CN102513023A - Trimeric surfactant and its synthetic method - Google Patents
Trimeric surfactant and its synthetic method Download PDFInfo
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- CN102513023A CN102513023A CN2011103391709A CN201110339170A CN102513023A CN 102513023 A CN102513023 A CN 102513023A CN 2011103391709 A CN2011103391709 A CN 2011103391709A CN 201110339170 A CN201110339170 A CN 201110339170A CN 102513023 A CN102513023 A CN 102513023A
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Abstract
The invention discloses a trimeric surfactant and its synthetic method. the structural formula of the trimeric surfactant is as shown in the invention, wherein R indicates CnH2n+1 and n=8-16. With adamantane as a raw material, the synthetic method contains the following three-step reactions: firstly directly oxidizing adamantane to obtain 1,3,5-trihydroxy adamantine, then performing a reaction between trihydroxy adamantine and bromoacetyl bromide to prepare a key intermediate 1,3,5-tribromoacetyloxy adamantane, and finally performing a reaction between the intermediate and a long chain tertiary amine for quaternary amination to form the trimeric esteryl quaternary surfactant with adamantane being the linker. The critical micelle concentration of the synthesized trimeric surfactant is lower than that of other corresponding single-chain gemini surfactants by at least one order of magnitude, and the synthesized trimeric surfactant has substantial excellent characteristics. In addition, the reaction condition is mild, the raw material is easily available, the product has high purity, the synthetic method is simple and easy to operate, and the trimeric surfactant is suitable for industrial production and has a latent application prospect in the fields of biomedicine, pharmacy, nano-material, tertiary oil recovery, extraordinary washing and the like.
Description
Technical field
The present invention relates to a kind of terpolymer surfactant and synthetic method thereof.
Background technology
Oligo surfactant comprises that Shuangzi (being commonly referred to Gemini), trimerization, four gather and have a more amphiphile, amphiphilic molecule of high polymerization degree; It is an amphiphile, amphiphilic molecule identical by two or more or much at one, at its hydrophilic head base or one type of novel surfactant being connected together and forming through chemical bond-linking by spacer group near hydrophilic Ji Chu.Compare with traditional surfactant, oligo surfactant has higher surface-active, very low Krafft point and well water-soluble, and better application performance, is described as surfactant of new generation.The research of oligo surfactant at present focuses mostly in Shuangzi, tripolymer and the tetramer, and the oligo surfactant that the aggregation number is higher is because synthetic difficulty is studied seldom.Adamantane is highly symmetrical cage shape hydrocarbon, its fusing point high (269 ℃), and heat endurance is high, and is nontoxic, tasteless.4 end of the bridge hydrogen atoms (1,3,5,7) can be substituted and generate a series of Buddha's warrior attendant alkane derivatives in the adamantane molecule, and derivative kind and the quantity low but more potential than the benzene reactivity far surpass benzene derivative.Through introducing the connection base of adamantyl as oligo surfactant; Can design synthetic various types of surfactants; And give very particular performances of surfactant, be expected to prepare the surfactant of performance more superior, multi-functional (like superelevation surface-active, high stability, biocompatibility, ultralow toxicity).
In addition, because adamantane rigid structure characteristic, through introducing the connection base of adamantyl as oligo surfactant; Make the hydrophobic chain that contains a plurality of stereochemical structures in the surfactant molecule of its formation; Hydrophobicity is stronger, and the amphiphile, amphiphilic molecule chain that adamantyl can make connection is apart from shortening, and its rigidity stereochemical structure has produced very big sterically hindered; Coulomb repulsion tendency between ion head base is weakened because of being limited by stereoeffect greatly, arranges more tight on the surface of water like this.Therefore, theoretically, the amphiphile, amphiphilic molecule chain more (degree of polymerization is high more) that adamantyl connects, its surface-active is high more.And introduce ester group in the linking group, and make it more degraded easily and avoid environmental pollution, have foam performance preferably, foam stability is good.These are all indicating the great potential of adamantyl poly type surfactant.
It is raw material that the present invention adopts adamantane, and having synthesized through oxidation, esterification, quaternary ammoniated three-step reaction is the trimerization ester based quaternary ammonium salt type surfactant that connects base with the adamantane, and products therefrom purity is high, and operation is simple, is fit to suitability for industrialized production.
Summary of the invention:
The invention reside in provides a kind of terpolymer surfactant and synthetic method thereof.Technical scheme of the present invention is following:
A kind of terpolymer surfactant provided by the invention, its structural formula is:
In the formula: R=C
nH
2n+1, n=8～16.
