CN108976213A - A kind of halogen amine antibacterial agent and its preparation method and application containing double-active group - Google Patents
A kind of halogen amine antibacterial agent and its preparation method and application containing double-active group Download PDFInfo
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- CN108976213A CN108976213A CN201811029887.1A CN201811029887A CN108976213A CN 108976213 A CN108976213 A CN 108976213A CN 201811029887 A CN201811029887 A CN 201811029887A CN 108976213 A CN108976213 A CN 108976213A
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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
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Abstract
The invention discloses a kind of Halamine antibacterial agents containing double-active group, shown in the structure of the antibacterial agent such as general formula (1), in general formula (1), and R1、R2It each independently represents as Cl or Br, by 5,5- Dimethyl Hydan, 2-chloroethyl amine hydrochloride and alkali, it reacts and amine ethylhydantoin is made, obtained halogen amine antimicrobial presoma is reacted with to (β-ethyl sulfone sodium sulphate) aniline, Cyanuric Chloride etc. again later, the Halamine antibacterial agent is made after last liquor natrii hypochloritis's processing.The production method of antibacterial agent of the present invention is simple, low in raw material price, and purification of products is easy, and arrangement step is simple, and the product after arrangement has good antibiotic property and stability.
Description
Technical field
The present invention relates to antimicrobial technology field more particularly to a kind of halogen amine antibacterial agents and its preparation side containing double-active group
Method and application.
Background technique
With the rapid development of our people's living standard significantly improved with industry, people defend healthy and safe and environment
Raw consciousness is increasingly enhanced, and antibacterial also becomes more and more important in many fields.Cotton is presently most used natural fiber, because of it
Good performance is used for clothes, the occasion close with human contact such as home textile by people extensively.But the good hygroscopicity of cotton fiber and
Carbohydrate contained in fiber provides energy under certain condition (including humidity, temperature) for microbial reproduction, can be rapid
Growth and breeding.This can cause damages to the health of the mankind, and influence the wearability of fabric.Therefore, the antibacterial of cotton fabric is whole
The extensive concern by researcher is managed, many different types of antibacterial agents has been emerged, has been divided into inorganic antiseptic, organic antibacterial agent
With natural antibacterial agent three classes.But most of antibacterial agent has its disadvantage, the washability of inorganic antiseptic is poor, sterilizes rate
Slowly；Natural antibacterial agent extracts difficult；Most of organic antibacterial agent toxic side effect, is harmful to the human body.
Halamine antibacterial agent is one kind of organic antibacterial agent, and have the characteristics that most of ideal antibacterial agent has: raw material is just
Preferably, convieniently synthesized, easily stored, validity period is long, and germicidal efficiency is high, is not easily decomposed or is converted to noxious material, kill with wide spectrum
Bacterium property and antibacterial are renewable etc..Contain one or more N-X (X indicates Cl, F, Br) in the structure of Halamine antibacterial agent,
It contacts release X+ with microorganism to destroy or inhibit the metabolism of microorganism to achieve the purpose that sterilization, the N- in sterilization process
X is reduced into N-H, and acts on the N-X structure that it can be made to become to have anti-microbial property again by halogenating agent (such as sodium hypochlorite).
It commonly rolls baking finishing technique to be affected to cotton fabric performance, and contains many active hydroxyls on cotton fiber
Base can be reacted with some active groups.This just specifies direction to the selection of antibacterial agent and application.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the halogen amine antibacterial agent that the present invention provides a kind of containing double-active group and
Preparation method and application.Production method of the present invention is simple, low in raw material price, and purification of products is easy, and arrangement step is simple, and
Product after arrangement has good antibiotic property and stability.
Technical scheme is as follows:
A kind of Halamine antibacterial agent containing double-active group, shown in the structure of the antibacterial agent such as general formula (1):
In general formula (1), R1、R2It each independently represents as Cl or Br.
