CN105017045A - Bis-quaternary ammonium salt with linking groups that contain diester groups and application thereof as bactericide - Google Patents
Bis-quaternary ammonium salt with linking groups that contain diester groups and application thereof as bactericide Download PDFInfo
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Abstract
The present invention discloses a novel bis-quaternary ammonium salt compound with linking groups that contain diester groups. The bis-quaternary ammonium salt compound with linking groups that contain diester groups structurally comprises an ester group, and is environmentally friendly and easily degradable, and simple in preparation process. Compared to the commonly used quaternary ammonium bactericide, the bis-quaternary ammonium salt compound with linking groups that contain diester groups in the present invention has high surface activity, higher bactericidal activity, and less consumption. The structural formula of the compound is shown in the specification.
Description
Technical field:
The invention belongs to surfactant field, relate to a kind of Gemini cats product and preparation method thereof and application, specifically, the present invention relates to a kind of base that connects containing the bi-quaternary ammonium salt of di-ester-base and the application in sterilant thereof.
Background technology:
Quaternary surfactant has function that is antibacterial, sterilization, and toxicity is low, applied range, has longer history to its research as sterilant.But microorganism easily develops immunity to drugs to quaternary ammonium salt, if dodecyl benzyl dimethyl ammonium chloride (1227) is a kind of quaternary ammonium salt bactericide preferably, with No.2 Oil Production Factory, Xinjiang Petroleum Administration Bureau's No. 802 oily(waste)waters for sample, sterilization effect test is carried out to it, when 1227 content are 40%, when chemical feeding quantity is 80mg/L, can only by the sulphate reducing bacteria quantity in oily(waste)water by 10
4individual/mL is down to 10
3individual/mL, and iron bacteria number does not change, and is still 10
3individual/mL (oilfield chemistry, 1994,3:247).
Since the nineties in last century, a kind of novel tensio-active agent-Gemini surface active receives the concern of researchist day by day.Different from the molecular structure of conventional surfactants, at least containing two hydrophilic radicals and two hydrophobic groupings in Gemini surface active molecule, make this kind of tensio-active agent present high surfactivity.Organic diammonium compound belongs to cationic Gemini surfactants, there is higher surfactivity, composite coordinating effect water-soluble and stronger preferably, thus have broad application prospects in industries such as papermaking, ore dressing, coal washing, oil recovery, sewage disposal, food-processings.
Organic diammonium compound has stronger fungicidal activity.Be the existence owing to connecting base on the one hand, ion head base positively charged in Gemini surface active molecule is at a distance of being furthered, and in single surfactant molecule, positive charge density increases, thus the fungicidal activity that performance is higher.On the other hand, Gemini surface active has two hydrophobic alkane chains, and hydrophobic performance is stronger, stronger with the hydrophobic binding effect of cellular lipids layer, result also in stronger sterilization effect.
Mao Xueqiang etc. have studied the bi-quaternary ammonium salt Gemini surface active (m-2-m of different hydrophobic chain length, m=8,10,12,14) to the bactericidal property of oilfield sewage, research finds, compared with conventional sterilants 1227, bi-quaternary ammonium salt all has stronger bactericidal property (synthetic chemistry, 2011,19 (2): 180) to sulphate reducing bacteria, iron bacteria and saprophytic microorganism.Tatsumi etc. synthesize a series of with Aden's alkyl, crotonylidene and butynelene for connecting the bi-quaternary ammonium salt Gemini surface active of base, and study its fungicidal activity (J.Surf.Deterg. to aspergillus niger and Candida albicans bacterium, 2001,4 (3): 271).Subsequently, it is connect base with crotonylidene that Tatsumi etc. have synthesized, and hydrophobic chain containing the bi-quaternary ammonium salt Gemini surface active of ester group, and studies its fungicidal activity (J.Oleo Sci. to gram-positive microorganism and Gram-negative bacteria, 2014,63 (2): 137).Kuperkar have studied the fungicidal activity (J.Surf.Deterg., 2012,15:107) of m-s-m type (m=12,16, s=2,4,6) bi-quaternary ammonium salt Gemini surface active gram-positive microorganism, Gram-negative bacteria and fungi.CN103598186A discloses a kind of double-basis type metronidazole modification biquaternary ammonium salts bactericides and preparation method thereof.