The synthetic method of a kind of trimerization type surfactant provided by the invention may further comprise the steps:
(1) 1,3,5-trihydroxy adamantane synthetic: adamantane is joined in the glacial acetic acid; Be warming up to 60 ℃; Stir and drip the solution that chromium trioxide and water form down, the control temperature is not higher than 100 ℃, dropwises back constant temperature stirring reaction 1～3h under 80～120 ℃ of temperature conditions; Removal of solvent under reduced pressure, with in the sodium hydroxide solution of mass fraction 40% and residue, more than 70 ℃ with ethyl acetate extraction repeatedly, vacuum concentrates ethyl acetate solution, obtains 1,3,5-trihydroxy adamantane;
(2) 1,3,5-tribromo acetoxyl group adamantane synthetic: under nitrogen protection, with 1; 3,5-trihydroxy adamantane joins in pyridine, the acetonitrile to stir and forms suspension, adds catalyst, constant temperature to 0～20 ℃; Through the solution of 1h dropping acetonitrile and bromoacetyl bromide formation, be warming up to 30～80 ℃ of reaction 5～10h after dropwising, add 6M hydrochloric acid solution and carrene cessation reaction, use dichloromethane extraction; Concentrate organic layer, residue is dissolved in the carrene, the aqueous sodium carbonate washing with saturated aqueous common salt, 0.5M concentrates organic layer; Cross silicagel column, get yellow oil 1,3,5-tribromo acetoxyl group adamantane;
(3) trimerization type surfactant is synthetic: with 1,3,5-tribromo acetoxyl group adamantane is dissolved in the acetone, and the adding long chain tertiary amine stirs reaction 3h down under 30～85 ℃, get white precipitate.Cross and filter white solid, washing with acetone, drying gets trimerization type surfactant with acetonitrile/acetone recrystallization.
The adamantane in the above-mentioned steps (1) and the mol ratio of glacial acetic acid are 1: 15～18, and the mol ratio of adamantane and chromium trioxide is 1: 5～10, and the mol ratio of chromium trioxide and water is 1: 3.
In the above-mentioned steps (2) 1,3, the mol ratio of 5-trihydroxy adamantane and pyridine is 1: 1～5,1,3, the mol ratio of 5-trihydroxy adamantane and bromoacetyl bromide is 1: 3～6.
In the above-mentioned steps (3) 1,3,5-tribromo acetoxyl group adamantane and long chain tertiary amine mol ratio are 1: 3～6.
Catalyst in the above-mentioned steps (2) is the 4-dimethylamino naphthyridine.
Long chain tertiary amine general formula C in the above-mentioned steps (3)
nH
2n+1N (CH
3)
2, n=8～16.
The reaction scheme of said method is:
The present invention has following beneficial effect:
(1) the invention provides a kind of is raw material by adamantane, and having synthesized through oxidation, esterification, quaternary ammoniated three-step reaction is the trimerization ester based quaternary ammonium salt type surfactant that connects base with the adamantane.
(2) critical micelle concentration (CMC) of the terpolymer surfactant that synthesizes of the present invention has significant good characteristic than a low at least one magnitude of other corresponding strands, Gemini surface active agent.
(3) surfactant of gained of the present invention has the reaction condition gentleness; Raw material is easy to get, and product purity is high, and operation is simple; Be fit to suitability for industrialized production, have potential application prospect in fields such as biomedicine, pharmacy, nano material, tertiary oil recovery, extraordinary washings.
Description of drawings
Fig. 1 is terpolymer surfactant (R=C
10H
21) structural formula.
Fig. 2 is terpolymer surfactant (R=C
10H
21)
1The HNMR spectrogram.
Fig. 3 is terpolymer surfactant (R=C
12H
25)
1The HNMR spectrogram.
Fig. 4 is terpolymer surfactant (R=C
14H
29)
1The HNMR spectrogram.
Fig. 5 is terpolymer surfactant (R=C
16H
33)
1The HNMR spectrogram.
Fig. 6 is terpolymer surfactant (R=C
8H
17) surface tension with concentration curve figure.
Fig. 7 is terpolymer surfactant (R=C
10H
21) surface tension with concentration curve figure.
Fig. 8 is terpolymer surfactant (R=C
12H
25) surface tension with concentration curve figure.
The specific embodiment
Below in conjunction with embodiment the present invention is made further and to specify.
