A compound with surfactant function and its preparation method and application, a surfactant and its application

Abstract

The present invention relates to the field of surfactants and discloses a compound with surfactant functionality, its preparation method, and application, as well as a surfactant and its application. The compound has the structure represented by Formula (A). The surfactant-functional compound provided by the present invention exhibits good water solubility, pH responsiveness, strong aggregation ability, and high solubilization capacity for condensed aromatic hydrocarbons. It also exhibits the advantage of being readily biodegradable. The preparation method provided by the present invention operates under mild reaction conditions, utilizes amino-functionalized cyclodextrin as a raw material, and can produce a product with a yield exceeding 95% in a single step. #imgabs0#

Description

Technical Field

[0001] The present invention relates to the field of surfactants, in particular to a compound with surfactant function, a preparation method and application thereof, a surfactant and application thereof. Background Art

[0002] Surfactants are highly effective adjuvants commonly used in pharmaceuticals and household chemicals. Traditional surfactants are generally composed of a hydrophilic head group and a hydrophobic tail chain. This unique amphiphilic structure enables multiple surfactant molecules to spontaneously aggregate in aqueous solution to form aggregates with hydrophobic microdomains, thereby solubilizing and encapsulating water-insoluble organic matter. Therefore, solubilization capacity is one of the most important performance parameters of surfactants. However, the solubilization capacity of the hydrophobic microdomains of traditional surfactant aggregates for polycyclic aromatic hydrocarbons needs to be improved. To achieve this, further strengthening the interaction between surfactants and water-insoluble organic matter is necessary. In addition, with the continuous improvement of national environmental protection requirements, the water pollution caused by the difficulty of degradation of traditional petroleum-based surfactants has gradually attracted attention. In this context, the development of green and easily degradable surfactants has become a trend.

[0003] Cyclodextrin (CD) is a natural cyclic polysaccharide obtained from microbial fermentation of starch. It has a spatial truncated cone structure and is a commonly used functional host molecule. Cyclodextrin can form host-guest complexes with water-insoluble organic matter through host-guest interactions. Host-guest complexation is another effective way to solubilize hydrophobic organic matter in addition to the solubilization effect of surfactants. By introducing the cyclodextrin structure into the surfactant molecular structure, synergistic solubilization of the hydrophobic microdomains of the aggregates and the host-guest complexation can be achieved, thereby significantly improving the solubilization effect of surfactants on water-insoluble organic matter.

[0004] Currently, most of the relevant reports in the literature and patents are about complex systems of surfactants and cyclodextrins, and there are very few reports on host-guest synergistic surfactants obtained by chemically modifying the cyclodextrin backbone. CN109836512A discloses a novel cationic gemini surfactant prepared based on cyclodextrin with host-guest interaction. It has good viscoelasticity and excellent temperature resistance, and is a promising clean fracturing fluid. However, its synthesis method is carried out in three steps, which is difficult to synthesize and has a low yield. The cationic gemini surfactant disclosed in CN113600095A also has similar effects, but its synthesis method also requires a multi-step reaction.

[0005] Sun et al. from Shandong University prepared a cationic quaternary ammonium salt-type cyclodextrin-modified surfactant using cyclodextrin as a raw material (Journal of Dispersion Science and Technology, 31:1067–1071, 2010). However, the quaternary ammonium salt product requires purification on a silica gel column, which suffers from significant adsorption losses and makes separation and purification difficult, resulting in high application costs and limited effectiveness.

[0006] Currently, nonionic surfactants are widely used in daily chemical products and are the fastest-growing class of surfactants. Literature (Langmuir 1996, 12, 4046-4049) reports that host-guest synergistic nonionic amphiphilic compounds can be prepared by reacting iodinated or p-toluenesulfonyl-substituted cyclodextrins with fatty amines. However, these compounds have poor solubility in water, hindering their practical application.

[0007] Therefore, there is an urgent need to develop a host-guest synergistic nonionic surfactant with simple preparation method, good water solubility and easy biodegradation to expand its application in the pharmaceutical and daily chemical industries. Summary of the Invention

[0008] The purpose of the present invention is to solve the problems of complex preparation methods, difficult separation and purification, poor solubilization effect and poor biodegradability of surfactant products in the methods for preparing surfactants provided in the prior art.

