CN115521219B - Multi-hydrophilic head-based surfactant, and composition, preparation method and application thereof - Google Patents
Multi-hydrophilic head-based surfactant, and composition, preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a multi-hydrophilic head-based surfactant, a composition, a preparation method and application thereof. The multi-hydrophilic head-based surfactant has a structure shown in a formula (I):wherein R is 1 An aromatic group which is a C1-C30 linear or branched hydrocarbon group, a C3-C30 cyclic hydrocarbon group, a linear or branched hydrocarbon group having a C1-C30; m is a cation or a cationic group. The product of the invention has good acid and alkali resistance, good compatibility of the surfactant, and the compounded product solution has ultralow oil-water interfacial tension and very high interfacial activity. Has good application prospect in the tertiary oil recovery process.
Description
Technical Field
The invention relates to the technical field of surfactants, in particular to a multi-hydrophilic head-based surfactant, a composition, a preparation method and application thereof.
Background
The chelating surfactant is a novel surfactant which has both a hydrophobic chain structure and a hydrophilic chelating structure, has excellent surface activity and better capability of chelating calcium and magnesium ions, and can avoid the problems of water pollution, poor degradability and the like of the conventional chelating agent, so that more attention is paid in recent years. The various characteristics of the chelating surfactant lead the chelating surfactant to have good application prospect in three applications of high-salinity and high-mineralization oil reservoirs.
CN1698942a discloses iminodisuccinate derivative surfactants, which are obtained by reacting iminodisuccinic acid with fatty alcohol or fatty amine in the presence of a catalyst, can improve the salt tolerance and hard water resistance of a mixed system, and are suitable for heavy-duty detergents and steel surface protection.
CN101961620a discloses a preparation method of rosin-based chelating gemini surfactant, which is a functional green surfactant and is easy to biodegrade. Firstly esterifying rosin and polyethylene glycol, adding conjugated double bonds in the rosin through D-A, and neutralizing with alkali to obtain the rosin-based chelating surfactant. The bio-based chelating surfactants are extremely easy to decompose in a high-temperature alkaline environment by using amide bonds or ester bonds to connect hydrophilic and hydrophobic groups, so that the bio-based chelating surfactants have hard water resistance only in a mild environment, and the application prospect of the bio-based chelating surfactants in the tertiary oil recovery process is severely limited.
CN102001956a describes a class of gemini surfactant double-chain alkyl diamine diacetic acid surfactants with chelating ability, which react with diamine by adopting alkyl haloalkane to obtain an N, N-dialkyl diamine intermediate, which reacts with halogenated carboxylic acid to generate dialkyl diamine diacetic acid sodium salt, adjusting pH value to obtain precipitate, recrystallizing with ethanol, having good wetting and emulsifying effects, but having the problem of poor solubility under alkaline conditions, not having better oil-water interface performance, and being difficult to be applied to tertiary oil recovery.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a chelate multi-hydrophilic head-based surfactant which is compounded with a cationic surfactant and can be used in tertiary oil recovery.
One of the objects of the present invention is to provide a multi-hydrophilic head-based surfactant having a structure as shown in formula (I):
wherein R is 1 An aromatic group which is a C1-C30 linear or branched hydrocarbon group, a C3-C30 cyclic hydrocarbon group, a linear or branched hydrocarbon group having a C1-C30; m is a cation or a cationic group;
preferably, R 1 An aromatic group which is a C1-C18 linear or branched hydrocarbon group, a C3-C18 cyclic hydrocarbon group, a linear or branched hydrocarbon group having a C1-C18; m is hydrogen ion, lithium ion, sodium ion, potassium ion;
more preferably, wherein the aryl is phenyl, naphthyl.
The second purpose of the invention is to provide a preparation method of the multi-hydrophilic head-based surfactant, which comprises the following steps:
1) Mixing monoamine and epichlorohydrin with the solvent 1 for reaction;
2) Adding diethyl iminodiacetate into the reaction system of the step 1) to react to obtain a tetraester compound of the multi-hydrophilic head group surfactant;
3) Mixing the tetraester compound obtained in the step 2) with inorganic base and a solvent 2, and purifying after reaction to obtain the multi-hydrophilic head-based surfactant.