A kind of preparation method of the Halamine antibacterial agent containing double-active group, the preparation method comprises the following steps:
(1) 5,5- Dimethyl Hydan and 2-chloroethyl amine hydrochloride are dissolved in water or organic solvent, alkali is then added, 60
Under the conditions of~70 DEG C, it is stirred at reflux 12~16h, steams solvent after reaction, and cleaned just with acetone or alcohol
Then product filters, by steaming acetone or alcohol in filtrate, obtain amine ethylhydantoin；
(2) suspension of (β-ethyl sulfone sodium sulphate) aniline will be added drop-wise in the water or organic solvent containing Cyanuric Chloride,
2~4h is reacted under the conditions of 0~5 DEG C, the aqueous solution of the resulting amine ethylhydantoin of step (1) is then added, at 30~50 DEG C
Under the conditions of react 3~5h；It is 5.0~6.0 that acid binding agent, which is added dropwise, and adjusts pH, and suction filtration of saltouing after reaction is purified and dried, obtains
Halogen amine antimicrobial presoma (II)；
(3) halogen amine antimicrobial presoma (II) is placed in aqueous sodium hypochlorite solution, stands 0.5 under the conditions of 20~40 DEG C
~4h, after filter and dry, obtain the Halamine antibacterial agent.
Alkali described in step (1) is one or both of sodium hydroxide, potassium hydroxide mixture；The 5,5- dimethyl
The molar ratio of glycolylurea, 2-chloroethyl amine hydrochloride and alkali is 1:1:2.
Organic solvent described in step (1) is one of ethyl alcohol, n,N-Dimethylformamide, acetone or a variety of, is used
Amount is that the concentration of reaction raw materials in a solvent is made to reach 1~10w/v%.
In step (2), the Cyanuric Chloride is 1 to the molar ratio of (β-ethyl sulfone sodium sulphate) aniline and amine ethylhydantoin:
1:1。
In step (2), the organic solvent be one of acetone, carbon tetrachloride, ether, ethyl alcohol, dioxanes, chloroform or
It is a variety of；Concentration of the Cyanuric Chloride in water or organic solvent is 1~20w/v%；The acid binding agent is sodium hydroxide, hydrogen-oxygen
Change one of potassium, calcium hydroxide, sodium carbonate, sodium bicarbonate or a variety of.
The structural formula of the halogen amine antimicrobial presoma (II) is as follows:
A kind of application of the Halamine antibacterial agent containing double-active group, the Halamine antibacterial agent are whole for antibacterial textile
Manage technical field.
The method of the application includes the following steps:
(1) by halogen amine antimicrobial presoma and metal salt obtained antibiotic finishing solution soluble in water, by textile to be processed in
Room temperature immersion 10~60min in the finishing fluid；
(2) solid alkaline agent is added, in 60~80 DEG C of 2~5h of dipping, takes out textile, washing, drying；
(3) finally the textile is impregnated in the liquor natrii hypochloritis of 0.1~1wt% of concentration and carries out halogenation, taken
It out and dries, antibacterial fabric is made.
Halamine antibacterial agent precursor concentration described in step (1) is 0.1~5% (w/v)；The metal salt is sulfuric acid
One of sodium, calcium sulfate, magnesium sulfate, zinc sulfate, sodium chloride, magnesium chloride, calcium chloride are a variety of, final concentration of 50~200g/
L；Solid alkaline agent described in step (2) be one of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, sodium bicarbonate or
It is a variety of, final concentration of 1~5g/L.
The present invention is beneficial to be had the technical effect that
(1) 5,5- Dimethyl Hydan and 2-chloroethyl amine hydrochloric acid reactant salt are first generated amine ethylhydantoin by the present invention, are solved
The problem of 5,5- Dimethyl Hydan cannot directly be reacted with Cyanuric Chloride；
(2) replace first chlorine on Cyanuric Chloride with to (β-ethyl sulfone sodium sulphate) aniline, solve in amine ethylhydantoin
Hydroxyl problem inactive at low temperature；
(3) introducing to (β-ethyl sulfone sodium sulphate) aniline is so that halogen amine antibacterial presoma has double-active group, increase
The dye-uptake stability of halogen amine antibacterial presoma；
(4) after tested the result shows that, the fabric highest chlorinity through antibiotic finish of the present invention is up to 0.52%；Entire synthesis
Technological operation is simple, does not generate harmful by-products, and synthesis material is cheap；
(5) antibacterial presoma of the present invention has had more an active group compared to reactive antibacterial agent presoma before,
Probability in conjunction with fabric is bigger, has saved the dosage of antibacterial presoma, can be in lower temperature (60~80 DEG C) and plant fiber
Nucleophilic displacement of fluorine or the formed Covalent bonding together of nucleophilic addition occur for the hydroxyl on molecule on fiber.Reaction process letter
It is single, it is high-efficient and do not generate toxic or polluter, meet ecological textile processing request.