[0009] In order to achieve the above object, the first aspect of the present invention provides a compound having a surfactant function, which has a structure shown in formula (A):

[0010]

[0011] Wherein, in formula (A),

[0012] m is any integer selected from 4 to 12;

[0013] One of R1 and R2 is a hydroxyl group, and the other is and each R is independently selected from H, C 1-18 Alkyl, C 2-18 alkenyl, C containing at least one oxygen atom 2-18 of alkyl.

[0014] A second aspect of the present invention provides a method for preparing a compound having surfactant function, wherein the compound has a structure represented by formula (A), the method comprising:

[0015] In the presence of a solvent, the amino-functionalized cyclodextrin represented by formula (B) is contacted with the 1,2-epoxyalkane represented by formula (C).

[0016]

[0017] Wherein, in formula (B), one of R3 and R4 is -OH and the other is -NH2;

[0018] In formula (A), formula (B) and formula (C), m, R, R1 and R2 are as defined in the first aspect.

[0019] The third aspect of the present invention provides a compound having surfactant function prepared by the method described in the second aspect.

[0020] The fourth aspect of the present invention provides use of the compound having surfactant function described in the first aspect or the third aspect as a water-soluble nonionic gemini surfactant.

[0021] The fifth aspect of the present invention provides a surfactant, which contains an active ingredient in an effective amount for surface active function, wherein the active ingredient is the compound having surfactant function as described in the first aspect.

[0022] The sixth aspect of the present invention provides the use of the compound having surfactant function described in the first aspect or the third aspect and the surfactant described in the fourth aspect in medicine and daily chemicals.

[0023] The inventors of the present invention have discovered that the water-soluble surfactant-functional compound provided by the present invention can achieve a synergistic effect of host-guest encapsulation and hydrophobic microdomain solubilization, thereby possessing efficient solubilization capabilities. Furthermore, the preparation method of the surfactant-functional compound provided by the present invention is completed in one step, with simple separation and purification, and a yield of over 95%. Furthermore, the cyclodextrin head group in the compound imparts strong biocompatibility, is easily biodegradable, and does not produce secondary pollution. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 This is the mass spectrum of compound Z1 with surfactant function prepared in Example 1 of the present invention.

[0025] Figure 2 This is the mass spectrum of compound Z2 with surfactant function prepared in Example 2 of the present invention.

[0026] Figure 3 This is the mass spectrum of compound Z3 with surfactant function prepared in Example 3 of the present invention. DETAILED DESCRIPTION

[0027] The endpoints of the ranges and any values ​​disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoints of each range, the endpoints of each range and individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered to be specifically disclosed herein.

[0028] The following terms are explained for the present invention:

[0029] In this article, the wavy lines in the groups Indicates the bonding position.

[0030] “C 1-18 "Alkyl" means an alkyl group with a total carbon atom count of 1-18, including C1-18 straight chain alkyl, C 1-18 For example, a straight chain alkyl group having a total number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18, a branched chain alkyl group having a total number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18, for example, etc. Regarding “C 8-18 The "alkyl" has a similar explanation, except that the number of carbon atoms is different.

[0031] “C 2-18 The term "alkenyl" refers to a hydrocarbon group formed by removing one or more hydrogen atoms from an olefin molecule, and the total number of carbon atoms in the alkenyl group is 2-18. The double bond in the group can be at any position, for example, etc. Regarding “C 6-12 The "alkenyl" has a similar explanation, except that the number of carbon atoms is different.

[0032] "C containing at least one oxygen atom 2-18 "alkyl" means an alkyl group having a total carbon number of 2 to 18, including straight-chain alkyl and branched-chain alkyl groups, and the C 2-18 The carbon atoms in the alkyl group may be interrupted by one or more oxygen atoms. For example, CH3OCH2-, etc. Regarding “C containing at least one oxygen atom 4-16 The "alkyl" has a similar explanation, except that the number of carbon atoms is different.

[0033] As mentioned above, the first aspect of the present invention provides a compound having surfactant function, which has a structure shown in formula (A):

[0034]

[0035] Wherein, in formula (A),

[0036] m is any integer selected from 4 to 12;

[0037] One of R1 and R2 is a hydroxyl group, and the other is and each R is independently selected from H, C 1-18 Alkyl, C 2-18 alkenyl, C containing at least one oxygen atom 2-18 of alkyl.

[0038] Preferably, m is any integer selected from 5 to 7.

[0039] Preferably, each R is independently selected from H, C 8-18 Alkyl, C 6-12 alkenyl, C containing at least one oxygen atom 4-16 of alkyl.

