CN113788799B - Preparation method and application of antibacterial flame retardant - Google Patents
Preparation method and application of antibacterial flame retardant Download PDFInfo
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- CN113788799B CN113788799B CN202110940841.0A CN202110940841A CN113788799B CN 113788799 B CN113788799 B CN 113788799B CN 202110940841 A CN202110940841 A CN 202110940841A CN 113788799 B CN113788799 B CN 113788799B
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 53
- 239000003063 flame retardant Substances 0.000 title claims abstract description 52
- 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 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 21
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims abstract description 18
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims abstract description 14
- PGSVNTIDEZRNES-UHFFFAOYSA-N 2,4-dibromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C(Br)=C1 PGSVNTIDEZRNES-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000005770 Eugenol Substances 0.000 claims abstract description 9
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229960002217 eugenol Drugs 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 238000004440 column chromatography Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims description 14
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 6
- 229910015900 BF3 Inorganic materials 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 4
- 239000004744 fabric Substances 0.000 abstract description 21
- 238000000576 coating method Methods 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 6
- 238000005580 one pot reaction Methods 0.000 abstract description 5
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000009987 spinning Methods 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 231100000956 nontoxicity Toxicity 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 230000002195 synergetic effect Effects 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract 1
- 238000005192 partition Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000012796 inorganic flame retardant Substances 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 206010059866 Drug resistance Diseases 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000011825 aerospace material Substances 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000004746 geotextile Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000008379 phenol ethers Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
-
- 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
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34922—Melamine; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/18—Fireproof paints including high temperature resistant paints
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Plant Pathology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a preparation method and application of an antibacterial flame retardant, which comprises the following steps: 2,4-dibromobenzaldehyde and a catalyst are added into a dichloromethane solution containing melamine and eugenol, the mixture is stirred and reacted for a period of time at a certain temperature, after the reaction is finished, the solvent is dried by spinning, and the antibacterial flame retardant is obtained by column chromatography separation. The antibacterial flame retardant prepared by the invention is prepared by a one-pot method, and the method has the advantages of simple and convenient operation and high yield. And the 2,4-dibromobenzaldehyde is used for connecting the eugenol and the melamine together, so that the flame retardant effect is achieved, and the antibacterial effect is achieved. The added 2,4-dibromobenzaldehyde can play a role in synergistic flame retardance with melamine. The antibacterial flame retardant can be applied to curtain cloth, soft-packaged wall cloth, antibacterial coating, medical partition cloth, biomedical films and the like, and has the advantages of strong functionality, no toxicity, environmental protection and wide application prospect.
Description
Technical Field
The invention relates to the field of flame-retardant materials, in particular to a preparation method and application of an antibacterial flame retardant.
Background
Nowadays, the multifunctionality of the material is gradually a new industrial requirement, the flame retardance and the antibacterial property of the material are increasingly outstanding among various functional requirements, and the material can be widely applied to the aspects of aerospace materials, living goods, coatings, textile products and the like, but at present, people mainly focus on the research of adding the flame-retardant material or the antibacterial material into a matrix, and the research on the screening of the flame-retardant material and the antibacterial material and the research on the flame-retardant antibacterial composite material are less.
The antibacterial agents on the market are mainly divided into two categories of organic antibacterial agents and inorganic antibacterial agents. The organic antibacterial agent mainly comprises ammonium salt, phenol ethers, phenols and the like. It can play a role in high sterilization speed, strong sterilization capability, convenient processing and the like, but also has the defects of poor heat resistance (easy decomposition and failure at plastic processing temperature, and secondary pollution caused by decomposition products), easy generation of drug resistance, toxic decomposition products and the like. Most of inorganic antibacterial agents are release antibacterial mechanisms, and the nano silver is widely used, but the problems of aggregation and color change exist because of being metal, and no good solution is obtained all the time. However, the current flame retardant products mainly focus on the research on some phosphorus and metal inorganic flame retardants, and the phosphorus flame retardants can generate toxic and corrosive gases during combustion, which have great adverse effects on human bodies and the environment, so that the application of the phosphorus flame retardants is increasingly limited. The metal inorganic flame retardant has bright color, causes limited application range, is easy to oxidize and release harmful and highly toxic gas, generates dust during combustion, is easy to explode, has general flame retardance and heat resistance and is high in cost. Therefore, a novel efficient environment-friendly antibacterial flame retardant is developed, and has important significance in the aspect of life application.
