3.22 dL/g.
4. Use according to claim 1, wherein the polymethylpentyldiallylammonium chloride has a characteristic viscosity of 1.23 dL/g.
5. The use of claim 1, wherein the polymethylheptyldiallylammonium chloride has an intrinsic viscosity of 1.03 dL/g.
6. The use according to claim 1, wherein the concentration of methyl-substituted diallyl quaternary ammonium salt homopolymer in the bactericide is 0.03-0.25 mg/L.
7. The use according to claim 1, wherein the concentration of methyl-substituted diallyl quaternary ammonium salt homopolymer in the bactericide is 0.15mg/L to 0.25 mg/L.
8. The use according to claim 1, wherein the bactericidal object of the bactericide is Escherichia coli or Staphylococcus aureus.
Priority Applications (1)
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|---|---|---|---|---|
| GB1287489A (en) * | 1969-06-19 | 1972-08-31 | Calgon Corp | Water purification |
| JPS54157826A (en) * | 1978-05-30 | 1979-12-13 | Mitsubishi Chem Ind Ltd | Pesticide for controlling viral diseases of plants |
| US5192451A (en) * | 1991-05-06 | 1993-03-09 | Calgon Corporation | Method for controlling zebra mussels in ship ballast tanks |
| CN105145566A (en) * | 2015-07-18 | 2015-12-16 | 广州大学 | Quaternary ammonium salt antibacterial agent and structural type antibacterial resin |
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2022
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| GB1287489A (en) * | 1969-06-19 | 1972-08-31 | Calgon Corp | Water purification |
| JPS54157826A (en) * | 1978-05-30 | 1979-12-13 | Mitsubishi Chem Ind Ltd | Pesticide for controlling viral diseases of plants |
| US5192451A (en) * | 1991-05-06 | 1993-03-09 | Calgon Corporation | Method for controlling zebra mussels in ship ballast tanks |
| CN105145566A (en) * | 2015-07-18 | 2015-12-16 | 广州大学 | Quaternary ammonium salt antibacterial agent and structural type antibacterial resin |
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| 刘立华等: "聚(N,N-二烯丙基-N-丁氧羰甲基氯化铵)的合成及其杀菌性能", 《应用化学》 * |
| 张秀娟: "聚甲基烷基二烯丙基氯化铵的制备及其构效关系研究", 《南京理工大学硕士学位论文》 * |
| 赵晓蕾等: "聚二甲基二烯丙基氯化铵的静态杀菌性能", 《精细化工》 * |
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