In the step 1), the chemical structural formula of the monoamine is R 1 NH 2 Wherein R is 1 An aromatic group which is a C1-C30 linear or branched hydrocarbon group, a C3-C30 cyclic hydrocarbon group, a linear or branched hydrocarbon group having a C1-C30; preferably, R 1 An aromatic group which is a C1-C18 linear or branched hydrocarbon group, a C3-C18 cyclic hydrocarbon group, a linear or branched hydrocarbon group having a C1-C18; more preferably, the aryl is phenyl, naphthyl.
In the step 1), the solvent 1 is preferably one or more of methanol, ethanol, isopropanol, acetonitrile, benzene, toluene, chloroform, N-dimethylformamide, and azamethylpyrrolidone.
In the step 1), the molar ratio of the epichlorohydrin to the monoamine is (2.0-10.0): 1, preferably (2.0 to 4.0): 1, more preferably (2.1 to 2.5): 1, for example, may be 2.0: 1. 2.5: 1. 3.0: 1. 4.0: 1. 5.0: 1. 6.0: 1. 7.0: 1. 8.0: 1. 9.0: 1. 10.0, etc.
In the step 1), the mass ratio of the solvent 1 to the monoamine is (0.01-100.0): 1, preferably (1.0 to 10.0): 1, for example, may be 0.01: 1. 0.1: 1. 1.0: 1. 5.0: 1. 8.0: 1. 10.0: 1. 20.0: 1. 50.0: 1. 80.0: 1. 100.0:1, etc.
In the step 1), the reaction temperature is 20-80 ℃, preferably 30-50 ℃; the reaction time is 60 to 600 minutes, preferably 240 to 480 minutes.
In the step 2), the molar ratio of the iminodiacetic acid diethyl ester to the monoamine is (2.0-10.0): 1, a step of; preferably (2.0 to 4.0): 1, more preferably (2.1 to 3.0): 1, for example, may be 2.0: 1. 2.5: 1. 3.0: 1. 4.0: 1. 5.0: 1. 6.0: 1. 7.0: 1. 8.0: 1. 9.0: 1. 10.0:1, etc.
In the step 2), the reaction temperature is 50-120 ℃, preferably 70-100 ℃; the reaction time is 60 to 600 minutes, preferably 240 to 480 minutes.
In the step 3), the inorganic base is preferably at least one of lithium hydroxide, sodium hydroxide, potassium hydroxide, lithium carbonate, sodium carbonate, and potassium carbonate.
In the step 3), the solvent 2 is preferably one or more of methanol, ethanol, isopropanol, acetonitrile, water, N-dimethylformamide, and azamethylpyrrolidone.
In the step 3), the molar ratio of the inorganic base to the monoamine is (4.0-10.0): 1, a step of; preferably (4.4 to 9.0): 1, more preferably (5.0 to 8.0): 1, for example, may be 4.0: 1. 4.5: 1. 5.0: 1. 5.5: 1. 6.0: 1. 6.5: 1. 7.0: 1. 7.5: 1. 8.0: 1. 8.5: 1. 9.0:1, etc.
In the step 3), the reaction temperature is 50-100 ℃, preferably 70-90 ℃; the reaction time is 30 to 300 minutes, preferably 60 to 180 minutes.
The preparation method of the multi-hydrophilic head-based surfactant specifically comprises the following steps:
1) Mixing monoamine, epichlorohydrin and solvent 1 at a certain temperature, and then reacting for a certain time at a certain temperature;
2) Adding a certain proportion of diethyl iminodiacetate into the reaction system of the step 1), and continuing to react for a certain time at a certain temperature to obtain a tetraester compound corresponding to the chelating surfactant;
3) Mixing the tetraester compound obtained in the step 2) with an inorganic base and a solvent 2 in a certain proportion, and reacting for a certain time at a certain temperature. The chelate surfactant (basic) can be obtained through purification, or the chelate surfactant (acid type, M is hydrogen ion) can be obtained through acidification and purification.
In the method for producing the multi-hydrophilic head-based surfactant of the present invention, the purification is not particularly limited, and a purification method common in the art can be employed.
