CN103599729A - Rosinyl quaternary ammonium salt dimeric surfactant as well as preparation method and application thereof - Google Patents
Rosinyl quaternary ammonium salt dimeric surfactant as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a rosinyl quaternary ammonium salt dimeric surfactant as well as a preparation method and application thereof. The molecular structural formula of the rosinyl quaternary ammonium salt dimeric surfactant is as shown in the specification, wherein R is a rosinyl tricyclic phenanthrene structure, and n is equal to 3, 4, 5 or 6. The rosinyl quaternary ammonium salt dimeric surfactant which takes rosin as a raw material satisfies the demand of environment-friendly raw materials for preparation of the surfactant. The surfactant prepared by the invention has good surface activity and antibacterial activity. The CMC (Critical Micelle Concentration) value of the surfactant is (2.28-3.38)*10<-5>mol/L, the gamma cmc value is 24.7-32.3mN/m, and the Krafft point ranges from 12 to 23 DEG C. The time of separating turpentine and water in an aqueous emulsion is 42-53 hours. The initial foaming height is 128-137mm. The foam height in 5 minutes is 121-131mm. The antibacterial activity of the surfactant to escherichia coli is superior to that of the marketed bacteriostatic agent bromogeramine.
Description
Technical field
The present invention relates to a kind of Abietyl quaternary ammonium salt heterogemini surfactant and its preparation method and application, belong to surfactant science and application.
Background technology
The Gemini surface active agent (Gemini surfactants) with high surface is the study hotspot in surfactant field in recent years.Conventionally the Gemini surface active agent of research is by connecting base at hydrophilic group or approaching the symmetrical structure that hydrophilic group place is joined together to form, the i.e. Gemini surface active agent of molecular structure symmetry by 2 identical surfactant molecules.And the asymmetric heterogemini surfactant of molecular structure (Heterogemini surfactants) is because containing a base of different chemical structures, the alkane main chain of different length and the various coupling link of variation, therefore become the new varieties that likely obtain the surfactant that performance is more superior, and understanding molecule self-organizing mechanism, the aspects such as orderly molecular aggregates of constructing novel structure play a significant role.But due to the synthetic difficulty of heterogemini surfactant, at present relevant research report is relatively less.
Rosin is a kind of abundant natural reproducible resource, and its main component is resin acid, is the monocarboxylic acid that contains two two keys of the luxuriant and rich with fragrance skeleton of a kind of three ring.The luxuriant and rich with fragrance skeleton of three rings has very strong hydrophobicity, usings two keys and carboxylic acid can introduce hydrophilic radical as reaction center.At present, about symmetric form abietyl Gemini surface active agent, also there is report, but there is not yet report about the research of abietyl heterogemini surfactant.
Summary of the invention
The object of this invention is to provide a kind of Abietyl quaternary ammonium salt heterogemini surfactant and its preparation method and application,
For solving the problems of the technologies described above, technical scheme of the present invention is:
An Abietyl quaternary ammonium salt heterogemini surfactant, its molecular structural formula is:
Wherein, R is the luxuriant and rich with fragrance structure of abietyl three ring, n=3,4,5 or 6.
For convenient preparation, the synthetic route of above-mentioned Abietyl quaternary ammonium salt heterogemini surfactant is as follows:
Wherein, R is the luxuriant and rich with fragrance structure of abietyl three ring, n=3,4,5 or 6.
The preparation method of above-mentioned Abietyl quaternary ammonium salt heterogemini surfactant, described Abietyl quaternary ammonium salt heterogemini surfactant is by N, and N-dimethyl lauryl amine and bromo alkyl abietyl dimethyl ammonium bromide quaterisation make.
In order to improve the combined coefficient of product, described N, the mol ratio of N-dimethyl lauryl amine and bromo alkyl abietyl dimethyl ammonium bromide is (1.05～5): 1.
For easy to prepare, guarantee product quality simultaneously, the preparation method of above-mentioned Abietyl quaternary ammonium salt heterogemini surfactant is: take acetone as solvent, by mol ratio, be (1.05～5): 1 N, N-dimethyl lauryl amine reacts 10～36h with bromo alkyl abietyl dimethyl ammonium bromide stirring and refluxing, then by product purification processes, obtain Abietyl quaternary ammonium salt heterogemini surfactant.Purification processes comprises decompression distillation, recrystallization and vacuum drying etc. successively.
Applicant finds after deliberation, by above-mentioned preparation method, just can prepare Abietyl quaternary ammonium salt heterogemini surfactant, and preparation technology is simple, and yield is high, and excellent product performance efficiently solves heterogemini surfactant in prior art and prepares difficult problem.
