A novel alkyl glycerolamine gemini surfactant and its preparation method and application

Abstract

The present invention discloses a novel alkylglycerolamine gemini surfactant, its preparation method, and application. The novel alkylglycerolamine gemini surfactant has a simplified structural formula of #imgabs0#. The novel alkylglycerolamine gemini surfactant of the present invention has excellent emulsifying properties and antibacterial activity. The simple two-step synthesis method has the advantages of a simple process flow, high yield, and pure product. The prepared product can be used as a novel alkylglycerolamine gemini surfactant with antibacterial activity.

Description

Technical Field

[0001] The present invention relates to the field of industrial auxiliary materials, specifically to the technical field of novel alkyl glycerol amine gemini surfactants, and in particular to a novel alkyl glycerol amine gemini surfactant and a preparation method and application thereof. Background Art

[0002] Surfactants possess fixed hydrophilic and lipophilic groups that can be arranged in fixed phases within a solution, significantly altering the interfacial state of the solution system. They play an indispensable role in industrial production and are often referred to as "industrial MSG." Nonionic surfactants, among them, do not generate ions in aqueous solutions. Their solubility is determined by their functional groups' strong affinity for water. Compared to other surfactants, they possess a higher emulsifying capacity and a certain degree of hard water resistance. They are an essential component in detergent and emulsifier formulations, and as a result, are attracting increasing attention.

[0003] However, traditional nonionic surfactants are composed of a polar, hydrophilic head group and a nonpolar, lipophilic, hydrophobic carbon chain. With the development of the times, the properties of traditional surfactants have become limited. In some applications, such as sterilization and oil extraction, they are no longer able to meet production and industrial needs. Therefore, the development of novel alkylglycerolamine gemini surfactants with novel structures has attracted increasing attention.

[0004] New alkylglycerolamine gemini surfactants, which combine two or more monomeric surfactants through a chemical bond using a linking group, are becoming a hot topic among researchers. These surfactants possess increased surface activity, lower cmc and Krafft temperatures, enhanced solubilization, and improved wettability, detergency, and emulsification, resulting in significant potential for applications in cleaning, sterilization, emulsification, dispersion, cosmetics, antimicrobial treatment, and oil recovery.

[0005] Given the exceptional properties of novel alkylglycerolamine gemini surfactants, the design and development of structurally diverse novel alkylglycerolamine gemini surfactants is a current research priority, as they can help discover novel structural types with functional or application specificity. Currently, the synthesis of novel alkylglycerolamine gemini surfactants is primarily cationic and amphoteric, but these surfactants exhibit poor performance and complex synthesis processes. Summary of the Invention

[0006] The main purpose of the present invention is to propose a novel alkyl glycerolamine gemini surfactant and its preparation method and application, aiming to design and synthesize a novel alkyl glycerolamine gemini surfactant with excellent performance, simple synthesis process and novel structure.

[0007] To achieve the above objectives, the present invention provides a novel alkyl glycerolamine gemini surfactant, which has the following structure:

[0008]

[0009] Wherein, R is a hydrocarbon group of 8 to 12 carbon atoms;

[0010] X is a positive integer from 1 to 2.

[0011] Optionally, X is 1 or 2.

[0012] Alternatively, R is an alkyl group of 8 or 12 carbon atoms.

[0013] The present invention also provides a method for preparing a gemini surfactant, comprising the following steps:

[0014] S1. mixing glycidol with an ethanol solution of alkylamine to react and generate monoalkylglycerolamine;

[0015] S2. In the presence of a base, a mono-chain alkyl glycerolamine is reacted with a dibromoalkane to generate a new alkyl glycerolamine gemini surfactant.

[0016] Optionally, in step S1, the molar ratio of the alkylamine to glycidol is 1:(1-2); and / or,

[0017] In step S2, the molar ratio of the monoalkyl glycerolamine to the dibromoalkane is (2-3):1.

[0018] Optionally, in step S2, the base comprises any one of triethylamine, sodium carbonate and potassium carbonate; and / or,

[0019] The dibromoalkane includes any one of 1,3-dibromopropane and 1,4-dibromobutane.

[0020] Optionally, in step S1, the reaction time is 2 to 10 hours; and / or,

[0021] The reaction temperature is 20-30°C.