The reaction route of the preparation method of the invention is as follows:
step 1):
step 2):
step 3):
the preparation method of the hydrophilic head-based surfactant can be carried out in a reaction kettle with a temperature control system, firstly, raw monoamine and a solvent are added into a reaction bottle, uniformly stirred and dissolved, then epichlorohydrin is added, and after uniform mixing, the temperature is controlled to react for a period of time; then adding iminodiacetic acid diethyl ester, and controlling the temperature to react for a period of time; after the solvent is removed, inorganic alkali and the solvent are added and stirred uniformly to form suspension, and the reaction is carried out by controlling the temperature until the reaction is finished. And after the reaction is finished, acidifying with concentrated hydrochloric acid, and carrying out suction filtration and drying to obtain a chelate type hydrophilic head-based surfactant product.
It is still another object of the present invention to provide a complex surfactant composition comprising the multi-hydrophilic head-based surfactant and a cationic surfactant, wherein the cationic surfactant preferably has a structure as shown in formula (II):
R 2 、R 3 、R 4 、R 5 independently selected from C1-C32 alkyl, benzyl and X - Is an anion or an anionic group, R 2 、R 3 、R 4 、R 5 May be partially or wholly identical; preferably X - Is chloride, bromide, iodide, sulfate, nitrate, hydroxide.
The cationic surfactants include, but are not limited to, for example, dioctadecyl dimethyl ammonium chloride, octadecyl dimethyl benzyl ammonium chloride, cetyl trimethyl ammonium chloride, tetrabutyl ammonium chloride, tetraethyl ammonium chloride, dodecyl trimethyl ammonium chloride, and the like.
The molar ratio of the cationic surfactant to the multi-hydrophilic head-based surfactant is 1: (0.01 to 1.0), for example, may be 0.01: 1. 0.05: 1. 0.1: 1. 0.2: 1. 0.3: 1. 0.4: 1. 0.5: 1. 0.6: 1. 0.7: 1. 0.8: 1. 009: 1. 1.0:1, etc.
The complex surfactant composition may be used in the form of an aqueous solution of a multi-hydrophilic head-based surfactant and a cationic surfactant, or in other forms suitable for use in tertiary applications.
It is a fourth object of the present invention to provide a process for preparing the complex surfactant composition comprising mixing the multi-hydrophilic head-based surfactant with a cationic surfactant.
The preparation method of the composite surfactant composition can be that the cationic surfactant and the multi-hydrophilic head-based surfactant are respectively dissolved in water, and then the following steps are carried out according to 1: (0.01-1.0).
The fifth object of the present invention is to provide the use of said complex surfactant composition in tertiary oil recovery.
The chelate hydrophilic head-based surfactant provided by the invention has the advantages of short production process flow, mild and easily controlled conditions, higher atom economy, no generation of a large number of toxic and harmful byproducts, and a greener chemical process. The product has good acid and alkali resistance, good compatibility of the surfactant, and the compounded product solution has ultralow oil-water interfacial tension and very high interfacial activity. Therefore, the method has good application prospect in the tertiary oil recovery process.
Detailed Description
The present invention is described in detail below with reference to specific embodiments, and it should be noted that the following embodiments are only for further description of the present invention and should not be construed as limiting the scope of the present invention, and some insubstantial modifications and adjustments of the present invention by those skilled in the art from the present disclosure are still within the scope of the present invention.
In addition, any combination of the various embodiments of the present invention can be made, so long as the concept of the present invention is not deviated, and the technical solution formed thereby is a part of the original disclosure of the present specification, and also falls within the protection scope of the present invention.
The raw materials used in the examples and comparative examples of the present invention are all disclosed in the prior art, if not particularly limited, and may be obtained, for example, directly or prepared according to the preparation method disclosed in the prior art.
Example 1
12.9 g of n-octylamine and 100 g of ethanol are added into a reaction bottle, stirred and dissolved uniformly, 19.5 g of epichlorohydrin is added at room temperature, and then the system temperature is controlled to be 40 ℃ for reaction for 4 hours.
Then 39.7 g of diethyl iminodiacetate was added to the reaction vessel, followed by controlling the reaction temperature to 80℃for 5 hours.
The solvent was removed by rotary evaporation, and 20 g of sodium hydroxide, 100 g of methanol and 20 g of deionized water were added to the reaction flask and stirred well. The reaction temperature was controlled to 90℃and the reaction was carried out for 1 hour. The reaction was stopped, acidified by adding concentrated hydrochloric acid, and dried by suction filtration to give 43.7 g of the white solid product C8NEPC2NC4 in 86% yield.
