CN116589772A - Antibacterial PE material and preparation process thereof - Google Patents
Antibacterial PE material and preparation process thereof Download PDFInfo
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- CN116589772A CN116589772A CN202310561669.7A CN202310561669A CN116589772A CN 116589772 A CN116589772 A CN 116589772A CN 202310561669 A CN202310561669 A CN 202310561669A CN 116589772 A CN116589772 A CN 116589772A
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- Prior art keywords
- geraniol
- antibacterial
- grafted
- halamine
- reaction
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- 239000000463 material Substances 0.000 title claims abstract description 55
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical class CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims abstract description 175
- 239000005792 Geraniol Substances 0.000 claims abstract description 81
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims abstract description 81
- 229940113087 geraniol Drugs 0.000 claims abstract description 81
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 31
- 239000002243 precursor Substances 0.000 claims abstract description 16
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000005708 Sodium hypochlorite Substances 0.000 claims abstract description 11
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 35
- 239000000243 solution Substances 0.000 claims description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 238000001035 drying Methods 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 18
- 238000001746 injection moulding Methods 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 7
- 239000008367 deionised water Substances 0.000 claims description 7
- 229910021641 deionized water Inorganic materials 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 238000002791 soaking Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 6
- 230000009977 dual effect Effects 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 7
- 238000001125 extrusion Methods 0.000 description 6
- 238000005469 granulation Methods 0.000 description 6
- 230000003179 granulation Effects 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- 235000010493 xanthan gum Nutrition 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
- 229930008411 3,7-dimethylocta-2,6-dien-1-ol Natural products 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229920006052 Chinlon® Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- -1 wool Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
- C07D233/82—Halogen atoms
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
-
- 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
- A01P3/00—Fungicides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- General Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to the technical field of PE materials, and discloses an antibacterial PE material and a preparation process thereof. The 5, 5-dimethyl hydantoin reacts with the brominated geraniol to obtain a geraniol grafted halamine precursor, then reacts with sodium hypochlorite to obtain a geraniol grafted halamine antibacterial agent, then the PE material and the geraniol grafted halamine antibacterial agent are uniformly mixed, and are placed in a double-screw extruder to be extruded, granulated, dried and injection-molded into sheets, so that the PE antibacterial material is obtained, the stability of geraniol is improved, the dual antibacterial effect is achieved, the stability of geraniol is enhanced, the comprehensive antibacterial effect of the antibacterial agent is enhanced, the antibacterial effect and the antibacterial stability of the antibacterial agent mixed in the PE material are improved, and the antibacterial performance of the PE material is improved.
Description
Technical Field
The invention relates to the technical field of PE materials, in particular to an antibacterial PE material and a preparation process thereof.
Background
The PE material is thermoplastic resin prepared by ethylene polymerization, has the excellent characteristics of low temperature resistance, chemical stability, acid and alkali corrosion resistance and the like, and is widely applied to a plurality of fields such as films, packaging materials, daily necessities, daily water parts, cover plates and the like, so that the research on the antibacterial property of the PE material is one of the important points of research. The invention discloses an antibacterial PE material and a preparation method thereof, and belongs to the technical field of plastics, and the prepared antibacterial PE resin has good antibacterial and bacteriostatic properties, excellent flame retardant property, good mechanical property, good oxidation resistance and aging resistance and wide application prospect, as disclosed in the patent application No. CN 113603990A.
Geraniol is a natural plant source alcohol, also called 3, 7-dimethyl-2, 6-octadien-1-ol, has the advantages of rose fragrance, antibiosis, insect expelling and the like, and is widely applied to the fields of foods, medicines, cosmetics and the like. The halamine compound is a compound containing one or more nitrogen-halogen bonds, has the advantages of durability, high efficiency, low toxicity and reproducibility, and is widely applied to the finishing of fibers and fabrics such as cotton, wool, chinlon, terylene and the like. For example, the literature 'preparation and performance of polyvinyl alcohol/xanthan gum antibacterial film based on N-halamine compound' discloses that N-halamine antibacterial agent 1-chloro-2, 5-tetramethyl-imidazoline is added into a polyvinyl alcohol and xanthan gum antibacterial film mixed system by adopting a blending method, and the prepared film has excellent antibacterial performance.