Sterilant conventional in oil field water and industrial circulating cooling water is at present still dodecyl benzyl dimethyl ammonium chloride (1227), due to life-time service, bacterium develops immunity to drugs to it, drug effect is constantly declined, injected volume constantly increases, production cost rises year by year, and causes environmental pollution.
Summary of the invention:
The object of the present invention is to provide a kind of organic diammonium compound connecting base and contain di-ester-base, can be used for sterilization, described connection base is as follows containing the general structure of the organic diammonium compound of di-ester-base:
Wherein, Y is
or
n=5-13.
Described connection base is as follows containing the synthetic method of the organic diammonium compound of di-ester-base:
(1) add organic solvent and Isosorbide-5-Nitrae-terephthalyl alcohol or Resorcinol in a kettle., then add acid binding agent, finally add chloroacetyl chloride, maintain reaction 3 ~ 5h, reaction produces tan precipitate; After reaction terminates, filter, after filtrate revolving evaporates solvent, with anhydrous methanol washing, drying two chloracetate.
Organic solvent described in step (1) is anhydrous dioxane or anhydrous tetrahydro furan;
Described acid binding agent is triethylamine, sodium carbonate, sodium hydroxide or pyridine;
The mol ratio of described Isosorbide-5-Nitrae-terephthalyl alcohol or Resorcinol and chloroacetyl chloride is 1:2.5 ~ 3.
Control temperature 0 ~ 10 DEG C when described chloroacetyl chloride drips, the temperature of reaction after being added dropwise to complete is 30 ~ 45 DEG C;
(2) the two chloracetate of step (1) gained and Long carbon chain tertiary amine react in organic solvent, temperature of reaction is at 80 ~ 110 DEG C, reaction times 30 ~ 48h, after reaction terminates, filter, filter cake anhydrous propanone recrystallization, drying can obtain the organic diammonium compound of described connection base containing di-ester-base;
Organic solvent described in step (2) is anhydrous ethylene dichloride, dioxane, acetonitrile or ethanol;
Described two chloracetate and the mol ratio of Long carbon chain tertiary amine are 1:2.2 ~ 3.
Reaction expression is as follows:
In, Y is
or
n=5-13.
The present invention also provides described connection base containing the application of bi-quaternary ammonium salt in sterilization of di-ester-base, and described connection base is 5 ~ 50ppm containing the concentration of bi-quaternary ammonium salt in water of di-ester-base.
Beneficial effect:
(1) the present invention disclose a kind of connection base newly containing in the bi-quaternary ammonium salt structure of di-ester-base containing ester group, environmentally friendly easy degraded, preparation technology is simple;
(2) compared with conventional quaternary ammonium salt bactericide, linking group of the present invention is containing the bi-quaternary ammonium salt good surface activity of di-ester-base, and have higher fungicidal activity, consumption is few.
Accompanying drawing illustrates:
Fig. 1 is the infrared spectrogram of bi-quaternary ammonium salt (I)
Fig. 2 is bi-quaternary ammonium salt (I)
1h NMR spectrogram
Fig. 3 is the ESI-MS spectrogram of bi-quaternary ammonium salt (I)
Fig. 4 is the infrared spectrogram of bi-quaternary ammonium salt (II)
Fig. 5 is bi-quaternary ammonium salt (II)
1h NMR spectrogram
Fig. 6 is the ESI-MS spectrogram of bi-quaternary ammonium salt (II)
Fig. 7 is the infrared spectrogram of bi-quaternary ammonium salt (III)
Fig. 8 is bi-quaternary ammonium salt (III)
1h NMR spectrogram
Fig. 9 is the ESI-MS spectrogram of bi-quaternary ammonium salt (III)
Figure 10 is the infrared spectrogram of bi-quaternary ammonium salt (IV)
Figure 11 is bi-quaternary ammonium salt (IV)
1h NMR spectrogram
Figure 12 is the ESI-MS spectrogram of bi-quaternary ammonium salt (IV)
Figure 13 is that the surface tension of bi-quaternary ammonium salt is to concentration relationship figure
Embodiment:
Example 1: the synthesis of bi-quaternary ammonium salt (I)
1, the synthesis of two Mono Chloro Acetic Acid terephthaldehyde alcohol ester
11.10g (0.1mol) terephthalyl alcohol is added in the four-hole bottle of 250mL, 100mL anhydrous dioxane, ice-water bath controls temperature of reaction under 0 ~ 10 DEG C of condition, add 30.32g (0.3mol) triethylamine, start stirring, dissolve completely until total material, slowly drip 28.25g (0.25mol) chloroacetyl chloride, drip completely until chloroacetyl chloride, be warming up to 30 DEG C of reaction 3h.After question response terminates, suction filtration, revolves solvent evaporated by filtrate, obtains brown solid.By 3 × 10mL anhydrous methanol washing brown solid, suction filtration, obtains white solid, i.e. two Mono Chloro Acetic Acid terephthaldehyde alcohol ester.