Disclosure of Invention
In order to solve the problems in the prior art, the invention aims to provide a preparation method of a novel efficient environment-friendly antibacterial flame retardant, the antibacterial flame retardant obtained by the preparation method has good antibacterial and flame retardant effects, and is prepared by a one-pot method, so that the method is simple and convenient to operate and high in yield.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method and application of an antibacterial flame retardant are disclosed, which comprises the following steps:
adding 0.5-5mmol of 2, 4-dibromobenzaldehyde and 1-20mol% of catalyst into a dichloromethane solution containing 1-10mmol of melamine and 1-10mmol of eugenol, and stirring to react for 6-24 hours at the temperature of 20-80 ℃; after the reaction is finished, spin-drying the solvent, and separating by column chromatography to obtain a product with the yield of 70-90%;
the main reaction equation is as follows:
preferably, the catalyst is one or more of Lewis acid such as boron trifluoride, ferric chloride and copper trifluoromethanesulfonate.
Preferably, the melamine, 2,4-dibromobenzaldehyde structure is introduced to assist in flame retardance.
Preferably, the preparation method is a nitrogen-containing Friedel-crafts reaction and is prepared by adopting a one-pot method.
The invention also provides an antibacterial flame retardant prepared by the preparation method.
Preferably, the fabric can be applied to the field of textile products, wherein the textile products comprise curtain cloth, soft packing wall cloth, table cloth, bedding cloth, vehicle interior cloth, electric power industry cloth, energy industry cloth, underwater geotextile and the like.
Preferably, the antibacterial material can be applied to the field of biomedical materials, and the materials comprise medical antibacterial coatings, medical separating cloth, disposable medical protective clothing, biomedical films and the like.
Compared with the prior art, the invention has the beneficial effects that:
1. compared with the traditional flame retardant, the antibacterial flame retardant is based on melamine, the melamine salt integrates an acid source and a gas source, has good expansion flame retardant efficiency, can form an expansion type flame retardant, can release a large amount of inert gases capable of diluting combustible gas and reducing the temperature of the combustible gas after being decomposed by heating, has the characteristics of no toxicity, low smoke, high flame retardant efficiency, environmental friendliness and the like, and is better than other flame retardants in the application process.
2. Eugenol is a natural ingredient with excellent antibacterial and calming effects, and is more green, environment-friendly and safe than other antibacterial ingredients. The melamine is connected with 2,4-dibromobenzaldehyde, so that the final product has the effects of antibiosis and flame retardance at the same time, and is prepared by a one-pot method, the method is simple and convenient to operate, and the yield is high.
3. In the preparation process, 2,4-dibromobenzaldehyde participates in the reaction, so that the reaction product and melamine play a role in synergistic flame retardance on the basis of connecting antibacterial and flame retardant components. Meanwhile, 2,4-dibromobenzaldehyde is low in price and easy to purchase, and has more advantages in actual production. The antibacterial flame retardant prepared by the invention can be applied to various aspects, such as soft packing wall cloth, table cloth, medical antibacterial coating, disposable medical protective clothing and the like.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
A preparation method and application of an antibacterial flame retardant are disclosed, which comprises the following steps:
adding 0.5-5mmol of 2, 4-dibromobenzaldehyde and 1-20mol% of catalyst into a dichloromethane solution containing 1-10mmol of melamine and 1-10mmol of eugenol, and stirring to react for 6-24 hours at the temperature of 20-80 ℃; after the reaction is finished, spin-drying the solvent, and separating by column chromatography to obtain a product with the yield of 70-90%;
the main reaction equation is as follows:
wherein the catalyst is one or more of Lewis acid such as boron trifluoride, ferric chloride and copper trifluoromethanesulfonate.
Wherein bromine atoms and melamine structure in the product molecule assist in flame retardancy.
Wherein, the preparation method is a nitrogen-doped Friedel-crafts reaction and is prepared by adopting a one-pot method.
An antibacterial flame retardant prepared by the preparation method.
The prepared antibacterial flame retardant can be applied to curtain cloth, soft-packaged wall cloth, table cloth, bedding cloth, traffic tool interior cloth and the like, and can also be applied to antibacterial coating, medical separation cloth, disposable medical protective clothing, biomedical films and the like.
Example 1
A preparation method and application of an antibacterial flame retardant are disclosed, which comprises the following steps:
adding 0.5mmol of 2, 4-dibromobenzaldehyde and 5mol% of boron trifluoride into a dichloromethane solution containing 1mmol of melamine and 1mmol of eugenol, and stirring to react for 6 hours at the temperature of 20 ℃; after the reaction is finished, spin-drying the solvent, and separating by column chromatography to obtain a product; the yield was 70%.