[0040] More preferably, each R is independently selected from n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, 7-octenyl, n-decyl-O-CH2-,

[0041]

[0042] Preferably, formula (A) is a structure represented by formula (I) or formula (II),

[0043]

[0044] In order to make the compound with surfactant function provided by the present invention have a better solubilization effect, the present invention provides several preferred specific embodiments below to illustrate the preferred conditions of the compound represented by formula (A) of the present invention.

[0045] Preferred embodiment 1:

[0046] In formula (A),

[0047] m is any integer selected from 5 to 7;

[0048] One of R1 and R2 is a hydroxyl group, and the other is and each R is independently selected from H, C 8-18 Alkyl, C 6-12 alkenyl, C containing at least one oxygen atom4-16 of alkyl.

[0049] Preferred embodiment 2:

[0050] In formula (A),

[0051] m is any integer selected from 5 to 7;

[0052] One of R1 and R2 is a hydroxyl group, and the other is Each R is independently selected from n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, 7-octenyl, n-decyl-O-CH2-,

[0053] Preferred embodiment 3:

[0054] Formula (A) is a structure represented by formula (I) or formula (II).

[0055] As mentioned above, the second aspect of the present invention provides a method for preparing a compound having surfactant function, wherein the compound has a structure represented by formula (A), the method comprising:

[0056] In the presence of a solvent, the amino-functionalized cyclodextrin represented by formula (B) is contacted with the 1,2-epoxyalkane represented by formula (C).

[0057]

[0058] Wherein, in formula (B), one of R3 and R4 is -OH and the other is -NH2;

[0059] In formula (A), formula (B) and formula (C), the definitions of m, R, R1 and R2 are the same as those in the first aspect. They are not described here in detail and should not be construed as limiting the present invention by those skilled in the art.

[0060] Preferably, the amino-functionalized cyclodextrin is selected from one of amino-functionalized α-cyclodextrin, amino-functionalized β-cyclodextrin, and amino-functionalized γ-cyclodextrin.

[0061] It should be noted that the amino functionalization position can be at the 3-hydroxyl position or the 6-hydroxyl position of the cyclodextrin.

[0062] More preferably, the formula (B) is a structure represented by formula (III) or formula (IV):

[0063]

[0064] The aforementioned preparation method of the present invention may also involve various post-processing operations known in the art, such as rotary evaporation, extraction, washing, filtration, recrystallization, column chromatography, etc. The present invention has no particular limitation thereto, and those skilled in the art should not understand this as a limitation of the present invention.

[0065] For example, after the amino-functionalized cyclodextrin of formula (B) and the 1,2-epoxyalkane of formula (C) are contacted and reacted, the solvent is removed by rotary evaporation, and then the product is recrystallized or purified by column chromatography to obtain the purified target product. The mixed solvent used for the recrystallization can be one of methanol-ethyl acetate, methanol-acetone, ethanol-ethyl acetate, and ethanol-acetone; the eluent used for the column chromatography is dichloromethane and ethanol in a volume ratio of 5 to 20:1.

[0066] The amino-functionalized cyclodextrin and the 1,2-epoxyalkane in the preparation method of the present invention can be prepared by methods known in the art or purchased.

[0067] Preferably, the 1,2-epoxyalkane is selected from 1,2-epoxydecane, 1,2-epoxydodecane, 1,2-epoxytetradecane, 1,2-epoxyhexadecane, 1,2-epoxyoctadecane, 1,2-epoxyeicosane, 1,2-epoxy-9-decene, Octyl glycidyl ether.

[0068] Preferably, the molar ratio of the amino-functionalized cyclodextrin to the 1,2-alkylene oxide is 1:(1-20).

[0069] More preferably, the molar ratio of the amino-functionalized cyclodextrin to the 1,2-epoxyalkylene is 1:(2.05-5).

[0070] Preferably, the volume of the solvent used is 10-30 mL relative to 1 mmol of amino-functionalized cyclodextrin.

[0071] Preferably, the solvent is selected from at least one of methanol, ethanol, isopropanol, n-butanol, water, tetrahydrofuran, 1,4-dioxane, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and ethylene glycol.

[0072] Preferably, the contact reaction conditions at least meet the following requirements: temperature of 30 to 100° C. and time of 24 to 168 h.

[0073] More preferably, the contact reaction conditions at least meet the following requirements: temperature of 60 to 90° C. and time of 48 to 120 h.

[0074] The contact reaction of the present invention is preferably carried out under stirring. There is no particular requirement for the stirring speed, and the reaction can be carried out using parameters known in the art.

