A three-head surfactant and its preparation method and application

By designing the molecular structure and preparation method of the tri-head-based surfactant, the problems of difficult and poor results in the preparation of existing low-foam surfactants are solved, and good surfactant with foam inhibition and low-foam properties are achieved, and foam control is suitable for foam control in industrial cleaning and other fields.

CN116903510BActive Publication Date: 2025-08-15SHANDONG UNIV
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Patent Information

Application Number
CN202310501905.6
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2023-04-28
Publication Date
2025-08-15
Estimated Expiration
2043-04-28

AI Technical Summary

Technical Problem

The existing research on low-foam surfactants is mainly based on the compound formulation of a variety of substances, which has the problem of difficult preparation technology and poor use effect, especially in the fields of industrial cleaning and other fields, foam control is difficult to achieve.

Method used

A trihead-based surfactant was designed, and its molecular structure contained a variety of hydrophilic groups such as carboxylic acid group, sulfonate group, nitrogen-containing heterocycle, cyclic amide group and quaternary ammonium group. Combined with lipophilic groups of different carbon chain lengths, a new structural trihead-based surfactant was prepared through specific synthesis steps such as intermediate reaction and recrystallization purification.

Benefits of technology

It achieves good surfactivity with foam inhibition and low foam properties, has low production cost, low energy consumption, simple preparation technology, and is suitable for foam control in industrial cleaning and other fields.

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Abstract

The present invention discloses a three-headed surfactant having a general molecular structure formula (DA-n-MX): #imgabs0# wherein n is 12, 14, 16 or 18; M is Na or K; and X is Cl or Br. The three-headed surfactant provided by the present invention has a plurality of hydrophilic groups in its molecular structure, such as a carboxylic acid group, a sulfonate group, a nitrogen-containing heterocycle, an amide group on a ring, and a quaternary ammonium salt group. The plurality of hydrophilic groups are combined with lipophilic groups of different carbon chain lengths to form a three-headed surfactant with a novel structure. The three-headed surfactant provided by the present invention exhibits anti-foaming properties, low-foaming properties, and good surface activity.
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Description

Technical Field

[0001] The present invention relates to the technical field of surfactants, and in particular to a three-head surfactant and a preparation method and application thereof. Background Art

[0002] The information disclosed in this background technology section is only intended to enhance understanding of the overall background of the invention and should not necessarily be regarded as an admission or any form of suggestion that the information constitutes the prior art already known to those skilled in the art.

[0003] Low-foaming surfactants are chemical surfactants that exhibit low foaming properties in specific applications, such as industrial cleaning. For example, in the low-foaming antibacterial surfactant, dishwasher tablets containing the same, and their preparation method (Publication No. CN112552509A), the low-foaming antibacterial surfactant is a modified fatty amine polyoxyethylene ether.

[0004] However, the existing research on low-foaming surfactants mainly focuses on the compound formulation of multiple substances. There are few reports on those with independent chemical compositions. At the same time, there are the disadvantages of high difficulty in preparation technology and poor performance. Summary of the Invention

[0005] In order to overcome the above problems, the present invention provides a three-headed surfactant and its preparation method and application. The three-headed surfactant provided by the present invention has the characteristics of a low-foaming surfactant and has good foam suppression and surface activity.

[0006] In order to achieve the above technical objectives, the present invention adopts the following technical solutions:

[0007] The first aspect of the present invention provides a three-head surfactant, the molecular structure of which is generally formulated as (DA-n-MX):

[0008]

[0009] wherein n is 12, 14, 16 or 18; M is Na or K; and X is Cl or Br.

[0010] The three-headed group in the three-headed surfactant refers to the propionic acid group, propanesulfonate group, and carboxyl group on the nitrogen-containing heterocycle in the molecular structure. The three-headed surfactant has a large spatial volume and a wide spatial action range. It can form intermolecular hydrogen bonds with solvent water molecules, has a strong action force, and has a good effect.

