CN108353898B - Gemini surfactant and 1, 2-hexanediol antibacterial compound - Google Patents
Gemini surfactant and 1, 2-hexanediol antibacterial compound Download PDFInfo
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- CN108353898B CN108353898B CN201810107392.XA CN201810107392A CN108353898B CN 108353898 B CN108353898 B CN 108353898B CN 201810107392 A CN201810107392 A CN 201810107392A CN 108353898 B CN108353898 B CN 108353898B
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
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Abstract
The invention provides a Gemini surfactant and 1, 2-hexanediol antibacterial compound, which comprises the following components: the cationic n-s-n type Gemini surfactant and 1, 2-hexanediol are adopted, and the molar concentration ratio of the Gemini cationic surfactant to the 1, 2-hexanediol is 1-20 mu M/L: 20 to 50 mM/L. According to the antibacterial composition, the addition of the Gemini surfactant with extremely low concentration enables the dosage of the 1, 2-hexanediol to be reduced by one order of magnitude, and the antibacterial activity is still high, and the two compounds have a good inhibition effect on various bacteria and fungi.
Description
Technical Field
The invention relates to a Gemini surfactant and 1, 2-hexanediol antibacterial compound, belonging to the technical field of preparation of antibacterial agents.
Background
The Gemini surfactant has a special structure, the molecule of the Gemini surfactant contains two hydrophilic groups and two hydrophobic chains, and the two hydrophilic groups are connected together through a chemical bond by a connecting group. This structure both enhances the hydrophobic interaction between the hydrophobic tails and greatly weakens the electrostatic repulsion between the ionic hydrophilic groups due to the restriction of the linking groups. Therefore, compared with the traditional single-chain surfactant, the Gemini surfactant shows more excellent physicochemical properties such as good surface activity, wettability, calcium soap dispersibility, extremely low CMC, rich aggregation forms, special phase behaviors and the like, and the specific properties enable the Gemini surfactant to have a very wide application prospect. The antibacterial ability of cationic surfactants ranging from single chain to Gemini is also significantly improved, for example, the MIC of dodecyltrimethylammonium bromide, which is a single-chain cationic surfactant, is about 250. mu.M, while the MIC of Gemini surfactants 12-4-12 with the same carbon number is about 24. mu.M, which is also reduced by almost an order of magnitude.
The 1, 2-hexanediol is colorless transparent to light yellow liquid at normal temperature, has good affinity to a surfactant, is commonly used as a humectant in personal care products, has certain antibacterial performance, and can replace benzoic acids, formaldehyde donors and phenoxyethanol preservatives to inhibit the growth of microorganisms in cosmetics. In general, 1, 2-hexanediol is used as an antibacterial agent in a large amount, and if necessary, 2.5 to 5% by mass (i.e., 200mM/L to 400mM/L molarity) is added to achieve a good antibacterial effect.
Disclosure of Invention
The object of the present invention is to provide a novel antibacterial composition.
The invention adopts the following technical scheme:
an antimicrobial complex of a Gemini surfactant and 1, 2-hexanediol, comprising: gemini surfactant and 1, 2-hexanediol.
Further, the antibacterial compound of the Gemini surfactant and the 1, 2-hexanediol can also have the following characteristics: wherein the Gemini surfactant is a quaternary ammonium salt cationic surfactant.
Further, the antibacterial compound of the Gemini surfactant and the 1, 2-hexanediol can also have the following characteristics: the general formula of the cationic Gemini surfactant is n-s-n (n is the carbon atom number of a hydrophobic tail chain, and s is the carbon atom number of a connecting group), and any one of the following can be selected:
12-s-12，n＝12，s＝2,4,6,8,10；
14-s-14，n＝14，s＝4；
16-s-16，n＝16，s＝4。
further, the antibacterial compound of the Gemini surfactant and the 1, 2-hexanediol can also have the following characteristics: wherein the Gemini cationic surfactant is 12-6-12.
