CN108976213B - Halamine antibacterial agent containing double active groups and preparation method and application thereof - Google Patents
Halamine antibacterial agent containing double active groups and preparation method and application thereof Download PDFInfo
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- CN108976213B CN108976213B CN201811029887.1A CN201811029887A CN108976213B CN 108976213 B CN108976213 B CN 108976213B CN 201811029887 A CN201811029887 A CN 201811029887A CN 108976213 B CN108976213 B CN 108976213B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
Abstract
The invention discloses a halamine antibacterial agent containing double active groups, which has a structure shown as a general formula (1), wherein in the general formula (1), R1、R2The antibacterial agent is independently expressed as Cl or Br, 5-dimethylhydantoin, 2-chloroethylamine hydrochloride and alkali are reacted to prepare aminoethylhydantoin, then the aminoethylhydantoin is reacted with para (β -ethyl sulfone sodium sulfate) aniline, cyanuric chloride and the like to prepare a halamine antibacterial precursor, and finally the halamine antibacterial agent is prepared after the treatment of a sodium hypochlorite solution.
Description
Technical Field
The invention relates to the technical field of antibiosis, in particular to a halamine antibacterial agent containing double active groups and a preparation method and application thereof.
Background
Along with the remarkable improvement of the living standard of people in China and the rapid development of industry, the awareness of people on health safety and environmental sanitation is increasingly strengthened, and the antibiosis becomes more and more important in many fields. Cotton is the most commonly used natural fiber at present, and is widely used by people in clothes, home textiles and other occasions closely contacted with human bodies due to good performance. However, the good hygroscopicity of the cotton fiber and the saccharides contained in the fiber provide energy for the propagation of microorganisms under certain conditions (including humidity and temperature), so that the microorganisms can grow and propagate rapidly. This can be a health hazard to humans and affect the wearability of the fabric. Therefore, the antibacterial finishing of cotton fabrics is receiving extensive attention from researchers, and many different antibacterial agents are emerging, which are classified into three types, inorganic antibacterial agents, organic antibacterial agents and natural antibacterial agents. However, most of the antibacterial agents have the defects of poor washing fastness and slow sterilization rate; extraction of natural antibacterial agents is difficult; most organic antibacterial agents have toxic and side effects and are harmful to human bodies.
The halamine antibacterial agent is one of organic antibacterial agents, and has the characteristics of most ideal antibacterial agents: cheap raw materials, simple and convenient synthesis, easy storage, long validity period, high sterilization efficiency, difficult decomposition or conversion into toxic substances, broad-spectrum sterilization, antibiosis, regeneration and the like. The structure of the halamine antibacterial agent contains one or more than one N-X (X represents Cl, F and Br), the halamine antibacterial agent is contacted with microorganisms to release X < + > to destroy or inhibit the metabolism of the microorganisms so as to achieve the aim of sterilization, and the N-X is reduced into N-H in the sterilization process, and can be changed into an N-X structure with antibacterial property again through the action of a halogenating agent (such as sodium hypochlorite).
The common rolling baking finishing technology has great influence on the performance of cotton fabrics, and cotton fibers contain a plurality of active hydroxyl groups and can react with some active groups. This gives direction to the selection and application of the antimicrobial agent.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a halamine antibacterial agent containing double active groups, and a preparation method and application thereof. The preparation method is simple, the raw materials are low in price, the product is simple and convenient to purify, the finishing step is simple, and the finished product has good antibacterial property and stability.
The technical scheme of the invention is as follows:
a halamine antibacterial agent containing double active groups has a structure shown as a general formula (1):
in the general formula (1), R1、R2Each independently represents Cl or Br.
A preparation method of a halamine antibacterial agent containing double active groups comprises the following steps:
(1) dissolving 5, 5-dimethylhydantoin and 2-chloroethylamine hydrochloride in water or an organic solvent, adding alkali, stirring and refluxing for 12-16 h at 60-70 ℃, distilling under reduced pressure after the reaction is finished to evaporate the solvent, washing the primary product with acetone or ethanol, filtering, and distilling out the acetone or ethanol in the filtrate through reduced pressure distillation to obtain aminoethyl hydantoin;
(2) adding the suspension liquid of p- (β -ethyl sulfone sodium sulfate) aniline into water or an organic solvent containing cyanuric chloride, reacting for 2-4 h at 0-5 ℃, then adding the aqueous solution of aminoethyl hydantoin obtained in the step (1), reacting for 3-5 h at 30-50 ℃, adding an acid binding agent dropwise to adjust the pH value to 5.0-6.0, salting out, filtering, purifying and drying after the reaction is finished, and obtaining a halamine antibacterial precursor (II);
(3) and (3) placing the halamine antibacterial precursor (II) in a sodium hypochlorite aqueous solution, standing for 0.5-4 h at the temperature of 20-40 ℃, filtering, and drying to obtain the halamine antibacterial agent.