2, the synthesis of bi-quaternary ammonium salt (I)
Step 1 gained 2.93g (10mmol) two Mono Chloro Acetic Acid terephthaldehyde alcohol ester is added in the four-hole bottle of 100mL, 40mL anhydrous dioxane, stir, be warming up to backflow, until completely dissolved, drip 5.34g (25mmol) dimethyl dodecyl base tertiary amine, under reflux conditions react 48h.Treat that system is cooled to room temperature, suction filtration after reaction terminates, filter cake washing with acetone, obtains white solid, obtains bi-quaternary ammonium salt (I).Adopt infrared spectroscopy, proton nmr spectra and high resolution mass spectrum to carry out structural characterization, its infrared spectra is shown in Fig. 1, and proton nmr spectra is shown in Fig. 2, and high resolution mass spec is shown in Fig. 3.
Infrared analysis result:
FT-IR(KBr,cm
-1):2917,2850,1747,1517,1465,1241,1191,813,719。
Nuclear-magnetism:
1h NMR (CDCl
3, ppm) and 0.874-0.916 (t, 6H, 2CH
3), 1.269-1.341 (m, 36H, 2CH
3(CH
2)
9), 1.720 (m, 4H, 2CH
3(CH
2)
9cH
2), 3.545 (m, 12H, 2N (CH
3)
2), 3.838 (m, 4H, 2CH
3(CH
2)
9cH
2cH
2), 5.158 (m, 4H, 2N (CH
3)
2cH
2cOO), 5.330 (m, 4H, CH
2arCH
2), 7.346 (m, 4H, ArH).
Mass spectrum: ESI-MS (positive): m/z 681.53569 [M-Cl]
+, 323.28080 [M-2Cl]
2+/ 2.
Example 2: the synthesis of bi-quaternary ammonium salt (II)
1, the synthesis of two Mono Chloro Acetic Acid Resorcinol ester
11.10g (0.1mol) Resorcinol is added in the four-hole bottle of 250mL, 100mL anhydrous tetrahydro furan, ice-water bath controls temperature of reaction under 0 ~ 10 DEG C of condition, add 19.78g (0.25mol) pyridine, start stirring, dissolve completely until total material, slowly drip 28.25g (0.25mol) chloroacetyl chloride, drip completely until chloroacetyl chloride, be warming up to 40 DEG C of reaction 4h.After question response terminates, suction filtration, revolves solvent evaporated by filtrate, obtains brown solid.By 3 × 10mL anhydrous methanol washing brown solid, suction filtration, obtains white solid, i.e. two Mono Chloro Acetic Acid Resorcinol ester.
2, the synthesis of bi-quaternary ammonium salt (II)
Step 1 gained 2.63g (10mmol) two Mono Chloro Acetic Acid Resorcinol ester is added in the four-hole bottle of 100mL, the anhydrous ethylene dichloride of 40mL, stir, be warming up to backflow, until completely dissolved, drip 6.76g (28mmol) dimethyl tetradecyl base tertiary amine, under reflux conditions react 42h.Treat that system is cooled to room temperature, suction filtration after reaction terminates, filter cake washing with acetone, obtains white solid, obtains bi-quaternary ammonium salt (II).Adopt infrared spectroscopy, proton nmr spectra and high resolution mass spectrum to carry out structural characterization, its infrared spectra is shown in Fig. 4, and proton nmr spectra is shown in Fig. 5, and high resolution mass spec is shown in Fig. 6.