The invention provides a preparation process of a novel antibacterial agent, which is prepared by grafting a geraniol natural antibacterial agent and a haloamine antibacterial agent, wherein the prepared novel geraniol grafted haloamine antibacterial agent is applied to a PE material, and the prepared antibacterial PE material has excellent antibacterial performance.
Disclosure of Invention
(one) solving the technical problems
Aiming at the defects of the prior art, the invention provides an antibacterial PE material and a preparation process thereof, and the novel geraniol grafted halamine antibacterial agent is prepared and applied to the PE material, so that the antibacterial performance of the PE material is improved.
(II) technical scheme
A preparation process of an antibacterial PE material, which comprises the following steps:
(1) At room temperature, geraniol is dissolved in anhydrous diethyl ether, pyridine catalyst is added into the geraniol, stirring and dissolving are carried out for 5 to 15 minutes, phosphorus tribromide is added into the geraniol for reaction, deionized water, sodium bicarbonate solution and saturated sodium chloride are sequentially used for washing after the reaction is finished, and the geraniol bromide is obtained through drying and rotary evaporation.
(2) Dissolving 5, 5-dimethyl hydantoin in an ether solution filled with sodium hydroxide at 170-200 ℃, carrying out reflux reaction for 20-40min, adding geraniol bromide into the solution after the reaction is finished, carrying out constant-temperature stirring reaction for 20-30h at 50-70 ℃, filtering, distilling under reduced pressure to obtain a geraniol grafted halamine precursor, soaking the geraniol grafted halamine precursor in a sodium hypochlorite solution at 20-35 ℃ for 1-3h, and drying to obtain the geraniol grafted halamine antibacterial agent.
(3) Adding PE material and geraniol grafted halamine antibacterial agent into a high-speed mixer, uniformly mixing, placing into a double-screw extruder, melting, extruding, granulating, drying at 150-200 ℃, and finally putting the mixture into an injection molding machine for injection molding into slices to obtain the PE antibacterial material.
Preferably, the molar ratio of the geraniol to the phosphorus tribromide to the pyridine catalyst is 1:0.4-0.6:0.01-0.05.
Preferably, the mass fraction of the sodium bicarbonate solution in the step (1) is 8-15%.
Preferably, the reaction temperature in the step (1) is 50-100 ℃ and the reaction time is 2-5h.
Preferably, the mass fraction of the sodium hypochlorite solution in the step (2) is 10-15%.
Preferably, in the step (2), the molar ratio of the 5, 5-dimethyl hydantoin, the sodium hydroxide and the brominated geraniol is 1:0.8-1.2:1-1.8.
Preferably, in the step (3), the mass ratio of the PE material to the geraniol grafted haloamine antibacterial agent is 1:0.005-0.01.
(III) beneficial technical effects
The geraniol and phosphorus tribromide undergo substitution reaction under the catalysis of pyridine to obtain the brominated geraniol. Geraniol has lipid solubility, and can dissolve cell membrane or cell wall, so that macromolecular substances in cells flow out, and cells are cracked and dead. The 5, 5-dimethyl hydantoin reacts with the brominated geraniol to obtain a geraniol grafted halamine precursor, and then reacts with sodium hypochlorite to obtain the geraniol grafted halamine antibacterial agent, wherein when the halamine structure acts with water molecules, nitrogen-halogen bonds are broken, released halogen atoms are adsorbed on the surfaces of cells due to the electrostatic effect and enter the cells, so that enzymes in the cells lose activity, biological metabolism is influenced, nutrient supply in the cells is influenced, the activity of the cells is destroyed, and the purposes of resisting and inhibiting bacteria are achieved. The geraniol is a volatile substance, and is combined with the halamine compound, so that the stability of the geraniol is improved, the dual antibacterial effect is achieved, the PE material and the geraniol grafted halamine antibacterial agent are uniformly mixed, and then the PE material and the geraniol grafted halamine antibacterial agent are placed in a double-screw extruder, extruded, granulated, dried and injection-molded into slices, and the PE antibacterial material is obtained. The geraniol is used as a natural antibacterial agent and is easy to volatilize, and the geraniol and the 5, 5-dimethyl hydantoin are subjected to chemical reaction, so that the stability of the geraniol is enhanced, the comprehensive antibacterial effect of the antibacterial agent is enhanced, and the geraniol is applied to PE materials, so that the antibacterial performance of the PE materials is improved.
