CN103949185B - A kind of anion surfactant possessing bactericidal activity and preparation method thereof - Google Patents
A kind of anion surfactant possessing bactericidal activity and preparation method thereof Download PDFInfo
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- CN103949185B CN103949185B CN201410108295.4A CN201410108295A CN103949185B CN 103949185 B CN103949185 B CN 103949185B CN 201410108295 A CN201410108295 A CN 201410108295A CN 103949185 B CN103949185 B CN 103949185B
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- anion surfactant
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- ZZPWCROYQRXOMZ-UHFFFAOYSA-N CN(c1nc(Cl)nc(Cl)n1)I Chemical compound CN(c1nc(Cl)nc(Cl)n1)I ZZPWCROYQRXOMZ-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention discloses a kind of anion surfactant with bactericidal activity, there is the structure that following general formula represents.This surfactant is with Cyanuric Chloride, fatty amine, sulfamic acid, and aminobenzimidazole is raw material, and with rational rate of charge, synthesize through three-step reaction, it had both had the character of surfactant, the more important thing is to possess bactericidal activity.The anion surfactant of what the present invention protected have bactericidal activity; not only solve surfactant and the undesirable problem of bactericide compatibility; and solve the restriction of electric charge; widen the range of application of the surfactant of bactericidal activity; the later stage is used to be easy to process; consumption is few, has important theory and realistic meaning.
described R
1for-(CH
2)
5cH
3,-(CH
2)
7cH
3,-(CH
2)
9cH
3,-(CH
2)
11cH
3in any one, described R
2for-CH
2-,-(CH
2)
2-,-(CH
2)
3-,-C
6h
4-in any one.
Description
Technical field:
The present invention relates to a kind of surfactant, particularly a kind of anion surfactant with bactericidal activity.
Background technology
Surfactant is a kind of functional fine chemicals, due to the special construction that its molecule is amphipathic, under dissolved state can oriented attachment at two-phase interface, thus significantly reduce the interfacial tension between the surface tension of solution and interface.Surfactant purposes is very extensive, relate to field from oil exploitation, industry cleaning link, papermaking, wastewater treatment, to the use of agricultural chemicals agriculturally, chemical fertilizer, the washing of medical field, sterilization, hydrotropy, arrive the cleaning supplies of daily life, cosmetics etc. again, be extended to the high-technology fields such as Novel environment-friendlymaterial material at present.
As far back as 20 middle of century, part surface activating agent is just detected possesses sterilizing function, and therefore it is widely used as bactericide all the time.The surfactant with bactericidal activity having studied report has cationic surface active agent and amphoteric surfactant two class.Quaternary ammonium salt cationic surfactant is a kind of cationic surface active agent, is also industry-wide a kind of bactericide.
In oil exploitation process, need in oil pipeline, to inject waste water to increase oil displacement pressure, but the microorganisms such as bacterium wherein, fungi and metabolite thereof not only can affect grade of oil, also can have corrosiveness to oil pipeline, the time one for a long time also can accumulated plugging pipeline.Conventional quaternary ammonium salt surface active agent is as bactericide at present, by being adsorbed on bacterium surface, destroys its phospholipid bilayer, and then carrys out kill bacteria and control its growth.But Long-Time Service, not only addition is huge, and immunity appears in microorganism, and in the last handling process of displacement of reservoir oil waste water, this type of surfactant is not easily removed, and then the mixture of meeting emulsification Residual oil and waste water, cause profit not easily separated, waste water not easily processes, seriously polluted; And due to electric charge, its application also will be subject to certain restrictions.
Heveatex is a kind of broad-spectrum industrial raw materials, but is easy to because of the effect of microorganism putrid and deteriorated, and rubber hydrocarbon is also unstable, and meeting is coagulation because external environment changes.Therefore, in its initial stage preservation process, need to add as ammoniacal liquor, penta sodium pentachlorophenate, TT/ZnO or other bactericide (single or composite) carry out bacteria growing inhibiting, sometimes also need to add surfactant emulsifies and increase steady.But some bactericide and latex-compatible undesirable, affect the physical and chemical performance of latex following process; Also not only cost is higher for some bactericide, and harmful, environmental pollution is serious, and dosage is wayward, and glue-preparing exhausted water also not easily processes; If separately add surfactant, though its emulsification can be played, latex is stablized, and then reduce the consumption of bactericide, but cannot ensure that itself and bactericide well coexist; Because latex is anionic colloid, therefore quaternary ammonium salt surface active agent is inapplicable.Therefore, research and development have the bactericide of specific function, namely have bactericidal activity and good surface-active bactericide concurrently, and the problems referred to above solving actual production existence become very important.
