CN117903118A - Triazine antibacterial agent, preparation method and application thereof - Google Patents
Triazine antibacterial agent, preparation method and application thereof Download PDFInfo
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- CN117903118A CN117903118A CN202211251574.7A CN202211251574A CN117903118A CN 117903118 A CN117903118 A CN 117903118A CN 202211251574 A CN202211251574 A CN 202211251574A CN 117903118 A CN117903118 A CN 117903118A
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- 239000003242 anti bacterial agent Substances 0.000 title claims abstract description 65
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 38
- 229920000139 polyethylene terephthalate Polymers 0.000 claims abstract description 38
- 239000005020 polyethylene terephthalate Substances 0.000 claims abstract description 38
- -1 polyethylene terephthalate Polymers 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 21
- 230000000845 anti-microbial effect Effects 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 16
- 229920005989 resin Polymers 0.000 claims description 16
- 239000011347 resin Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 239000011159 matrix material Substances 0.000 claims description 13
- 239000000314 lubricant Substances 0.000 claims description 12
- 239000003963 antioxidant agent Substances 0.000 claims description 11
- 230000003078 antioxidant effect Effects 0.000 claims description 11
- 229920000877 Melamine resin Polymers 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002994 raw material Substances 0.000 claims description 9
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
- 239000004599 antimicrobial Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000012298 atmosphere Substances 0.000 claims description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 4
- 229910021641 deionized water Inorganic materials 0.000 claims description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
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- 238000012545 processing Methods 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 claims description 2
- ZPRQXVPYQGBZON-UHFFFAOYSA-N 2-bromo-1h-indole Chemical compound C1=CC=C2NC(Br)=CC2=C1 ZPRQXVPYQGBZON-UHFFFAOYSA-N 0.000 claims description 2
- HBZHNVUMFPGVHW-UHFFFAOYSA-N 2-chloro-1h-indole Chemical compound C1=CC=C2NC(Cl)=CC2=C1 HBZHNVUMFPGVHW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000002193 fatty amides Chemical class 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
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- 235000013872 montan acid ester Nutrition 0.000 claims description 2
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 claims 1
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
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- 238000002156 mixing Methods 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 2
- 235000012141 vanillin Nutrition 0.000 description 2
- WIRLVLFYTTULCM-UHFFFAOYSA-N 2-Bromo-1H-indole-3-carboxaldehyde Chemical compound C1=CC=C2C(C=O)=C(Br)NC2=C1 WIRLVLFYTTULCM-UHFFFAOYSA-N 0.000 description 1
- XYSSNBNFOBVMAU-UHFFFAOYSA-N 2-chloro-1h-indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(Cl)NC2=C1 XYSSNBNFOBVMAU-UHFFFAOYSA-N 0.000 description 1
- 240000003291 Armoracia rusticana Species 0.000 description 1
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
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- 229920002101 Chitin Polymers 0.000 description 1
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- 241000195493 Cryptophyta Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- JPFSNUBRFGFBAR-UHFFFAOYSA-N N-[3-[1-[(4-methylphenyl)methyl]benzimidazol-2-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(=CC=C1)C1=NC2=C(N1CC1=CC=C(C=C1)C)C=CC=C2 JPFSNUBRFGFBAR-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
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- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical class CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The application discloses a triazine antibacterial agent, a preparation method and application thereof. The structure of the antibacterial agent is shown as a formula (I): Wherein R 1、R2 is independently selected from H, substituted or unsubstituted alkyl, or halogen. The triazine antibacterial agent provided by the application has excellent antibacterial performance, high temperature resistance and thermal stability, good compatibility with polyethylene terephthalate (PET), uniform dispersion in PET, precipitation resistance and migration resistance, long-acting and broad-spectrum antibacterial performance of an antibacterial product, and particularly, the mechanical properties such as tensile strength, impact strength and the like of the antibacterial PET product can be obviously improved.
Description
Technical Field
The application relates to an antibacterial agent, in particular to a triazine antibacterial agent, and a preparation method and application thereof.