[0011] The development strategy of this invention incorporates a variety of hydrophilic groups into the surfactant's molecular structure, including carboxylic acid, sulfonate, nitrogen-containing heterocycles, cyclic amides, and quaternary ammonium salts. These groups are combined with lipophilic groups of varying carbon chain lengths to create a novel three-head surfactant. This molecule exhibits anti-foaming and low-foaming properties, as well as excellent surface activity.

[0012] The second aspect of the present invention provides a method for preparing the above-mentioned three-head surfactant, comprising the following steps:

[0013] S1: Add N-alkyl-1,3-propylene diamine and itaconic acid to organic solvent A, mix and react to obtain intermediate ZB1-n. The general structural formula of intermediate ZB1-n is:

[0014]

[0015] Wherein, n is 12, 14, 16 or 18;

[0016] S2: Add acrylic acid to the intermediate ZB1-n, mix and react to obtain the intermediate ZB2-n. The general structural formula of the intermediate ZB2-n is:

[0017]

[0018] Wherein, n is 12, 14, 16 or 18;

[0019] S3: Add 2-haloethylsulfonate aqueous solution to the intermediate ZB2-n, mix and react. After the reaction is completed, evaporate the organic solvent A and water under normal pressure, and then purify by recrystallization with organic solvent B to obtain the pure product DA-n-MX.

[0020] The third aspect of the present invention provides a three-head surfactant prepared by the above preparation method.

[0021] A fourth aspect of the present invention provides the use of the above-mentioned tri-head surfactant as a foam suppressant, low-foaming surfactant, or emulsifier. For example, in specific fields such as industrial cleaning, the generation of large amounts of foam can make production difficult to control and cause environmental pollution.

[0022] The beneficial effects of the present invention are:

[0023] (1) The three-head surfactant provided by the present invention has a variety of hydrophilic groups in its molecular structure, such as carboxylic acid groups, sulfonate groups, nitrogen-containing heterocycles, ring amide groups, and quaternary ammonium salt groups. The multiple hydrophilic groups are combined with lipophilic groups of different carbon chain lengths to form a novel three-head surfactant structure. The three-head surfactant provided by the present invention exhibits anti-foaming properties, low foaming properties, and good surface activity.

[0024] (2) The raw materials used in the present invention are widely available and inexpensive, so the production cost is low.

[0025] (3) The heating reaction temperature is low, the energy consumption is low, and no pressure reaction is required.

[0026] (4) The preparation process is simple and the technology is practical. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] The accompanying drawings, which constitute a part of the present invention, are used to provide a further understanding of the present invention. The exemplary embodiments of the present invention and their descriptions are used to explain the present invention and do not constitute improper limitations on the present invention.

[0028] Figure 1 This is the infrared spectrum of the product DA-18-NaCl after recrystallization and purification in Example 1 of the present invention;

[0029] Figure 2 This is the NMR spectrum of the product DA-18-NaCl after recrystallization and purification in Example 1 of the present invention;

[0030] Figure 3 This is the mass spectrum of the product DA-18-NaCl after recrystallization and purification in Example 1 of the present invention;

[0031] Figure 4 This is a graph showing the relationship between surface tension and logarithmic concentration of the product DA-18-NaCl after recrystallization and purification in Example 1 of the present invention;

[0032] Figure 5 This is the general formula of the reaction of Examples 1 and 2 of the present invention. DETAILED DESCRIPTION

[0033] It should be noted that the following detailed descriptions are exemplary and intended to provide further explanation of the present invention. Unless otherwise specified, all technical and scientific terms used in the present invention have the same meanings as those commonly understood by those skilled in the art to which the present invention belongs.

[0034] It should be noted that the terms used herein are only for describing specific embodiments and are not intended to limit the exemplary embodiments according to the present application; as used herein, unless the context clearly indicates otherwise, the singular form is also intended to include the plural form, and it should be understood that when the terms "comprise" and / or "include" are used in this specification, they indicate the presence of features, steps, operations, devices, components and / or their combinations.