Further, the antibacterial compound of the Gemini surfactant and the 1, 2-hexanediol can also have the following characteristics: wherein the molar concentration ratio of the Gemini cationic surfactant to 1, 2-hexanediol is 1-20 mu M/L: 20 to 50 mM/L.
Further, the Gemini surfactant and 1, 2-hexanediol antibacterial compound can also have the following characteristics: wherein the Gemini cationic surfactant and the 1, 2-hexanediol are mixed according to the concentration ratio of: 1 μ M/L: 50 mM/L.
Detailed Description
The technical solution of the present invention is further explained by the following specific examples.
< example one >
The bacteriostasis effect of the 1 mu M12-6-12 and 50mM 1, 2-hexanediol complex system on Escherichia coli (ATCC8739) and Candida albicans (ATCC10231) is illustrated, and the operation method is illustrated by taking Escherichia coli as an example.
1. 4 μ M/L of 12-6-12 solution and 200mM/L of 1, 2-hexanediol in PBS buffer solution, and the polypeptide-containing PBS solution was sterilized, cooled and filtered through a 0.45 μ M filter into a conical flask.
2. The medium was lowered to the appropriate temperature (before coagulation) and the plates were decanted.
3. Grouping experiments:
(1) 100 μ L of 12-6-12 solution with concentration of 4 μ M/L is put into a centrifuge tube of 1.5ml, 100 μ L of 1, 2-hexanediol with concentration of 200mM/L is added, 200 μ L of Escherichia coli with different colony counts is added, and reaction is carried out for 30 minutes.
(2) 200 mul of Escherichia coli liquid with concentration of 2 mul/L and 12-6-12 and 200 mul of Escherichia coli liquid with different concentrations are respectively added.
(3) 200 mul of 1, 2-hexanediol with the concentration of 100mM/L and 200 mul of Escherichia coli liquid with different concentrations are respectively added. The negative control sample is 200 mu L PBS solution and 200 mu L Escherichia coli liquid with different concentrations; at least 3 replicates were prepared per sample.
4. A pipette gun was used to remove 100. mu.L of the total mixture from the system and place it on the surface of the solidified medium and spread it with a spreader.
5. After culturing for 24 hours at 37 ℃, counting colonies, and comparing with a negative control sample to calculate the bacteriostasis rate
Wherein A is the average colony number of the negative control sample, and B is the average colony number of the experimental sample.
6. In the experimental steps of the candida albicans, the culture time needs at least 48 hours, and the rest operation steps and groups and the concentration of reagents are the same as those of the escherichia coli.
7. The results are shown in Table 1:
TABLE 1 Gemini surfactant and 1, 2-hexanediol antimicrobial efficacy
< example two >
The bacteriostatic effect of a 5 mu M12-6-12 and 20mM 1, 2-hexanediol complex system on Escherichia coli (ATCC8739) and Candida albicans (ATCC10231), and the operation method is illustrated by taking Escherichia coli as an example.
1. A20. mu.M/L solution of 12-6-12 and 80 mM/L1, 2-hexanediol in PBS buffer was used, and the polypeptide-containing PBS solution was sterilized, cooled and filtered through a 0.45. mu.M filter into a conical flask.
2. The medium was lowered to the appropriate temperature (before coagulation) and the plates were decanted.
3. Grouping experiments:
(1) 100 μ L of 12-6-12 solution with concentration of 20 μ M/L is put into a centrifuge tube of 1.5ml, 100 μ L of 1, 2-hexanediol with concentration of 80mM/L is added, 200 μ L of Escherichia coli with different colony counts is added, and reaction is carried out for 30 minutes.
(2) 200 mul of 10 mul/L Escherichia coli liquid 12-6-12 and 200 mul of different concentrations were added.
(3) 200 mul of 1, 2-hexanediol with the concentration of 40mM/L and 200 mul of Escherichia coli liquid with different concentrations are respectively added. The negative control sample is 200 mu L PBS solution and 200 mu L Escherichia coli liquid with different concentrations; at least 3 replicates were prepared per sample.