Background
Antimicrobial agents (anti-bacterial agents) are chemical substances that can maintain the growth or propagation of certain microorganisms (bacteria, fungi, yeasts, algae, viruses, etc.) at or below a necessary level for a certain period of time, and have been widely used in various fields such as industry and agriculture.
The antibacterial agent commonly used at present is mainly inorganic antibacterial agent, organic antibacterial agent, biological antibacterial agent and the like. Typical inorganic antibacterial agents include metals such as silver, copper, and zinc. Typical organic antibacterial agents are mainly vanillin or ethyl vanillin compounds and the like. Typical natural antibacterial agents are mainly extracted from natural plants such as chitin, mustard, castor oil, horseradish, etc. However, if existing inorganic and organic antibacterial agents are used for plastic products and coating products, certain antibacterial performance can be given to the products, but other problems often occur. For example, inorganic antibacterial agents typified by silver ion antibacterial agents or nano silver antibacterial agents have poor compatibility with matrix resins in plastic products, film-forming polymers in coatings, and the like, and are liable to agglomerate, and may cause deterioration in mechanical properties and the like of these products, and a uniform antibacterial effect cannot be obtained. However, organic antibacterial agents such as vanillin have better compatibility with matrix resins and film-forming polymers and are more easily and uniformly dispersed, but have high toxicity, poor thermal stability and easy decomposition, and thus are difficult to be widely used in plastic products.
Disclosure of Invention
The application mainly aims to provide a triazine antibacterial agent, and a preparation method and application thereof, so as to overcome the defects in the prior art.
In order to achieve the purpose of the application, the technical scheme adopted by the application comprises the following steps:
In one aspect, the present application provides a triazine antibacterial agent comprising a compound represented by formula (I):
Wherein R 1、R2 is independently selected from H, substituted or unsubstituted alkyl, or halogen.
In another aspect, the present application provides a method for preparing a triazine antibacterial agent, comprising: reacting melamine with a compound shown in a formula (II) at 100-140 ℃ in the presence of a solvent to obtain the triazine antibacterial agent with a structure shown in the formula (I),
Wherein R 1、R2 is independently selected from H, substituted or unsubstituted alkyl, or halogen.
In another aspect, the application provides the use of the triazine antibacterial agent in the manufacture of a product having antibacterial properties. Such antimicrobial products include, but are not limited to, antimicrobial PET materials or articles thereof, antimicrobial coatings or antimicrobial coatings formed therefrom, and the like.
Compared with the prior art, the application has the following advantages:
(1) The triazine antibacterial agent provided not only has excellent antibacterial performance, but also has excellent high temperature resistance and thermal stability, has good compatibility with polyethylene terephthalate (PET), can be uniformly dispersed in the PET, is resistant to precipitation and migration, can endow an antibacterial product with long-acting and broad-spectrum antibacterial performance, and particularly can also remarkably improve the mechanical properties such as tensile strength, impact strength and the like of the antibacterial PET product.
(2) The triazine antibacterial agent has the advantages of simple and convenient preparation process, high yield, safety, environmental protection, wide raw material sources and low cost.
Detailed Description
Aiming at the defects of the existing inorganic antibacterial agent and organic antibacterial agent, the technical scheme provided by the application mainly comprises the following steps: the melamine is selected to react with indole-3-formaldehyde or derivatives thereof to prepare a triazine antibacterial agent, and the triazine antibacterial agent and the corresponding antibacterial product are used for preparing products with antibacterial functions, and the performances of the triazine antibacterial agent and the corresponding antibacterial products can be seen from the above and the following.
The technical scheme, implementation process and principle of the application will be further explained as follows. It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the application. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.
Some embodiments of the present application provide a triazine-based antibacterial agent comprising a compound represented by formula (I):
Wherein R 1、R2 is independently selected from H, substituted or unsubstituted alkyl, or halogen. The halogen includes fluorine, chlorine, bromine, etc.
In one embodiment, R 1、R2 is H.
In one embodiment, R 1、R2 is independently selected from H, C C3 alkyl or halogen.
In one embodiment, one of R 1、R2 is H and the remainder are selected from C1-C3 alkyl or halogen.