In the step (1), the alkali is one or a mixture of sodium hydroxide and potassium hydroxide; the molar ratio of the 5, 5-dimethylhydantoin, the 2-chloroethylamine hydrochloride to the alkali is 1:1: 2.
In the step (1), the organic solvent is one or more of ethanol, N-dimethylformamide and acetone, and the dosage of the organic solvent is such that the concentration of the reaction raw material in the solvent reaches 1-10 w/v%.
In the step (2), the molar ratio of cyanuric chloride to p- (β -ethyl sulfone sodium sulfate) aniline to aminoethyl hydantoin is 1:1: 1.
In the step (2), the organic solvent is one or more of acetone, carbon tetrachloride, diethyl ether, ethanol, dioxane and chloroform; the concentration of the cyanuric chloride in water or an organic solvent is 1-20 w/v%; the acid-binding agent is one or more of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate and sodium bicarbonate.
The structural formula of the halamine antibacterial precursor (II) is as follows:
an application of a halamine antibacterial agent containing double active groups, wherein the halamine antibacterial agent is used in the technical field of antibacterial finishing of textiles.
The application method comprises the following steps:
(1) dissolving a halamine antibacterial precursor and a metal salt in water to prepare an antibacterial finishing liquid, and soaking the textile to be treated in the finishing liquid at room temperature for 10-60 min;
(2) adding a solid alkaline agent, soaking at 60-80 ℃ for 2-5 h, taking out the textile, washing with water, and drying;
(3) and finally, soaking the textile in a sodium hypochlorite solution with the concentration of 0.1-1 wt% for halogenation reaction, taking out and drying to obtain the antibacterial textile.
The concentration of the precursor of the halamine antibacterial agent in the step (1) is 0.1-5% (w/v); the metal salt is one or more of sodium sulfate, calcium sulfate, magnesium sulfate, zinc sulfate, sodium chloride, magnesium chloride and calcium chloride, and the final concentration is 50-200 g/L; in the step (2), the solid alkaline agent is one or more of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate and sodium bicarbonate, and the final concentration is 1-5 g/L.
The beneficial technical effects of the invention are as follows:
(1) according to the invention, 5-dimethylhydantoin is reacted with 2-chloroethylamine hydrochloride to generate aminoethyl hydantoin, so that the problem that 5, 5-dimethylhydantoin cannot be directly reacted with cyanuric chloride is solved;
(2) the first chlorine on cyanuric chloride is replaced by p- (β -ethyl sulfone sodium sulfate) aniline, so that the problem that hydroxyl in aminoethyl hydantoin is inactive at low temperature is solved;
(3) the introduction of (β -ethyl sulfone sodium sulfate) aniline enables the halamine antibacterial precursor to have double active groups, and the stability of the dye uptake of the halamine antibacterial precursor is improved;
(4) test results show that the maximum chlorine content of the fabric subjected to antibacterial finishing can reach 0.52 percent; the whole synthesis process is simple to operate, no toxic by-product is generated, and the synthesis raw material is low in price;
(5) compared with the prior reactive antibacterial agent precursor, the antibacterial precursor has the advantages that one more active group is added, the probability of combination with the fabric is higher, the using amount of the antibacterial precursor is saved, and the antibacterial precursor can perform nucleophilic substitution or nucleophilic addition reaction with hydroxyl on plant fiber molecules at a lower temperature (60-80 ℃) to form a covalent bond with the hydroxyl to be combined with the fibers. The reaction process is simple, the efficiency is high, no toxic or pollutant is generated, and the processing requirement of the ecological textile is met.
Drawings
FIG. 1 is a synthetic route and a chlorination reaction equation of a diamine halide antibacterial precursor containing a double active group in example 1 of the present invention;
FIG. 2 is an infrared spectroscopic analysis chart of cotton fabric before and after finishing, wherein: a is cotton fabric before finishing, B is cotton fabric after finishing;
FIG. 3 is a scanning electron micrograph of cotton fabric before and after finishing, wherein: a is cotton fabric before finishing, and B is cotton fabric after finishing.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings and examples.