Embodiment 1: terpolymer surfactant (R=C
8H
17) synthetic
Get adamantane (13.6g, 0.1mol), the 86mL glacial acetic acid join the 500mL there-necked flask (dress thermometer; Condenser pipe, constant pressure funnel, magnetic agitation) in; Be warming up to 60 ℃, (100g 1mol) is dissolved in the solution that 54mL water forms to drip chromium trioxide under stirring; The control temperature is not higher than 100 ℃, is warming up to 90 ℃ after dropwising, constant temperature stirring reaction 3h.Removal of solvent under reduced pressure, with in 40% the sodium hydroxide solution and residue, more than 70 ℃ with ethyl acetate (5 * 200mL) extraction products, vacuum concentrates ethyl acetate solution, white 1,3,5-trihydroxy adamantane white crystal 8.50g.Yield 46%.
With 1,3, and 5-trihydroxy adamantane (2.3g, 12.5mmol), pyridine (3.02mL; 37.5mmol), acetonitrile (12mL) forms suspension in there-necked flask (dress thermometer, constant pressure funnel, condenser pipe, magnetic agitation); Add catalyst, constant temperature to 0 ℃ under nitrogen protection and the stirring condition, drips the solution of 12mL acetonitrile and the formation of 3.28mL bromoacetyl bromide through 1h, dropwises to be warming up to 60 ℃ and to react 5h; Add 6M hydrochloric acid solution and 20mL carrene cessation reaction, (3 * 20mL) extractions concentrate organic layer, and residue is dissolved in the 20mL carrene, use saturated aqueous common salt with carrene; 0.5M aqueous sodium carbonate washing, organic layer becomes brownish black, concentrates organic layer, crosses silicagel column; Get yellow oil 1,3,5-tribromo acetoxyl group adamantane 4.98g, yield 73%.
With 1,3, (2.23g 4.10mmol) is dissolved in the 30mL acetone 5-tribromo acetoxyl group adamantane, adds N, and (1.93g 12.27mmol) reacts 3h under the stirring down in 30 ℃ to N-dimethyl-1-octylame, and the adularescent deposition produces.Cross and filter white solid, washing with acetone, drying gets white crystal 3.80g with acetonitrile/acetone recrystallization, yield 91%.Be terpolymer surfactant (R=C
8H
17).
Embodiment 2: terpolymer surfactant (R=C
10H
21) synthetic
Get adamantane (13.6g, 0.1mol), the 100mL glacial acetic acid join the 500mL there-necked flask (dress thermometer; Condenser pipe, constant pressure funnel, magnetic agitation) in; Be warming up to 60 ℃, (50g 0.5mol) is dissolved in the solution that 27mL water forms to drip chromium trioxide under stirring; The control temperature is not higher than 100 ℃, is warming up to 120 ℃ after dropwising, constant temperature stirring reaction 1h.Removal of solvent under reduced pressure, with in 40% the sodium hydroxide solution and residue, more than 70 ℃ with ethyl acetate (5 * 200mL) extraction products, vacuum concentrates ethyl acetate solution, white 1,3,5-trihydroxy adamantane white crystal 9.05g.Yield 49%.With 1,3, and 5-trihydroxy adamantane (2.3g, 12.5mmol), pyridine (1.01mL; 12.5mmol), acetonitrile (12mL) forms suspension in there-necked flask (dress thermometer, constant pressure funnel, condenser pipe, magnetic agitation); Add catalyst, constant temperature to 10 ℃ under nitrogen protection and the stirring condition, drips the solution of 12mL acetonitrile and the formation of 4.37mL bromoacetyl bromide through 1h, dropwises to be warming up to 30 ℃ and to react 10h; Add 6M hydrochloric acid solution and 20mL carrene cessation reaction, (3 * 20mL) extractions concentrate organic layer, and residue is dissolved in the 20mL carrene, use saturated aqueous common salt with carrene; 0.5M aqueous sodium carbonate washing, organic layer becomes brownish black, concentrates organic layer, crosses silicagel column; Get yellow oil 1,3,5-tribromo acetoxyl group adamantane 4.53g, yield 67%.
With 1,3, (2.23g 4.10mmol) is dissolved in the 40mL acetone 5-tribromo acetoxyl group adamantane, adds N, and (4.55g 24.60mmol) reacts 3h under the stirring down in 50 ℃ to N-dimethyl-1-decyl amine, and the adularescent deposition produces.Cross and filter white solid, washing with acetone, drying gets white crystal 3.85g with acetonitrile/acetone recrystallization, yield 85%.Be terpolymer surfactant (R=C
10H
21).