Benzimidazole is a kind of widely used fine chemical material, all plays important role in a lot of field, has extremely strong bactericidal action to bacterium, fungi, virus etc.Commercially available carbendazim series bactericidal agent is with it for parent carries out derivative synthesis, and because it has high-efficiency low-toxicity, the duration is long, to features such as ambient influnence are little, is widely used in the numerous areas such as industrial or agricultural.
Summary of the invention
The object of this invention is to provide a kind of anion surfactant with bactericidal activity and preparation method thereof.Specifically with Cyanuric Chloride, fatty amine, sulfamic acid, aminobenzimidazole is raw material, a kind of containing triazine ring anionic surface activity bactericide with rational rate of charge synthesis, has both had the character of surfactant, and the more important thing is to possess bactericidal activity.
The general structure with the anion surfactant of bactericidal activity of the present invention is as follows:
Described R
1for-(CH
2)
5cH
3,-(CH
2)
7cH
3,-(CH
2)
9cH
3,-(CH
2)
11cH
3in any one,
Described R
2for-CH
2-,-(CH
2)
2-,-(CH
2)
3-,-C
6h
4-in any one.
The anion surfactant with bactericidal activity that above-mentioned general formula of the present invention represents is with Cyanuric Chloride, fatty amine, sulfamic acid, and aminobenzimidazole is raw material, and synthesize through three-step reaction, its concrete synthetic method is:
The straight-chain fatty amine that Cyanuric Chloride and general formula (II) represent is reacted, obtains the compound that general formula (III) represents,
R
1—NH
2（Ⅱ）
Described R
1for-(CH
2)
5cH
3,-(CH
2)
7cH
3,-(CH
2)
9cH
3,-(CH
2)
11cH
3in any one.
The compound that general formula (III) represents reacts with sulfamic acid again, obtains general formula (IV)
Described R
2for-CH
2-,-(CH
2)
2-,-(CH
2)
3-,-C
6h
4-in any one.
The compound that general formula (IV) represents then reacts with aminobenzimidazole, namely obtains the anion surfactant with bactericidal activity that general formula (I) represents.
Its concrete course of reaction is:
R in synthetic route
1, R
2implication identical with front.
Preparing the concrete grammar with the anion surfactant of bactericidal activity of the present invention is:
(1) add with acetone successively in the reactor, or chloroform, or toluene, or oxolane, or DMF, or ethyl acetate is as the Cyanuric Chloride solution of solvent, and (general formula is R to fatty amine
1-NH
2) and aqueous sodium carbonate, under the condition of 0 DEG C-30 DEG C, react 1-8 hour, obtain first step intermediate CT through suitable post processing, be i.e. the compound that represents of general formula (III);
(2) with ethanol, or acetone, or acetonitrile, or water, or DMF, or dimethyl sulfoxide (DMSO) is as solvent, the first step intermediate CT obtained in step (1) is dissolved in wherein, then sulfamic acid solution and aqueous sodium carbonate are added in reactor successively, under the condition of 40 DEG C-60 DEG C, react 5-10 hour, through concentrated, precipitation, drying obtains second step intermediate SCT, i.e. the compound that represents of general formula (IV);
(3) with toluene, or dioxanes, or water or 1-METHYLPYRROLIDONE are as solvent, are dissolved in by aminobenzimidazole wherein; Add the second step intermediate SCT and NaOH and catalyst that obtain in step (2) again, under the condition of 70 DEG C-98 DEG C, heating using microwave reaction 1-5 hour, obtains final products BSCT through concentrated, cooling, i.e. the compound that represents of general formula (I).
Described catalyst is any one in triethylamine, triethylene diamine, DMA.
Beneficial effect:
(1) the present invention utilizes the special construction of Cyanuric Chloride as skeleton, utilizes the mode of the affine replacement of three steps, connects different functional groups respectively, synthesizes a kind of anionic surfactant possessing bactericidal activity.First, the triazine ring of Cyanuric Chloride has higher stability, and three chlorine atoms have higher reactivity because being subject to C=N impact, and reaction condition is easy to control; Secondly, the cheaper starting materials chosen is easy to get, and synthetic route is reasonable in design; Product Status is good, and post-processing approach is simple.
