A surfactant and its preparation method and application

Abstract

The application provides a surfactant, a preparation method and application thereof, and the surfactant has a structure shown in formula (I). The raw material of the surfactant is derived from phloretic acid, ferulic acid and hydrogenated ferulic acid, and the surfactant has the characteristics of green environmental protection and biological safety. The hydrophobic part in the structure contains an ester group functional group, and has the characteristics of biological degradability. In addition to the hydrophilicity, the surface activity of the surfactant can be adjusted by controlling the length of polyoxyethylene, and the hydrophobicity and the surface activity of the surfactant can be adjusted by selecting different carbon number fatty alcohols for esterification.

Description

Technical Field

[0001] This invention belongs to the field of fine chemical materials, and relates to a surfactant, its preparation method and application, and more particularly to a bio-based biodegradable surfactant, its preparation method and application. Background Technology

[0002] Surfactants are known as "industrial MSG" and have a wide range of applications in industrial production, daily chemical products, and medical and health fields.

[0003] Surfactants are substances that, when added in very small amounts, can reduce the surface tension of a solvent. Surfactants are structurally characterized by a lipophilic tail group and a hydrophilic head group. Surface-active substances that can associate molecules in aqueous solutions to form micelles or other aggregates, exhibiting high surface activity, and also possessing wetting, emulsifying, foaming, and detergency properties are called surfactants.

[0004] Alkylphenol polyoxyethylene ether surfactants (APEO) are an important type of polyoxyethylene nonionic surfactant. They are characterized by stable properties, acid and alkali resistance, and low cost. They are mainly used to produce high-performance detergents and are one of the most commonly used raw materials in printing and dyeing auxiliaries. For a long time, alkylphenol polyoxyethylene ethers have been required to be added to various printing and dyeing auxiliaries, such as detergents, scouring agents, spinning oils, softeners, wool oils, and metal cleaning agents. OP-10 (octylphenol polyoxyethylene ether 10) and NP-10 (nonylphenol polyoxyethylene ether 10) are excellent representatives of APEO surfactants. They are easily soluble in water, resistant to acids, alkalis, salts, and hard water, and have good emulsifying, leveling, wetting, dispersing, and detergency properties. They can be mixed with various surfactants and dye preforms and are widely used as leveling agents and dispersing agents in printing and dyeing processes, degreasing agents for leather and wool, emulsifiers for crude oil and fuel oil, penetrants for oil extraction acidification, emulsifiers for styrene-butadiene latex and emulsion polymerization, lubricants and emulsifiers for glass fiber textiles, and emulsifiers, detergents, penetrants, and wetting agents in cosmetics.

[0005] However, the environmental hormone issue of alkylphenol polyoxyethylene ethers (APEOs) has also attracted widespread attention. Environmental hormones are chemical substances that can enter the human body through various pathways, have estrogen-like effects, and harm the body's normal hormone secretion. NP and OP have been included in the US Environmental Protection Agency's list of 70 environmental hormone chemicals. In 2016, Annex XVII of the EU's REACH law imposed corresponding restrictions and regulations on the use, distribution, and emission of alkylphenol polyoxyethylene ethers (APEOs). The regulations typically restrict four APEOs: NPEO (nonylphenol polyoxyethylene ether), NP (nonylphenol), OPEO (octylphenol polyoxyethylene ether), and OP (octylphenol), with a limit of 100 ppm. Products exceeding these limits are prohibited from being placed on the EU market.

[0006] Many attempts have been made to find good alternatives to APEO. One important method is to use bio-based cashew nutshellol to prepare cashew nutshellol polyoxyethylene ether nonionic surfactants. Bruce et al. (Journal of Surfactants & Detergents, 2009, 12:337-344.) synthesized cashew nutshellol polyoxyethylene ether sulfate salts by reacting cashew nutshellol with methanol as a solvent and vinyl sulfate, achieving a yield of 78%. The synthetic route is as follows:

[0007]

[0008] CN 200910017035 discloses a method for preparing cashew phenol polyoxyethylene ether sulfate ammonium salt from cashew phenol polyoxyethylene ether as a raw material, and the structural formula of the product is as follows:

[0009]

[0010] CN200910017036.X and CN202110352871.X both disclose a cashew phenol polyoxyethylene ether and its preparation method; CN200910052239.2 and CN202011342639.X disclose a method for preparing cashew phenol sulfonate surfactant by sulfonating cashew phenol and then neutralizing it with alkali.