Embodiment 3: terpolymer surfactant (R=C
12H
25) synthetic
Get adamantane (13.6g, 0.1mol), the 100mL glacial acetic acid join the 500mL there-necked flask (dress thermometer; Condenser pipe, constant pressure funnel, magnetic agitation) in; Be warming up to 60 ℃, (100g 1mol) is dissolved in the solution that 54mL water forms to drip chromium trioxide under stirring; The control temperature is not higher than 100 ℃, is warming up to 100 ℃ after dropwising, constant temperature stirring reaction 1h.Removal of solvent under reduced pressure, with in 40% the sodium hydroxide solution and residue, more than 70 ℃ with ethyl acetate (5 * 200mL) extraction products, vacuum concentrates ethyl acetate solution, white 1,3,5-trihydroxy adamantane white crystal 9.04g.Yield 49%.
With 1,3, and 5-trihydroxy adamantane (2.3g, 12.5mmol), pyridine (5.02mL; 62.5mmol), acetonitrile (12mL) forms suspension in there-necked flask (dress thermometer, constant pressure funnel, condenser pipe, magnetic agitation); Add catalyst, constant temperature to 0 ℃ under nitrogen protection and the stirring condition, drips the solution of 12mL acetonitrile and the formation of 6.55mL bromoacetyl bromide through 1h, dropwises to be warming up to 50 ℃ and to react 6h; Add 6M hydrochloric acid solution and 20mL carrene cessation reaction, (3 * 20mL) extractions concentrate organic layer, and residue is dissolved in the 20mL carrene, use saturated aqueous common salt with carrene; 0.5M aqueous sodium carbonate washing, organic layer becomes brownish black, concentrates organic layer, crosses silicagel column; Get yellow oil 1,3,5-tribromo acetoxyl group adamantane 4.75g, yield 70%.
With 1,3, (2.23g 4.10mmol) is dissolved in the 30mL acetone 5-tribromo acetoxyl group adamantane, and (3.49g 16.40mmol) reacts 3h under the stirring down in 70 ℃, and the adularescent deposition produces to add the dodecyl dimethyl tertiary amine.Cross and filter white solid, washing with acetone, drying gets white crystal 3.83g with acetonitrile/acetone recrystallization, yield 83%.Be terpolymer surfactant (R=C
12H
25).
Embodiment 4: terpolymer surfactant (R=C
14H
29) synthetic
Get adamantane (13.6g, 0.1mol), the 100mL glacial acetic acid join the 500mL there-necked flask (dress thermometer; Condenser pipe, constant pressure funnel, magnetic agitation) in; Be warming up to 60 ℃, (90g 0.9mol) is dissolved in the solution that 49mL water forms to drip chromium trioxide under stirring; The control temperature is not higher than 100 ℃, is warming up to 110 ℃ after dropwising, constant temperature stirring reaction 2h.Removal of solvent under reduced pressure, with in 40% the sodium hydroxide solution and residue, more than 70 ℃ with ethyl acetate (5 * 200mL) extraction products, vacuum concentrates ethyl acetate solution, white 1,3,5-trihydroxy adamantane white crystal 9.20g.Yield 50%.
With 1,3, and 5-trihydroxy adamantane (2.3g, 12.5mmol), pyridine (5.02mL; 62.5mmol), acetonitrile (12mL) forms suspension in there-necked flask (dress thermometer, constant pressure funnel, condenser pipe, magnetic agitation); Add catalyst, constant temperature to 0 ℃ under nitrogen protection and the stirring condition, drips the solution of 12mL acetonitrile and the formation of 4.37mL bromoacetyl bromide through 1h, dropwises to be warming up to 70 ℃ and to react 6h; Add 6M hydrochloric acid solution and 20mL carrene cessation reaction, (3 * 20mL) extractions concentrate organic layer, and residue is dissolved in the 20mL carrene, use saturated aqueous common salt with carrene; 0.5M aqueous sodium carbonate washing, organic layer becomes brownish black, concentrates organic layer, crosses silicagel column; Get yellow oil 1,3,5-tribromo acetoxyl group adamantane 4.97g, yield 73%.
With 1,3, (2.23g 4.10mmol) is dissolved in the 30mL acetone 5-tribromo acetoxyl group adamantane, and (4.37g 20.50mmol) reacts 3h under the stirring down in 60 ℃, and the adularescent deposition produces to add the myristyl dimethyl tertiary amine.Cross and filter white solid, washing with acetone, drying gets white crystal 3.77g with acetonitrile/acetone recrystallization, yield 82%.Be terpolymer surfactant (R=C
14H
29).