(2) surfactant possessing bactericidal activity of this method synthesis, not only possess good bactericidal properties and surface-active, the more important thing is, under dissolved state, its surface-active makes it between two-phase interface, play oriented attachment effect, especially in the colloidal dispersion of O/W, hydrophobic segment can be adsorbed in hydrophobic one phase, hydrophilic radical is adsorbed in a hydrophilic phase, not only serve stable emulsifying effect, the more important thing is, sterilization group can be concentrated in critical position and play its bactericidal action, compares that not possess surface-active bactericide consumption less.
(3) product of the present invention overcomes the limitation of conventional surface active bactericide electric charge, makes the application of this fine chemicals of Surface Active Germicide more extensive, therefore has important practical significance and actual use value.
In a word; the anion surfactant of what the present invention protected have bactericidal activity; not only solve surfactant and the undesirable problem of bactericide compatibility; and its sterilization mechanism is innovated; also solve the restriction of conventional surface active bactericide electric charge, widened the range of application of the surfactant of bactericidal activity, and use the later stage to be easy to process; consumption is few, has important theory and realistic meaning.
Accompanying drawing explanation
Fig. 1 is embodiment 2 gained BSC
8the infrared spectrogram (KBr compressing tablet, An Hemeng development in science and technology Co., Ltd FTIR7600 type determination of infrared spectroscopy) of T;
At 1500cm
-1near be the stretching vibration of triazine ring; At 1210cm
-1neighbouring is sulfonic acid S=O asymmetric stretching vibration; 1060cm
-1place is sulfonic acid S=O symmetrical stretching vibration; 3000cm
-1near be the stretching vibration of alkyl; 1500cm
-1, 1580cm
-1, 1600cm
-1neighbouring absworption peak proves the existence having phenyl ring; And 1650-1550cm
-1near show the existence of aromatic series and fragrant heterocycle, 1468cm
-1, 1455cm
-1place is imidazole ring stretching vibration peak.
Fig. 2 is embodiment 2 gained BSC
8eSI-MS figure (Bruker company of Switzerland APEX IV type ESI source high-resolution organic mass spectrometer mensuration) of T
In conjunction with ESI-MS(negative) known, 461.20981 is product B SC
8t [M+H
+] quasi-molecular ions.
γ-logc the curve of Fig. 3 product obtained by embodiment 1,2,3.
Detailed description of the invention:
Below in conjunction with embodiment, the specific embodiment of the present invention is described in further detail.Following examples for illustration of the present invention, but are not used for limiting the scope of the invention.
Embodiment 1
Prepare the anion surfactant with bactericidal activity of following structure:
Name is called:
2-(4-(1H-benzimidazolyl-2 radicals-Ji) the own amino of amino-6--1,3,5-triazines-2-amino) ethyl sulfonic acid sodium
Concrete preparation method is as follows:
(1) 0.1mol Cyanuric Chloride is added successively in the reactor, 500mL toluene, 0.12mol n-hexylamine and mass concentration are the aqueous sodium carbonate (containing solute 0.1mol) of 5%, react 6 hours at 0 DEG C-5 DEG C, utilize TLC to follow the tracks of reaction monitoring terminal, solvent is toluene: acetone=1:1-5(V/V).Through dilute hydrochloric acid solution after reaction terminates, sodium bicarbonate solution and washed with de-ionized water, dry, obtain first step intermediate C after concentrated
6t;
(2) 0.12molC is added successively in the reactor
6t, 500mL acetone, 0.1mol tarine and mass concentration are the aqueous sodium carbonate (containing solute 0.1mol) of 5%, react 8 hours at 40 DEG C-50 DEG C, utilize TLC to follow the tracks of reaction monitoring terminal, solvent is acetone: toluene: water=6:1-5:0.5-3(V/V/V).Through concentrated after reaction terminates, cooling, washing obtains second step intermediate SC
6t;
(3) in microwave reactor, 0.1molSC is added successively
6t, 0.1mol triethylene diamine, 500mL deionized water, 0.15mol2-aminobenzimidazole, reacts 3 hours at 90 DEG C-95 DEG C, and utilize TLC to monitor reaction end, solvent is methyl alcohol: toluene=1-5:1(V/V).Through concentrated after reaction terminates, cooling, watery hydrochloric acid process, filtration drying obtains final products BSC
6t.