In one embodiment, R 1、R2 is independently selected from H or halogen.
Some embodiments of the application also provide the use of a compound of formula (I) in the preparation of an antibacterial agent.
Some embodiments of the present application also provide a method for preparing a triazine antibacterial agent, comprising: reacting melamine with a compound shown in a formula (II) at 100-140 ℃ in the presence of a solvent to obtain the triazine antibacterial agent with a structure shown in the formula (I),
Wherein R 1、R2 is independently selected from H, C C3 alkyl or halogen, preferably from H, -CH 3 or halogen.
In one embodiment, the molar ratio of melamine to the compound of formula (II) is from 1:1 to 10.
In one embodiment, the solvent includes any one or more of DMSO, ethanol, DMF, and deionized water, and is not limited thereto.
In one embodiment, the reaction time is from 6 to 12 hours.
In one embodiment, the compound represented by the formula (II) includes any one or more of indole 3-carbaldehyde, chloroindole 3-carbaldehyde, bromoindole 3-carbaldehyde, 8-methyl-indole-trioxane, 8-ethyl-indole-2-carbaldehyde, 8-propyl-indole-2-carbaldehyde, and is not limited thereto.
In one embodiment, the preparation method specifically includes: dissolving melamine and a compound shown in a formula (II) in the solvent, carrying out reflux reaction for 6-12 h at 100-140 ℃ in protective atmosphere, and carrying out aftertreatment after the reaction is finished to obtain the triazine antibacterial agent.
Further, the post-processing includes: and after the reaction is finished, dropwise adding the obtained reaction solution into toluene or deionized water for recrystallization, standing, suction filtering and drying in a vacuum oven to obtain the triazine antibacterial agent.
Further, the protective atmosphere includes inert atmosphere such as nitrogen atmosphere, argon atmosphere, or a mixed atmosphere thereof.
Some embodiments of the present application also provide the use of a compound represented by formula (I) in the preparation of an antibacterial product, which may include, but is not limited to, an antibacterial PET material or article thereof, an antibacterial paint or coating formed therefrom, and the like.
Some embodiments of the present application provide an antimicrobial polyethylene terephthalate material comprising: matrix resin, antibacterial agent, antioxidant and lubricant. The matrix resin comprises, preferably consists of, polyethylene terephthalate.
Further, the antioxidant includes any one or more of pentaerythritol tetrakis [ beta- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ], triethylene glycol bis [ triethylene glycol t-butyl-4-hydroxy-5-methylphenyl) propionate ], N' -bis- (3, 5-di-t-butyl-4-hydroxyphenyl) propionyl) hexamethylenediamine, and 1,3, 5-tris (3, 5-di-t-butyl-4-hydroxybenzyl) isocyanuric acid, and is not limited thereto.
Further, the lubricant may be selected from any one or more of lubricants commonly known in the art, such as montanic acid esters or salts, stearates (e.g., calcium stearate, etc.), fatty amides or polyol esters, and is not limited thereto.
In one embodiment, the raw materials of the antibacterial polyethylene terephthalate material comprise the following components in parts by mass: 100 parts of matrix resin, 0.5 to 3 parts of antibacterial agent, 0.1 to 0.3 part of antioxidant and 0.2 to 1.0 part of lubricant.
Some embodiments of the present application also provide a method of preparing an antimicrobial polyethylene terephthalate material, comprising: it comprises the following steps: the matrix resin, the antibacterial agent, the antioxidant and the lubricant are fully and uniformly mixed and then added into a double-screw extruder, and the mixture is mixed and extruded, wherein the processing temperature of the adopted double-screw extruder is 260-280 ℃.
Some embodiments of the present application also provide an antimicrobial coating formed from the antimicrobial coating.
The triazine antibacterial agent provided by the embodiment of the application has the advantages of wide antibacterial range, strong antibacterial capability, excellent heat stability, biological sources of main raw materials, safety, environmental protection and wide sources, can be compounded with matrix resins such as PET (polyethylene terephthalate) in a mode of blending, melting, extrusion and the like, is not easy to be decomposed by heat, has good compatibility with the matrix resins such as PET, can effectively guarantee and promote the antibacterial performance, mechanical property and the like of antibacterial PET products, is safe and reliable, has no peculiar smell, and has low harm and pollution degree to human bodies and environment. The preparation process of the triazine antibacterial agent and the antibacterial PET material provided by the embodiment of the application has the advantages of simplicity and easiness in operation control, high yield, safety, environmental protection, low cost, suitability for industrial production and the like.