[0011] Scorzza et al. (Journal of Surfactants & Detergents, 2010, 13(1):27) prepared two types of cashew nut shell phenol carboxylate surfactants using cashew nut shell phenol as a raw material. The specific synthetic routes are as follows:

[0012]

[0013] This carboxylate surfactant has strong hydrophilicity, good surface activity, and a low critical micelle concentration.

[0014] Wang Jun et al. (Chemical and Biological Engineering, 2013, (4):33-35) prepared a novel cashew phenol cationic surfactant using cashew phenol, epichlorohydrin and trimethylamine as raw materials, with a yield of 56% and a quaternary ammonium salt content of 80%. The synthetic route is as follows:

[0015]

[0016] While cashew phenol can be used to prepare various alkylphenol surfactants, it has the following drawbacks: First, its alkyl chain is a 15-carbon unsaturated segment, much longer than the 8- and 9-carbon alkyl chains in OP-10 and NP-10 structures, affecting its surface activity efficiency. Second, the meta position of the alkyl chain on the benzene ring, unlike the para position of the alkyl chain on the benzene ring in OP-10 and NP-10, also affects its emulsifying and dispersing abilities. Therefore, there is a need to find superior APEO surfactants. Summary of the Invention

[0017] To address the shortcomings of existing technologies, the present invention aims to provide a surfactant, its preparation method, and its application, particularly a bio-based biodegradable surfactant, its preparation method, and its application.

[0018] To achieve this objective, the present invention adopts the following technical solution:

[0019] On the one hand, the present invention provides a surfactant having the structure shown in formula (I):

[0020]

[0021] Wherein, R1 is an alkyl group with 4 to 16 carbon atoms, R2 is hydrogen or methoxy, X is a carbon-carbon single bond or carbon-carbon double bond, and n is a natural number from 3 to 30.

[0022] In this invention, the surfactant is a nonionic surfactant derived from phloretic acid, and its raw materials are derived from phloretic acid, ferulic acid and hydrogenated ferulic acid. It has the characteristics of being green, environmentally friendly and biosafe, and is biodegradable.

[0023] In this invention, R1 is an alkyl group having 4 to 16 carbon atoms, for example, the number of carbon atoms can be 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 or 16. n is a natural number from 3 to 30, for example, it can be 3, 4, 5, 6, 8, 10, 12, 14, 15, 17, 19, 20, 22, 24, 25, 26, 28 or 30, etc.

[0024] Preferably, the surfactant is any one of the following compounds:

[0025]

[0026]

[0027] On the other hand, the present invention provides a method for preparing the surfactant as described above, the method comprising the following steps:

[0028] (1) Compound A reacts with compound B to give compound C, and the reaction equation is as follows:

[0029]

[0030] (2) Compound C reacts with ethylene oxide to obtain the surfactant shown in formula (I), as follows:

[0031]

[0032] The constraints R1, R2, X, and n are the same as those above.

[0033] Preferably, compound A is any one of phloroglucinic acid, ferulic acid, or hydrogenated ferulic acid.

[0034] This invention uses bio-based phloroglucinic acid, ferulic acid, and hydrogenated ferulic acid as raw materials, and prepares bio-based nonionic surfactants through esterification and oxyethylation to replace traditional alkylphenol surfactants.

[0035] Phlorenic acid, ferulic acid, and hydrogenated ferulic acid (structural formulas below) all have the structure of p-carboxyethylphenol, which has a structure and properties similar to alkylphenols. They can be modified and prepared into bio-based materials and raw materials.

[0036] In this invention, the structures of phloric acid, ferulic acid, or hydrogenated ferulic acid are as follows:

[0037]

[0038] Preferably, the molar ratio of compound A to compound B is 1:(0.85-2.0), for example, it can be 1:0.85, 1:0.9, 1:0.95, 1:1, 1:1.2, 1:1.4, 1:1.5, 1:1.7, 1:1.8, 1:1.9 or 1:2.0, etc.

[0039] Preferably, the reaction temperature in step (1) is 80-180℃, for example 80℃, 90℃, 100℃, 110℃, 120℃, 130℃, 140℃, 150℃, 160℃, 170℃ or 180℃, and the reaction time is 8-28 hours, for example 8 hours, 10 hours, 12 hours, 14 hours, 16 hours, 18 hours, 20 hours, 22 hours, 24 hours, 26 hours or 28 hours.