[0022] Optionally, in step S2, the reaction time is 5 to 20 hours; and / or,

[0023] The reaction temperature is 50-80°C.

[0024] The present invention also provides an industrial auxiliary agent, which includes the novel alkyl glycerolamine gemini surfactant. The novel alkyl glycerolamine gemini surfactant has the following structure:

[0025]

[0026] Wherein, R is a hydrocarbon group of 8 to 12 carbon atoms;

[0027] X is a positive integer from 1 to 2.

[0028] Optionally, the industrial additives include antibacterial agents and emulsifiers.

[0029] In the technical solution provided by the present invention, the novel alkylglycerolamine gemini surfactant has an alkylglycerolamine gemini structure with excellent performance, simple synthesis process, and novel structure. It does not generate ions in aqueous solution, has functional groups with strong affinity for water, and has good water solubility and emulsification ability as well as excellent antibacterial activity. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the following briefly introduces the drawings required for use in the embodiments or the description of the prior art. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on the structures shown in these drawings without paying any creative work.

[0031] Figure 1 Product diagram of the C8-3-C8, C12-3-C12, C8-4-C8, and C12-4-C12 novel alkyl glycerolamine gemini surfactants synthesized in accordance with the present invention;

[0032] Figure 2 Infrared spectra of the C8-3-C8, C12-3-C12, C8-4-C8, and C12-4-C12 novel alkyl glycerolamine gemini surfactants synthesized in accordance with the present invention;

[0033] Figure 3 This is a high-resolution mass spectrum of the novel alkyl glycerolamine gemini surfactant (C8-3-C8) of di-n-octylglycerolamine synthesized in Example 1 of the present invention;

[0034] Figure 4 This is a high-resolution mass spectrum of the novel alkyl glycerolamine gemini surfactant (C12-3-C12) of didodecylglycerolamine synthesized in Example 2 of the present invention;

[0035] Figure 5 This is a high-resolution mass spectrum of the novel alkyl glycerolamine gemini surfactant (C8-4-C8) of di-n-octylglycerolamine synthesized in Example 3 of the present invention;

[0036] Figure 6 This is a high-resolution mass spectrum of the novel alkyl glycerolamine gemini surfactant (C12-4-C12) of didodecylglycerolamine synthesized in Example 4 of the present invention;

[0037] Figure 7 Surface tension performance diagram of the novel alkyl glycerolamine gemini surfactant prepared in Examples 1-4 of the present invention at different concentrations;

[0038] Figure 8 This is a graph showing the emulsification performance of the new alkyl glycerolamine gemini surfactant prepared in Examples 1-4 of the present invention at a concentration of 2 mg / mL.

[0039] The purpose, features and advantages of the present invention will be further described with reference to the accompanying drawings and in conjunction with the embodiments. DETAILED DESCRIPTION

[0040] In order to make the purpose, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. Where specific conditions are not specified in the embodiments, they are carried out according to conventional conditions or the conditions recommended by the manufacturer. Where the reagents or instruments used are not specified by the manufacturer, they are all conventional products that can be purchased commercially. In addition, the meaning of "and / or" appearing in the full text includes three parallel schemes. Taking "A and / or B" as an example, it includes scheme A, or scheme B, or schemes that A and B meet at the same time. In addition, the technical solutions between the various embodiments can be combined with each other, but must be based on the ability of ordinary technicians in this field to achieve. When the combination of technical solutions is contradictory or cannot be achieved, it should be considered that the combination of such technical solutions does not exist and is not within the scope of protection required by the present invention. Based on the embodiments in the present invention, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention.

[0041] New alkylglycerolamine gemini surfactants, which combine two or more monomeric surfactants through a chemical bond using a linking group, are becoming a hot topic among researchers. These surfactants possess increased surface activity, lower cmc and Krafft temperatures, enhanced solubilization, and improved wettability, detergency, and emulsification, resulting in significant potential for applications in cleaning, sterilization, emulsification, dispersion, cosmetics, antimicrobial treatment, and oil recovery.

