CN103113251A - N,N-p-benzocarboxyl hydroxyphenyl methyl quaternary ammonium salt and preparation method thereof - Google Patents
N,N-p-benzocarboxyl hydroxyphenyl methyl quaternary ammonium salt and preparation method thereof Download PDFInfo
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- CN103113251A CN103113251A CN2013100302971A CN201310030297A CN103113251A CN 103113251 A CN103113251 A CN 103113251A CN 2013100302971 A CN2013100302971 A CN 2013100302971A CN 201310030297 A CN201310030297 A CN 201310030297A CN 103113251 A CN103113251 A CN 103113251A
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Abstract
The invention discloses N,N-p-benzocarboxyl hydroxyphenyl methyl quaternary ammonium salt, wherein the structure is shown in the specification; two compounds with good anti-bacterial property namely p-aminobenzoic acid and p-hydroxy benzaldehyde are organically combined and subjected to quaternization to obtain novel quaternary ammonium salt containing N positive charges; the quaternary ammonium salt has good anti-bacterial activity on bacteria and fungi; the minimal inhibitory concentration against staphylococcus aureus and salmonella is 8mg/L, and the minimal inhibitory concentration against escherichia coli and aspergillus niger is 16mg/L; a strong inhibition effect is also realized in the strain growth process; and after 40 hours of culture, 100% inhibition can be realized basically against three bacteria, and the inhibition ratio against aspergillus niger also exceeds 95%. The physical and chemical indexes of the compound are that the compound is light yellow powder solid and is soluble to water, methanol and acetic acid at normal temperature and slightly soluble to acetone and dichloromethane, and the molecular weight is about 399. The N,N-p-benzocarboxyl hydroxyphenyl methyl quaternary ammonium salt has the characteristics of good solubility, anti-bacterial activity, stability and the like, and can be added into a medical product as an anti-bacterial agent.
Description
Technical field
The invention belongs to chemical field, be specifically related to N, the preparation method of N-to benzene carboxyl hydroxyphenyl methyl quaternary ammonium, and the application aspect medicinal antibiosis.
Background technology
The physico-chemical property that the quaternary ammonium salt antimicrobial substance is good with it is approved by increasing people, its solid-state form non-volatility, can be good at being dissolved in water, in industries such as medicine, food, fine chemistry industries, as aspects such as sterilization and disinfection, catalysis, emulsifications, application is comparatively widely arranged.Efficient, nontoxic, nothing accumulation property that this sterilant has, be not subject to the impact that the pH value changes, easy to use, slime layer is had to the stronger effect of peeling off, the characteristics such as stable chemical performance, dispersion and corrosion inhibition are better, can be used as the pharmaceutical products antiseptic-germicide and be applicable to the medicinal antibiosis aspect.
The present invention combines two kinds of compound molecules with strong anti-microbial activity, make the quaternary ammonium compound that simultaneously contains carboxyl and hydroxyl, this compound dissolution is good, and possesses positively charged N ion, show larger surfactivity, more be conducive to the absorption of biocide molecules at bacterium surface, thereby change the perviousness of cell walls, make the thalline death of breaking, true confirmed that the quarternary ammonium salt compound with this structure compares with traditional quarternary ammonium salt compound, there is stronger anti-microbial property, and also particularly evident to the growth-inhibiting effect of bacterium and fungi.
Summary of the invention
The objective of the invention is to overcome the problem that antiseptic-germicide is insoluble in water, a kind of quarternary ammonium salt compound with good anti-microbial activity be provided, in conjunction with its have no side effect, the characteristics such as good stability can be used as antiseptic-germicide and add in pharmaceutical products.
The present invention is completed by following technical scheme, has developed a kind of N, and N-, to benzene carboxyl hydroxyphenyl methyl quaternary ammonium, is characterized in that: its structure is,
The physical and chemical indexes of this compound: pale yellow powder shape solid, water soluble under normal temperature, methyl alcohol and acetic acid, be slightly soluble in acetone and methylene dichloride, and molecular weight is about 399.N, N-, can be used as antiseptic-germicide and makes an addition in pharmaceutical products due to characteristics such as its good solubility, anti-microbial activity and stability benzene carboxyl hydroxyphenyl methyl quaternary ammonium.