Infrared analysis result:
FT-IR(KBr,cm
-1):2917,2848,1762,1502,1465,1240,1182,1157,835,719。
Nuclear-magnetism:
1h NMR (CDCl
3, ppm) and 0.852-0.893 (t, 6H, 2CH
3),
1.248-1.349(m,44H,2CH
3(CH
2)
11),1.816(m,4H,2CH
3(CH
2)
11CH
2),
3.636(m,12H,2N(CH
3)
2),3.853(m,4H,2CH
3(CH
2)
11CH
2CH
2),
6.005(m,4H,2N(CH
3)
2CH
2COO),7.272(m,4H,ArH)。
Mass spectrum: ESI-MS (positive): m/z 709.56539 [M-Cl]
+, 337.29789 [M-2Cl]
2+/ 2.
Example 3: the synthesis of bi-quaternary ammonium salt (III)
1, the synthesis of two Mono Chloro Acetic Acid terephthaldehyde alcohol ester
11.10g (0.1mol) terephthalyl alcohol is added in the four-hole bottle of 250mL, 100mL anhydrous dioxane, ice-water bath controls temperature of reaction under 0 ~ 10 DEG C of condition, add 25.25g (0.25mol) triethylamine, start stirring, dissolve completely until total material, slowly drip 33.90g (0.30mol) chloroacetyl chloride, drip completely until chloroacetyl chloride, be warming up to 30 DEG C of reaction 3h.After question response terminates, suction filtration, revolves solvent evaporated by filtrate, obtains brown solid.By 3 × 10mL anhydrous methanol washing brown solid, suction filtration, obtains white solid, i.e. two Mono Chloro Acetic Acid terephthaldehyde alcohol ester.
2, the synthesis of bi-quaternary ammonium salt (III)
Step 1 gained 2.93g (10mmol) two Mono Chloro Acetic Acid terephthaldehyde alcohol ester is added in the four-hole bottle of 100mL, 40mL anhydrous acetonitrile, stir, be warming up to backflow, until completely dissolved, drip 6.03g (25mmol) dimethyl tetradecyl base tertiary amine, under reflux conditions react 36h.Treat that system is cooled to room temperature, suction filtration after reaction terminates, filter cake washing with acetone, obtains white solid, obtains bi-quaternary ammonium salt.Adopt infrared spectroscopy, proton nmr spectra and high resolution mass spectrum to carry out structural characterization, its infrared spectra is shown in Fig. 7, and proton nmr spectra is shown in Fig. 8, and high resolution mass spec is shown in Fig. 9.
Infrared analysis result:
FT-IR(KBr,cm
-1):2915,2848,1747,1519,1467,1243,1189,811,719。
Nuclear-magnetism:
1h NMR (CDCl
3, ppm) and 0.852-0.891 (t, 6H, 2CH
3),
1.247-1.323(m,44H,2CH
3(CH
2)
11),1.719(m,4H,2CH
3(CH
2)
11CH
2),
3.531(m,12H,2N(CH
3)
2),3.814(m,4H,2CH
3(CH
2)
9CH
2CH
2),
5.125(m,4H,2N(CH
3)
2CH
2COO),5.354(m,4H,CH
2ArCH
2),
7.268-7.306(m,4H,ArH)。
Mass spectrum: ESI-MS (positive): m/z 737.59819 [M-Cl]
+, 351.31347 [M-2Cl]
2+/ 2.
Example 4: the synthesis of (IV) of bi-quaternary ammonium salt
1, the synthesis of two Mono Chloro Acetic Acid Resorcinol ester
11.10g (0.1mol) Resorcinol is added in the four-hole bottle of 250mL, 100mL anhydrous tetrahydro furan, ice-water bath controls temperature of reaction under 0 ~ 10 DEG C of condition, add 10.15g (0.25mol) sodium hydroxide, start stirring, dissolve completely until total material, slowly drip 33.92g (0.30mol) chloroacetyl chloride, drip completely until chloroacetyl chloride, be warming up to 40 DEG C of reaction 4h.After question response terminates, suction filtration, revolves solvent evaporated by filtrate, obtains brown solid.By 3 × 10mL anhydrous methanol washing brown solid, suction filtration, obtains white solid, i.e. two Mono Chloro Acetic Acid Resorcinol ester.