[0035] A first typical embodiment of the present invention provides a three-head surfactant, the general molecular structure of which is (DA-n-MX):

[0036]

[0037] wherein n is 12, 14, 16 or 18; M is Na or K; and X is Cl or Br.

[0038] The three-headed group in the three-headed surfactant refers to the propionic acid group, propanesulfonate group, and carboxyl group on the nitrogen-containing heterocycle in the molecular structure. The three-headed surfactant has a large spatial volume and a wide spatial action range. It can form intermolecular hydrogen bonds with solvent water molecules, has a strong action force, and has a good effect.

[0039] A second typical embodiment of the present invention provides a method for preparing the above-mentioned three-head surfactant, comprising the following steps:

[0040] S1: Add N-alkyl-1,3-propylene diamine and itaconic acid to organic solvent A, mix and react to obtain intermediate ZB1-n. The general structural formula of intermediate ZB1-n is:

[0041]

[0042] Wherein, n is 12, 14, 16 or 18;

[0043] S2: Add acrylic acid to the intermediate ZB1-n, mix and react to obtain the intermediate ZB2-n. The general structural formula of the intermediate ZB2-n is:

[0044]

[0045] Wherein, n is 12, 14, 16 or 18;

[0046] S3: Add 2-haloethylsulfonate aqueous solution to the intermediate ZB2-n, mix and react. After the reaction is completed, evaporate the organic solvent A and water under normal pressure, and then purify by recrystallization with organic solvent B to obtain the pure product DA-n-MX.

[0047] In one or more embodiments, in S1, the N-alkyl-1,3-propylene diamine is N-octadecyl-1,3-propylene diamine, N-hexadecyl-1,3-propylene diamine, N-tetradecyl-1,3-propylene diamine or N-dodecyl-1,3-propylene diamine.

[0048] In one or more embodiments, in S1, the organic solvent A is ethanol and / or isopropanol, preferably isopropanol.

[0049] In one or more embodiments, in S1, the reaction temperature is 62-82° C., preferably 75° C.; and the reaction time is 3-5 hours, preferably 4 hours.

[0050] In one or more embodiments, in S2, the reaction temperature is 62-82° C., preferably 75° C.; the reaction time is 2-4 hours, preferably 3 hours.

[0051] In one or more embodiments, in S3, the mass fraction of 2-haloethylsulfonate in the 2-haloethylsulfonate aqueous solution is 27-37%, preferably 32.7%.

[0052] In one or more embodiments, in S3, the 2-haloethylsulfonate is sodium 2-chloroethylsulfonate, sodium 2-bromoethylsulfonate, potassium 2-chloroethylsulfonate or potassium 2-bromoethylsulfonate.

[0053] In one or more embodiments, in S3, the reaction temperature is 62-82° C., preferably 75° C.; and the reaction time is 8-10 hours, preferably 9 hours.

[0054] In one or more embodiments, in S3, the temperature for evaporating the organic solvent A is 62-82°C, preferably 75°C.

[0055] In one or more embodiments, in S3, the organic solvent B is methanol, petroleum ether or ethyl acetate, preferably methanol.

[0056] In one or more embodiments, the molar ratio of the N-alkyl-1,3-propylene diamine, organic solvent A, itaconic acid, acrylic acid, 2-haloethyl sulfonate, and water is 1:(9.5-19.5):(1.01-1.07):(1.01-1.08):(1.01-1.09):(15-29), preferably 1:11.8:1.03:1.05:1.05:22.