[0042] The excellent properties and structural diversity of new alkyl glycerolamine gemini surfactants. The design and development of new alkyl glycerolamine gemini surfactants is a current research focus, which helps to discover new structural types with functional specificity or application specificity. Currently, the synthesis of new alkyl glycerolamine gemini surfactants is mainly cationic and amphoteric, and non-ionic new alkyl glycerolamine gemini surfactants are relatively rare. In view of this, the present invention proposes a new alkyl glycerolamine gemini surfactant. The new alkyl glycerolamine gemini surfactant has excellent performance, a simple synthesis process, and a novel alkyl glycerolamine gemini structure. Specifically, the new alkyl glycerolamine gemini surfactant has the following structure:

[0043]

[0044] Wherein, R is a hydrocarbon group of 8 to 12 carbon atoms;

[0045] X is a positive integer from 1 to 2.

[0046] In the technical solution provided by the present invention, the novel alkyl glycerolamine gemini surfactant has an alkyl glycerolamine gemini structure, and has good water solubility and emulsification ability as well as excellent antibacterial activity.

[0047] Furthermore, X is 1 or 2. The obtained novel alkyl glycerolamine gemini surfactant has better foaming performance.

[0048] Furthermore, R is an alkyl group with 8 or 12 carbon atoms. It should be noted that the R groups can be the same alkyl group or different alkyl groups, preferably the same alkyl group, and the obtained new alkyl glycerolamine gemini surfactant has better emulsification performance.

[0049] In the technical solution provided by the present invention, the novel alkylglycerolamine gemini surfactant has an alkylglycerolamine gemini structure with excellent performance, simple synthesis process, and novel structure. It does not generate ions in aqueous solution, has functional groups with strong affinity for water, and has good water solubility and emulsification ability as well as excellent antibacterial activity.

[0050] The present invention also provides a method for preparing a novel alkyl glycerolamine gemini surfactant, comprising the following steps:

[0051] S1, mixing drops of glycidol with an ethanol solution of alkylamine to react and form monoalkylglycerolamine;

[0052] S2. In the presence of a base, a mono-chain alkyl glycerolamine is reacted with a dibromoalkane to generate a new alkyl glycerolamine gemini surfactant.

[0053] The novel alkyl glycerolamine gemini surfactant prepared by the present invention has an alkyl glycerolamine gemini structure and can be efficiently synthesized through a simple two-step method. The process flow is simple, the yield is high, and the product is pure. The novel alkyl glycerolamine gemini surfactant has excellent emulsification ability and antibacterial activity and has a wide range of applications.

[0054] It should be noted that alkylamine and glycidol react at room temperature for a certain period of time to produce monoalkylglycerolamine. Alkylamine refers to a linear or branched, saturated or unsaturated hydrocarbon amine having 8 to 12 carbon atoms. Preferably, glycidol is added dropwise to an ethanol solution of the alkylamine to react to produce monoalkylglycerolamine. The resulting monoalkylglycerolamine has a higher purity.

[0055] Furthermore, in step S1, the reaction time is 2 to 10 hours and the reaction temperature is 20 to 30° C. Under these reaction conditions, the yield of monoalkyl glycerolamine is higher and the purity is better; the reaction time is preferably 5 hours, and the yield of monoalkyl glycerolamine is the highest and the purity is the best.

[0056] Furthermore, in the presence of a base, a mono-chain alkyl glycerolamine and a dibromoalkane are stirred and reacted at a certain temperature for a certain time to synthesize an alkyl glycerolamine novel alkyl glycerolamine gemini surfactant. In step S2, the reaction temperature is 50-100° C. and the reaction time is 5-20 hours. Under these reaction conditions, the obtained novel alkyl glycerolamine gemini surfactant has higher purity and better reaction efficiency. Preferably, the reaction temperature is 80° C., which gives the obtained novel alkyl glycerolamine gemini surfactant the highest purity and the best reaction efficiency.

[0057] Furthermore, in step S1, the molar ratio of the alkylamine to glycidol is 1:(1-2). At this ratio, the obtained product monoalkyl glycerolamine has a higher purity. Preferably, the ratio is 1:1, which gives the product monoalkyl glycerolamine with the best purity.

[0058] Furthermore, in step S2, the molar ratio of the monoalkyl glycerolamine to the dibromoalkane is (2-3):1; at this ratio, the obtained product, the novel alkyl glycerolamine gemini surfactant, has a higher purity. Preferably, the ratio is 2:1, which results in the obtained product, the novel alkyl glycerolamine gemini surfactant, having the highest purity.