Embodiment 5: terpolymer surfactant (R=C
16H
33) synthetic
Get adamantane (13.6g, 0.1mol), the 100mL glacial acetic acid join the 500mL there-necked flask (dress thermometer; Condenser pipe, constant pressure funnel, magnetic agitation) in; Be warming up to 60 ℃, (80g 0.8mol) is dissolved in the solution that 43mL water forms to drip chromium trioxide under stirring; The control temperature is not higher than 100 ℃, is warming up to 100 ℃ after dropwising, constant temperature stirring reaction 3h.Removal of solvent under reduced pressure, with in 40% the sodium hydroxide solution and residue, more than 70 ℃ with ethyl acetate (5 * 200mL) extraction products, vacuum concentrates ethyl acetate solution, white 1,3,5-trihydroxy adamantane white crystal 9.30g.Yield 52%.
With 1,3, and 5-trihydroxy adamantane (2.3g, 12.5mmol), pyridine (2.01mL; 25.0mmol), acetonitrile (12mL) forms suspension in there-necked flask (dress thermometer, constant pressure funnel, condenser pipe, magnetic agitation); Add catalyst, constant temperature to 20 ℃ under nitrogen protection and the stirring condition, drips the solution of 12mL acetonitrile and the formation of 5.67mL bromoacetyl bromide through 1h, dropwises to be warming up to 50 ℃ and to react 8h; Add 6M hydrochloric acid solution and 20mL carrene cessation reaction, (3 * 20mL) extractions concentrate organic layer, and residue is dissolved in the 20mL carrene, use saturated aqueous common salt with carrene; 0.5M aqueous sodium carbonate washing, organic layer becomes brownish black, concentrates organic layer, crosses silicagel column; Get yellow oil 1,3,5-tribromo acetoxyl group adamantane 5.00g, yield 74%.
With 1,3, (2.23g 4.10mmol) is dissolved in the 30mL acetone 5-tribromo acetoxyl group adamantane, and (3.31g 12.30mmol) reacts 3h under the stirring down in 85 ℃, and the adularescent deposition produces to add the hexadecyldimethyl benzyl ammonium tertiary amine.Cross and filter white solid, washing with acetone, drying gets white crystal 4.22g with acetonitrile/acetone recrystallization, yield 76%.Be terpolymer surfactant (R=C
16H
33).
Analytical test
Adopt
1HNMR is to terpolymer surfactant (R=C
10H
21R=C
12H
25R=C
14H
29R=C
16H
33) analyze.Respectively like Fig. 2, like Fig. 3, like Fig. 4, as shown in Figure 5.
Adopt ring detachment method to terpolymer surfactant (R=C
8H
17R=C
10H
21R=C
12H
25) test.25 ℃ down its surface tension with the change in concentration result respectively like Fig. 6, Fig. 7, shown in Figure 8.
The nucleus magnetic hydrogen spectrum analysis (
1HNMR)
By the analysis result of proton nmr spectra, can confirm to adopt the inventive method: by adamantane is raw material, and successfully synthesizing with the adamantane through oxidation, esterification, quaternary ammoniated three-step reaction is the trimerization ester based quaternary ammonium salt type surfactant that connects base.
The surface tension test
Surface tension adopts ring detachment method to measure on KSV Sigma 700 surface tension instrument, 25 ℃ down its surface tension with the change in concentration result respectively like Fig. 6, Fig. 7, shown in Figure 8.
Terpolymer surfactant (R=C
8H
17) CMC=2 * 10 of sample
-3Mol/L, surface tension 32.6mN/m.
Terpolymer surfactant (R=C
10H
21) CMC=1 * 10 of sample
-3Mol/L, surface tension 44.5mN/m.
Terpolymer surfactant (R=C
12H
25) CMC=0.5 * 10 of sample
-3Mol/L, surface tension 41.6mN/m.
Contrast the hot alkoxyl of traditional cationic surfactant 3--2-Hydroxyproyl Trimethyl ammonium bromide (C
8-TAB), its CMC=290 * 10
-3Mol/L, C
10The CMC=65 of-TAB * 10
-3Mol/L, C
12The CMC=14.6 of-TAB * 10
-3Mol/L contrasts Shuangzi cationic surfactant 8-s-8 ([C in addition
8H
17(CH
3)
2N
+(CH
2)
sN
+(CH
3)
2C
8H
17] 2Br
-, s=2,6), the CMC=55 of 8-2-8 * 10 wherein
-3The CMC=51 of mol/L, 8-2-8 * 10
-3Mol/L.Show other corresponding strands of ratio of the CMC of the terpolymer surfactant that the present invention obtains, a low at least one magnitude of Gemini surface active agent, have significant good characteristic.