Detailed description of the invention
Fig. 1 is halogen amine antibacterial precursor synthesis route and chlorination reaction equation of the embodiment of the present invention 1 containing double-active group
Formula；
Fig. 2 is the infrared spectrum analysis figure for arranging front and back cotton fabric, in which: A is cotton fabric before arranging, and B is cotton after arranging
Fabric；
Fig. 3 is the scanning electron microscope (SEM) photograph for arranging front and back cotton fabric, in which: A is cotton fabric before arranging, and B is cotton fabric after arranging.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
Embodiment 1
Referring to Fig.1, a kind of Halamine antibacterial agent containing double-active group, preparation method include the following steps:
(1) 2.34g 2-chloroethyl amine hydrochloride, 1.66g sodium hydroxide and 2.61g 5 are weighed, 5- Dimethyl Hydan is in ethyl alcohol
Middle reaction 12h, after filtering removal sodium chloride, be evaporated under reduced pressure, drying, be made amine ethylhydantoin；
(3) 3.64g Cyanuric Chloride is weighed, is dissolved in 25mL acetone, weighs 5.64g to (β-ethyl sulfone sodium sulphate) benzene
Amine and 1.06g sodium carbonate, are dissolved in 20mL water, and the two is mixed with 250mL three-necked flask, is in 0~5 DEG C of pH value
2h is reacted under conditions of 2.5~3.5, and 25mL amine ethylhydantoin obtained above is then dissolved in 25mL water and pours into reaction solution
In, be warming up to 40 DEG C, pH value be 5.0~6.0 under conditions of react 4h, after be added 20% solid sodium chloride (to anti-
Answer liquid weight) saltout, after filter, cleaned with ethyl alcohol and acetone, dry, save, be made halogen amine antimicrobial presoma 2-
Chloro- 4- (4- (β-ethyl sulfone sodium sulphate) phenylamino) -6- amine ethylhydantoin -1,3,5- triazine.
Embodiment 2
Referring to Fig.1, a kind of Halamine antibacterial agent containing double-active group, preparation method include the following steps:
(1) by 2.61g 5,5- Dimethyl Hydan and 0.83g sodium hydroxide flow back 10min in ethanol, are added to 2.34g
In the ethanol solution of 2-chloroethyl amine hydrochloride and 1.06g powdered sodium carbonate, 14h is reacted, then filters and removes sodium chloride, decompression is steamed
It evaporates and dries, amine ethylhydantoin is made；
(2) 3.64g Cyanuric Chloride is weighed, is added into 25mL water and stirs, amine ethylhydantoin obtained above is dissolved in
In 25mL water and it is added drop-wise in Cyanuric Chloride suspension.5.64g is added to (β-ethyl sulfone sodium sulphate) after reacting 3h under ice bath
The aqueous solution of aniline and 1.06g sodium carbonate, reacts 2h at 40 DEG C, full adjustment pH in 5-7, after be added 20% chlorination
Sodium solid (to reaction solution weight) is saltoutd, after filter, cleaned, dried with ethyl alcohol and acetone, saved, it is anti-that halogen amine is made
The chloro- 4- of bacterium presoma 2- (4- (β-ethyl sulfone sodium sulphate) phenylamino) -6- amine ethylhydantoin -1,3,5- triazine.
Embodiment 3
A kind of antibacterial agent presoma, preparation method include the following steps:
(1) 3.64g Cyanuric Chloride is weighed, 5.64g is added to (β-ethyl sulfone sodium sulphate) aniline and 1.06g sodium carbonate
In 50mL water, 5h is reacted, adjusting pH is 2.5~3.5, filters and is cleaned with ethyl alcohol and methanol, is dried；
(2) by 2.61g 5,5- Dimethyl Hydan and 0.83g sodium hydroxide flow back 10min in ethanol, are added to 2.34g
In the ethanol solution of 2-chloroethyl amine hydrochloride and 1.06g powdered sodium carbonate, the water of solid obtained in the previous step is added after reaction 16h
Solution adjusts pH 5~6, reacts 4h, after filter, cleaned, dried with ethyl alcohol, saved, the antibacterial agent forerunner is made
Body.
Application examples:
Application Example 1
0.5g cotton fabric is impregnated in the antibacterial presoma and 1g sodium sulphate by preparing in 0.05g embodiment 1 at room temperature
It is dissolved in 0.5h in the antibiotic finishing solution configured in 20mL water；60 DEG C of addition 0.1g sodium hydroxides are warming up to, after impregnating 3h, taking-up is knitted
Object is soaped, and washes, drying；Modified cotton fabric after drying is impregnated in the commercialization time sodium chloride solution of 10% that pH is 7
1h is made antibacterial cotton fabric, measures chlorinity 0.32%.Chlorination reaction is referring to Fig. 1.