Dioctadecyl dimethyl ammonium chloride and the C8NEPC2NC4 anionic sodium salt prepared in example 1 of the invention were dissolved in water respectively, and stirred for 30 minutes to prepare a 5.0wt% aqueous solution. The surfactant solution is then mixed according to cations: and mixing the anionic surfactants in a molar ratio of 1:0.1 to obtain a compound solution for oil-water interfacial tension measurement.
Example 2
18.5 g of dodecyl amine and 200 g of isopropanol are added into a reaction bottle, stirred and dissolved uniformly, 22.6 g of epichlorohydrin is added at room temperature, and then the system temperature is controlled to be 45 ℃ for reaction for 3.5 hours.
Then, 38 g of diethyl iminodiacetate was added to the reaction vessel, followed by controlling the reaction temperature to 90℃for 4 hours.
The solvent was removed by rotary evaporation, 25 g sodium hydroxide, 100 g ethanol and 20 g deionized water were added to the reaction flask and stirred well. The reaction temperature was controlled at 80℃and the reaction was carried out for 2 hours. Stopping the reaction, adding concentrated hydrochloric acid for acidification, and carrying out suction filtration and drying to obtain 52.4 g of white solid product C12NEPC2NC4, wherein the yield is 93%.
Octadecyldimethylbenzyl ammonium chloride and the sodium salt of the C12NEPC2NC4 anion prepared in example 2 of the present invention were dissolved in water, respectively, and stirred for 30 minutes to prepare a 5.0wt% aqueous solution. The surfactant solution is then mixed according to cations: and mixing the anionic surfactants in a molar ratio of 1:0.5 to obtain a compound solution for oil-water interfacial tension measurement.
Example 3
24.1 g of hexadecylamine and 50 g of toluene are added into a reaction bottle, stirred and dissolved uniformly, 20.3 g of epichlorohydrin is added at room temperature, and then the system temperature is controlled to be 40 ℃ for reaction for 4 hours.
45.3 g of diethyl iminodiacetate was then added to the reaction vessel, and the reaction was continued at 70℃for 8 hours.
The solvent was removed by rotary evaporation, 30 g of sodium hydroxide, 100 g of acetonitrile and 20 g of deionized water were added to the reaction flask and stirred well. The reaction temperature was controlled at 70℃to conduct the reaction for 3 hours. Stopping the reaction, adding concentrated hydrochloric acid for acidification, and carrying out suction filtration and drying to obtain 53.9 g of white solid product C16NEPC2NC4, wherein the yield is 87%.
Cetyl trimethyl ammonium chloride and the sodium salt of C16NEPC2NC4 anion prepared in example 3 of the present invention were dissolved in water, respectively, and stirred for 30 minutes to prepare a 5.0wt% aqueous solution. The surfactant solution is then mixed according to cations: and mixing the anionic surfactants in a molar ratio of 1:0.5 to obtain a compound solution for oil-water interfacial tension measurement.
Example 4
27 g of octadecylamine and 150 g of chloroform are added into a reaction bottle, stirred and dissolved uniformly, 21.7 g of epichlorohydrin is added at room temperature, and then the system temperature is controlled to be 35 ℃ for reaction for 7 hours.
Then 50.3 g of diethyl iminodiacetate was added to the reaction vessel, followed by controlling the reaction temperature to 70℃for further 8 hours.
The solvent was removed by rotary evaporation, and 20 g of sodium hydroxide, 100 g of methanol and 20 g of deionized water were added to the reaction flask and stirred well. The reaction temperature was controlled to 90℃and the reaction was carried out for 1 hour. The reaction was stopped, acidified by adding concentrated hydrochloric acid, and dried by suction filtration to give 59 g of a white solid product C18NEPC2NC4 in 91% yield.
Tetrabutylammonium chloride and the sodium salt of the C18NEPC2NC4 anion prepared in example 4 of the present invention were dissolved in water, respectively, and stirred for 30 minutes to prepare a 5.0wt% aqueous solution. The surfactant solution is then mixed according to cations: and mixing the anionic surfactants in a molar ratio of 1:0.2 to obtain a compound solution for oil-water interfacial tension measurement.
Example 5
26.8 g of oleylamine and 100 g of DMF are added into a reaction bottle, stirred and dissolved uniformly, 22.1 g of epichlorohydrin is added at room temperature, and then the system temperature is controlled to be 40 ℃ for reaction for 5 hours.