[0040] Preferably, the molar ratio of compound C to ethylene oxide in step (2) is 1:3-30, for example, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:11, 1:12, 1:13, 1:14, 1:15, 1:18, 1:20, 1:22, 1:24, 1:26, 1:28 or 1:30, etc.

[0041] Preferably, the reaction in step (2) is carried out in the presence of a catalyst.

[0042] Preferably, the catalyst is selected from at least one of sodium hydroxide, potassium hydroxide, boron trifluoride, or boron trifluoride diethyl ether.

[0043] Preferably, the reaction temperature in step (2) is 50-80℃, for example 50℃, 55℃, 58℃, 60℃, 65℃, 70℃, 75℃ or 80℃, and the reaction time is 3-8 hours, for example 3 hours, 4 hours, 5 hours, 6 hours, 7 hours or 8 hours.

[0044] Compared with the prior art, the present invention has the following beneficial effects:

[0045] The surfactant of this invention is derived from phlorenic acid, ferulic acid, and hydrogenated ferulic acid, and is characterized by being green, environmentally friendly, and biosafe. The hydrophobic part of its structure contains ester functional groups, which makes it biodegradable. In addition to adjusting its hydrophilicity and surface activity by controlling the length of the polyoxyethylene, the surfactant of this invention can also adjust its hydrophobicity and surface activity by selecting fatty alcohols with different carbon numbers for esterification. Attached Figure Description

[0046] Figure 1 The NMR spectrum of hexyl phloroglucinate is shown.

[0047] Figure 2 The hydrogen nuclear magnetic spectrum of bio-based surfactant #1.

[0048] Figure 3 The NMR spectrum of isooctyl ferulic acid is 1H NMR.

[0049] Figure 4 The hydrogen nuclear magnetic spectrum of bio-based surfactant #2.

[0050] Figure 5 The image shows the proton NMR spectrum of hexyl ferulic acid ester.

[0051] Figure 6 The hydrogen nuclear magnetic spectrum of bio-based surfactant #3. Detailed Implementation

[0052] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0053] Example 1

[0054] In this embodiment, bio-based surfactant 1# is prepared by the following method:

[0055] (1) Add 256 g (1.54 mol) of phloroglucinic acid, 133.6 g (1.308 mol) of n-hexanol, 3.8 g (1 wt%) of p-toluenesulfonic acid monohydrate, and 600 mL of cyclohexane to a 2000 mL four-necked flask. Collect the water generated during the reaction using a water separator, heat to 80 °C in an oil bath, and reflux for 8 h. Wash three times with 2000 mL of 5 wt% NaHCO3 aqueous solution to remove excess phloroglucinic acid and n-hexanol. Collect the organic phase, dry with 100 g of anhydrous magnesium sulfate, filter, and remove the solvent by rotary evaporation of the mother liquor to obtain the intermediate phloroglucinic acid n-hexanol ester. The proton NMR spectrum is shown in the figure. Figure 1 Its NMR data are as follows:

[0056] 1 HNMR (400MHz, DMSO) δ9.16 (s, 1H, -OH); δ7.00~6.96 (d, 2H, Ar-H); δ6.64~6.66 (d, 2H, Ar-H); δ3.99~3.96 (t, 2H, CH2CH2OCO); δ 2.74~2.70(s,2H,Ar-CH2CH2CO), δ2.55~2.50(s,2H,Ar-CH2CH2CO), δ1.51~1.24(d,8H,(CH2)4CH3); δ1.06~0.84(s,3H,CH3).

[0057] (2) 200 g (0.8 mol) of hexanol terpenoid intermediate was added to a metal reactor along with 50 g of anhydrous KOH tablets. While stirring, a mixture of ethylene oxide (253 g, 10 mol) and nitrogen was gradually introduced until the reaction system pressure reached 0.5 MPa. During the reaction, the pressure of the reaction system gradually decreased as the ethylene oxide was consumed. Nitrogen was continuously introduced to maintain the reaction pressure at 0.5 MPa until the pressure stabilized and no longer decreased, indicating that the ethylene oxide reaction was complete. Acetic acid was added to adjust the pH of the reaction system to a weak acid (pH = 6). After adding diatomaceous earth adsorbent, the mixture was filtered and dehydrated to obtain bio-based surfactant #1. The hydrogen nuclear magnetic resonance spectrum is shown in [reference needed]. Figure 2 Its NMR data are as follows:

[0058] 1HNMR (400MHz, DMSO) δ9.16(-OH); δ7.00~6.64(Ar-H); δ3.99~3.96(CH2CH2OCO); δ3.579~3.42(CH2CH2O) 10 ); δ1.51~1.24((CH2)4CH3); δ1.06~0.84(CH3).