By two kinds of combinations that have good anti-microbial property compound para-amino benzoic acid and p-Hydroxybenzaldehyde itself, then obtain the novel N containing the N positive charge after it is quaternized, N-is to benzene carboxyl hydroxyphenyl methyl quaternary ammonium.The principal reaction the present invention relates to is:
Described N, the preparation method of N-to benzene carboxyl hydroxyphenyl methyl quaternary ammonium, its preparation process is as follows:
(1) the para-amino benzoic acid of weighing is dissolved in 50-65 ℃ of distilled water to hot suction filtration; Filtrate cool to room temperature, at room temperature suction filtration; Get filter cake, vacuum-drying, obtain pure para-amino benzoic acid;
(2) the p-Hydroxybenzaldehyde of weighing is dissolved in 50-65 ℃ of distilled water to hot suction filtration; Filtrate cool to room temperature, at room temperature suction filtration; Get filter cake, vacuum-drying, obtain pure p-Hydroxybenzaldehyde;
(3) accurately take a certain amount of para-amino benzoic acid of having purified and p-Hydroxybenzaldehyde and put into the there-necked flask to 250ml, the dehydrated alcohol that adds certain volume with the every gram 20ml of mixture ratio, mixture dissolves fully, with Glacial acetic acid regulator solution pH to 4.5-5.0, bath temperature is set as 40-60 ℃, stirring and refluxing reaction 3h, obtain yellow solution;
By step (3) in solution be placed in 0 ℃ and spend the night, crystallize out, suction filtration, absolute ethanol washing, obtain faint yellow solid, vacuum-drying obtains the Schiff's base intermediate;
(5) get a certain amount of step (4) in product put into the round-bottomed flask to 250ml, add the certain volume dissolve with ethanol with every gram 30ml ratio, sodium borohydride-the ethanolic soln (sodium borohydride and ethanol mass ratio are 1:20) that dropwise adds 1.5 times of Schiff's base molar weights, the adjusting bath temperature is 40-60 ℃, at the uniform velocity stir 3h, reaction solution is transferred in Rotary Evaporators, evaporate solvent, revolve steam after liquid be added in methylene dichloride extraction 3-5 time, merge organic phase, use anhydrous magnesium sulfate drying, filter, the concentrated product that obtains;
(6) the product after (5) concentrating by the anhydrous alcohol solution step, to dropwise adding in solution diluted sodium hydroxide solution to regulate pH, be 8-9, controlling bath temperature is 40-60 ℃ of stirring and refluxing 1.5h, the methyl iodide that adds 2.4 times of para-amino benzoic acid molar weights, the sodium iodide that simultaneously adds 0.5 times of methyl iodide molar weight, stirring and refluxing reaction 3-4h;
By step (6) in product move in Rotary Evaporators, solvent evaporated, obtain yellow solid product, add washing with acetone with every gram 50ml ratio, suction filtration, solid sample ethanol Soxhlet extraction, suction filtration, obtain faint yellow product, vacuum-drying obtains product N, and N-is to benzene carboxyl hydroxyphenyl methyl quaternary ammonium.
Described step (1) and (2) in the processing condition of suction filtration be: dry 1-3h with filter flask and Büchner funnel in 50-65 ℃ of baking oven, at 50-65 ℃ of lower suction filtration solution, after the suction filtration end, rapidly filtrate be poured in clean beaker;
Described step (4) and (7) in suction filtration processing condition all: dry 1-3h with filter flask and Büchner funnel in 50-65 ℃ of baking oven, suction filtration reaction solution under room temperature condition, after the suction filtration end, wash and collect gained solid in Büchner funnel.
Described step revolve in (5) and steam after the volume ratio of liquid and methylene dichloride be 1:(10-20).
Described para-amino benzoic acid: p-Aminobenzaldehyde: sodium borohydride: the amount of substance fed intake of methyl iodide is than being 1:1:(1.5-2): (2-3).
Described step (6) in enriched product and dehydrated alcohol weight ratio be 1:(20-30).
(5) and revolve (7) that to steam temperature be 80-90 ℃, vacuum tightness is 0.06Mpa to described step.
The processing condition that described step Soxhlet is (7) extracted are: 65-75 ℃ of heating in water bath, extract 24-30h.