Embodiment 2
Prepare the anion surfactant with bactericidal activity of following structure:
Its name is called:
2-(4-(1H-benzimidazolyl-2 radicals-Ji) the pungent amino of amino-6--1,3,5-triazines-2-amino) ethyl sulfonic acid sodium
Concrete preparation method is as follows:
(1) 0.1mol Cyanuric Chloride is added successively in the reactor, 500mL toluene, 0.12mol n-octyl amine and mass concentration are the aqueous sodium carbonate (containing solute 0.1mol) of 5%, react 6 hours at 0 DEG C-5 DEG C, utilize TLC to follow the tracks of reaction monitoring terminal, solvent is toluene: acetone=1:1-5(V/V).Through dilute hydrochloric acid solution after reaction terminates, sodium bicarbonate solution and washed with de-ionized water, dry, obtain first step intermediate C after concentrated
8t;
(2) 0.12molC is added successively in the reactor
8t, 500mL acetone, 0.1mol tarine and mass concentration are the aqueous sodium carbonate (containing solute 0.1mol) of 5%, react 8 hours at 40 DEG C-50 DEG C, utilize TLC to follow the tracks of reaction monitoring terminal, solvent is acetone: toluene: water=6:1-5:0.5-3(V/V/V).Through concentrated after reaction terminates, cooling, washing obtains second step intermediate SC
8t;
(3) in microwave reactor, 0.1molSC is added successively
8t, 0.1mol triethylene diamine, 500mL deionized water, 0.15mol2-aminobenzimidazole, reacts 3 hours at 90 DEG C-95 DEG C, and utilize TLC to monitor reaction end, solvent is methyl alcohol: toluene=1-5:1(V/V).Through concentrated after reaction terminates, cooling, watery hydrochloric acid process, filtration drying obtains final products BSC
8t.
Embodiment 3
Prepare the anion surfactant with bactericidal activity of following structure:
Its name is called:
2-(4-(1H-benzimidazolyl-2 radicals-Ji) amino-6-dodecane amino-1,3,5-triazines-2-amino) ethyl sulfonic acid sodium
Concrete preparation method is as follows:
(1) 0.1mol Cyanuric Chloride is added successively in the reactor, 500mL toluene, 0.12mol n-dodecylamine and mass concentration are the aqueous sodium carbonate (containing solute 0.1mol) of 5%, react 6 hours at 0 DEG C-5 DEG C, utilize TLC to follow the tracks of reaction monitoring terminal, solvent is toluene: acetone=1:1-5(V/V).Through dilute hydrochloric acid solution after reaction terminates, sodium bicarbonate solution and washed with de-ionized water, dry, obtain first step intermediate C after concentrated
12t;
(2) 0.12molC is added successively in the reactor
12t, 500mL acetone, 0.1mol tarine and mass concentration are the aqueous sodium carbonate (containing solute 0.1mol) of 5%, react 8 hours at 40 DEG C-50 DEG C, utilize TLC to follow the tracks of reaction monitoring terminal, solvent is acetone: toluene: water=6:1-5:0.5-3(V/V/V).Through concentrated after reaction terminates, cooling, washing obtains second step intermediate SC
12t;
(3) in microwave reactor, 0.1molSC12T is added successively, 0.1mol triethylene diamine, 500mL deionized water, 0.15mol2-aminobenzimidazole, react 3 hours at 90 DEG C-95 DEG C, utilize TLC to monitor reaction end, solvent is methyl alcohol: toluene=1-5:1(V/V).Through concentrated after reaction terminates, cooling, watery hydrochloric acid process, filtration drying obtains final products BSC
12t.
Performance test
1, choose Escherichia coli, staphylococcus aureus as instruction bacterial classification, with embodiment 2, embodiment 3 products obtained therefrom BSC
8t, BSC
12t is example, utilizes disk diffusion method to test its bacteriostasis property, and show that minimal inhibitory concentration MIC(utilizes intermediate SC respectively
8t, SC
12t, deionized water are in contrast).Inhibition zone is greater than 7mm and can repeats to be considered as there is inhibitory action to bacterial growth.Test and draw (as table 1-4): BSC
8t product is 44mg/mL to colibacillary MIC, is 38mg/mL to the MIC of staphylococcus aureus, and BSC
12t is 40mg/mL to colibacillary MIC, is 36mg/mL to the MIC of staphylococcus aureus, and SC
8t, SC
12t does not have fungistatic effect.As can be seen from the results, two kinds of products all serve certain inhibitory action to two kinds of bacteriums under variable concentrations, and intermediate and deionized water do not affect fungistatic effect; Two kinds of products comparatively speaking, BSC
12the fungistatic effect of T product compares BSC
8t is good.