[0059]

[0060] Example 2

[0061] In this embodiment, bio-based surfactant #2 was prepared by the following method:

[0062] (1) Add 388.2 g (2 mol) of ferulic acid, 234.36 g (1.9 mol) of isooctanol (2-ethylhexanol), 6.2 g (1 wt%) of p-toluenesulfonic acid monohydrate, and 1000 mL of cyclohexane to a 2500 mL four-necked flask. Collect the water generated during the reaction using a water separator. Heat the mixture in an oil bath at 105 °C and reflux for 28 h. Wash three times with 2000 mL of 5 wt% NaHCO3 aqueous solution to remove excess ferulic acid and isooctanol. After collecting the organic phase, dry it with 200 g of anhydrous magnesium sulfate, filter, and remove the solvent by rotary evaporation to obtain the intermediate isooctyl ferulic acid. The hydrogen NMR spectrum is shown in […]. Figure 3

[0063] 1 HNMR (400MHz, DMSO) δ9.21(s,1H,-OH); δ7.56~7.33(s,1H,Ar-H); δ7.33~7.12(s,1H,Ar-H); δ6.8~6.46(s,1H,Ar-H); δ4.06~4.04(s,2H,Ar-CH) ＝ CHCO), δ3.82(s,3H,Ar-OCH3), δ1.36~1.34(m,1H,-O-CH2CH(CH2CH3)CH2CH2CH2CH3);

[0064] δ1.32~1.29(d,2H,-O-CH2CH(CH2CH3)CH2CH2CH2CH3);

[0065] δ1.28~1.26(d,8H,-O-CH2CH(CH2CH3)CH2CH2CH2CH3);

[0066] δ0.90~0.86(d,6H,-O-CH2CH(CH2CH3)CH2CH2CH2CH3).

[0067] 306.2 g (1 mol) of isooctyl ferulic acid intermediate was added to a metal reactor along with 52 g of anhydrous KOH tablets. While stirring, a mixture of 220 g (5 mol) of ethylene oxide and nitrogen was gradually introduced until the reaction system pressure reached 0.5 MPa. During the reaction, the pressure gradually decreased as the ethylene oxide was consumed. Nitrogen was continuously introduced to maintain the reaction pressure at 0.5 MPa until it stabilized and no longer decreased, indicating that the ethylene oxide reaction was complete. Acetic acid was added to adjust the pH of the reaction system to a weakly acidic state (pH = 6). After adding diatomaceous earth adsorbent, the mixture was filtered and dehydrated to obtain bio-based surfactant #2. The hydrogen nuclear magnetic resonance (NMR) spectrum is shown below. Figure 4 . 1 HNMR (400MHz, DMSO) δ3.57-3.52 is the peak of methylene (CH2CH2O) in the polyether segment, and δ1.38-0.87 is the peak of alkyl groups in isooctanol ester.

[0068]

[0069] Example 3

[0070] In this embodiment, bio-based surfactant #3 was prepared by the following method:

[0071] (1) Add 392.4 g (2 mol) of hydrogenated ferulic acid, 408.4 g (4 mol) of n-hexanol, and 0.4 g (0.5 wt%) of tetrabutyl titanate to a 2500 mL four-necked flask. Purge the air from the reaction flask with nitrogen gas, raise the temperature to 200 °C, and evacuate to -0.05 MPa with a water pump to remove the water generated during the reaction. React for 10 hours. Raise the temperature to 230 °C, evacuate to -0.1 MPa with an oil pump, and remove excess n-hexanol from the reaction system. Maintain this for 5 hours until no more water or hexanol is removed. Cool the reaction system to room temperature. The resulting oily product is washed three times with 5 wt% NaHCO3 aqueous solution to remove excess hydrogenated ferulic acid and hexanol. Collect the organic phase, dry it with 200 g of anhydrous magnesium sulfate, filter, and the mother liquor is the product, yielding the intermediate hydrogenated ferulic acid n-hexanol. The hydrogen NMR spectrum is shown in [reference needed]. Figure 5 .