[0059] Furthermore, in step S2, the base comprises any one of triethylamine, sodium carbonate and potassium carbonate. Under such alkaline conditions, the reaction rate is better. Triethylamine is preferred, as it has the best reaction rate under such alkaline conditions.

[0060] Furthermore, in step S2, the dibromoalkane includes 1,3-dibromopropane and 1,4-dibromobutane; the new alkyl glycerolamine gemini surfactant prepared from the dibromoalkane under these conditions has better performance.

[0061] The present invention also provides an industrial additive comprising the novel alkyl glycerolamine gemini surfactant. The industrial additive incorporates all the technical solutions of the novel alkyl glycerolamine gemini surfactant and, therefore, possesses all the beneficial effects of the aforementioned technical solutions, which will not be further detailed here.

[0062] Furthermore, the industrial additives include antibacterial agents and emulsifiers.

[0063] The technical solutions of the present invention are further described in detail below in conjunction with specific embodiments and drawings. It should be understood that the following embodiments are only used to explain the present invention and are not used to limit the present invention.

[0064] Example 1 Preparation of a new type of alkyl glycerolamine gemini surfactant (C8-3-C8)

[0065] Dissolve 77.5 g of n-octylamine in 50 mL of ethanol and stir at 20°C until dissolved. Slowly add 40.7 g of glycidol dropwise and stir at room temperature for 5 hours. After the reaction is complete, remove the ethanol by rotary evaporation under reduced pressure to obtain an oily single-chain n-octylglycerolamine.

[0066] 40.6 g of single-chain n-octylglycerolamine and 20.2 g of 1,3-dibromopropane were mixed in a round-bottom flask, 22.3 g of triethylamine was added, and the mixture was reacted in a 50°C oil bath for 12 hours. Then, 100 mL of ethyl acetate was added and stirred for 30 minutes. The insoluble triethylamine hydrobromide was removed by suction filtration, and the filtrate was distilled under reduced pressure to remove ethyl acetate to obtain an oily di-n-octylglycerolamine, a new alkyl glycerolamine gemini surfactant, wherein R is a hydrocarbon group with 8 carbon atoms and X is 1 (C8-3-C8).

[0067] The new alkyl glycerolamine gemini surfactant prepared in Example 1 is as follows Figure 1 As shown, the infrared spectrum is as follows Figure 2 As shown, the high-resolution mass spectrum is as follows Figure 3 shown. Figure 2 It can be analyzed that 3353cm -1 Belongs to the associated OH peak, the peak shape is broad and blunt; 2918cm -1 is the CH antisymmetric stretching vibration; 2849cm -1 1640cm is the CH symmetric stretching vibration; -1 Left and right are CN stretching vibrations; 1456cm -1 is CH bending vibration; 1375cm -1 1107cm is the symmetrical bending vibration of the CH of the methyl group; -1 Belongs to the CO stretching vibration of secondary alcohol; 1048cm -1 is the CO stretching vibration of the primary alcohol. Figure 3 The molecular ion peak of the high-resolution mass spectrum of C8-3-C8 is 447.41553[M+1] + , the theoretical value is 447.41563[M+1] + , indicating that the molecular structure of the compound is consistent with C8-3-C8.

[0068] Example 2 Preparation of a novel alkyl glycerolamine gemini surfactant (C12-3-C12)

[0069] Dissolve 80.9 g of dodecylamine in 60 mL of ethanol and stir at 25°C until dissolved. Slowly add 20.4 g of glycidol dropwise and stir at room temperature for 10 hours. After the reaction is complete, remove the ethanol by rotary evaporation under reduced pressure to obtain single-chain dodecylglycerolamine as a white solid.

[0070] 51.9 g of single-chain dodecylglycerolamine and 20.2 g of 1,3-dibromopropane were mixed in a round-bottom flask, 22.3 g of triethylamine was added, and the mixture was reacted in an 80°C oil bath for 20 hours. Then, 100 mL of ethyl acetate was added and stirred for 30 minutes. The insoluble triethylamine hydrobromide was removed by suction filtration, and the filtrate was distilled under reduced pressure to remove ethyl acetate to obtain an oily didodecanolamine, a new alkyl glycerolamine gemini surfactant, wherein R is a hydrocarbon group with 12 carbon atoms and X is 1 (C12-3-C12).