4. A pipette gun was used to remove 100. mu.L of the total mixture from the system and place it on the surface of the solidified medium and spread it with a spreader.
5. After culturing for 24 hours at 37 ℃, counting colonies, and comparing with a negative control sample to calculate the bacteriostasis rate
Wherein A is the average colony number of the negative control sample, and B is the average colony number of the experimental sample.
6. In the experimental steps of the candida albicans, the culture time needs at least 48 hours, and the rest operation steps and groups and the concentration of reagents are the same as those of the escherichia coli.
7. The results are shown in Table 2:
TABLE 2 Gemini surfactant and 1, 2-hexanediol antimicrobial efficacy
< example three >
2.5 mu M of 12-6-12 and 40mM of 1, 2-hexanediol are compounded to achieve the bacteriostatic effect on Escherichia coli (ATCC8739) and Candida albicans (ATCC10231), and the operation method is illustrated by taking Escherichia coli as an example.
1. 10 μ M/L of 12-6-12 solution and 160mM/L of 1, 2-hexanediol in PBS buffer solution, and the polypeptide-containing PBS solution was sterilized, cooled and filtered through a 0.45 μ M filter into a conical flask.
2. The medium was lowered to the appropriate temperature (before coagulation) and the plates were decanted.
3. Grouping experiments:
(1) 100 μ L of 12-6-12 solution with concentration of 10 μ M/L is put into a centrifuge tube of 1.5ml, 100 μ L of 1, 2-hexanediol with concentration of 160mM/L is added, 200 μ L of Escherichia coli with different colony counts is added, and reaction is carried out for 30 minutes.
(2) 200 mul of Escherichia coli liquid with concentration of 5 mul/L and 12-6-12 and 200 mul of Escherichia coli liquid with different concentrations are respectively added.
(3) 200 mul of 1, 2-hexanediol with the concentration of 80mM/L and 200 mul of Escherichia coli liquid with different concentrations are respectively added. The negative control sample is 200 mu L PBS solution and 200 mu L Escherichia coli liquid with different concentrations; at least 3 replicates were prepared per sample.
4. A pipette gun was used to remove 100. mu.L of the total mixture from the system and place it on the surface of the solidified medium and spread it with a spreader.
5. After culturing for 24 hours at 37 ℃, counting colonies, and comparing with a negative control sample to calculate the bacteriostasis rate
Wherein A is the average colony number of the negative control sample, and B is the average colony number of the experimental sample.
6. In the experimental steps of the candida albicans, the culture time needs at least 48 hours, and the rest operation steps and groups and the concentration of reagents are the same as those of the escherichia coli.
7. The results are shown in Table 3:
TABLE 3 Gemini surfactant and 1, 2-hexanediol antimicrobial efficacy
In other embodiments, the cationic Gemini surfactant can also adopt 12-4-12 or 14-4-14 Gemini surfactant and can achieve better sterilization effect.
Effects and effects of the embodiments
In general, 1, 2-hexanediol needs to be added with a mass concentration of 2.5-5% (namely 200 mM/L-400 mM/L molarity) to exert antibacterial performance, but when the 1 mu M/L12-6-12 and 50 mM/L1, 2-hexanediol compound system and the 5 mu M/L12-6-12 and 20 mM/L1, 2-hexanediol compound system are compounded, the antibacterial performance is close to 100% on various bacteria and fungi. It is noted that 12-6-12 and 1, 2-hexanediol alone had no significant bactericidal effect on the above mentioned species at their experimental concentrations. In the invention, the addition of the Gemini surfactant with extremely low concentration enables the dosage of the 1, 2-hexanediol to be reduced by one order of magnitude and still maintain high antibacterial activity, and the two compounds have good inhibition effect on various bacteria and fungi. The interaction of alcohol and surfactant in aqueous solution can affect the surface activity and the size and shape of aggregate, and the research work of Tang Neng Qiang et al reveals the interaction of alcohol and a series of cationic Gemini surfactants (Tang Neng Qiang, Zhulin I, Korea Yu Chun, Wang Yilin. branched alcohol affects the surface activity and micellization behavior of Gemini surfactants [ J ] Chemicals, 2014 (72): 673-. In the invention, the surfactant with extremely low concentration is added into the mixture formed by the surfactant and the 1, 2-hexanediol, so that the surfactant can more efficiently penetrate through cell membranes and destroy the barrier function of the cell membranes, and the antibacterial efficiency of the cell membranes is improved.