For Reaction time shorten, improve reaction efficiency, guarantee product quality, the preparation method of above-mentioned Abietyl quaternary ammonium salt heterogemini surfactant is simultaneously: under microwave condition, take acetone as solvent, at power, be 60～300W, temperature is, under the condition of 40～50 ℃, by mol ratio, to be (1.05～5): 1 N, and N-dimethyl lauryl amine reacts 5～60min with bromo alkyl abietyl dimethyl ammonium bromide, then by product purification processes, obtain Abietyl quaternary ammonium salt heterogemini surfactant.Purification processes comprises decompression distillation, recrystallization and vacuum drying etc. successively.
Applicant finds after deliberation, under microwave condition, significantly Reaction time shorten, improve reaction yield, and products obtained therefrom excellent performance.
For easy to use, guarantee product quality simultaneously, the synthetic method of bromo alkyl abietyl dimethyl ammonium bromide is: take absolute ethyl alcohol as solvent, by mol ratio, be 1:(1～8) N, N-dimethyl rosin amine and two bromoalkanes react after 4～50h at 30～60 ℃, under reflux temperature, reaction 4～50h, then by the decompression distillation of product process, with the dry bromo alkyl abietyl dimethyl ammonium bromide that to obtain of 3～5 final vacuums of petroleum ether.
N, the synthetic method of N-dimethyl rosin amine is: take carrene as solvent, is 1:(1～4 by mol ratio) rosin acid and SOCl
2under reflux temperature, react 3～5h, obtain rosin acid acyl chlorides; Again rosin acid acyl chlorides and 40% dimethylamine agueous solution are reacted to the synthetic N of 2～5h at-5～0 ℃, N-dimethyl rosin acid acid amides, the mol ratio of rosin acid acyl chlorides and dimethylamine is 1:(3～6); By mol ratio, be finally (1～5): 1 lithium aluminium hydride and N, N-dimethyl rosin acid acid amides, at 40～80 ℃, reacts 2～8h, obtains N, N-dimethyl rosin tertiary amine.The method obtains more highly purified N than traditional formaldehyde formic acid method, N-dimethyl rosin amine.
In order to improve the quality of products, described two bromoalkanes are 1,3-dibromopropane, Isosorbide-5-Nitrae-dibromobutane, 1, the mixture of one or more any proportionings in pentamethylene bromide or 1,6-dibromo-hexane.
By above-mentioned Abietyl quaternary ammonium salt heterogemini surfactant, as the application of bacteriostatic agent.
Applicant finds that above-mentioned Abietyl quaternary ammonium salt heterogemini surfactant has good fungistatic effect and foaming properties after deliberation.
The not specified technology of the present invention is prior art.
Beneficial effect of the present invention:
1, Abietyl quaternary ammonium salt heterogemini surfactant of the present invention be take rosin as raw material, rosin is a kind of abundant natural reproducible resource, there is environment friendly, meet the requirement of " raw material greenization " prepared by surfactant, and preparation method of the present invention is simple, easy to operate;
2, the Abietyl quaternary ammonium salt heterogemini surfactant that prepared by the inventive method has good surface-active and bacteriostasis property, and its CMC value is 2.28～3.38 * 10
-5mol/L, γ
cmcvalue is 24.7～32.3mN/m; Krafft point is 12～23 ℃; The time that separates 10mL water in turpentine oil/aqueous emulsion is 42～53h; Initial foam height is 128～137mm, and after 5min, foam height is 121～131mm; For colibacillary biocidal property, be superior to commercially available bacteriostatic agent bromogeramine.
3, the present invention adopts microwave irradiation to prepare Abietyl quaternary ammonium salt heterogemini surfactant to compare with popular response, has short, efficiency advantages of higher of time.
Accompanying drawing explanation
Fig. 1 is the hydrogen spectrogram of Abietyl quaternary ammonium salt heterogemini surfactant A.
Fig. 2 is the FT-IR figure of Abietyl quaternary ammonium salt heterogemini surfactant A.
Fig. 3 is the hydrogen spectrogram of Abietyl quaternary ammonium salt heterogemini surfactant B.
Fig. 4 is the FT-IR figure of Abietyl quaternary ammonium salt heterogemini surfactant B.
Fig. 5 is the hydrogen spectrogram of Abietyl quaternary ammonium salt heterogemini surfactant C.
Fig. 6 is the FT-IR figure of Abietyl quaternary ammonium salt heterogemini surfactant C.
Fig. 7 is γ-C figure of Abietyl quaternary ammonium salt heterogemini surfactant A.