The technical solution of the present application will be described in further detail below with reference to several preferred embodiments, and it is apparent that the described embodiments are only some embodiments of the present application, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the application without making any inventive effort, are intended to be within the scope of the application. Unless otherwise indicated, reagents and starting materials used in the following examples were obtained commercially, and test methods in which specific conditions were not noted were generally conducted under conventional conditions or under conditions recommended by the respective manufacturers. Further, unless otherwise indicated, the experimental methods, detection methods, and preparation methods disclosed in the present application all employ techniques conventional in the art. These techniques are well described in the prior art.
The antimicrobial agent used in the following examples was prepared mainly by the following method, including: dissolving melamine and indole 3-formaldehyde or derivatives thereof in a molar ratio of 1:1, 1:2, 1:3, 1:8 and 1:10 in DMSO, ethanol, deionized water, DMF or a mixed solvent of a plurality of solvents, respectively stirring and reacting at 100 ℃, 110 ℃, 120 ℃, 130 ℃, 140 ℃ for 6 hours, 8 hours and 12 hours, and after the reaction is finished, carrying out suction filtration from a reaction system to obtain a precipitate, namely the target product triazine antibacterial agent.
Wherein the indole 3-formaldehyde derivative is selected from bromoindole 3-formaldehyde, chloroindole 3-formaldehyde, 8-methyl-indole-trioxymethylene, 8-ethyl-indole-2-formaldehyde, 8-propyl-indole-2-formaldehyde and the like. By regulating the types, the reaction temperature and the reaction time of indole 3-formaldehyde and derivatives thereof, a series of antibacterial agent products are obtained, and the structural general formula of the antibacterial agent products is shown as formula (I).
More specifically:
one of the triazine antibacterial products has the following structural formula:
The nuclear magnetic characterization information of the antibacterial agent is as follows: 1 H-NMR (300 MHz, DMSO, ppm): 11.28 (-NH, indole ring, 3H), 7.07 (-CH, indole ring, 3H), 7.19 (-CH, indole ring, 3H), 7.40 (-CH, indole ring, 3H), 7.63 (-CH, indole ring, 3H), 8.43 (-CH, indole ring ,3H),8.46(-CH,1H),9.32(-CH,2H);13C-NMR(100MHz,CDCl3,ppm)：137.1,137.1,137.1,130.7,130.7,130.7,126.3,126.3,126.3,110.4,110.4,110.4,166.2,166.2,166.2,111.1,111.1,111.1,121.8,121.8,121.8,121.7,121.7,121.7,119.8,119.8,119.8,160.0,160.0,160.0. which is defined as antimicrobial agent 1 in tables 1, 4.
The nuclear magnetic characterization information of one triazine antibacterial product (R 1 is Cl and R 2 is H) is as follows: 1 H-NMR (300 MHz, DMSO, ppm): 10.85 (-NH, indole ring, 3H), 6.87 (-CH, indole ring, 3H), 7.22 (-CH, indole ring, 3H), 7.63 (-CH, indole ring, 3H), 8.08 (-CH, indole ring ,3H),8.46(-CH,1H),9.32(-CH,2H);13C-NMR(100MHz,CDCl3,ppm)：136.8,136.8,136.8,130.7,130.7,130.7,127.7,127.7,119.6,119.6,119.6,166.2,166.2,166.2,119.9,119.9,119.9,119.9,119.9,119.9,120.6,120.6,120.6,160.0,160.0.160.0. which is defined as antimicrobial 2 in tables 1, 4.