Example 1
Referring to fig. 1, a method for preparing a halamine-based antibacterial agent containing a double active group includes the following steps:
(1) weighing 2.34g of 2-chloroethylamine hydrochloride, 1.66g of sodium hydroxide and 2.61g of 5, 5-dimethyl hydantoin, reacting in ethanol for 12h, filtering to remove sodium chloride after the reaction is finished, and carrying out reduced pressure distillation and drying to obtain aminoethyl hydantoin;
(3) weighing 3.64g of cyanuric chloride, dissolving the cyanuric chloride in 25mL of acetone, weighing 5.64g of p- (β -ethyl sulfone sodium sulfate) aniline and 1.06g of sodium carbonate, dissolving the cyanuric chloride and the sodium carbonate in 20mL of water, mixing the two, reacting in a 250mL three-neck flask at 0-5 ℃ under the condition that the pH value is 2.5-3.5 for 2h, then dissolving the obtained 25mL of aminoethyl hydantoin in 25mL of water, pouring the mixture into a reaction solution, heating to 40 ℃, reacting for 4h under the condition that the pH value is 5.0-6.0, adding 20% of sodium chloride solid (relative to the weight of the reaction solution) for salting out, filtering after finishing, cleaning with ethanol and acetone, drying and storing to obtain the haloamine antibacterial precursor 2-chloro-4- (4- (β -ethyl sulfone sodium sulfate) phenylamino) -6-aminoethyl hydantoin-1, 3, 5-triazine.
Example 2
Referring to fig. 1, a method for preparing a halamine-based antibacterial agent containing a double active group includes the following steps:
(1) refluxing 2.61g of 5, 5-dimethylhydantoin and 0.83g of sodium hydroxide in ethanol for 10min, adding the mixture into an ethanol solution of 2.34g of 2-chloroethylamine hydrochloride and 1.06g of sodium carbonate powder, reacting for 14h, then performing suction filtration to remove sodium chloride, and performing reduced pressure distillation and drying to obtain aminoethyl hydantoin;
(2) weighing 3.64g of cyanuric chloride, adding the cyanuric chloride into 25mL of water, stirring, dissolving the obtained aminoethyl hydantoin in 25mL of water, dropwise adding the cyanuric chloride into the cyanuric chloride suspension, reacting for 3h in an ice bath, adding 5.64g of p- (β -ethyl sulfone sodium sulfate) aniline and 1.06g of sodium carbonate aqueous solution, reacting for 2h at 40 ℃, adjusting the pH to be 5-7 in the whole process, adding 20% of sodium chloride solid (relative to the weight of the reaction solution) after the reaction is finished, salting out, filtering, washing with ethanol and acetone, drying and storing to obtain the halamine antibacterial precursor 2-chloro-4- (4- (β -ethyl sulfone sodium sulfate) phenylamino) -6-aminoethyl hydantoin-1, 3, 5-triazine.
Example 3
An antibacterial agent precursor, the preparation method comprises the following steps:
(1) weighing 3.64g of cyanuric chloride, 5.64g of p- (β -ethyl sulfone sodium sulfate) aniline and 1.06g of sodium carbonate, adding the materials into 50mL of water, reacting for 5 hours, adjusting the pH value to 2.5-3.5, performing suction filtration, cleaning with ethanol and methanol, and drying;
(2) refluxing 2.61g of 5, 5-dimethylhydantoin and 0.83g of sodium hydroxide in ethanol for 10min, adding the obtained mixture into an ethanol solution of 2.34g of 2-chloroethylamine hydrochloride and 1.06g of sodium carbonate powder, reacting for 16h, adding the solid aqueous solution obtained in the previous step, adjusting the pH value to 5-6, reacting for 4h, performing suction filtration after the reaction is finished, cleaning with ethanol, drying and storing to obtain the antibacterial agent precursor.
Application example:
application example 1
0.5g of cotton fabric is immersed in an antibacterial finishing liquid prepared by dissolving 0.05g of the antibacterial precursor prepared in the example 1 and 1g of sodium sulfate in 20mL of water at room temperature for 0.5 h; heating to 60 ℃, adding 0.1g of sodium hydroxide, soaking for 3h, taking out the fabric, soaping, washing with water and drying; and (3) soaking the dried modified cotton fabric in a 10% commercial sodium hypochlorite solution with the pH value of 7 for 1h to prepare the antibacterial cotton fabric, and measuring the chlorine content to be 0.32%. The chlorination reaction is shown in figure 1.