Then 39.7 g of diethyl iminodiacetate was added to the reaction vessel, followed by controlling the reaction temperature to 80℃for 5 hours.
The solvent was removed by rotary evaporation, and 20 g of sodium hydroxide, 100 g of DMF and 20 g of deionized water were added to the reaction flask and stirred well. The reaction temperature was controlled to 90℃and the reaction was carried out for 1 hour. Stopping the reaction, adding concentrated hydrochloric acid for acidification, and carrying out suction filtration and drying to obtain 52.3 g of a pale yellow solid product C18xNEPC2NC4, wherein the yield is 81%.
Tetraethylammonium chloride and the C18xNEPC2NC4 anionic sodium salt prepared in example 5 of the present invention were dissolved in water, respectively, and stirred for 30 minutes to prepare a 5.0wt% aqueous solution. The surfactant solution is then mixed according to cations: and mixing the anionic surfactants in a molar ratio of 1:0.1 to obtain a compound solution for oil-water interfacial tension measurement.
Example 6
31.8 g of 4-hexadecyl aniline and 100 g of ethanol are added into a reaction bottle, evenly stirred and dissolved, 22.6 g of epichlorohydrin is added at room temperature, and then the system temperature is controlled to be 50 ℃ for reaction for 8 hours.
Then 39.7 g of diethyl iminodiacetate was added to the reaction vessel, followed by controlling the reaction temperature to 78℃for further 7 hours.
The solvent was removed by rotary evaporation, and 20 g of sodium hydroxide, 100 g of methanol and 20 g of deionized water were added to the reaction flask and stirred well. The reaction temperature was controlled to 90℃and the reaction was carried out for 1 hour. Stopping the reaction, adding concentrated hydrochloric acid for acidification, and carrying out suction filtration and drying to obtain 53.6 g of a tan solid product C16 BNCEPC 2NC4, wherein the yield is 77%.
Dodecyl trimethyl ammonium chloride and the C16 BNECT 2NC4 anion sodium salt prepared in the embodiment 6 of the invention are respectively dissolved in water and stirred for 30 minutes to prepare 5.0wt% aqueous solution. The surfactant solution is then mixed according to cations: and mixing the anionic surfactants in a molar ratio of 1:0.3 to obtain a compound solution for oil-water interfacial tension measurement.
Measurement of oil-water interfacial tension
Diluting the compound solution in different embodiments to insoluble weight percentage concentration by using Henan oilfield produced water, and then measuring the oil-water interfacial tension of the diluted compound solution and Henan oilfield crude oil by using a TX-500C rotary drop interfacial tensiometer.
The specific oil-water interfacial tension is shown in Table 1 below.
TABLE 1 oil-water interfacial tension data (mN/m) for different concentrations of the formulated solutions of the different examples and crude oil from Henan oilfield
| Examples | 0.3wt％ | 0.2wt％ | 0.1wt％ | 0.05wt％ |
| 1 | 0.00771 | 0.00585 | 0.00399 | 5.19908E-4 |
| 2 | 0.00728 | 0.00455 | 0.00183 | 9.771E-4 |
| 3 | 0.00728 | 0.00683 | 0.00638 | 2.508E-4 |
| 4 | 0.00601 | 0.00471 | 0.00339 | 9.771E-4 |
| 5 | 0.00483 | 0.00325 | 0.00167 | 6.96295E-4 |
| 6 | 0.00728 | 0.00537 | 0.00337 | 4.52185E-4 |
Claims (16)
1. A multi-hydrophilic head-based surfactant having a structure according to formula (I):
wherein R is 1 An aromatic group which is a C1-C30 linear or branched hydrocarbon group, a C3-C30 cyclic hydrocarbon group, a linear or branched hydrocarbon group having a C1-C30; m is a cation or a cationic group.
2. The multi-hydrophilic head-based surfactant of claim 1, wherein:
R 1 a C1-C18 linear or branched hydrocarbon group, a C3-C18 cyclic hydrocarbon group,Aromatic groups with straight-chain hydrocarbon groups or branched-chain hydrocarbon groups of C1-C18; m is hydrogen ion, lithium ion, sodium ion, potassium ion.