The nuclear magnetic characterization information of one triazine antibacterial product (R 2 is Br and R 1 is H) is as follows: 1 H-NMR (300 MHz, DMSO, ppm): 11.53 (-NH, indole ring, 3H), 7.64 (-CH, indole ring, 3H), 7.00 (-CH, indole ring, 3H), 7.05 (-CH, indole ring, 3H), 8.47 (-CH, indole ring ,3H),8.46(-CH,1H),9.32(-CH,2H);13C-NMR(100MHz,CDCl3,ppm)：112.0,112.0,112.0,135.5,135.5,135.5,126.3,126.3,126.3,110.4,110.4,110.4,166.2,166.2,166.2,111.1,111.1,111.1,121.8,121.8,121.8,121.7,121.7,121.7,119.8,119.8,119.8,160.0,160.0,160.0. which is defined as antimicrobial 3 in tables 1, 4).
The nuclear magnetic characterization information of one triazine antibacterial product (R 1 is methyl and R 2 is H) is as follows: 1 H-NMR (300 MHz, DMSO, ppm): 10.85 (-NH, indole ring, 3H), 7.11 (-CH, indole ring, 3H), 6.88 (-CH, indole ring, 3H), 8.10 (-CH, indole ring, 3H), 7.63 (-CH, indole ring ,3H),8.46(-CH,1H),9.32(-CH,2H),2.70(-CH,9H);13C-NMR(100MHz,CDCl3,ppm)：136.5,136.5,136.5,130.7,130.7,130.7,126.2,126.2,126.2,110.4,110.4,110.4,166.2,166.2,166.2,120.5,120.5,120.5,118.8,118.8,118.8,120.1,120.1,120.1,122.2,122.2,122.2,160.0,160.0,160.0,16.6,16.6,16.6. which is defined as antimicrobial agent 4 in tables 1, 4.
The antibacterial PET product can be prepared by utilizing the various triazine antibacterial agents in the embodiment, and the corresponding preparation method comprises the following steps: adding PET resin, an antibacterial agent, an antioxidant and a lubricant into a mixer, mixing for 10-15 min, and adding the uniformly mixed materials into a double-screw extruder for mixing and extruding to obtain the antibacterial PET material, wherein the adopted double-screw extrusion processing temperature is 260-280 ℃. The dosage proportion of the PET resin, the antibacterial agent, the antioxidant and the lubricant, the types of the PET resin, the antibacterial agent, the antioxidant and the lubricant, the extrusion temperature and the like can be adjusted according to actual production requirements.
Further, the present inventors prepared a series of antibacterial PET products using the aforementioned triazine antibacterial agent products (abbreviated as "antibacterial agent" in tables 1 and 2) according to the process conditions shown in Table 1, and the results of the performance test of these antibacterial PET products can be seen in Table 1. Wherein the antibacterial performance, the secondary pulling performance and the impact strength of each product are respectively tested according to the methods specified in GB/T31402-2015, GB/T1040.1-2018 and GB/T1043.2-2018.
TABLE 1 raw material composition of various antibacterial PET products in examples of the application and results of performance test
Note that: the data shown in column D, G of Table 1 are all averages of the samples after testing.
The results of performance testing of a series of PET products prepared using the process conditions shown in table 2 without the addition of any of the triazine based antimicrobial products described above can also be seen in table 2.
TABLE 2 raw material composition and Performance test results for various PET products of comparative example 1 of the present application
Note that: the data shown in column D, G of Table 2 are all averages of the samples after testing.
In the case of replacing the aforementioned triazine based antimicrobial products with commercially available inorganic silver ion antimicrobial agents, the results of performance testing of a series of PET products prepared using the process conditions shown in table 3 can be seen in table 3.
TABLE 3 raw material composition and Performance test results for various PET products of comparative example 2 of the present application
Note that: the data shown in column D, G of Table 3 are all averages of the samples after testing.
If other types of matrix resins are used in combination with the triazine antimicrobial products, the performance test results of a series of antimicrobial plastic products prepared using the process conditions shown in table 4 can be seen in table 4.
TABLE 4 raw material composition and Performance test results for various antibacterial Plastic products of comparative example 3 of the present application
Note that: the data shown in column D, G of Table 4 are all averages of the samples after testing.