[0057] In one or more embodiments, the preparation method of the multi-head surfactant specifically comprises the following steps:

[0058] S1: Add N-alkyl-1,3-propylene diamine to a reaction vessel, add organic solvent A, heat and stir to dissolve, then add itaconic acid in 5-10 batches. After the addition is complete, stir and react at 62-82°C for 3-5 hours to obtain intermediate ZB1-n;

[0059] S2: Add acrylic acid to the intermediate ZB1-n in 5 to 10 batches. After the addition is complete, stir and react at 62 to 82°C for 2 to 4 hours to obtain the intermediate ZB2-n;

[0060] S3: Add 2-haloethylsulfonate aqueous solution to the intermediate ZB2-n in 5 to 10 batches. After the addition is completed, stir and react at 62 to 82°C for 8 to 10 hours. After the reaction is completed, evaporate the organic solvent A and water at 62 to 82°C under normal pressure, and then recrystallize and separate and purify with organic solvent B for 3 to 4 times to obtain the pure product DA-n-MX of the multi-head surfactant.

[0061] The reaction equation is:

[0062]

[0063] A third typical embodiment of the present invention provides a three-head surfactant prepared by the above preparation method.

[0064] A fourth typical embodiment of the present invention provides the use of the above-mentioned three-headed surfactant as a foam suppressant, a low-foaming surfactant, and an emulsifier.

[0065] In order to enable those skilled in the art to more clearly understand the technical solution of the present invention, the technical solution of the present invention will be described in detail below with reference to specific embodiments and experimental examples.

[0066] Example 1

[0067] Preparation of tri-head surfactant (product DA-18-NaCl)

[0068] S1: Add 163.0 g of N-octadecyl-1,3-propylene diamine and 355.0 g of isopropanol to a reactor, heat and stir at 75°C to dissolve, add 67.0 g of itaconic acid in 8 batches, and stir at 75°C for 4 hours to obtain the intermediate (ZB1-18).

[0069] S2: 37.85 g of acrylic acid was added to the intermediate (ZB1-18) in 8 batches, and the mixture was stirred at 75° C. for 3 hours to obtain the intermediate (ZB2-18).

[0070] S3: Dissolve 98.9 g of sodium 2-chloroethylsulfonate monohydrate (98.0% purity) in 197.8 g of water to obtain an aqueous solution of sodium 2-chloroethylsulfonate. This aqueous solution of sodium 2-chloroethylsulfonate was added to the reaction intermediate (ZB2-18) in eight batches. The mixture was stirred at 75°C for 9 hours to obtain the tris-head surfactant product, DA-18-NaCl.

[0071] Isopropyl alcohol and water were evaporated under normal pressure, and the product was purified by recrystallization from methanol three times to obtain pure product DA-18-NaCl.

[0072] The reaction equation is:

[0073]

[0074] Infrared analysis (see Figure 1 ): 3471cm -1 (peak 1) is the OH stretching vibration absorption peak, 2950cm -1 (peak 2) is the asymmetric stretching vibration absorption peak of methyl, 2922 cm -1 (peak 3) is the asymmetric stretching vibration absorption peak of methylene, 2852 cm -1 (peak 4) is the symmetrical stretching vibration peak of methylene, 1718 cm -1 (peak 5) is the stretching vibration peak of carboxyl C=O, 1630 cm -1 (peak 6) is the C=O stretching vibration absorption peak of the amide ring, 1207 cm -1 (peak 7) is the stretching vibration absorption peak of CN, 1053 cm -1 (peak 8) is the asymmetric stretching vibration absorption peak of sulfonic acid group S=O, 721 cm -1 (peak 9) is the in-plane rocking vibration of the methylene group, 602 cm -1 (peak 10) is the stretching vibration absorption peak of SO.