[0071] The novel alkyl glycerolamine gemini surfactant prepared in Example 2 is as follows Figure 1 As shown, the infrared spectrum is as follows Figure 2 As shown, the high-resolution mass spectrum is as follows Figure 4 shown. Figure 2 It can be analyzed that 3353cm -1 Belongs to the associated OH peak, the peak shape is broad and blunt; 2918cm -1 is the CH antisymmetric stretching vibration; 2849cm -1 1640cm is the CH symmetric stretching vibration; -1 Left and right are CN stretching vibrations; 1456cm -1 is CH bending vibration; 1375cm -1 1107cm is the CH symmetric bending vibration of the methyl group; -1 Belongs to the CO stretching vibration of secondary alcohol; 1048cm -1 is the CO stretching vibration of the primary alcohol. Figure 4 The molecular ion peak of the high-resolution mass spectrum of C12-3-C12 is 559.54077[M+1] + , the theoretical value is 559.54084[M+1] + , indicating that the molecular structure of the compound is consistent with C12-3-C12.

[0072] Example 3 Preparation of a new type of alkyl glycerolamine gemini surfactant (C8-4-C8)

[0073] Dissolve 77.5 g of n-octylamine in 50 mL of ethanol and stir at 28°C until dissolved. Slowly add 40.7 g of glycidol dropwise and stir at room temperature for 2 hours. After the reaction is complete, remove the ethanol by rotary evaporation under reduced pressure to obtain an oily single-chain n-octylglycerolamine.

[0074] 40.6 g of single-chain n-octylglycerolamine and 21.6 g of 1,4-dibromobutane were mixed in a round-bottom flask, 22.3 g of triethylamine was added, and the mixture was reacted in an oil bath at 60°C for 8 hours. Then, 100 mL of ethyl acetate was added and stirred for 30 minutes. The insoluble triethylamine hydrobromide was removed by suction filtration, and the filtrate was distilled under reduced pressure to remove ethyl acetate to obtain an oily di-n-octylglycerolamine, a new alkyl glycerolamine gemini surfactant, wherein R is a hydrocarbon group with 8 carbon atoms and X is 2 (C8-4-C8).

[0075] The new alkyl glycerolamine gemini surfactant prepared in Example 3 is as follows Figure 1 As shown, the infrared spectrum is as follows Figure 2 As shown, the high-resolution mass spectrum is as follows Figure 5 shown. Figure 2 It can be analyzed that 3353cm -1 Belongs to the associated OH peak, the peak shape is broad and blunt; 2918cm -1 is the CH antisymmetric stretching vibration; 2849cm -1 1640cm is the CH symmetric stretching vibration; -1 Left and right are CN stretching vibrations; 1456cm -1 is CH bending vibration; 1375cm -1 1107cm is the CH symmetric bending vibration of the methyl group; -1 Belongs to the CO stretching vibration of secondary alcohol; 1048cm -1 is the CO stretching vibration of the primary alcohol. Figure 5 The molecular ion peak of the high-resolution mass spectrum of C8-4-C8 is 461.43076[M+1] + , the theoretical value is 461.43128[M+1] + , indicating that the molecular structure of the compound is consistent with C8-4-C8.

[0076] Example 4 Preparation of a novel alkyl glycerolamine gemini surfactant (C12-4-C12)

[0077] 80.9 g of dodecylamine was dissolved in 60 mL of ethanol and stirred at 30°C until dissolved. 20.4 g of glycidol was slowly added dropwise and stirred at room temperature for 8 hours. After the reaction was complete, the ethanol was removed by rotary evaporation under reduced pressure to obtain single-chain dodecylglycerolamine as a white solid.

[0078] 51.9 g of single-chain dodecylglycerolamine and 21.6 g of 1,4-dibromobutane were mixed in a round-bottom flask, 22.3 g of triethylamine was added, and the mixture was reacted in an oil bath at 70°C for 5 hours. Then, 100 mL of ethyl acetate was added and stirred for 30 minutes. The insoluble triethylamine hydrobromide was removed by suction filtration, and the filtrate was distilled under reduced pressure to remove ethyl acetate to obtain an oily didodecanolamine, a new alkyl glycerolamine gemini surfactant, wherein R is a hydrocarbon group with 12 carbon atoms and X is 2(C12-4-C12).