Example 2
A preparation method and application of an antibacterial flame retardant are disclosed, which comprises the following steps:
adding 3mmol of 2, 4-dibromobenzaldehyde and 10mol percent of ferric chloride into a dichloromethane solution containing 5mmol of melamine and 5mmol of eugenol, and stirring for reaction for 12 hours at the temperature of 50 ℃; after the reaction is finished, the solvent is dried by spinning, and the product is obtained by column chromatography and chromatographic separation, wherein the yield is 80%.
Example 3
A preparation method and application of an antibacterial flame retardant are disclosed, which comprises the following steps:
adding 5mmol of 2, 4-dibromobenzaldehyde and 20mol% of copper trifluoromethanesulfonate into a dichloromethane solution containing 10mmol of melamine and 10mmol of eugenol, and stirring to react for 6-24 hours at the temperature of 80 ℃; after the reaction is finished, the solvent is dried by spinning, and the product is obtained by column chromatography and chromatographic separation, wherein the yield is 90%.
Because the raw material proportion of the antibacterial flame retardant is different, the flame retardant and antibacterial performances of the antibacterial flame retardant are different to different degrees. Therefore, the inventors used the antibacterial flame retardants of preparation examples 1, 2 and 3 and polyvinyl chloride as a base resin in an amount of 30 parts, and applied the flame retardants to polyvinyl chloride (PVC) materials. Thus, the antibacterial and flame retardant property test is carried out, and the measured data are as follows:
(1) Test for antibacterial Property
TABLE 1 antibacterial Property test results
(2) Flame retardancy test
The combustion behavior was determined by the oxygen index method according to GB/T-2406.2-2009, part 2: the flame retardant effect of the material was determined by room temperature testing.
TABLE 2 flame retardance test results
As can be seen from tables 1 and 2, the antibacterial flame retardant prepared by the invention has excellent antibacterial and flame retardant effects, and can be applied to medical antibacterial coatings, medical barrier cloth, disposable medical protective clothing, biomedical films and the like.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Claims (5)
1. The preparation method of the antibacterial flame retardant is characterized by comprising the following steps: the preparation steps are as follows:
adding 0.5-5mmol of 2, 4-dibromobenzaldehyde and 1-20mol% of catalyst into a dichloromethane solution containing 1-10mmol of melamine and 1-10mmol of eugenol, and stirring to react for 6-24 hours at the temperature of 20-80 ℃; after the reaction is finished, spin-drying the solvent, and separating by column chromatography to obtain a product with the yield of 70-90%;
the main reaction equation is as follows:
2. the method for preparing the antibacterial flame retardant according to claim 1, characterized in that: the catalyst is one or more of boron trifluoride, ferric chloride and copper trifluoromethanesulfonate.
3. An antibacterial flame retardant prepared by the preparation method according to any one of claims 1 to 2, characterized in that: the structure of the antibacterial flame retardant is as follows:
4. use of the antibacterial flame retardant of claim 3, characterized in that: the antibacterial flame retardant is applied to the field of textile products.
5. Use of the antibacterial flame retardant of claim 3, characterized in that: the antibacterial flame retardant is applied to the field of biomedical materials.
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| EP0882720B1 (en) * | 1995-12-27 | 2001-08-22 | Nissan Chemical Industries, Limited | Methods for modifying 1,3,5-triazine derivatives |
| CN109336753B (en) * | 2018-11-29 | 2021-08-10 | 丽水学院 | Synthetic method of alpha-benzyl substituted 1, 3-diketone compound |
| CN111170899B (en) * | 2020-01-14 | 2022-03-01 | 丽水学院 | Synthesis method of N-diaryl methyl sulfonamide compound |
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| CN113788799A (en) | 2021-12-14 |
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Effective date of registration: 20240603 Address after: 056000 Middle section of Fuqiang Street East, Qiuxian Economic Development Zone, Handan City, Hebei Province Patentee after: Hebei Hongdu Shengshi Garment Technology Co.,Ltd. Country or region after: China Address before: 323000 No. 1 College Road, Liandu District, Lishui City, Zhejiang Province Patentee before: LISHUI University Country or region before: China |
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Denomination of invention: Preparation method and application of an antibacterial flame retardant Granted publication date: 20230418 Pledgee: Bank of China Limited by Share Ltd. Handan branch Pledgor: Hebei Hongdu Shengshi Garment Technology Co.,Ltd. Registration number: Y2024980042771 |