Claims (4)
1. An antimicrobial complex of a Gemini surfactant and 1, 2-hexanediol, comprising: a Gemini surfactant and 1, 2-hexanediol;
the Gemini surfactant is selected from Gemini surfactants shown in the following structural formula:
the general formula is n-s-n, n is the carbon atom number of the hydrophobic tail chain, s is the carbon atom number of the connecting group,
wherein n is 12 and s is 6;
the molar concentration ratio of the Gemini surfactant to 1, 2-hexanediol is 1-5 mu M/L: 20 to 50 mM/L.
2. The Gemini surfactant and 1, 2-hexanediol antimicrobial complex of claim 1, wherein:
the concentration ratio of the Gemini surfactant to the 1, 2-hexanediol is 1 mu M/L: 50 mM/L.
3. The Gemini surfactant and 1, 2-hexanediol antimicrobial complex of claim 1, wherein:
the concentration ratio of the Gemini surfactant to the 1, 2-hexanediol is 5 mu M/L: 20 mM/L.
4. The Gemini surfactant and 1, 2-hexanediol antimicrobial complex of claim 1, wherein:
the concentration ratio of the Gemini surfactant to the 1, 2-hexanediol is 2.5 mu M/L: 40 mM/L.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4444790A (en) * | 1982-05-27 | 1984-04-24 | Millmaster Onyx Group, Inc. | Quaternary ammonium disinfectants |
| CN101279219A (en) * | 2008-01-03 | 2008-10-08 | 天津师范大学 | Bis-quaternary ammonium salt cationic surfactant, preparation and use thereof |
| US20120034287A1 (en) * | 2010-08-03 | 2012-02-09 | Napolitano Lisa A | Quaternary Ammonium Glycol Ether Disinfectant Wipes |
| CN107372579A (en) * | 2017-08-13 | 2017-11-24 | 上海应用技术大学 | Asymmetric Shuangzi silicone Quaternary Ammonium Salt Antimicrobial Agent and preparation method thereof |
-
2018
- 2018-02-02 CN CN201810107392.XA patent/CN108353898B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4444790A (en) * | 1982-05-27 | 1984-04-24 | Millmaster Onyx Group, Inc. | Quaternary ammonium disinfectants |
| CN101279219A (en) * | 2008-01-03 | 2008-10-08 | 天津师范大学 | Bis-quaternary ammonium salt cationic surfactant, preparation and use thereof |
| US20120034287A1 (en) * | 2010-08-03 | 2012-02-09 | Napolitano Lisa A | Quaternary Ammonium Glycol Ether Disinfectant Wipes |
| CN107372579A (en) * | 2017-08-13 | 2017-11-24 | 上海应用技术大学 | Asymmetric Shuangzi silicone Quaternary Ammonium Salt Antimicrobial Agent and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| Effect of N,N′-Bis(alkyldimethyl)-α,ω-alkanediammonium Dibromides on Bacteria of the Genus Clostridium;V Cigáneková等;《Folia Microbiologica》;19891231;第34卷(第3期);全文 * |
| Relationship between critical micelle concentrations and minimum inhibitory concentrations for some non-aromatic quaternary ammonium salts and amine oxides;F Devinsky等;《Tenside Detergents》;19851231;第22卷(第1期);全文 * |
| 季铵盐杀菌剂的现状与发展趋势;李俊等;《日用化学品科学》;20150930;第38卷(第9期);第33页第3段 * |
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