Application example 2
0.5g of cotton fabric is dipped into an antibacterial finishing liquid prepared by dissolving 0.1g of the antibacterial precursor 2-chloro-4- (4- (β -ethyl sulfone sodium sulfate) phenylamino) -6-aminoethylhydantoin-1, 3, 5-triazine and 2g of sodium chloride in 20mL of water at room temperature for 10min, the temperature is increased to 80 ℃, 0.02g of potassium hydroxide is added, after dipping for 2h, the fabric is taken out, soaped, washed and dried, and the dried modified cotton fabric is dipped in a commercial sodium hypochlorite solution with the pH of 50 percent of 7 for 1h to prepare the antibacterial cotton fabric, and the chlorine content is measured to be 0.37 percent.
Application example 3
0.5g of cotton fabric is dipped into an antibacterial finishing liquid prepared by dissolving 0.1g of the antibacterial precursor 2-chloro-4- (4- (β -ethyl sulfone sodium sulfate) phenylamino) -6-aminoethylhydantoin-1, 3, 5-triazine and 4g of magnesium sulfate prepared in example 1 in 20mL of water at room temperature for 1h, the temperature is raised to 70 ℃, 0.05g of sodium hydroxide is added, after dipping for 5h, the fabric is taken out, soaped, washed and dried, the dried modified cotton fabric is dipped for 1h in a commercial sodium hypochlorite solution with the pH of 7 to prepare the antibacterial cotton fabric, and the chlorine content is measured to be 0.17%.
In conclusion, the antibacterial cotton fabric prepared by the application example has excellent antibacterial performance according to the judgment of the effective chlorine content, wherein the application example 2 has higher chlorine content and is the best application example.
Test example:
(1) FT-IRATR infrared spectroscopic analysis of cotton fabric
The characterization of the cotton fabric before and after finishing in application example 2 was performed by a Nicolet is 10 fourier infrared transform spectrometer, and the results are shown in fig. 2.
Comparing the infrared spectra of the cotton fabric (A) before finishing and the cotton fabric (B) finished by the invention in FIG. 2, the latter can be seen in 1572cm-1An absorption peak is added, which is the absorption peak of carbonyl and benzene ring on the antibacterial agent, and proves that the antibacterial finishing agent is grafted on the cotton fabric.
(2) Scanning electron microscopy analysis of cotton fabrics
The surface morphology of the cotton fabric before and after finishing in application example 2 was characterized by SU-1510 scanning electron microscopy and the results are shown in fig. 3.
From the analysis of FIG. 3, it can be seen that the natural texture of the cotton fibers on the surface of the fibers of cotton fabric (B) finished with the antimicrobial agent of the present invention is masked and rougher compared to the cotton fabric (A) before finishing, indicating that the antimicrobial finishing agent is grafted to the surface of the fabric.
(3) Test of antibacterial property of cotton fabric
The test was performed according to the method described in the modified AATCC100-1999 test Standard for antibacterial Performance. The cotton fabric was given an antibacterial finish according to the method described in application example 2, using the last cotton fabric as a blank sample without halogenation. The non-halogenated cotton fabric and the cotton fabric prepared in application example 2 were subjected to an antibacterial test, and the inoculated bacteria were staphylococcus aureus and escherichia coli O157: h7, test results are shown in tables 1 and 2.
TABLE 1 antibacterial property test of antibacterial cotton fabric against Staphylococcus aureus
Note: the inoculation concentration of Staphylococcus aureus is 1.03 × 106cfu/sample。
Table 2 antimicrobial cotton fabric versus escherichia coli O157: antibacterial property test of H7
Note: escherichia coli O157: the inoculation concentration of H7 was 1.00X 106cfu/sample
The test data in tables 1 and 2 show that the antibacterial cotton fabric prepared by the application example 2 of the invention has good antibacterial performance and high antibacterial efficiency, and can completely kill golden yellow staphylococcus and escherichia coli O157 within 1 min: H7.
the raw materials involved in the above examples and application examples are all commercially available products, and the equipment used is conventional in the art, wherein the ratio of staphylococcus aureus to escherichia coli O157: h7 was purchased from American Type Culture Collection (ATCC).
What has been described above is only a preferred embodiment of the present invention, and the present invention is not limited to the above examples. It is to be understood that other modifications and variations directly derivable or suggested by those skilled in the art without departing from the spirit and concept of the present invention are to be considered as included within the scope of the present invention.
Claims (9)
1. The halamine antibacterial agent containing the double active groups is characterized in that the structure of the antibacterial agent is shown as a general formula (1):
in the general formula (1), R1、R2Each independently represents Cl or Br.