2, the synthesis of bi-quaternary ammonium salt (IV)
In the four-hole bottle of 100mL, add step 1 gained 2.63g (10mmol) two Mono Chloro Acetic Acid Resorcinol ester, 40mL dehydrated alcohol, stir, be warming up to backflow, until completely dissolved, drip 6.42g (30mmol) dimethyl dodecyl base tertiary amine, under reflux conditions react 30h.Treat that system is cooled to room temperature, suction filtration after reaction terminates, filter cake washing with acetone, obtains white solid, obtains bi-quaternary ammonium salt.Adopt infrared spectroscopy, proton nmr spectra and high resolution mass spectrum to carry out structural characterization, its infrared spectra is shown in Figure 10, and proton nmr spectra is shown in Figure 11, and high resolution mass spec is shown in Figure 12.
Infrared analysis result:
FT-IR(KBr,cm
-1):2917,2848,1766,1502,1463,1243,1180,1155,833,719。
Nuclear-magnetism:
1h NMR (CDCl
3, ppm) and 0.865 (t, 6H, 2CH
3),
1.240-1.344(m,36H,2CH
3(CH
2)
9),1.817(m,4H,2CH
3(CH
2)
9CH
2),
3.625(m,12H,2N(CH
3)
2),3.846(m,4H,2CH
3(CH
2)
9CH
2CH
2),
5.977(m,4H,2N(CH
3)
2CH
2COO),6.849(m,4H,ArH)。
Mass spectrum: ESI-MS (positive): m/z 653.50289 [M-Cl]
+, 309.26644 [M-2Cl]
2+/ 2.
Example 5: the determination of surface activity of bi-quaternary ammonium salt
The determination of surface activity method of bi-quaternary ammonium salt is as follows:
When measuring such Gemini surface active surfactivity, the surfactant soln of a series of different concns is configured with ultrapure water, be placed in 100mL beaker, spend the night with insurance film phonograph seal, utilize K100 automatic surface tensiometer to adopt the equilibrium surface tension of the platinum around-France chart surface-active agent aqueous solution.First liquid to be measured is placed in water bath with thermostatic control constant temperature for some time during test, then removes preservative film, be placed on test board gently.After having surveyed a sample, platinum loop ultrapure water is cleaned, and then uses spirit lamp calcination to micro-red, to ensure that it is absolute clean.The surface tension of bi-quaternary ammonium salt I, II, III, IV and the graph of a relation of concentration are as shown in Figure 13.
The micelle-forming concentration that can obtain I, II, III, IV of 4 kinds of bi-quaternary ammonium salts prepared by embodiment from Figure 13 is respectively 0.58,0.10,0,09 and 0.65mmol/L, and N under the same terms, the micelle-forming concentration of N-dimethyl benzyl ammonium chloride (1227) is 8.8mmol/L, and prepared connection base has higher surfactivity containing the bi-quaternary ammonium salt of di-ester-base than 1227.
Embodiment 6: bactericidal property evaluation
1. strain culturing
Get intestinal bacteria (E.coli) and subtilis (B.subtilis) respectively in slant culture 72h.Substratum is prepared: 15 grams, agar, add appropriate distilled water heating for dissolving, adding peptone 10 grams successively, extractum carnis 3 grams, 5 grams, sodium-chlor, and stir, adding distil water is settled to 1 liter, about pH to 7.2, while hot packing is regulated, in 121 DEG C of high pressure steam sterilizations 30 minutes by 1M HCl and 1M NaOH solution.
2. bacteria suspension processed
Be transferred in Erlenmeyer flask by the bacterial strain stroke-physiological saline solution of inoculation culture, fully shake, make lawn be well-dispersed in physiological saline, the colony number of each experimental bacteria suspension is 1 × 10
7~ 1 × 10
8cfu/mL.
3. fungicidal activity evaluation
Prepare certain density microbicide solution, get 10mL bacteria suspension, add a certain amount of microbicide solution, be placed in 34 DEG C of shaking tables and cultivate, adopt 10 times of dilution method dilutions, measure the colony number under the existence of different concns sterilant.Make blank sample simultaneously, calculate sterilizing rate.