Table 1BSC
8the MIC of T measures
Table 2BSC
8the biocidal property control experiment of T
Table 3:BSC
12the MIC of T measures
Table 4BSC
12the biocidal property control experiment of T
2, the full-automatic surface tension instrument of German Kruss company K100 type is utilized to measure BSC respectively
6t, BSC
8t, BSC
12the surface tension of the T aqueous solution at 25 DEG C, and obtain respective critical micelle concentration CMC, as shown in Figure 3.Before and after curve break, two linear intersections corresponding concentration are the CMC value of product at 25 DEG C, and the surface tension of curve minimum point is product water solution lowest surface tension γ
cMC, as shown in table 5.
The CMC of table 5 different product and lowest surface tension γ
cMCdata
As shown in Fig. 3 and table 5, different product all possesses good surface-active in the aqueous solution of 25 DEG C, γ
cMCbe less than the surface tension of 25 DEG C of pure water.Different product compares, and CMC shows the trend of reduction, γ along with the growth of hydrophobic segment
cMCthere is no fixing rule.Comprehensively draw in conjunction with bacteriostatic experiment: along with the growth of hydrophobic segment, products C MC reduces, and the MIC of corresponding product also shows the trend of reduction, shows that the fungistatic effect of product is better.
Claims (3)
1. there is an anion surfactant for bactericidal activity, there is the structure that following general formula represents:
（Ⅰ）
Described R
1for-(CH
2)
5cH
3,-(CH
2)
7cH
3,-(CH
2)
9cH
3,-(CH
2)
11cH
3in any one,
Described R
2for-CH
2-,-(CH
2)
2-,-(CH
2)
3-,-C
6h
4-in any one.
2. a preparation method with the anion surfactant of bactericidal activity according to claim 1, is characterized in that:
Be with Cyanuric Chloride, straight-chain fatty amine, sulfamic acid, aminobenzimidazole is raw material, and synthesize through three-step reaction, concrete synthetic method is:
The straight-chain fatty amine that Cyanuric Chloride and general formula (II) represent is reacted, obtains the compound that general formula (III) represents,
R
1—NH
2（Ⅱ）
（Ⅲ）
Described R
1for-(CH
2)
5cH
3,-(CH
2)
7cH
3,-(CH
2)
9cH
3,-(CH
2)
11cH
3in any one;
The compound that general formula (III) represents reacts with sulfamic acid again, obtains the compound that general formula (IV) represents
（Ⅳ）
Described R
2for-CH
2-,-(CH
2)
2-,-(CH
2)
3-,-C
6h
4-in any one;
The compound that general formula (IV) represents then reacts with aminobenzimidazole, namely obtains the anion surfactant with bactericidal activity that general formula (I) represents.
3. the preparation method with the anion surfactant of bactericidal activity according to claim 2, is characterized in that:
Concrete preparation method is as follows:
(1) add successively with acetone in the reactor, or chloroform, or toluene, or oxolane, or DMF, or ethyl acetate is as the Cyanuric Chloride solution of solvent, straight-chain fatty amine and aqueous sodium carbonate, react 1-8 hour under the condition of 0 DEG C-30 DEG C, through processing the compound obtaining general formula (III) and represent;
(2) with ethanol, or acetone, or acetonitrile, or water, or DMF, or dimethyl sulfoxide (DMSO) is as solvent, the compound that the general formula (III) obtained in step (1) represents is dissolved in wherein, again sulfamic acid solution and aqueous sodium carbonate are added in reactor successively, under the condition of 40 DEG C-60 DEG C, react 5-10 hour, through concentrated, precipitation, drying obtains the compound that general formula (IV) represents;
(3) with toluene, or dioxanes, or water, or 1-METHYLPYRROLIDONE is as solvent, is dissolved in by aminobenzimidazole wherein; Add compound and NaOH and catalyst that the general formula (IV) that obtains in step (2) represents again, under the condition of 70 DEG C-98 DEG C, heating using microwave reaction 1-5 hour, obtains through concentrated, cooling the compound that general formula (I) represents; Described catalyst is triethylamine, triethylene diamine, any one in DMA.
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| CN101659634A (en) * | 2009-09-09 | 2010-03-03 | 中国海洋石油总公司 | Synthetic method of anion sulfoacid gemini surfactant DTM |
| CN102311657A (en) * | 2011-06-25 | 2012-01-11 | 山东大学 | Low-water-solubility fluorescent whitening agent with bactericidal action as well as synthesis method and application thereof |
| CN103554085A (en) * | 2013-10-12 | 2014-02-05 | 江南大学 | Reaction-type halogen amine antibacterial agent, and synthetic method and application thereof |
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| CN102311657A (en) * | 2011-06-25 | 2012-01-11 | 山东大学 | Low-water-solubility fluorescent whitening agent with bactericidal action as well as synthesis method and application thereof |
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