Described step (1), vacuum drying processing condition are (2) and (7): under 30-50 ℃, vacuum tightness is 0.08Mpa.
Described N, N-is applied in pharmaceutical products as antiseptic-germicide benzene carboxyl hydroxyphenyl methyl quaternary ammonium.
Positively effect of the present invention is: two kinds of compound molecules with strong anti-microbial activity are combined, make the quaternary ammonium compound that simultaneously contains carboxyl and hydroxyl, this compound dissolution is good, stability is strong, have no side effect, and possessing positively charged N ion, more traditional quarternary ammonium salt compound has stronger anti-microbial activity, and also particularly evident to the growth-inhibiting effect of mushroom.
The accompanying drawing explanation
The infrared spectrogram that Fig. 1 is sodium borohydride reduction Schiff's base after product.
Fig. 2 is prepared N, the infrared spectrogram of N-to benzene carboxyl hydroxyphenyl methyl quaternary ammonium.
Fig. 3 is prepared N, the ultraviolet spectrogram of N-to benzene carboxyl hydroxyphenyl methyl quaternary ammonium.
Fig. 4 is prepared N, and N-is to benzene carboxyl hydroxyphenyl methyl quaternary ammonium
1h NMR spectrogram.
Fig. 5 is different concns N, and N-is the inhibiting rate to streptococcus aureus, intestinal bacteria, Salmonellas and black-koji mould to benzene carboxyl hydroxyphenyl methyl quaternary ammonium.
Fig. 6 is N, and N-is the growth-inhibiting effect to streptococcus aureus, intestinal bacteria, Salmonellas and black-koji mould to benzene carboxyl hydroxyphenyl methyl quaternary ammonium.
In Fig. 3, by N, N-is dissolved in methyl alcohol and water (1:1) and makes 10 μ g/ml solution benzene carboxyl hydroxyphenyl methyl quaternary ammonium, carries out the uv scan analysis, and it is 0.350 that there is maximum absorbance at the 291.0nm place, uptake factor
be 350, accordingly this compound carried out to the ultraviolet discriminating.
In Fig. 4, by N, N-is dissolved in CD to benzene carboxyl hydroxyphenyl methyl quaternary ammonium
3cOOD and D
2in the mixture of O, measured, from spectrogram, the multiplet at 1.42-1.95ppm place is-CH
3middle proton uptake peak, it at multi-absorption peak, 6.43-7.72ppm place, is proton uptake peak in two contraposition disubstituted benzene rings in compound, 9.48ppm locate the fignal center of absorption peak for hydrogen in-OH, 12.29ppm locate the charateristic avsorption band into hydrogen in compound-COOH, prove and successfully make N, N-is to benzene carboxyl hydroxyphenyl methyl quaternary ammonium.
Fig. 5 bacteriostasis rate curve shows, product all has good restraining effect to four kinds of bacterium, its minimum inhibitory concentration to streptococcus aureus and Salmonellas is 8mg/L, minimum inhibitory concentration to intestinal bacteria and black-koji mould is 16mg/L, proof N, N-all has good restraining effect to bacterium and fungi to benzene carboxyl hydroxyphenyl methyl quaternary ammonium in low strength range, and its scope of restraining fungi and effect are more superior than other like products.
N in Fig. 6, N-is obvious to four kinds of fungus grown restraining effect to benzene carboxyl hydroxyphenyl methyl quaternary ammonium, cultivation 24h can reach more than 99% to the inhibiting rate of streptococcus aureus, intestinal bacteria and Salmonellas, and the inhibiting rate of black-koji mould is also reached to 89.3%, after cultivating 40h, three kinds of bacteriums are reached to 100% inhibition substantially, the inhibiting rate of black-koji mould also is increased to more than 95%.Proof N, N-is obvious to four kinds of fungus grown process restraining effect to benzene carboxyl hydroxyphenyl methyl quaternary ammonium.
Embodiment
Embodiment 1:
Get dry para-amino benzoic acid 1.2g and the p-Hydroxybenzaldehyde 1.0g crossed and put into the there-necked flask to 250ml, add the 44ml dehydrated alcohol, regulating PH with Glacial acetic acid is 4.5, stirring reaction 3h under the water bath condition of 55 ℃, solution is placed in 0 ℃ and spends the night, suction filtration, absolute ethanol washing, 50 ℃ of vacuum-dryings, obtain yellow product Schiff's base intermediate.