Fig. 8 is γ-C figure of Abietyl quaternary ammonium salt heterogemini surfactant B.
Fig. 9 is γ-C figure of Abietyl quaternary ammonium salt heterogemini surfactant C.
The specific embodiment
In order to understand better the present invention, below in conjunction with embodiment, further illustrate content of the present invention, but content of the present invention is not only confined to the following examples.
N, N-dimethyl rosin amine synthetic:
Take carrene as solvent, SOCl
2(2.4g, 20mmol) reacts 4h with rosin acid (3.0g, 10mmol) under reflux temperature, except desolventizing and excessive SOCl
2obtain rosin acid acyl chlorides.Again the rosin acid acyl chlorides of gained is dissolved in the oxolane of 20mL, at 0 ℃, slowly drips in 40% dimethylamine agueous solution (4.5g, 40mmol) and react 4h, filter after completion of the reaction, filtrate is reduced pressure and is steamed solvent after acidifying, alkalization, washing, makes N, N-dimethyl dehydrogenation fir acid amides.Finally, by N, N-dimethyl dehydrogenation fir acid amides is dissolved in tetrahydrofuran solvent, stirs and add lithium aluminium hydride (0.8g, 20mmol) at 0 ℃, reacts 6h after being slowly warming up to 70 ℃.After completion of the reaction, continue to drip and be equal to the water of lithium aluminium hydride quality and 15% sodium hydroxide solution reaction 0.5h at 0 ℃, filter after adding excessive anhydrous magnesium sulfate to stir 0.5h, filtrate decompression steams solvent, makes N, N-dimethyl rosin amine.
Synthesizing of bromo alkyl abietyl dimethyl ammonium bromide:
(1) synthetic (n=3) of 3-bromopropyl abietyl dimethyl ammonium bromide:
Get N, N-dimethyl rosin amine (3.1g, 10mmol), in filling the reactor of absolute ethyl alcohol, stirs lower 1, the 3-dibromopropane (2.0g, 10mmol) that drips, and reacts after 30h at 50 ℃, is warming up to 80 ℃, then reacts 8h.React complete, decompression steams solvent, with the excessive dibromopropane of benzinum eccysis, is drying to obtain 3-bromopropyl abietyl dimethyl ammonium bromide.
(2) synthetic (n=4) of 4-brombutyl abietyl dimethyl ammonium bromide:
Get N, N-dimethyl rosin amine (3.1g, 10mmol), in filling the reactor of absolute ethyl alcohol, stirs the lower Isosorbide-5-Nitrae-dibromobutane (7.4g, 35mmol) that drips, and reacts 24h after reacting 24h at 50 ℃ at 80 ℃ again.React complete, decompression steams solvent, with the excessive dibromobutane of benzinum eccysis, is drying to obtain 4-brombutyl abietyl dimethyl ammonium bromide.
(3) synthetic (n=5) of 5-bromine amyl group abietyl dimethyl ammonium bromide:
Get N, N-dimethyl rosin amine (3.1g, 10mmol), in filling the reactor of absolute ethyl alcohol, stirs and to drip 1 down, and pentamethylene bromide (18.5g, 80mmol) reacts 24h after reacting 24h at 50 ℃ at 80 ℃ again.React complete, decompression steams solvent, with the excessive dibromo pentane of benzinum eccysis, is drying to obtain 5-bromine amyl group abietyl dimethyl ammonium bromide.
Synthesizing of Abietyl quaternary ammonium salt heterogemini surfactant:
(1) conventional heating Abietyl quaternary ammonium salt heterogemini surfactant A's is synthetic:
In the there-necked flask of 100ml that thermometer, drying tube, changes in temperature return duct are housed, add N, N-dimethyl lauryl amine (2.3g, 10.5mmol), 3-bromopropyl abietyl dimethyl ammonium bromide (4.1g, 10mmol) with 100ml acetone, heating, stirring and refluxing reaction 36h.React complete, decompression steams solvent, then makes Abietyl quaternary ammonium salt heterogemini surfactant A through recrystallization, vacuum drying, and productive rate is 70%.
(2) microwave Abietyl quaternary ammonium salt heterogemini surfactant A's is synthetic:
In the round bottom single port bottle of 100ml, add N, N-dimethyl lauryl amine (2.3g, 10.5mmol) with 3-bromopropyl abietyl dimethyl ammonium bromide (4.1g, 10mmol), in 40ml acetone, dissolve and put into microwave reactor, microwave reaction power is 100W, and reaction temperature is 50 ℃, and the reaction time is 30min.React complete, decompression steams solvent, then makes Abietyl quaternary ammonium salt heterogemini surfactant A (in spectrogram checking and (1), conventional method is same product) through recrystallization, vacuum drying, and productive rate is 81%.