[0075] As mentioned above, the third aspect of the present invention provides a compound having surfactant function prepared by the method described in the second aspect.

[0076] As mentioned above, the fourth aspect of the present invention provides the use of the compound having surfactant function described in the first aspect or the third aspect as a water-soluble nonionic gemini surfactant.

[0077] As mentioned above, the fifth aspect of the present invention provides a surfactant, which contains an active ingredient in an effective amount for surface active function, and the active ingredient is the compound with surfactant function as described in the first aspect.

[0078] Preferably, the content of the active ingredient is 0.1-99.9% by weight. Exemplarily, the content of the active ingredient is 0.3%, 0.5%, 1%, 3%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, etc.

[0079] More preferably, the content of the active ingredient is 0.1-10% by weight.

[0080] As mentioned above, the sixth aspect of the present invention provides the use of the compound having surfactant function described in the first aspect or the third aspect, or the surfactant described in the fourth aspect in medicine and daily chemicals.

[0081] Compared with the prior art, the technical solution of the present invention has the following advantages:

[0082] (1) The compound with surfactant function provided by the present invention contains a cyclodextrin polysaccharide head group, and its alkyl chain contains hydroxyl groups, which makes it water-soluble and pH-responsive, and aggregates of different morphologies can be constructed by adjusting the pH value.

[0083] (2) The critical aggregation concentration of the compound provided by the present invention is as low as 0.005 mM, which is 2 orders of magnitude lower than that of traditional single-chain non-ionic surfactants. In addition, the compound exhibits efficient solubilization ability, and the solubilization amount can reach 10 times that of the same type of single-chain surfactants.

[0084] (3) The preparation method provided by the present invention uses amino-functionalized cyclodextrin as raw material and can prepare the product through a one-step reaction, which has the advantages of being simple and efficient.

[0085] (4) The compounds with surfactant function provided by the present invention are easily biodegradable, do not cause secondary pollution, are green and efficient, and have good application prospects in the fields of medicine and daily chemicals.

[0086] The technical solutions of the present invention are described in detail below through specific examples. Unless otherwise specified, all raw materials used are commercially available and of analytical grade. The experimental methods and detection methods involved in the following examples, unless otherwise specified, are conventional experimental methods and detection methods in the prior art.

[0087] The main raw materials used in the examples are shown in Table 1:

[0088] Table 1

[0089]

[0090]

[0091] Example 1

[0092] In formula (A), when m=6, R1 is When R2 is a hydroxyl group and R is a n-dodecyl group, the structure shown in formula (A) is compound Z1;

[0093]

[0094] Preparation of compound Z1 with surfactant function based on amino β-cyclodextrin:

[0095] Weigh 1.134 g of mono-(6-amino-6-deoxy)-β-cyclodextrin and 0.85 g of 1,2-epoxytetradecane into a reaction flask, then add 20 mL of anhydrous ethanol and stir thoroughly. Stir the reaction at 75°C for 72 hours, then stop the reaction and remove the solvent by rotary evaporation. The residue is recrystallized from an ethanol / acetone mixture to obtain Compound Z1 with a yield of 97%.

[0096] Compound Z1 was characterized by MALDI-TOF-MS. Figure 1 As shown, the product spectrum has the highest peak at 1558.580, which is the molecular ion peak of compound Z1, proving that the product was successfully prepared.

[0097] Example 2

[0098] In formula (A), when m=6, R1 is hydroxyl, R2 is When R is n-dodecyl, the structure shown in formula (A) is compound Z2;

[0099] Preparation of compound Z2 with surfactant function based on amino β-cyclodextrin:

[0100] Weigh 1.134 g of 3A-amino-3A-deoxy-(2AS,3AS)-β-cyclodextrin hydrate and 0.85 g of 1,2-epoxytetradecane into a reaction flask. Add 20 mL of anhydrous ethanol and stir thoroughly. Stir the reaction at 75°C for 72 hours, then stop the reaction and remove the solvent by rotary evaporation. The residue is recrystallized from an ethanol / acetone mixture to obtain Compound Z2 in a 98% yield.

[0101] Compound Z2 was characterized by MALDI-TOF-MS. Figure 2 As shown, the product spectrum has the highest peak at 1558.8942, which is the molecular ion peak of compound Z2, proving that the product was successfully prepared.