Get the 1.0g Schiff's base and put into the round-bottomed flask to 250ml, add 50ml ethanol.Dropwise add 25ml sodium borohydride-ethanolic soln under stirring, regulating bath temperature is 60 ℃, and stirring reaction 3h, revolve steaming, revolves to steam liquid and be added in the 50ml methylene dichloride extraction 3 times, merges organic phase, use anhydrous magnesium sulfate drying, filters, and concentrates.
Above-mentioned enriched product is dissolved in the 45ml dehydrated alcohol, and adding diluted sodium hydroxide solution to regulate PH is 8.2, return stirring 1.5h under 50 ℃ of water bath condition, add the 1.2ml methyl iodide, add the 1.4g sodium iodide simultaneously, continue stirring reaction 3.5h, revolve steaming, sample adds in 75ml acetone and washs, suction filtration, get filter cake and carry out the Soxhlet extraction with ethanol, sample vacuum-drying under 45 ℃ of conditions, obtain yellow product N, N-is to benzene carboxyl hydroxyphenyl methyl quaternary ammonium.
Embodiment 2:
Products therefrom N of the present invention, N-under benzene carboxyl hydroxyphenyl methyl quaternary ammonium different concns to the suppression efficiency (%) of streptococcus aureus, intestinal bacteria, Salmonellas and black-koji mould
The measuring method of above-mentioned antibacterial efficiency: the sample solution (take 0.5% methanol solution as solvent) of preparation different concns.Respectively the sample solution of 0.1 ml bacteria suspension and 0.1 ml different concns is uniformly coated on culture medium flat plate, blank for not adding the bacteria suspension of sample solution.All flat boards are cultivated 24 h in 37 ℃ of constant incubators, take out the bacterial growth situation of observing on each flat board, calculate bacteriostasis rate:
I = (n
1-n
2)/ n
1×100%
Wherein, n
1and n
2be respectively the colony number on the blank flat board with scribbling sample.
For aspergillus niger, adopt the dry weight method to measure the antibacterial efficiency of quaternary ammonium salt.Respectively the sample solution of 1 ml black-koji mould suspension and 2 ml different concns is added in sabouraud culture medium, blank for not adding the bacteria suspension of sample solution, cultivate 36 h in 28 ℃ of constant-temperature shaking incubators, suction filtration, drying also claims dry cell weight, calculates bacteriostasis rate:
I = (m
1-m
2)/ m
1×100%
Wherein, m
1and m
2be respectively and do not add in the sample nutrient solution and add the mycelia dry weight in sample cultivation liquid.
Embodiment 3:
Products therefrom N of the present invention, N-is the growth-inhibiting effect (%) to streptococcus aureus, intestinal bacteria, Salmonellas and black-koji mould to benzene carboxyl hydroxyphenyl methyl quaternary ammonium
The measuring method of above-mentioned growth-inhibiting effect: add a certain amount of sample solution (take 0.5% methanol solution as solvent) in the liquid nutritional broth culture, making its concentration is 1mg/L, and access concentration is 10
7the bacteria suspension 0.2ml of individual/ml, 37 ℃ of constant-temperature shaking culture, timing sampling is measured its absorbancy under 620nm, measure and do not add sample bacterium liquid absorbancy simultaneously, reflect the variation of bacterial number with the variation of absorbance, the absorbance measurement blank is the liquid nutritional broth culture of not inoculated bacteria, calculates inhibiting rate:
Wherein, OD
0, OD
1and OD
2represent respectively not inoculated bacteria, do not add sample liquid and add the broth culture absorbance of sample liquid.
Adopt the dry cell weight method for mould, add the sample solution of a certain amount of (take 0.5% methanol solution be solvent) in the liquid sabouraud culture medium, making its concentration is 1mg/L, and access aspergillus niger suspension 1ml, 28 ℃ of constant-temperature shaking culture, timing sampling, use the Büchner funnel suction filtration, the dry and dry cell weight of weighing, weigh simultaneously and do not add the dry cell weight of sample liquid mould, blank is the liquid sabouraud culture medium of not inoculated aspergillus niger suspension, calculates bacteriostasis rate:
Wherein, M1 and M2 represent respectively and do not add in the sample nutrient solution and add mycelia dry weight in sample cultivation liquid.