[0072] 1HNMR (400MHz, DMSO) δ9.56(s,1H,-OH); δ7.61~7.57(s,1H,Ar-H); δ7.38(s,1H,Ar-H); δ7.18~7.15(s,1H,Ar-H); δ6.85~6.51(s,2H,Ar-CH2CH2CO), δ4.18~4.15(s,3H,Ar-OCH 3), δ3.87(m,2H,Ar-CH2CH2CO); δ1.69~1.65(d,4H,-O-CH2CH2CH2CH2CH2CH3); δ1.28~ 1.26(d,6H,-O-CH2CH2CH2CH2CH2CH3); .δ0.94~0.91(q,3H,-O-CH2CH2CH2CH2CH2CH3).

[0073] (2) 280.2 g (1 mol) of hydrogenated ferulic acid n-hexyl ester intermediate was added to a metal reactor along with 40 g of anhydrous KOH tablets. While stirring, a mixture of ethylene oxide (880 g, 20 mol) and nitrogen was gradually introduced until the reaction system pressure reached 0.5 MPa. During the reaction, the pressure of the reaction system gradually decreased as the ethylene oxide was consumed. Nitrogen was continuously introduced to maintain the reaction pressure at 0.5 MPa until the pressure stabilized and no longer decreased, indicating that the ethylene oxide reaction was complete. Acetic acid was added to adjust the pH of the reaction system to a weak acid (pH = 6). After adding diatomaceous earth adsorbent, the mixture was filtered and dehydrated to obtain bio-based surfactant #3. The hydrogen nuclear magnetic resonance spectrum is shown in [reference needed]. Figure 6 . 1 ¹H NMR (400MHz, DMSO), where δ3.57-3.52 are the peaks of methylene (CH₂CH₂O) in the polyether segment.

[0074]

[0075] Example 4

[0076] In this embodiment, bio-based surfactant #4 was prepared by the following method:

[0077] (1) Add 392.4 g (2 mol) of hydrogenated ferulic acid, 296.4 g (4 mol) of n-butanol, and 0.3 g (0.5 wt‰) of tetrabutyl titanate to a 2500 mL four-necked flask. Purge the air from the reaction flask with nitrogen gas, raise the temperature to 100 °C, and evacuate to -0.05 MPa with a water pump to remove the water generated during the reaction. React for 12 hours. Raise the temperature to 110 °C, evacuate to -0.1 MPa with an oil pump, and remove excess n-butanol from the reaction system. Maintain this temperature for 5 hours until no more water or n-butanol is removed. Cool the reaction system to room temperature. The resulting oily product is washed three times with 5 wt% NaHCO3 aqueous solution to remove excess hydrogenated ferulic acid and n-butanol. Collect the organic phase, dry it with 200 g of anhydrous magnesium sulfate, filter, and the mother liquor is the product, yielding 424 g of the intermediate hydrogenated ferulic acid n-butyl ester.

[0078] (2) 252.1 g (1 mol) of hydrogenated ferulic acid n-butyl ester intermediate and 5 g of boron trifluoride diethyl ether were added to a metal reactor. After purging with nitrogen three times, the system was evacuated to -0.1 MPa. The vacuum was then closed, and the temperature was raised to 50°C. A mixture of ethylene oxide (1320 g, 30 mol) and nitrogen was slowly introduced. The reaction temperature was maintained at 50-70°C, and the pressure of the reaction system did not exceed 0.2 MPa. During the reaction, the pressure of the reaction system gradually decreased as the ethylene oxide was consumed. Nitrogen was continuously introduced, and the temperature was raised to 70-80°C. The reaction pressure was maintained at 0.5 MPa. The system was aged until the pressure stabilized and no longer decreased. The product was then cooled and discharged to obtain bio-based surfactant #4.

[0079]

[0080] Examples 5-19

[0081]

[0082]

[0083] The structures of the compounds prepared in Examples 5-19 are as follows:

[0084]

[0085]

[0086] Furthermore, all of the above compounds have been verified by 1H NMR spectroscopy.