Drawings
FIG. 1 is a route to geraniol grafted haloamine antimicrobial agents.
Detailed Description
Example 1
(1) At room temperature, 15mol of geraniol is dissolved in anhydrous diethyl ether, then 0.15mol of pyridine catalyst is added into the geraniol, stirring and dissolving are carried out for 12min, then 8mol of phosphorus tribromide is added into the geraniol at 80 ℃ for reaction for 3h, deionized water, sodium bicarbonate solution with the mass fraction of 12% and saturated sodium chloride are used for washing in sequence after the reaction is finished, and the geraniol bromide is obtained through drying and rotary evaporation.
(2) Dissolving 6mol of 5, 5-dimethyl hydantoin in an ether solution filled with 6mol of sodium hydroxide at 190 ℃, carrying out reflux reaction for 30min, adding 9mol of brominated geraniol into the solution after the reaction is finished, carrying out constant-temperature stirring reaction for 25h at 60 ℃, filtering, distilling under reduced pressure to obtain a geraniol grafted halamine precursor, soaking the geraniol grafted halamine precursor in a sodium hypochlorite solution with the mass fraction of 12% at 35 ℃ for 2h, and drying to obtain the geraniol grafted halamine antibacterial agent.
(3) Adding 120g of PE material and 0.6g of geraniol grafted halamine antibacterial agent into a high-speed mixer, uniformly mixing, placing the mixture into a double-screw extruder, carrying out melt extrusion granulation and drying at 150 ℃, and finally putting the mixture into an injection molding machine for injection molding into sheets to obtain the PE antibacterial material.
Example 2
(1) At room temperature, 15mol of geraniol is dissolved in anhydrous diethyl ether, then 0.15mol of pyridine catalyst is added into the geraniol, stirring and dissolving are carried out for 5min, then 6mol of phosphorus tribromide is added into the geraniol at 50 ℃ for reaction for 2h, deionized water, sodium bicarbonate solution with the mass fraction of 8% and saturated sodium chloride are used for washing in sequence after the reaction is finished, and the geraniol bromide is obtained through drying and rotary evaporation.
(2) Dissolving 6mol of 5, 5-dimethyl hydantoin in an ether solution containing 7.2mol of sodium hydroxide at 200 ℃, carrying out reflux reaction for 20min, adding 9mol of brominated geraniol into the solution after the reaction is finished, carrying out constant-temperature stirring reaction for 25h at 60 ℃, filtering, distilling under reduced pressure to obtain a geraniol grafted halamine precursor, soaking the geraniol grafted halamine precursor in a sodium hypochlorite solution with the mass fraction of 12% at 20 ℃ for 2h, and drying to obtain the geraniol grafted halamine antibacterial agent.
(3) Adding 120g of PE material and 0.75g of geraniol grafted halamine antibacterial agent into a high-speed mixer, uniformly mixing, placing the mixture into a double-screw extruder, carrying out melt extrusion granulation and drying at 180 ℃, and finally putting the mixture into an injection molding machine for injection molding into sheets to obtain the PE antibacterial material.
Example 3
(1) At room temperature, 15mol of geraniol is dissolved in anhydrous diethyl ether, then 0.75mol of pyridine catalyst is added into the geraniol, stirring and dissolving are carried out for 15min, then 9mol of phosphorus tribromide is added into the geraniol at 100 ℃ for reaction for 5h, deionized water, 15% sodium bicarbonate solution and saturated sodium chloride are used for washing in sequence after the reaction is finished, and the geraniol bromide is obtained through drying and rotary evaporation.
(2) Dissolving 6mol of 5, 5-dimethyl hydantoin in an ether solution containing 7.2mol of sodium hydroxide at 200 ℃, carrying out reflux reaction for 40min, adding 10.8mol of brominated geraniol into the solution after the reaction is finished, carrying out constant-temperature stirring reaction for 30h at 70 ℃, filtering, distilling under reduced pressure to obtain a geraniol grafted halamine precursor, soaking the geraniol grafted halamine precursor in a sodium hypochlorite solution with the mass fraction of 15% at 30 ℃ for 3h, and drying to obtain the geraniol grafted halamine antibacterial agent.