Application Example 2
0.5g cotton fabric is impregnated in the chloro- 4- (4- of antibacterial presoma 2- by preparing in 0.1g embodiment 1 at room temperature
(β-ethyl sulfone sodium sulphate) phenylamino) -6- amine ethylhydantoin -1,3,5- triazine and 2g sodium chloride be dissolved in configured in 20mL water it is anti-
10min in bacterium finishing fluid；80 DEG C of addition 0.02g potassium hydroxide are warming up to, after impregnating 2h, fabric is taken out, soaps, wash, drying；
Modified cotton fabric after drying is impregnated into 1h in the commercialization time sodium chloride solution of 50% that pH is 7, antibacterial cotton fabric is made, surveys
Obtain chlorinity 0.37%.
Application Example 3
0.5g cotton fabric is impregnated in the chloro- 4- (4- of antibacterial presoma 2- by preparing in 0.1g embodiment 1 at room temperature
(β-ethyl sulfone sodium sulphate) phenylamino) -6- amine ethylhydantoin -1,3,5- triazine and 4g magnesium sulfate be dissolved in configured in 20mL water it is anti-
1h in bacterium finishing fluid；70 DEG C of addition 0.05g sodium hydroxides are warming up to, after impregnating 5h, fabric is taken out, soaps, wash, drying；It will
Modified cotton fabric after drying impregnates 1h in the commercialization time sodium chloride solution that pH is 7, and antibacterial cotton fabric is made, measures chlorinity
0.17%.
To sum up, it can determine whether according to available chlorine content, the made antibacterial cotton fabric of use above embodiment is provided with excellent resist
Bacterium performance, wherein the chlorinity with higher of Application Example 2 is best applications embodiment.
Test case:
(1) cotton fabric FT-IRATR infrared spectrum analysis
By 10 Fourier transform infrared spectrometer of Nicolet is to the cotton fabric for arranging front and back in Application Example 2
It is characterized, as a result sees Fig. 2.
Compare cotton fabric (A) and the latter known to the infrared spectrogram of the cotton fabric (B) arranged through the present invention before arranging in Fig. 2
In 1572cm-1An absorption peak is had more, this is the absorption peak of carbonyl and phenyl ring on antibacterial agent, it was demonstrated that be grafted on cotton fabric anti-
Bacterium finishing agent.
(2) cotton fabric scanning electron microscope analysis
Configuration of surface table is carried out to front and back cotton fabric is arranged in Application Example 2 by SU-1510 scanning electron microscope
Sign, is as a result shown in Fig. 3.
Cotton fabric (B) fiber it is found that before arranging compared with cotton fabric (A), arranged through antibacterial agent of the present invention is analyzed by Fig. 3
Surface cotton fiber native texture is covered, and more coarse, illustrates that antibacterial finishing agent has been grafted to fabric surface.
(3) cotton fabric anti-microbial property test
It is tested according to modified AATCC100-1999 anti-microbial property test standard the method.According to application implementation
2 the method for example carries out antibiotic finish to cotton fabric, use finally the cotton fabric without halogenation as blank sample.To without
The above-mentioned cotton fabric and the made cotton fabric of Application Example 2 of halogenation carry out antibacterial test, and inoculated bacteria is staphylococcus aureus
And Escherichia coli O 157: H7, test result are as shown in Table 1 and Table 2.
Anti-microbial property test of 1 antibacterial cotton fabric of table to staphylococcus aureus
Note: the inoculum density of staphylococcus aureus is 1.03 × 106cfu/sample。
2 antibacterial cotton fabric of table is to Escherichia coli O 157: the anti-microbial property detection of H7
Note: Escherichia coli O 157: the inoculum density of H7 is 1.00 × 106cfu/sample
It is good that the test data of Tables 1 and 2 shows that the antibacterial cotton fabric that Application Example 2 of the present invention is prepared has
Anti-microbial property, antimicrobial efficiency is high, can kill completely Staphylococcus aureus and Escherichia coli O 157 in 1min: H7.
Each raw material involved by above-described embodiment and Application Example is commercial goods, and institute is this using each instrument and equipment
Field conventional equipment, wherein staphylococcus aureus and Escherichia coli O 157: H7 is purchased from American Type Culture collection warehousing
(ATCC)。
What has been described above is only a preferred embodiment of the present invention, and present invention is not limited to the above embodiments.It is appreciated that this
The other improvements and change that field technical staff directly exports or associates without departing from the spirit and concept in the present invention
Change, is considered as being included within protection scope of the present invention.