[0079] The novel alkyl glycerolamine gemini surfactant prepared in Example 4 is as follows Figure 1 As shown, the infrared spectrum is as follows Figure 2 As shown, the high-resolution mass spectrum is as follows Figure 6 shown. Figure 2 It can be analyzed that 3353cm -1 Belongs to the associated OH peak, the peak shape is broad and blunt; 2918cm -1 is the CH antisymmetric stretching vibration; 2849cm -1 1640cm is the CH symmetric stretching vibration; -1 Left and right are CN stretching vibrations; 1456cm -1 is CH bending vibration; 1375cm -1 1107cm is the CH symmetric bending vibration of the methyl group; -1 Belongs to the CO stretching vibration of secondary alcohol; 1048cm -1 is the CO stretching vibration of the primary alcohol. Figure 6 The molecular ion peak of the high-resolution mass spectrum of C12-4-C12 is 573.55566[M+1] + , the theoretical value is 573.55649[M+1] + , indicating that the molecular structure of the compound is consistent with C12-4-C12.

[0080] Comparative Example 1

[0081] Commercially available nonionic surfactant

[0082] Surfactant performance test

[0083] Determination of Surface Tension and Critical Micelle Concentration of New Alkylglycerolamine Gemini Surfactants

[0084] Aqueous solutions of alkylglycerolamine new alkylglycerolamine gemini surfactants with different concentrations were prepared and stirred at room temperature for 2 h. The surface tension was measured using an interfacial rheometer with a drop weight method at a test temperature of (25.0(0.1(℃). The results are shown in Table 1. Figure 7 shown.

[0085] Depend on Figure 7 It can be seen that the surface tension values of the new alkyl glycerolamine gemini surfactants Example 1 (C8-3-C8), Example 2 (C12-3-C12), Example 3 (C8-4-C8), and Example 4 (C12-4-C12) decrease with increasing concentration and then tend to stabilize. Their critical micelle concentrations are 5.25 mmol / L, 1.58 mmol / L, 1.41 mmol / L, and 4.57 mmol / L, respectively, and the surface tensions at the critical micelle concentrations are 26.83 mN / m, 26.38 mN / m, 25.45 mN / m, and 25.81 mN / m, respectively.

[0086] Determination of the emulsifying properties of new alkyl glycerolamine gemini surfactants

[0087] A 2 mg / mL aqueous solution of the surfactant prepared in Examples 1-6 was prepared at a constant temperature of 25°C. 20 mL of the above solution was poured into a 100 mL stoppered graduated cylinder. 20 mL of the oil phase (medium-chain triglycerides, cyclohexane, benzene, and rapeseed oil) was added to the cylinder. The stoppered graduated cylinder was shaken up and down vigorously for 60 seconds to completely mix the aqueous solution of the novel alkylglycerolamine gemini surfactant with the oil phase. The mixture was allowed to stand for 1 hour, and the volumes of the oil phase, aqueous phase, and emulsion phase were recorded. The results are shown in FIG. Figure 8 shown.

[0088] according to Figure 8 The four new alkylglycerolamine gemini surfactants showed the strongest emulsification ability for medium-chain triglycerides, while only C12-3-C12 (Example 2) and C12-4-C12 (Example 4) showed good emulsification of rapeseed oil. With the exception of C8-4-C8 (Example 3), all three new alkylglycerolamine gemini surfactants showed good emulsification of benzene. However, all four new alkylglycerolamine gemini surfactants showed poor emulsification of n-hexane. These experimental results demonstrate that the four new alkylglycerolamine gemini surfactants synthesized exhibit a certain degree of selectivity for the emulsified oil phase and can be selected based on application needs.

[0089] Determination of Foaming Properties of New Alkyl Glycerolamine Gemini Surfactants

[0090] Foamability was measured using the graduated cylinder method. 20 mL of the 2 mg / mL aqueous surfactant solutions prepared in Examples 1-4 and Comparative Example 1 were poured into a 100 mL stoppered graduated cylinder. After vigorous shaking for one minute, the initial foam volume (H0) was immediately recorded. After 3 and 5 minutes, the foam volumes (H3 and H5) were recorded, respectively. The results are shown in Table 1.