(3) microwave Abietyl quaternary ammonium salt heterogemini surfactant B's is synthetic:
In the round bottom single port bottle of 100ml, add N, N-dimethyl lauryl amine (6.4g, 30mmol) with 4-brombutyl abietyl dimethyl ammonium bromide (4.3g, 10mmol), in 40ml acetone, dissolve and put into microwave reactor, microwave reaction power is 300W, and reaction temperature is 40 ℃, and the reaction time is 15min.React complete, decompression steams solvent, then makes Abietyl quaternary ammonium salt heterogemini surfactant B through recrystallization and vacuum drying, and productive rate is 83%.
(4) conventional heating Abietyl quaternary ammonium salt heterogemini surfactant C's is synthetic:
In the there-necked flask of 100ml that thermometer, drying tube, changes in temperature return duct are housed, add N, N-dimethyl lauryl amine (10.6g, 50mmol), 5-bromine amyl group abietyl dimethyl ammonium bromide (4.4g, 10mmol) with 100ml acetone, heating, stirring and refluxing reaction 15h.React complete, decompression steams solvent, then makes Abietyl quaternary ammonium salt heterogemini surfactant C through recrystallization, vacuum drying, and productive rate is 71%.
Surface property test: by the Abietyl quaternary ammonium salt heterogemini surfactant A of preparation in embodiment 3, the aqueous solution that B, C are configured to the sample of a series of variable concentrations, in 25 ℃ of surface tension with the suspension ring method working sample aqueous solution in BZY-1 type surface tension instrument.By sample aqueous solution concentration and capillary graph of relation, obtain its critical micelle concentration (CMC) and surface tension (γ thereof
cmc).
Krafft point (KP) test: the aqueous solution of the sample that configuration quality mark is 1%, be heated to clarify completely, naturally cool to muddy appearance, record temperature for its Krafft point.Each sample repeats 3 times, gets its mean value.
The test of emulsifying capacity (EP): under room temperature, get respectively 40ml mass fraction and be in the aqueous solution of 0.1% Abietyl quaternary ammonium salt heterogemini surfactant A, B, C and tool plug graduated cylinder that 40ml benzene is poured 100ml into, stopper beyond the Great Wall, standing after thermal agitation 50 times, then record separates the time of 10ml water, repeats 3 times.
The test of foam ability (FP): under room temperature, getting respectively 20ml mass fraction is that 0.5% Abietyl quaternary ammonium salt heterogemini surfactant A, the aqueous solution of B, C are poured in the tool plug graduated cylinder of 100ml, add warm water to 30ml, stopper beyond the Great Wall, the foam height that thermal agitation records for 25 times afterwards represents frothing capacity, and foam height during standing 5min represents foam stability energy.
The some surface active property of table 1A, B, C
Biocidal property test:
Measure the Abietyl quaternary ammonium salt heterogemini surfactant A of preparation in embodiment 3, the bacteriostasis property of B, C.By dull and stereotyped doubling dilution, measure the minimum inhibitory concentration (MIC) of compound.Choose pharmacosensitive test bacterial strain and have 6 kinds: staphylococcus aureus, Pseudomonas aeruginosa, MRSE, klebsiella pneumoniae, aerobacteria, Escherichia coli.Control drug has 2 kinds: bromogeramine.
Sample (above-mentioned surfactant A, B, C and commercially available bromogeramine) is made into the dimethyl sulfoxide solution that concentration is 1280 μ g/ml, and dilution obtains respectively the series of samples solution that concentration is 1280,640,320,160,80,40,20 μ g/ml.Get respectively MH agar medium 9ml after above-mentioned sample solution 1ml and high-temperature sterilization and join on aseptic flat board and mix, the pastille that obtains being respectively containing sample concentration 128,64,32,16,8,4,2 μ g/ml after it solidifies is dull and stereotyped.With sterilized water, 6 kinds of cultured bacterial classifications are mixed with to bacteria suspension, then by with No. 0.5 Maxwell opacity tube than turbid, be diluted to concentration approximately 10
8cFU/mL.Respectively add 2 μ L bacteria suspensions in each pastille flat board after, be inverted in incubator, observe bacterial growth situation cultivate 30h at 30 ℃ after.Abietyl quaternary ammonium salt heterogemini surfactant A, B, C to staphylococcus aureus, Pseudomonas aeruginosa, MRSE, klebsiella pneumoniae, aerobacteria, colibacillary minimum inhibitory concentration (μ g/mL) as table 2.As shown in Table 2, A, B, C are superior to commercially available bacteriostatic agent bromogeramine for colibacillary biocidal property.