[0102] Example 3

[0103] In formula (A), when m=5, R1 is hydroxyl, R2 is When R is n-dodecyl, the structure shown in formula (A) is compound Z3;

[0104] Preparation of compound Z3 with surfactant function based on amino α-cyclodextrin:

[0105] Weigh 0.972 g of 3A-amino-3A-deoxy-(2AS,3AS)-α-cyclodextrin hydrate and 0.85 g of 1,2-epoxytetradecane into a reaction flask. Add 20 mL of anhydrous ethanol and stir thoroughly. Stir the reaction at 75°C for 72 hours, then stop the reaction and remove the solvent by rotary evaporation. The residue is recrystallized from an ethanol / acetone mixture to obtain Compound Z3 in a 95% yield.

[0106] Compound Z3 was characterized by MALDI-TOF-MS. Figure 3 As shown, the product spectrum has the highest peak value of 1396.76721, which is the molecular ion peak of compound Z3, proving that the product was successfully prepared.

[0107] Test Example 1: pH responsiveness test

[0108] 100 mg of the prepared surfactant compound sample was weighed into a glass bottle, 100 g of water was added, and the mixture was stirred thoroughly to completely dissolve it, resulting in a 0.1 wt% aqueous solution of the surfactant compound. Hydrochloric acid or sodium hydroxide solution was then added to the solution to adjust the pH to 3.0, 7.0, and 12.0, respectively. The turbidity was measured using a Hach 2100P turbidimeter. The results are shown in Table 2.

[0109] Table 2: Turbidity of compounds with surfactant functionality at different pH conditions

[0110]

[0111] Test Example 2: Surface activity test

[0112] The surface tension of three new surfactant compounds at different concentrations was measured using a K100 surface tension meter from KRUSS, Germany, using the hanging plate method. The test temperature was 25°C and the pH value of the samples was 7.0.

[0113] As the concentration of the compound increases, the surface tension value decreases continuously. After a certain critical concentration, the surface tension value remains basically constant. This critical concentration is defined as the critical aggregation concentration (CAC), and the surface tension value that remains constant is defined as the surface tension γ of the compound. CAC As a comparison, the CAC and γ CAC The test results are shown in Table 3.

[0114] Table 3: Surface tension of various surfactant-functional compounds

[0115]

[0116]

[0117] Test Example 3: Solubilization Ability Test

[0118] Solubilization capacity determination: Naphthalene is used as a water-insoluble organic matter simulation molecule to evaluate the solubilization capacity of compounds with surfactant function. 50 mg of naphthalene is added to 10 mL of a 2000 mg / L surfactant compound and stirred at 500 rpm for 24 hours. Undissolved naphthalene is removed by centrifugation. In order to further remove a small amount of naphthalene solid residue, the upper aqueous solution after centrifugation is filtered with a membrane with a pore size of 0.45 μm. The content of dissolved naphthalene in the solution is calculated using the Lambert-Beer law based on the peak value at 276 nm of the ultraviolet spectrum. The calculation formula is:

[0119] C=A / Kb,

[0120] Wherein, C is the molar concentration of naphthalene in the solution after passing through the membrane;

[0121] A is the UV absorption peak of the solution at 276 nm after passing through the membrane;

[0122] K is the molar absorption coefficient of naphthalene, and its value is 4920M -1 cm -1 ;

[0123] b is the thickness of the absorption layer, which is 2 cm.

[0124] The solubilization ability evaluation results of several compounds with surfactant function are shown in Table 4.

[0125] Table 4: Solubilization of naphthalene by different surfactant-functional compounds

[0126] Compounds with surfactant function Solubilizing naphthalene concentration / mM Compound Z1 1.12 Compound Z2 0.95 Compound Z3 0.71 AEO-9 0.11

[0127] Test Example 4: Biodegradability Test

[0128] The biodegradability of surfactants is evaluated by the ratio of their biological oxygen demand (BOD) to chemical oxygen demand (COD) (B / C ratio). The higher the B / C ratio of a surfactant, the better its biodegradability. A B / C ratio of 0.3 is usually used as a benchmark parameter; if a compound has a B / C ratio of 0.3 or greater, it is considered readily biodegradable. The BOD and COD ratios were measured according to the methods described in national standards HJ 505-2009 and HJ 828-2017, respectively. The results of BOD, COD, and B / C ratio measurements for several surfactants are shown in Table 5.