3. The multi-hydrophilic head-based surfactant according to claim 2, wherein:
the aryl is phenyl and naphthyl.
4. A method of preparing a multi-hydrophilic head-based surfactant according to any one of claims 1 to 3, comprising the steps of:
1) Mixing monoamine and epichlorohydrin with the solvent 1 for reaction;
2) Adding diethyl iminodiacetate into the reaction system of the step 1) to react to obtain a tetraester compound of the multi-hydrophilic head group surfactant;
3) Mixing the tetraester compound obtained in the step 2) with inorganic base and a solvent 2, and purifying after reaction to obtain the multi-hydrophilic head-based surfactant.
5. The method according to claim 4, wherein in the step 1):
the chemical structural formula of the monoamine is R 1 NH 2 Wherein R is 1 An aromatic group which is a C1-C30 linear or branched hydrocarbon group, a C3-C30 cyclic hydrocarbon group, a linear or branched hydrocarbon group having a C1-C30; and/or the number of the groups of groups,
the solvent 1 is one or more of methanol, ethanol, isopropanol, acetonitrile, benzene, toluene, chloroform, N-dimethylformamide and azomethyl pyrrolidone.
6. The method according to claim 4, wherein in the step 1):
the molar ratio of the epichlorohydrin to the monoamine is (2.0-10.0): 1, a step of; and/or the number of the groups of groups,
the mass ratio of the solvent 1 to the monoamine is (0.01-100.0): 1, a step of; and/or the number of the groups of groups,
the reaction temperature is 20-80 ℃; the reaction time is 60-600 minutes.
7. The method of manufacturing according to claim 6, wherein:
the molar ratio of the epichlorohydrin to the monoamine is (2.0-4.0): 1, a step of; and/or the number of the groups of groups,
the mass ratio of the solvent 1 to the monoamine is (1.0-10.0): 1, a step of; and/or the number of the groups of groups,
the reaction temperature is 30-50 ℃; the reaction time is 240-480 minutes.
8. The method according to claim 4, wherein in the step 2):
the molar ratio of the iminodiacetic acid diethyl ester to the monoamine is (2.0-10.0): 1, a step of; and/or the number of the groups of groups,
the reaction temperature is 50-120 ℃; the reaction time is 60-600 minutes.
9. The method of manufacturing according to claim 8, wherein:
the molar ratio of the iminodiacetic acid diethyl ester to the monoamine is (2.0-4.0): 1, a step of; and/or the number of the groups of groups,
the reaction temperature is 70-100 ℃; the reaction time is 240-480 minutes.
10. The method according to claim 4, wherein in the step 3):
the inorganic base is at least one of lithium hydroxide, sodium hydroxide, potassium hydroxide, lithium carbonate, sodium carbonate and potassium carbonate; and/or the number of the groups of groups,
the solvent 2 is one or more of methanol, ethanol, isopropanol, acetonitrile, water, N-dimethylformamide and azomethyl pyrrolidone.
11. The method according to claim 4, wherein in the step 3):
the molar ratio of the inorganic base to the monoamine is (4.0-10.0): 1, a step of; and/or the number of the groups of groups,
the reaction temperature is 50-100 ℃; the reaction time is 30-300 minutes.
12. The method of manufacturing according to claim 11, wherein:
the molar ratio of the inorganic base to the monoamine is (4.4-9.0): 1, a step of; and/or the number of the groups of groups,
the reaction temperature is 70-90 ℃; the reaction time is 60-180 minutes.
13. A complex surfactant composition comprising the multi-hydrophilic head-based surfactant of any one of claims 1 to 3 and a cationic surfactant, wherein the cationic surfactant has a structure as shown in formula (II):
R 2 、R 3 、R 4 、R 5 independently selected from C1-C32 alkyl, benzyl and X - Is an anion or an anionic group.
14. The complex surfactant composition of claim 13, wherein:
X - is chloride, bromide, iodide, nitrate, hydroxide; and/or the number of the groups of groups,
the molar ratio of the cationic surfactant to the multi-hydrophilic head-based surfactant is 1: (0.01-1.0).
15. A method of preparing a complex surfactant composition according to claim 13 or 14 comprising mixing the multi-hydrophilic head-based surfactant with a cationic surfactant.
16. Use of the complex surfactant composition of claim 13 or 14 in tertiary oil recovery.
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