Claims (10)
1. a kind of Halamine antibacterial agent containing double-active group, which is characterized in that the structure of the antibacterial agent such as general formula (1) institute
Show:
In general formula (1), R1、R2It each independently represents as Cl or Br.
2. a kind of preparation method of the Halamine antibacterial agent described in claim 1 containing double-active group, which is characterized in that the system
Preparation Method the following steps are included:
(1) 5,5- Dimethyl Hydan and 2-chloroethyl amine hydrochloride are dissolved in water or organic solvent, alkali is then added, 60~70
Under the conditions of DEG C, it is stirred at reflux 12~16h, steams solvent after reaction, and clean head product with acetone or alcohol,
Then it filters, by steaming acetone or alcohol in filtrate, obtains amine ethylhydantoin；
(2) suspension of (β-ethyl sulfone sodium sulphate) aniline will be added drop-wise in the water or organic solvent containing Cyanuric Chloride, 0~
2~4h is reacted under the conditions of 5 DEG C, the aqueous solution of the resulting amine ethylhydantoin of step (1) is then added, under the conditions of 30~50 DEG C
React 3~5h；It is 5.0~6.0 that acid binding agent, which is added dropwise, and adjusts pH, and suction filtration of saltouing after reaction purifies and dries, obtains halogen amine
Antibacterial presoma (II)；
(3) halogen amine antimicrobial presoma (II) is placed in aqueous sodium hypochlorite solution, under the conditions of 20~40 DEG C stand 0.5~
4h, after filter and dry, obtain the Halamine antibacterial agent.
3. according to right want 2 described in preparation method, which is characterized in that alkali described in step (1) be sodium hydroxide, potassium hydroxide
One or both of mixture；The molar ratio of the 5,5- Dimethyl Hydan, 2-chloroethyl amine hydrochloride and alkali is 1:1:2.
4. preparation method according to claim 2, which is characterized in that organic solvent described in step (1) is ethyl alcohol, N, N-
One of dimethylformamide, acetone are a variety of, and dosage is that the concentration of reaction raw materials in a solvent is made to reach 1~10w/
V%.
5. preparation method according to claim 2, which is characterized in that in step (2), the Cyanuric Chloride, to (β-ethyl
Sulfone sodium sulphate) molar ratio of aniline and amine ethylhydantoin is 1:1:1.
6. preparation method according to claim 2, which is characterized in that in step (2), the organic solvent is acetone, four
One of chlorination carbon, ether, ethyl alcohol, dioxanes, chloroform are a variety of；Concentration of the Cyanuric Chloride in water or organic solvent
For 1~20w/v%；The acid binding agent be one of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, sodium bicarbonate or
It is a variety of.
7. preparation method according to claim 2, which is characterized in that the structural formula of the halogen amine antimicrobial presoma (II)
It is as follows:
8. a kind of application of the Halamine antibacterial agent described in claim 1 containing double-active group, which is characterized in that the halogen amine
Class antibacterial agent is used for textiles antibacterial finishing technical field.
9. application according to claim 8, which is characterized in that the method for the application includes the following steps:
(1) by halogen amine antimicrobial presoma and metal salt obtained antibiotic finishing solution soluble in water, by textile to be processed in room temperature
It is impregnated in 10~60min in the finishing fluid；
(2) solid alkaline agent is added, in 60~80 DEG C of 2~5h of dipping, takes out textile, washing, drying；
(3) finally the textile is impregnated in the liquor natrii hypochloritis of 0.1~1wt% of concentration and carries out halogenation, taken out simultaneously
Antibacterial fabric is made in drying.
10. application according to claim 8, which is characterized in that Halamine antibacterial agent precursor concentration described in step (1)
For 0.1~5% (w/v)；The metal salt is sodium sulphate, calcium sulfate, magnesium sulfate, zinc sulfate, sodium chloride, magnesium chloride, calcium chloride
One of or a variety of, final concentration of 50~200g/L；Solid alkaline agent described in step (2) is sodium hydroxide, potassium hydroxide, hydrogen
One of calcium oxide, sodium carbonate, sodium bicarbonate are a variety of, final concentration of 1~5g/L.
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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 |
-
2018
- 2018-09-05 CN CN201811029887.1A patent/CN108976213B/en active Active
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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