[0129] Table 5: BOD, COD and B / C ratio of different compounds with surfactant function

[0130] Compounds with surfactant function BOD COD B / C ratio Compound Z1 91.66 241.2 0.38 Compound Z2 84.28 240.8 0.35 Compound Z3 77.50 242.2 0.32 AEO-9 35.77 630.7 0.056

[0131] The results of Examples 1-3 show that, through the preparation method provided by the present invention, the product can be efficiently prepared in a one-step reaction using amino-functionalized cyclodextrin as a raw material, and the reaction yield is over 95%.

[0132] The results of Test Examples 1-3 show that the surfactant-functional compound prepared by the present invention has the strongest aggregation ability near pH 7.0, with a critical aggregation concentration as low as 0.005mM, which is 2 orders of magnitude lower than that of traditional single-chain nonionic surfactants, and the aggregation ability is significantly improved. Accordingly, the solubilizing ability of the surfactant-functional compound provided by the present invention for the water-insoluble organic substance naphthalene is more than 6.45 times that of the industrial single-chain nonionic surfactant (AEO-9).

[0133] The results of Test Example 4 also demonstrate that, due to the presence of the cyclodextrin structure, the surfactant-functional compounds provided by the present invention have a B / C ratio greater than 0.3, demonstrating the advantage of readily biodegradable properties compared to traditional single-chain nonionic surfactants. Therefore, the surfactant-functional compounds provided by the present invention have promising application prospects in the fields of medicine and daily chemicals.

[0134] The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, various simple variations of the technical solution of the present invention may be made, including combining the various technical features in any other appropriate manner. These simple variations and combinations should also be regarded as disclosed in the present invention and fall within the scope of protection of the present invention.

Claims

1. A compound having surfactant function, characterized in that The compound has the structure shown in formula (A): Formula (A), Wherein, in formula (A), m is any integer selected from 4 to 12; One of R1 and R2 is a hydroxyl group, and the other is ; and each R is independently selected from C 6-18 Alkyl, C 6-18 of alkenyl.

2. The compound according to claim 1, wherein In formula (A), m is any integer selected from 5 to 7; One of R1 and R2 is a hydroxyl group, and the other is ; and each R is independently selected from C 8-18 Alkyl, C 6-12 of alkenyl.

3. The compound according to claim 2, wherein In formula (A), m is any integer selected from 5 to 7; One of R1 and R2 is a hydroxyl group, and the other is ; and each R is independently selected from n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, and 7-octenyl.

4. The compound according to any one of claims 1 to 3, wherein Formula (A) is a structure represented by formula (I) or formula (II), Formula (I), Formula (II).

5. A method for preparing a compound having surfactant function, characterized in that: The compound has a structure shown in formula (A), and the method comprises: In the presence of a solvent, the amino-functionalized cyclodextrin represented by formula (B) is contacted with the 1,2-epoxyalkane represented by formula (C). Formula (A), Formula (B), Formula (C), Wherein, in formula (B), one of R3 and R4 is -OH and the other is -NH2; In formula (A), formula (B) and formula (C), m, R, R1 and R2 have the same definitions as in any one of claims 1 to 4.

6. The method according to claim 5, wherein: The molar ratio of the amino-functionalized cyclodextrin to the 1,2-epoxyalkylene is 1:(1-20).

7. The method according to claim 6, wherein: The molar ratio of the amino-functionalized cyclodextrin to the 1,2-epoxyalkylene is 1:(2.05-5).

8. The method according to claim 5 or 6, wherein: The solvent is selected from at least one of methanol, ethanol, isopropanol, n-butanol, water, tetrahydrofuran, 1,4-dioxane, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and ethylene glycol.

9. The method according to any one of claims 5 to 7, wherein: The contact reaction conditions at least meet the following requirements: temperature of 30-100° C. and time of 24-168 h.

10. The method according to claim 9, wherein: The contact reaction conditions at least meet the following requirements: temperature of 60-90° C. and time of 48-120 h.

11. A compound having surfactant function prepared by the method according to any one of claims 5 to 10.

12. Use of the compound having surfactant function according to any one of claims 1 to 4 and 11 as a water-soluble nonionic gemini surfactant.

13. A surfactant, characterized in that The surfactant contains an active ingredient in an effective amount for surface active function, and the active ingredient is the compound with surfactant function according to any one of claims 1 to 4.

14. The surfactant according to claim 13, wherein The content of the active ingredient is 0.1-99.9% by weight.

15. The surfactant according to claim 14, wherein The content of the active ingredient is 0.1-10% by weight.

16. Use of the compound having surfactant function according to any one of claims 1 to 4 and 11, and the surfactant according to any one of claims 13 to 15 in daily chemicals.

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