Those of ordinary skill in the art can understand, and in protection scope of the present invention, for above-described embodiment, modifies, and it is all possible adding and replacing, and it does not all exceed protection scope of the present invention.
Claims (9)
1. a N, N-is to benzene carboxyl hydroxyphenyl methyl quaternary ammonium, and it is characterized in that: this derivative has structure shown in following formula,
A kind of as N as described in right 1, the preparation method of N-to benzene carboxyl hydroxyphenyl methyl quaternary ammonium, it is characterized in that: described preparation process is as follows:
(1) the para-amino benzoic acid of weighing is dissolved in 50-65 ℃ of distilled water to hot suction filtration; Filtrate cool to room temperature, at room temperature suction filtration; Get filter cake, vacuum-drying, obtain pure para-amino benzoic acid;
(2) the p-Hydroxybenzaldehyde of weighing is dissolved in 50-65 ℃ of distilled water to hot suction filtration; Filtrate cool to room temperature, at room temperature suction filtration; Get filter cake, vacuum-drying, obtain pure p-Hydroxybenzaldehyde;
(3) accurately take a certain amount of para-amino benzoic acid of having purified and p-Hydroxybenzaldehyde and put into the there-necked flask to 250ml, the dehydrated alcohol that adds certain volume with the every gram 20ml of mixture ratio, mixture dissolves fully, with Glacial acetic acid regulator solution pH to 4.5-5.0, bath temperature is set as 40-60 ℃, stirring and refluxing reaction 3h, obtain yellow solution;
By step (3) in solution be placed in 0 ℃ and spend the night, crystallize out, suction filtration, absolute ethanol washing, obtain faint yellow solid, vacuum-drying obtains the Schiff's base intermediate;
(5) get a certain amount of step (4) in product put into the round-bottomed flask to 250ml, add the certain volume dissolve with ethanol with every gram 30ml ratio, sodium borohydride-the ethanolic soln (sodium borohydride and ethanol mass ratio are 1:20) that dropwise adds 1.5 times of Schiff's base molar weights, the adjusting bath temperature is 40-60 ℃, at the uniform velocity stir 3h, reaction solution is transferred in Rotary Evaporators, evaporate solvent, revolve steam after liquid be added in methylene dichloride extraction 3-5 time, merge organic phase, use anhydrous magnesium sulfate drying, filter, the concentrated product that obtains;
(6) the product after (5) concentrating by the anhydrous alcohol solution step, to dropwise adding in solution diluted sodium hydroxide solution to regulate pH, be 8-9, controlling bath temperature is 40-60 ℃ of stirring and refluxing 1.5h, the methyl iodide that adds 2.4 times of para-amino benzoic acid molar weights, the sodium iodide that simultaneously adds 0.5 times of methyl iodide molar weight, stirring and refluxing reaction 3-4h;
By step (6) in product move in Rotary Evaporators, solvent evaporated, obtain yellow solid product, with every gram 50ml ratio, adds washing with acetone, suction filtration, solid sample ethanol Soxhlet extraction, suction filtration, obtain faint yellow product, vacuum-drying obtains product N, and N-is to carboxyl hydroxyphenyl methyl quaternary ammonium.
2. N according to claim 2, the preparation method of N-to carboxyl hydroxyphenyl methyl quaternary ammonium, is characterized in that: described
Step (1) and (2) in the processing condition of suction filtration be: dry 1-3h with filter flask and Büchner funnel in 50-65 ℃ of baking oven, at 50-65 ℃ of lower suction filtration solution, after the suction filtration end, rapidly filtrate be poured in clean beaker;
Described step (4) and (7) in suction filtration processing condition all: dry 1-3h with filter flask and Büchner funnel in 50-65 ℃ of baking oven, suction filtration reaction solution under room temperature condition, after the suction filtration end, wash and collect gained solid in Büchner funnel.