The calculation formula of sterilizing rate is as follows:
In formula, I is the average colony number of control sample, and II is the average colony number of the sample adding sterilant.
Table 1 lists the sterilizing rate of sterilant described in embodiment 1-4 and fungicide 1227.
The sterilization effect of table 1 bi-quaternary ammonium salt I, II, III, IV and " 1227 "
As can be seen from Table 1, no matter be gram-positive microorganism (subtilis B.Subtilis) or Gram-negative bacteria (intestinal bacteria E.Coli), prepared connection base has the better sterilization effect than 1227 containing the bi-quaternary ammonium salt of di-ester-base.
Claims (8)
1. connect the organic diammonium compound of base containing di-ester-base, it is characterized in that, described structural formula of compound is as follows:
Wherein, Y is
or
n=5-13.
2. a kind of preparation method connecting base and contain the organic diammonium compound of di-ester-base as claimed in claim 1, it is characterized in that, preparation method is as follows:
(1) add organic solvent and Isosorbide-5-Nitrae-terephthalyl alcohol or Resorcinol in a kettle., then add acid binding agent, finally add chloroacetyl chloride, maintain reaction 3 ~ 5h, reaction produces tan precipitate; After reaction terminates, filter, after filtrate revolving evaporates solvent, with anhydrous methanol washing, drying two chloracetate;
(2) two for step (1) gained chloracetate and Long carbon chain tertiary amine are reacted in organic solvent, temperature of reaction is at 80 ~ 110 DEG C, reaction times 30 ~ 48h, after reaction terminates, filter, filter cake anhydrous propanone recrystallization, drying can obtain the organic diammonium compound of described connection base containing di-ester-base.
3. a kind of preparation method connecting base and contain the organic diammonium compound of di-ester-base as claimed in claim 2, it is characterized in that, the organic solvent described in step (1) is anhydrous dioxane or anhydrous tetrahydro furan.
4. a kind of preparation method connecting base and contain the organic diammonium compound of di-ester-base as claimed in claim 2, it is characterized in that, described acid binding agent is triethylamine, sodium carbonate, sodium hydroxide or pyridine.
5. a kind of preparation method connecting base and contain the organic diammonium compound of di-ester-base as claimed in claim 2, it is characterized in that, the mol ratio of described Isosorbide-5-Nitrae-terephthalyl alcohol or Resorcinol and chloroacetyl chloride is 1:2.5 ~ 3.
6. a kind of preparation method connecting base and contain the organic diammonium compound of di-ester-base as claimed in claim 2, it is characterized in that, control temperature 0 ~ 10 DEG C when described chloroacetyl chloride drips, the temperature of reaction after being added dropwise to complete is 30 ~ 45 DEG C.
7. a kind of preparation method connecting base and contain the organic diammonium compound of di-ester-base as claimed in claim 2, it is characterized in that, described two chloracetate and the mol ratio of Long carbon chain tertiary amine are 1:2.2 ~ 3.
8. connect the organic diammonium compound application in sterilization of base containing di-ester-base as claimed in claim 1.
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Cited By (4)
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| CN107573316A (en) * | 2017-09-06 | 2018-01-12 | 荆门医药工业技术研究院 | The acylated derivatives and its preparation technology of a kind of genistein |
| CN114262273A (en) * | 2021-12-31 | 2022-04-01 | 安徽大学 | Novel degradable quaternary ammonium salt with high antibacterial activity and synthesis 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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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105817176A (en) * | 2016-03-25 | 2016-08-03 | 黑龙江幸福人生物合成树脂科技开发有限公司 | Quaternary ammonium salt surface active agent and preparation method thereof |
| CN105817176B (en) * | 2016-03-25 | 2017-06-16 | 黑龙江幸福人生物合成树脂科技开发有限公司 | Quaternary ammonium salt surface active agent and preparation method thereof |
| CN107573316A (en) * | 2017-09-06 | 2018-01-12 | 荆门医药工业技术研究院 | The acylated derivatives and its preparation technology of a kind of genistein |
| CN114262273A (en) * | 2021-12-31 | 2022-04-01 | 安徽大学 | Novel degradable quaternary ammonium salt with high antibacterial activity and synthesis 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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