[0075] NMR analysis (see Figure 2 ): 1 H NMR (400MHz, CD3OD), δ: 0.8838-0.9179 (3H, t, J = 6.82Hz, -CH3), 1.2888, (30H, s, CH3 (CH2) 15 CH2CH2-), 1.6677-1.7237(2H, m, -CH3(CH2) 15 CH2CH2-), 2.0568-2.1359(2H, m, -NCH2CH2CH2NCO-), 2.4650-2.4966 (4H, t, J=6.32Hz, -NCH2CH2CH2NCO-and CH3(CH2) 15CH2CH2N-), 2.5410-2.5781 (2H, t, J=7.42Hz, -CH2COOH), 2.6550-2.6724 (2H, d, -CH2CON-), 2.9550-2.9 894 (2H, t, J = 6.88Hz, -CH2CH2COOH), 3.1084-3.1331 (2H, t, J = 4.94Hz, -NCH2CH2SO3Na), 3.1928-3.2149 (2H, t, J = 4.42 Hz, -NCH2CH2SO3Na), 3.5341-3.5528 (2H, d, -CH2CHCOOH), 3.6274-3.6673 (2H, t, J = 7.98 Hz, -NCH2CH2CH2NCO-), 3.8136-3.8357 (2H, m, -CH2CHCOOH) ppm. 3.3100 ppm is the deuterated methanol solvent peak; 4.8636 ppm is the deuterated methanol water peak.

[0076] Mass spectrometry analysis (see Figure 3 ): HRMS(ESI)(negative)m / z:[M-Na + ] - Calcd for C 31 H 58 O8N2SCl, 653.3602; Found 653.4131.

[0077] Example 2

[0078] Preparation of three-head surfactant (product DA-12-NaCl):

[0079] S1: Add 121.0 g of N-dodecyl-1,3-propylene diamine and 355.0 g of isopropanol to a reactor, heat and stir at 75°C to dissolve, add 67.0 g of itaconic acid in 8 batches, and stir at 75°C for 4 hours to obtain the intermediate (ZB1-12).

[0080] S2: 37.85 g of acrylic acid was added to the intermediate (ZB1-12) in 8 batches, and the mixture was stirred at 75° C. for 3 hours to obtain the intermediate (ZB2-12).

[0081] S3: Dissolve 98.9 g of sodium 2-chloroethylsulfonate monohydrate (98.0% purity) in 197.8 g of water to obtain an aqueous solution of sodium 2-chloroethylsulfonate. This aqueous solution of sodium 2-chloroethylsulfonate was added to the reaction intermediate (ZB2-12) in eight batches. The mixture was stirred at 75°C for 9 hours to obtain the tris-head surfactant product, DA-12-NaCl.

[0082] Isopropyl alcohol and water were evaporated under normal pressure, and the product was purified by recrystallization from methanol three times to obtain pure product DA-12-NaCl.

[0083] The reaction equation is:

[0084]

[0085] Experimental Example 1

[0086] The foam suppression performance of the tri-head surfactant DA-18-NaCl prepared in Example 1 was measured: 10 mL of a 0.5% (mass fraction) aqueous solution of sodium dodecylbenzenesulfonate (LBS) and a predetermined amount of sample were poured into a 100 mL stoppered graduated cylinder. The cylinder was stoppered and vigorously shaken up and down 20 times. The foam volume was recorded. The foam suppression value (T) represents the sample's ability to suppress foam.

[0087] T=(V0-V1) / V0

[0088] Where V0 is the foam volume during the blank test (mL); V1 is the foam volume when the sample is added (mL).

[0089] The foam suppression performance of the three-head surfactant DA-18-NaCl and OP-10 (industrial product) is compared and shown in Tables 1 and 2. It can be seen that the three-head surfactant DA-18-NaCl prepared in Example 1 has better foam suppression ability.

[0090] Table 1. Foam suppression ability (before purification)

[0091]

[0092] Table 2. Antifoaming ability (after purification)

[0093]

[0094] Experimental Example 2

[0095] The emulsifying ability of the pure tris-head surfactant product DA-18-NaCl prepared in Example 1 was determined. 20 ml of a 0.1% (mass fraction) sample aqueous solution and 20 ml of liquid paraffin were poured into a 100 ml stoppered graduated cylinder. The cylinder was then stoppered and vigorously shaken up and down five times, then allowed to stand for one minute. This was repeated five times, and the time it took to separate 10 ml of water was measured.