(3) Adding 120g of PE material and 0.9g of geraniol grafted halamine antibacterial agent into a high-speed mixer, uniformly mixing, placing the mixture into a double-screw extruder, performing melt extrusion granulation at 180 ℃, drying, and finally putting the mixture into an injection molding machine for injection molding into sheets to obtain the PE antibacterial material.
Example 4
(1) At room temperature, 15mol of geraniol is dissolved in anhydrous diethyl ether, 0.4mol of pyridine catalyst is added into the geraniol, stirring and dissolving are carried out for 10min, 8mol of phosphorus tribromide is added into the geraniol at 70 ℃ for reaction for 3h, deionized water, 10% sodium bicarbonate solution and saturated sodium chloride are sequentially used for washing after the reaction is finished, and the geraniol bromide is obtained through drying and rotary evaporation.
(2) Dissolving 6mol of 5, 5-dimethyl hydantoin in an ether solution filled with 6mol of sodium hydroxide at 180 ℃, carrying out reflux reaction for 30min, adding 9.8mol of brominated geraniol into the solution after the reaction is finished, carrying out constant-temperature stirring reaction for 20h at 50 ℃, filtering, distilling under reduced pressure to obtain a geraniol grafted halamine precursor, soaking the geraniol grafted halamine precursor in a sodium hypochlorite solution with the mass fraction of 15% at 35 ℃ for 2h, and drying to obtain the geraniol grafted halamine antibacterial agent.
(3) Adding 120g of PE material and 1.05g of geraniol grafted halamine antibacterial agent into a high-speed mixer, uniformly mixing, placing the mixture into a double-screw extruder, performing melt extrusion granulation at 200 ℃, drying, and finally putting the mixture into an injection molding machine for injection molding into sheets to obtain the PE antibacterial material.
Example 5
(1) At room temperature, 15mol of geraniol is dissolved in anhydrous diethyl ether, then 0.15mol of pyridine catalyst is added into the geraniol, stirring and dissolving are carried out for 12min, then 9mol of phosphorus tribromide is added into the geraniol at 50-100 ℃ for reaction for 3h, after the reaction is finished, deionized water, sodium bicarbonate solution with the mass fraction of 12% and saturated sodium chloride are used for washing, drying and rotary steaming are carried out in sequence, and the brominated geraniol is obtained.
(2) Dissolving 6mol of 5, 5-dimethyl hydantoin in an ether solution containing 4.8mol of sodium hydroxide at 170 ℃, carrying out reflux reaction for 20min, adding 6mol of brominated geraniol into the solution after the reaction is finished, carrying out constant-temperature stirring reaction for 20h at 50 ℃, filtering, distilling under reduced pressure to obtain a geraniol grafted halamine precursor, soaking the geraniol grafted halamine precursor in a sodium hypochlorite solution with the mass fraction of 10% at 30 ℃ for 1h, and drying to obtain the geraniol grafted halamine antibacterial agent.
(3) Adding 120g of PE material and 1.2g of geraniol grafted halamine antibacterial agent into a high-speed mixer, uniformly mixing, placing the mixture into a double-screw extruder, carrying out melt extrusion granulation and drying at 180 ℃, and finally putting the mixture into an injection molding machine for injection molding into sheets to obtain the PE antibacterial material.
Comparative example 1
(1) Adding 120g of PE material into a high-speed mixer, uniformly mixing, placing the PE material into a double-screw extruder, performing melt extrusion granulation at 180 ℃, drying, and finally putting the mixture into an injection molding machine for injection molding into sheets to obtain the PE material.
Adding bacterial suspension into the center of PE material, covering with the same PE material, and immersing the sample in 5mL,0.02mol/L sterile sodium thiosulfate for centrifugation for 30min and 60min, diluting with buffer solution, culturing in a culture dish, culturing at 35 ℃ for 24h at constant temperature, and testing the antibacterial performance of the PE material.