The bacteriostatic activity of the various surfactants of table 2 (μ g/mL)
Note: a: Escherichia coli (CMCC-44102) b: staphylococcus aureus (CMCC-26003) c: kerekou pneumonia uncle bacterium (GIM-1.279) d: Pseudomonas aeruginosa (CMCC-10104) e: clostridium perfringen (GIM-1.234) f: MRSE (CMCC-26069).
Claims (10)
1. an Abietyl quaternary ammonium salt heterogemini surfactant, is characterized in that: its molecular structural formula is:
Wherein, R is the luxuriant and rich with fragrance structure of abietyl three ring, n=3,4,5 or 6.
2. Abietyl quaternary ammonium salt heterogemini surfactant as claimed in claim 1, is characterized in that: its synthetic route is as follows:
Wherein, R is the luxuriant and rich with fragrance structure of abietyl three ring, n=3,4,5 or 6.
3. the preparation method of the Abietyl quaternary ammonium salt heterogemini surfactant described in claim 1 or 2, it is characterized in that: described Abietyl quaternary ammonium salt heterogemini surfactant is by N, and N-dimethyl lauryl amine and bromo alkyl abietyl dimethyl ammonium bromide quaterisation make.
4. method as claimed in claim 3, is characterized in that: described N, the mol ratio of N-dimethyl lauryl amine and bromo alkyl abietyl dimethyl ammonium bromide is (1.05～5): 1.
5. method as claimed in claim 4, it is characterized in that: take acetone as solvent, is (1.05～5) by mol ratio: 1 N, N-dimethyl lauryl amine and bromo alkyl abietyl dimethyl ammonium bromide stirring and refluxing reaction 10～36h, then by product purification processes, obtain.
6. method as claimed in claim 4, it is characterized in that: under microwave condition, take acetone as solvent, at power, be 60～300W, temperature is, under the condition of 40～50 ℃, by mol ratio, to be (1.05～5): 1 N, N-dimethyl lauryl amine and bromo alkyl abietyl dimethyl ammonium bromide reaction 5～60min, then by product purification processes, obtain.
7. the method as described in claim 3-6 any one, it is characterized in that: the synthetic method of bromo alkyl abietyl dimethyl ammonium bromide is: take absolute ethyl alcohol as solvent, by mol ratio, be 1:(1～8) N, N-dimethyl rosin amine and two bromoalkanes react after 4～50h, under reflux temperature at 30～60 ℃, reaction 4～50h, then by the decompression distillation of product process, dry with 3～5 final vacuums of petroleum ether, obtain bromo alkyl abietyl dimethyl ammonium bromide.
8. method as claimed in claim 7, is characterized in that: N, the synthetic method of N-dimethyl rosin amine is: take carrene as solvent, is 1:(1～4 by mol ratio) rosin acid and SOCl
2under reflux temperature, react 3～5h, obtain rosin acid acyl chlorides; Again rosin acid acyl chlorides and 40% dimethylamine agueous solution are reacted to the synthetic N of 2～5h at-5～0 ℃, N-dimethyl rosin acid acid amides, the mol ratio of rosin acid acyl chlorides and dimethylamine is 1:(3～6); By mol ratio, be finally (1～5): 1 lithium aluminium hydride and N, N-dimethyl rosin acid acid amides, at 40～80 ℃, reacts 2～8h, obtains N, N-dimethyl rosin tertiary amine.
9. method as claimed in claim 8, is characterized in that: described two bromoalkanes are 1,3-dibromopropane, Isosorbide-5-Nitrae-dibromobutane, 1, the mixture of one or more any proportionings in pentamethylene bromide or 1,6-dibromo-hexane.
10. the Abietyl quaternary ammonium salt heterogemini surfactant described in claim 1 or 2 is as the application of bacteriostatic agent.
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| CN109772226A (en) * | 2019-01-23 | 2019-05-21 | 江南大学 | One kind by abietyl stabilized with amine oxide surfactant gel emulsion |
| CN109772226B (en) * | 2019-01-23 | 2020-06-09 | 江南大学 | Gel emulsion stabilized by rosin-based amine oxide surfactant |
| CN110590562A (en) * | 2019-09-17 | 2019-12-20 | 江西农业大学 | Synthetic method and antibacterial application of symmetrical gemini quaternary ammonium iron containing hydrogenated nopyl |
| CN114524736A (en) * | 2021-12-30 | 2022-05-24 | 福州大学 | Asymmetric Gemini cationic surfactant and preparation method thereof |
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