3. N according to claim 2, the preparation method of N-to carboxyl hydroxyphenyl methyl quaternary ammonium is characterized in that: described step revolve in (5) and steam after the volume ratio of liquid and methylene dichloride be 1:(10-20).
4. N according to claim 2, the preparation method of N-to carboxyl hydroxyphenyl methyl quaternary ammonium is characterized in that: described para-amino benzoic acid: p-Aminobenzaldehyde: sodium borohydride: the amount of substance fed intake of methyl iodide is than being 1:1:(1.5-2): (2-3).
5. N according to claim 2, the preparation method of N-to carboxyl hydroxyphenyl methyl quaternary ammonium is characterized in that: described step (6) in enriched product and dehydrated alcohol weight ratio be 1:(20-30).
According to claim 2 step (5) and revolve (7) that to steam temperature be 80-90 ℃, vacuum tightness is 0.06Mpa.
7. N according to claim 2, the preparation method of N-to carboxyl hydroxyphenyl methyl quaternary ammonium is characterized in that: the processing condition that described step Soxhlet is (7) extracted are: 65-75 ℃ of heating in water bath, extract 24-30h.
8. N according to claim 2, the preparation method of N-to carboxyl hydroxyphenyl methyl quaternary ammonium is characterized in that: described step (1), vacuum drying processing condition are (2) and (7): under 30-50 ℃, vacuum tightness is 0.08Mpa.
9. N according to claim 1, N-is the application as the pharmaceutical products antimicrobial additive to carboxyl hydroxyphenyl methyl quaternary ammonium.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015108091A (en) * | 2013-12-05 | 2015-06-11 | デクセリアルズ株式会社 | Compound, thermosetting resin composition, and thermosetting sheet |
| CN114524766A (en) * | 2021-12-29 | 2022-05-24 | 河南驼人医疗器械研究院有限公司 | Novel tridentate pyridine quaternary ammonium salt antibacterial compound and preparation method thereof |
| CN115353459A (en) * | 2022-07-27 | 2022-11-18 | 安徽启威生物科技有限公司 | Low-polymerization-degree polylactic acid quaternary ammonium salt and preparation method thereof |
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| EP0791575A1 (en) * | 1996-02-16 | 1997-08-27 | Nippon Paint Co., Ltd. | Method of synthesis of a quaternary ammonium salt |
| CN102153675A (en) * | 2011-03-15 | 2011-08-17 | 中国海洋大学 | N-para benzene hydroxyl carboxymethyl chitosan hyamine and preparation method thereof |
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2013
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| EP0791575A1 (en) * | 1996-02-16 | 1997-08-27 | Nippon Paint Co., Ltd. | Method of synthesis of a quaternary ammonium salt |
| CN102153675A (en) * | 2011-03-15 | 2011-08-17 | 中国海洋大学 | N-para benzene hydroxyl carboxymethyl chitosan hyamine and preparation method thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015108091A (en) * | 2013-12-05 | 2015-06-11 | デクセリアルズ株式会社 | Compound, thermosetting resin composition, and thermosetting sheet |
| WO2015083585A1 (en) * | 2013-12-05 | 2015-06-11 | デクセリアルズ株式会社 | Compound, heat-curable resin composition, and heat-curable sheet |
| CN105814090A (en) * | 2013-12-05 | 2016-07-27 | 迪睿合株式会社 | Compound, heat-curable resin composition, and heat-curable sheet |
| CN114524766A (en) * | 2021-12-29 | 2022-05-24 | 河南驼人医疗器械研究院有限公司 | Novel tridentate pyridine quaternary ammonium salt antibacterial compound and preparation method thereof |
| CN114524766B (en) * | 2021-12-29 | 2023-06-27 | 河南驼人医疗器械研究院有限公司 | Novel tridentate pyridine quaternary ammonium salt antibacterial compound and preparation method thereof |
| CN115353459A (en) * | 2022-07-27 | 2022-11-18 | 安徽启威生物科技有限公司 | Low-polymerization-degree polylactic acid quaternary ammonium salt and preparation method thereof |
| CN115353459B (en) * | 2022-07-27 | 2023-08-15 | 安徽启威生物科技有限公司 | Low-polymerization degree polylactic acid quaternary ammonium salt and preparation method thereof |
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Application publication date: 20130522 |