[0096] Results: The water separation time of the pure product DA-18-NaCl of the three-headed surfactant in Example 1 is 135 seconds, indicating that the sample has good emulsification ability.

[0097] Experimental Example 3

[0098] The foaming and foam stability properties of the pure product DA-18-NaCl of the three-head surfactant prepared in Example 1 were measured. 110 ml of an aqueous solution of the sample with a concentration of 0.001 mol / L was prepared. 20 ml of the solution was placed in a 100 ml stoppered measuring cylinder and kept at a constant temperature of 25°C for 10 minutes. The constant temperature solution was vigorously shaken up and down 20 times and allowed to stand, and the initial volume of the foam (H0), the volume of the foam after 5 minutes (H5), and the time required for the foam volume to decay to half of the initial volume (t 1 / 2 ).

[0099] The data are shown in Table 3. Compared with sodium dodecylbenzenesulfonate, the H0 of the pure product DA-18-NaCl of the three-headed surfactant prepared in Example 1 is 7 mL, which is a smaller value, indicating that the pure product DA-18-NaCl of the three-headed surfactant prepared in Example 1 is a low-foaming surfactant.

[0100] Table 3. Foamability and Foam Stability

[0101]

[0102] Experimental Example 4

[0103] The surface tension of the pure product DA-18-NaCl of the three-head surfactant prepared in Example 1 was measured. The surface tension was measured using an automatic surface tension meter to obtain a surface tension-log c curve (see Figure 4 ), calculate the critical micelle concentration (CMC), the surface tension at CMC (γ CMC ), C 20 、pC 20 and CMC / C 20 (See Table 4.) It can be seen that DA-18-NaCl has better surface properties.

[0104] Table 4. Surface performance parameters

[0105] product <![CDATA[CMC(mol·L -1 )]]> <![CDATA[γ CMC (mN·m -1 )]]> <![CDATA[C 20 (mol·L -1 )]]> <![CDATA[pC 20 ]]> <![CDATA[CMC / C 20 ]]> DA-18-NaCl <![CDATA[2.99×10 -3 ]]> 37.4 <![CDATA[5.61×10 -5 ]]> 4.25 53.30

[0106] Comparative Example 1

[0107] The following compounds were synthesized:

[0108]

[0109] The foam suppression performance of this compound (pure product) was measured using the same method as in Example 1. When 0.1 g was added, the foam volume was 72 ml, and the foam suppression value T was 0.14. When 0.05 g was added, the foam volume was 81 ml, and the foam suppression value T was 0.04. This foam suppression performance was poor.

[0110] The foregoing description is merely a preferred embodiment of the present invention and is not intended to limit the present invention. Those skilled in the art will readily appreciate that various modifications and variations of the present invention are possible. Any modifications, equivalent substitutions, or improvements made within the spirit and principles of the present invention are intended to be within the scope of protection of the present invention.

Claims

1. A three-head surfactant, characterized in that Its molecular structure formula (DA-n-MX) is: , DA-n-MX; Among them, C n H 2n+1 is dodecyl, tetradecyl, hexadecyl or octadecyl; M is Na or K; X is Cl or Br.