[0091] Table 1 Foaming test results of surfactants

[0092] <![CDATA[H0]]> <![CDATA[H3]]> <![CDATA[H5]]> Example 1 20.5 18 17.5 Example 2 38 36.5 36 Example 3 3 3 3 Example 4 54.5 51 51 Comparative Example 1 26 24 24

[0093] According to the data in Table 1, as the length of the hydrophobic alkyl chain increases (from C8 to C12), the foaming property increases; when the carbon chain length of the linker increases from 3 carbons to 4 carbons, the foaming property (H0) of C12-4-C12 increases by 43.4%, but the foaming property of C8-4-C8 decreases significantly. The experimental results show that the foaming property of the new alkyl glycerolamine gemini surfactant of this structural type is determined by both the alkyl chain length and the linker length. Figure 8 It can also be found that C8-4-C8 can be used as a new type of alkyl glycerolamine gemini surfactant with low foaming properties.

[0094] Determination of antibacterial activity of new alkylglycerolamine gemini surfactants

[0095] Escherichia coli and Staphylococcus aureus were used as target bacteria. The antibacterial activity of the novel alkylglycerolamine gemini surfactant was determined by the optical density (OD) method. The OD value at 596 nm was measured using an ultraviolet spectrophotometer to calculate the antibacterial rate.

[0096] Table 2 Antibacterial rate of new alkyl glycerolamine gemini surfactants

[0097]

[0098] - indicates that the inhibition rate was not determined.

[0099] Table 2 shows that all four gemini surfactants exhibited excellent antibacterial activity against Escherichia coli and Staphylococcus aureus. C8-3-C8, C12-3-C12, and C12-4-C12 exhibited excellent antibacterial properties against E. coli and S. aureus at relatively low concentrations, while C8-4-C8 required a higher concentration to effectively inhibit the growth of these bacteria. These experimental results demonstrate that all four novel alkylglycerolamine gemini surfactants exhibited excellent antibacterial activity.

[0100] In summary, the novel alkylglycerolamine gemini surfactant provided by the present invention has excellent performance, simple synthesis process, and novel structure of the alkylglycerolamine gemini structure. It does not generate ions in aqueous solution, has functional groups with strong affinity for water, and has good water solubility and emulsification ability as well as excellent antibacterial activity.

[0101] The above description is merely a preferred embodiment of the present invention and does not limit the scope of the present invention. Those skilled in the art will readily appreciate that the present invention is susceptible to various modifications and variations. Any modifications, equivalent substitutions, or improvements made within the spirit and principles of the present invention shall be included within the scope of the present invention.

Claims

1. A novel alkyl glycerolamine gemini surfactant, characterized in that: The gemini surfactant has the following structural formula: Wherein, R is an alkyl group of 8 or 12 carbon atoms; X is 1 or 2.

2. A method for preparing the novel alkyl glycerolamine gemini surfactant according to claim 1, characterized in that: The preparation method of the novel alkyl glycerolamine gemini surfactant comprises the following steps: S1. mixing glycidol with an ethanol solution of alkylamine to react and generate monoalkylglycerolamine; S2. In the presence of a base, reacting a mono-chain alkyl glycerolamine with a dibromoalkane to generate the novel alkyl glycerolamine gemini surfactant.

3. The method for preparing the novel alkyl glycerolamine gemini surfactant according to claim 2, wherein: In step S1, the molar ratio of the alkylamine to glycidol is 1:(1-2); and / or, In step S2, the molar ratio of the monoalkyl glycerolamine to the dibromoalkane is (2-3):

1.

4. The method for preparing the novel alkyl glycerolamine gemini surfactant according to claim 2, wherein: In step S2, the base is any one of triethylamine, sodium carbonate and potassium carbonate; and / or, The dibromoalkane is any one of 1,3-dibromopropane and 1,4-dibromobutane.

5. The method for preparing the novel alkyl glycerolamine gemini surfactant according to claim 2, wherein: In step S1, the reaction time is 2 to 10 hours; and / or, The reaction temperature is 20~30℃.

6. The method for preparing the novel alkyl glycerolamine gemini surfactant according to claim 2, wherein: In step S2, the reaction time is 5 to 20 hours; and / or, The reaction temperature is 50~80℃.

7. An industrial additive, characterized in that The industrial auxiliary agent comprises the novel alkyl glycerolamine gemini surfactant as claimed in claim 1.

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