In addition, the inventors have conducted experiments with other materials, process operations, and process conditions as described in this specification with reference to the foregoing examples, and have all obtained desirable results.
While the application has been described with reference to illustrative embodiments, it will be understood by those skilled in the art that various other changes, omissions and/or additions may be made and substantial equivalents may be substituted for the materials of the embodiments shown without departing from the spirit and scope of the application. In addition, many modifications may be made to adapt a particular situation or material to the teachings of the application without departing from the scope thereof. Therefore, it is intended that the application not be limited to the particular embodiment disclosed for carrying out this application, but that the application will include all embodiments falling within the scope of the appended claims.
Claims (10)
1. A triazine-based antibacterial agent, characterized in that the antibacterial agent comprises a compound represented by formula (I):
Wherein R 1、R2 is independently selected from H, substituted or unsubstituted alkyl, or halogen.
2. The triazine antibacterial agent of claim 1, wherein R 1、R2 is H; or one of R 1、R2 is H, the rest is selected from C1-C3 alkyl, fluorine, chlorine or bromine.
3. The use of a compound of formula (I) for the preparation of an antibacterial agent,
Wherein R 1、R2 is independently selected from H, substituted or unsubstituted alkyl, or halogen.
4. A method for preparing a triazine antibacterial agent, which is characterized by comprising the following steps: reacting melamine with a compound shown in a formula (II) at 100-140 ℃ in the presence of a solvent to obtain the triazine antibacterial agent with a structure shown in the formula (I),
Wherein R 1、R2 is independently selected from H, substituted or unsubstituted alkyl, or halogen.
5. The method of manufacturing according to claim 4, wherein: r 1、R2 is independently selected from H, C-C3 alkyl or halogen;
And/or the molar ratio of melamine to the compound of formula (II) is 1:1-10;
and/or the solvent comprises any one or more of DMSO, ethanol, DMF, and deionized water;
and/or the reaction time is 6-12 h;
And/or the compound shown in the formula (II) comprises any one or more of indole 3-formaldehyde, chloroindole 3-formaldehyde, bromoindole 3-formaldehyde, 8-methyl-indole-trioxymethylene, 8-ethyl-indole-2-formaldehyde and 8-propyl-indole-2-formaldehyde.
6. The preparation method according to claim 4, characterized by comprising the following steps: dissolving melamine and a compound shown in a formula (II) in the solvent, carrying out reflux reaction for 6-12 h at 100-140 ℃ in protective atmosphere, and carrying out aftertreatment after the reaction is finished to obtain the triazine antibacterial agent.
7. An antibacterial polyethylene terephthalate material, the raw materials of which comprise a matrix resin, an antioxidant, a lubricant and an antibacterial agent, wherein the matrix resin comprises polyethylene terephthalate, and the antibacterial agent is characterized in that the antibacterial agent comprises a compound shown in a formula (I):
wherein R 1、R2 is independently selected from H, C C3 alkyl or halogen.
8. The antibacterial polyethylene terephthalate material according to claim 7, wherein the raw materials of the antibacterial polyethylene terephthalate material comprise the following components in parts by mass: 100 parts of matrix resin, 0.5 to 3 parts of antibacterial agent, 0.1 to 0.3 part of antioxidant and 0.2 to 1.0 part of lubricant;
And/or the antioxidant comprises any one or more of pentaerythritol tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], triethylene glycol bis [ triethylene glycol tert-butyl-4-hydroxy-5-methylphenyl) propionate ], N-bis- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl) hexamethylenediamine and 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanuric acid;
And/or the lubricant comprises any one or more of montanic acid esters or salts, stearates, fatty amides or polyol esters.
9. A method for producing the antibacterial polyethylene terephthalate material according to any of claims 7-8, characterized by comprising: the matrix resin, the antibacterial agent, the antioxidant and the lubricant are fully and uniformly mixed and then added into a double-screw extruder, and the mixture is mixed and extruded, wherein the processing temperature of the adopted double-screw extruder is 260-280 ℃.
10. An antimicrobial polyethylene terephthalate wire formed from the antimicrobial polyethylene terephthalate material of any of claims 7-8.
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