Claims (7)
1. terpolymer surfactant is characterized in that its structural formula is:
In the formula: R=C
nH
2n+1, n=8～16.
2. according to the synthetic method of the said trimerization type of claim 1 surfactant, it is characterized in that may further comprise the steps:
(1) 1,3,5-trihydroxy adamantane synthetic: adamantane is joined in the glacial acetic acid; Be warming up to 60 ℃; Stir and drip the solution that chromium trioxide and water form down, the control temperature is not higher than 100 ℃, dropwises back constant temperature stirring reaction 1～3h under 80～120 ℃ of temperature conditions; Removal of solvent under reduced pressure, with in the sodium hydroxide solution of mass fraction 40% and residue, more than 70 ℃ with ethyl acetate extraction repeatedly, vacuum concentrates ethyl acetate solution, obtains 1,3,5-trihydroxy adamantane;
(2) 1,3,5-tribromo acetoxyl group adamantane synthetic: under nitrogen protection, with 1; 3,5-trihydroxy adamantane joins in pyridine, the acetonitrile to stir and forms suspension, adds catalyst, constant temperature to 0～20 ℃; Through the solution of 1h dropping acetonitrile and bromoacetyl bromide formation, be warming up to 30～80 ℃ of reaction 5～10h after dropwising, add 6M hydrochloric acid solution and carrene cessation reaction, use dichloromethane extraction; Concentrate organic layer, residue is dissolved in the carrene, the aqueous sodium carbonate washing with saturated aqueous common salt, 0.5M concentrates organic layer; Cross silicagel column, get yellow oil 1,3,5-tribromo acetoxyl group adamantane;
(3) trimerization type surfactant is synthetic: with 1,3,5-tribromo acetoxyl group adamantane is dissolved in the acetone, and the adding long chain tertiary amine stirs reaction 3h down under 30～85 ℃, get white precipitate.Cross and filter white solid, washing with acetone, drying gets trimerization type surfactant with acetonitrile/acetone recrystallization.
3. synthetic method according to claim 2 is characterized in that: the adamantane in the above-mentioned steps (1) and the mol ratio of glacial acetic acid are 1: 15～18, and the mol ratio of adamantane and chromium trioxide is 1: 5～10, and the mol ratio of chromium trioxide and water is 1: 3.
4. synthetic method according to claim 2 is characterized in that: 1,3 in the above-mentioned steps (2), and the mol ratio of 5-trihydroxy adamantane and pyridine is 1: 1～5,1,3, the mol ratio of 5-trihydroxy adamantane and bromoacetyl bromide is 1: 3～6.
5. synthetic method according to claim 2 is characterized in that: 1,3 in the above-mentioned steps (3), 5-tribromo acetoxyl group adamantane and long chain tertiary amine mol ratio are 1: 3～6.
6. synthetic method according to claim 2 is characterized in that: the catalyst in the above-mentioned steps (2) is the 4-dimethylamino naphthyridine.
7. synthetic method according to claim 2 is characterized in that: the long chain tertiary amine general formula C in the above-mentioned steps (3)
nH
2n+1N (CH
3)
2, n=8～16.
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| CN104525043A (en) * | 2014-12-19 | 2015-04-22 | 武汉工程大学 | Quaternary ammonium salt type trimeric surfactant and preparation method thereof |
| CN109836349A (en) * | 2017-11-27 | 2019-06-04 | 贺州学院 | A kind of Gemini surface active and its synthetic method containing adamantane |
| CN114573802A (en) * | 2020-12-02 | 2022-06-03 | 中国石油天然气股份有限公司 | Surfactant and preparation method thereof |
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| CN104525043B (en) * | 2014-12-19 | 2016-06-22 | 武汉工程大学 | A kind of quaternary terpolymer surfactant and preparation method thereof |
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| CN114573802A (en) * | 2020-12-02 | 2022-06-03 | 中国石油天然气股份有限公司 | Surfactant and preparation method thereof |
| CN114573802B (en) * | 2020-12-02 | 2024-03-26 | 中国石油天然气股份有限公司 | Surfactant and preparation method thereof |
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