2. A method for preparing the dual active group-containing halamine-type antibacterial agent of claim 1, comprising the steps of:
(1) dissolving 5, 5-dimethylhydantoin and 2-chloroethylamine hydrochloride in water or an organic solvent, adding alkali, stirring and refluxing for 12-16 h at 60-70 ℃, distilling under reduced pressure after the reaction is finished to evaporate the solvent, washing the primary product with acetone or ethanol, filtering, and distilling out the acetone or ethanol in the filtrate through reduced pressure distillation to obtain aminoethyl hydantoin;
(2) adding the suspension liquid of p- (β -ethyl sulfone sodium sulfate) aniline into water or an organic solvent containing cyanuric chloride, reacting for 2-4 h at 0-5 ℃, then adding the aqueous solution of aminoethyl hydantoin obtained in the step (1), reacting for 3-5 h at 30-50 ℃, adding an acid binding agent dropwise to adjust the pH value to 5.0-6.0, salting out, filtering, purifying and drying after the reaction is finished, and obtaining a halamine antibacterial precursor (II);
the structural formula of the halamine antibacterial precursor (II) is as follows:
(3) and (3) placing the halamine antibacterial precursor (II) in a sodium hypochlorite aqueous solution, standing for 0.5-4 h at the temperature of 20-40 ℃, filtering, and drying to obtain the halamine antibacterial agent.
3. The preparation method according to claim 2, wherein the alkali in the step (1) is one or a mixture of two of sodium hydroxide and potassium hydroxide; the molar ratio of the 5, 5-dimethylhydantoin, the 2-chloroethylamine hydrochloride to the alkali is 1:1: 2.
4. The preparation method according to claim 2, wherein the organic solvent in step (1) is one or more of ethanol, N-dimethylformamide and acetone, and the amount of the organic solvent is 1 to 10 w/v% of the concentration of the reaction raw material in the solvent.
5. The method according to claim 2, wherein in the step (2), the molar ratio of cyanuric chloride to p- (β -ethylsulfone sodium sulfate) aniline to aminoethyl hydantoin is 1:1: 1.
6. The method according to claim 2, wherein in the step (2), the organic solvent is one or more selected from acetone, carbon tetrachloride, diethyl ether, ethanol, dioxane and chloroform; the concentration of the cyanuric chloride in water or an organic solvent is 1-20 w/v%; the acid-binding agent is one or more of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate and sodium bicarbonate.
7. The application of the halamine antibacterial agent containing the double active groups as claimed in claim 1, wherein the halamine antibacterial agent is used in the technical field of antibacterial finishing of textiles.
8. The application according to claim 7, characterized in that the method of application comprises the steps of:
(1) dissolving a halamine antibacterial precursor (II) and a metal salt in water to prepare an antibacterial finishing liquid, and soaking the textile to be treated in the finishing liquid at room temperature for 10-60 min;
(2) adding a solid alkaline agent, soaking at 60-80 ℃ for 2-5 h, taking out the textile, washing with water, and drying;
(3) finally, soaking the textile in a sodium hypochlorite solution with the concentration of 0.1-1 wt% for halogenation reaction, taking out and drying to obtain the antibacterial textile;
the structural formula of the halamine antibacterial precursor (II) is as follows:
9. the use according to claim 8, wherein the concentration of the halamine-based antibacterial precursor (II) in step (1) is 0.1-5% (w/v); the metal salt is one or more of sodium sulfate, calcium sulfate, magnesium sulfate, zinc sulfate, sodium chloride, magnesium chloride and calcium chloride, and the final concentration is 50-200 g/L; in the step (2), the solid alkaline agent is one or more of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate and sodium bicarbonate, and the final concentration is 1-5 g/L.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105484064A (en) * | 2015-11-17 | 2016-04-13 | 江南大学 | Novel haloamine antibacterial reactive dye, and preparation method and application thereof |
| CN106359383A (en) * | 2016-08-08 | 2017-02-01 | 山东科技大学 | Bifunctional bactericide containing double bond, quaternary ammonium salt and halamine, and preparation method and application thereof |
| CN106632259A (en) * | 2016-09-19 | 2017-05-10 | 江南大学 | Triazine quaternary ammonium salt halamine antibacterial agent and preparation method thereof, and salt-free antibacterial finishing method |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105484064A (en) * | 2015-11-17 | 2016-04-13 | 江南大学 | Novel haloamine antibacterial reactive dye, and preparation method and application thereof |
| CN106359383A (en) * | 2016-08-08 | 2017-02-01 | 山东科技大学 | Bifunctional bactericide containing double bond, quaternary ammonium salt and halamine, and preparation method and application thereof |
| CN106632259A (en) * | 2016-09-19 | 2017-05-10 | 江南大学 | Triazine quaternary ammonium salt halamine antibacterial agent and preparation method thereof, and salt-free antibacterial finishing method |
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