2. The method for preparing the three-head surfactant according to claim 1, characterized in that: The steps include: S1: Add N-alkyl-1,3-propylene diamine and itaconic acid to organic solvent A, mix and react to obtain intermediate ZB1-n. The general structural formula of intermediate ZB1-n is: , Intermediate ZB1-n; Among them, C n H 2n+1 is dodecyl, tetradecyl, hexadecyl or octadecyl; The N-alkyl-1,3-propylene diamine is N-octadecyl-1,3-propylene diamine, N-hexadecyl-1,3-propylene diamine, N-tetradecyl-1,3-propylene diamine or N-dodecyl-1,3-propylene diamine; S2: Add acrylic acid to the intermediate ZB1-n, mix and react to obtain the intermediate ZB2-n. The general structural formula of the intermediate ZB2-n is: , Intermediate ZB2-n; Among them, C n H 2n+1 is dodecyl, tetradecyl, hexadecyl or octadecyl; S3: Adding an aqueous solution of 2-haloethylsulfonate to the intermediate ZB2-n, mixing and reacting, and after the reaction is completed, evaporating the organic solvent A and water under normal pressure, and then recrystallizing and purifying with organic solvent B to obtain the pure product DA-n-MX; The 2-haloethylsulfonate is sodium 2-chloroethylsulfonate, sodium 2-bromoethylsulfonate, potassium 2-chloroethylsulfonate or potassium 2-bromoethylsulfonate.

3. The preparation method according to claim 2, wherein In S1, the organic solvent A is ethanol and / or isopropanol.

4. The preparation method according to claim 3, wherein The organic solvent A is isopropyl alcohol.

5. The preparation method according to claim 2, wherein In the above-mentioned S1, the reaction temperature is 62-82° C. and the reaction time is 3-5 h.

6. The preparation method according to claim 5, wherein In S1, the reaction temperature is 75° C. and the reaction time is 4 h.

7. The preparation method according to claim 2, wherein In the step S2, the reaction temperature is 62-82° C., and the reaction time is 2-4 h.

8. The preparation method according to claim 7, wherein In S2, the reaction temperature is 75° C. and the reaction time is 3 h.

9. The preparation method according to claim 2, wherein In S3, the mass fraction of 2-haloethylsulfonate in the 2-haloethylsulfonate aqueous solution is 27-37%; Alternatively, in S3, the reaction temperature is 62-82° C. and the reaction time is 8-10 h; Alternatively, the organic solvent B is methanol, petroleum ether or ethyl acetate.

10. The preparation method according to claim 9, characterized in that In S3, the mass fraction of 2-haloethylsulfonate in the 2-haloethylsulfonate aqueous solution is 32.7%; Or, in S3, the reaction temperature is 75° C.; the reaction time is 9 h; Alternatively, the organic solvent B is methanol.

11. The preparation method according to claim 2, wherein The molar ratio of the N-alkyl-1,3-propylene diamine, organic solvent A, itaconic acid, acrylic acid, 2-haloethyl sulfonate and water is 1: (9.5-19.5): (1.01-1.07): (1.01-1.08): (1.01-1.09): (15-29).

12. The preparation method according to claim 11, characterized in that The molar ratio is 1:11.8:1.03:1.05:1.05:

22.

13. The preparation method according to claim 2, wherein The preparation method specifically comprises the following steps: S1: Add N-alkyl-1,3-propylene diamine to a reaction vessel, add organic solvent A, heat and stir to dissolve, then add itaconic acid in 5-10 batches. After the addition is complete, stir and react at 62-82°C for 3-5 hours to obtain intermediate ZB1-n; S2: Add acrylic acid to intermediate ZB1-n in 5-10 batches. After the addition is complete, stir and react at 62-82°C for 2-4 hours to obtain intermediate ZB2-n; S3: Add 2-haloethylsulfonate aqueous solution to the intermediate ZB2-n in 5 to 10 batches. After the addition is completed, stir and react at 62 to 82°C for 8 to 10 hours. After the reaction is completed, evaporate the organic solvent A and water under normal pressure, and then recrystallize and separate and purify with organic solvent B for 3 to 4 times to obtain the pure product DA-n-MX of the tri-head surfactant.

14. Use of the three-headed surfactant according to claim 1 and / or the three-headed surfactant prepared by the preparation method according to any one of claims 2 to 13 as a foam suppressant, low-foaming surfactant, or emulsifier.

Citation Information

Patent Citations

  • Low-foam antibacterial surfactant, dish-washing machine cleaning sheet containing same and preparation method thereof

    CN112552509A