The PE antibacterial material of example 5 has the best antibacterial effect against Staphylococcus aureus and Escherichia coli. The PE antibacterial material of comparative example 1 had the worst antibacterial effect against Staphylococcus aureus and Escherichia coli.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (7)
1. A preparation process of an antibacterial PE material is characterized by comprising the following steps of: the preparation process comprises the following steps:
(1) Dissolving geraniol in anhydrous diethyl ether at room temperature, adding pyridine catalyst, stirring and dissolving for 5-15min, adding phosphorus tribromide to react, washing with deionized water, sodium bicarbonate solution and saturated sodium chloride in sequence after the reaction is finished, drying, and steaming to obtain geraniol bromide;
(2) Dissolving 5, 5-dimethyl hydantoin in an ether solution filled with sodium hydroxide at 170-200 ℃, carrying out reflux reaction for 20-40min, adding geraniol bromide into the solution after the reaction is finished, carrying out constant-temperature stirring reaction for 20-30h at 50-70 ℃, filtering, distilling under reduced pressure to obtain a geraniol grafted halamine precursor, soaking the geraniol grafted halamine precursor in a sodium hypochlorite solution at 20-35 ℃ for 1-3h, and drying to obtain a geraniol grafted halamine antibacterial agent;
(3) Adding PE material and geraniol grafted halamine antibacterial agent into a high-speed mixer, uniformly mixing, placing into a double-screw extruder, melting, extruding, granulating, drying at 150-200 ℃, and finally putting the mixture into an injection molding machine for injection molding into slices to obtain the PE antibacterial material.
2. The process for preparing an antibacterial PE material according to claim 1, characterized in that: the molar ratio of the geraniol to the phosphorus tribromide to the pyridine catalyst in the step (1) is 1:0.4-0.6:0.01-0.05.
3. The process for preparing an antibacterial PE material according to claim 1, characterized in that: the mass fraction of the sodium bicarbonate solution in the step (1) is 8-15%.
4. The process for preparing an antibacterial PE material according to claim 1, characterized in that: the reaction temperature in the step (1) is 50-100 ℃ and the reaction time is 2-5h.
5. The process for preparing an antibacterial PE material according to claim 1, characterized in that: and (3) the mass fraction of the sodium hypochlorite solution in the step (2) is 10-15%.
6. The process for preparing an antibacterial PE material according to claim 1, characterized in that: the molar ratio of the 5, 5-dimethyl hydantoin, the sodium hydroxide and the brominated geraniol in the step (2) is 1:0.8-1.2:1-1.8.
7. The process for preparing an antibacterial PE material according to claim 1, characterized in that: the mass ratio of the PE material to the geraniol grafted halamine antibacterial agent in the step (3) is 1:0.005-0.01.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104396965A (en) * | 2014-11-11 | 2015-03-11 | 张家港互益染整有限公司 | Reaction type halamine antiseptic, preparation method, and applications thereof |
| CN104628665A (en) * | 2015-01-28 | 2015-05-20 | 复旦大学 | Double-bond-containing cyclic halamine antibacterial agent precursor as well as preparation method and application thereof |
| US11084841B1 (en) * | 2020-03-24 | 2021-08-10 | Jiangnan University | Chitooligosaccharide-N-geraniol derivatives, methods for preparing and application thereof |
| CN113527794A (en) * | 2021-08-05 | 2021-10-22 | 界首市锦丰塑业有限公司 | Processing technology of antibacterial toughened polyethylene plastic |
| CN115926297A (en) * | 2023-01-30 | 2023-04-07 | 广东中港印务有限公司 | Antibacterial food packaging film and preparation method thereof |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104396965A (en) * | 2014-11-11 | 2015-03-11 | 张家港互益染整有限公司 | Reaction type halamine antiseptic, preparation method, and applications thereof |
| CN104628665A (en) * | 2015-01-28 | 2015-05-20 | 复旦大学 | Double-bond-containing cyclic halamine antibacterial agent precursor as well as preparation method and application thereof |
| US11084841B1 (en) * | 2020-03-24 | 2021-08-10 | Jiangnan University | Chitooligosaccharide-N-geraniol derivatives, methods for preparing and application thereof |
| CN113527794A (en) * | 2021-08-05 | 2021-10-22 | 界首市锦丰塑业有限公司 | Processing technology of antibacterial toughened polyethylene plastic |
| CN115926297A (en) * | 2023-01-30 | 2023-04-07 | 广东中港印务有限公司 | Antibacterial food packaging film and preparation method thereof |
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