[0087] Performance testing

[0088] Testing of the dispersing performance of superdispersants

[0089] (1) Preparation of O / W type emulsion

[0090] In an indoor environment at 25°C, weigh 0.05g of the bio-based surfactant prepared in the example and dissolve it in 50mL of deionized water for later use. According to the set total oil / water volume (10mL) and oil / water volume ratio, weigh 5mL of the previously prepared bio-based surfactant solution and 5mL of the oil phase, put them into a small glass bottle (inner diameter = 1.6cm, height = 7.2cm), and homogenize and emulsify them using a homogenizer at a speed of 13,000 pm for 2min. Then let it stand for 0.5 hours and observe the stability and layering of the emulsion.

[0091] There are three oil phases in total. Oil phase 1# is a mixture of styrene, methyl methacrylate, ethyl acrylate, and butyl acrylate. V 苯乙烯 :V 甲基丙烯酸甲酯 :V 丙烯酸乙酯 :V 丙烯酸丁酯 = 1:1:1:1; Oil phase 2# is No. 36 white oil; Oil phase 3# is soybean oil.

[0092] (2) Preparation of W / O type emulsion

[0093] (a) Using n-hexadecane as the oil phase

[0094] First, prepare an oil solution of the bio-based surfactant. Weigh a certain amount of the bio-based surfactant and add it to the oil, then heat at 80°C to dissolve. Next, transfer the required amount of the bio-based surfactant oil solution and ultrapure water (total volume of oil and water: 10 mL) into a small vial, place it in a 25°C incubator, and allow it to cool for 24 hours to ensure the sample temperature has completely dropped to 25°C. Then, homogenize the sample using a homogenizer at 13,000 rpm for 2 minutes in a 25°C indoor environment, followed by standing for 0.5 hours to observe the emulsion stability and layering.

[0095] (b) Using edible oil as the oil phase

[0096] Due to the high viscosity of edible oil, a dropwise method was used to prepare the emulsion. First, the bio-based surfactant was dissolved in the edible oil at a high temperature (80°C). Then, a certain volume of the bio-based surfactant oil solution was quickly transferred using a pipette into a small bottle as described above, and placed in a constant temperature incubator at 25°C to cool. Next, at an ambient temperature of 25°C, 1 mL of ultrapure water was added dropwise to the oil dispersion over 30 seconds, and homogenized for 30 seconds. This process was repeated again over 30 seconds until all the ultrapure water was added to the oil dispersion. For example, when the oil / water volume ratio was 5:5, the total homogenization time was 5 minutes. The emulsion was then allowed to stand for 0.5 hours to observe its stability and layering.

[0097] (3) Determining the type of emulsion

[0098] The type of emulsion can be determined using the droplet dispersion method. Prepare two small bottles, one filled with purified water and the other with n-hexadecane. Drop the emulsion into the water and then into the n-hexadecane, respectively. If the emulsion disperses immediately in the water but does not disperse in the oil and sinks to the bottom of the n-hexadecane phase, then the emulsion is an O / W type emulsion. If the emulsion disperses immediately in the n-hexadecane but does not disperse in the water and floats on the surface as a sphere, then it is a W / O type emulsion.

[0099] (4) Emulsion stability assessment

[0100] When the emulsion is of the O / W type, demulsification and coalescence will occur. The stability of emulsion demulsification and coalescence can be characterized by measuring the volume or height of the precipitated aqueous and oil phases, and the parameter f can be obtained. w and f o :

[0101]

[0102]

[0103] In the formula, V w(t) and V o(t) V refers to the volumes of the aqueous and oil phases precipitated at time t, respectively; w(0) and V o(0) These refer to the volumes of the aqueous and oil phases before homogenization, respectively. Parameter f w and f o The smaller the value, the better the stability of the emulsion. w and f o The closer the value is to 1, the worse the surface emulsion stability.

[0104] Similarly, sedimentation and aggregation also occur when the emulsion is of the W / O type. The parameter f can be obtained similarly. w and f o , are used to represent coalescence and sedimentation stability, respectively.

[0105] Table 1

[0106]

[0107]

[0108] As shown in Table 1, except for Examples 5 and 10, the bio-based surfactants in the other examples can all be prepared as O / W emulsions. This was achieved by reacting OP-10 and NP-10 with f0 and f... wComparative analysis revealed that the oil-in-water emulsifiers prepared in Examples 1, 2, 6, 7, 11, 12, 13, and 16 all exhibited better surface activity than OP-10 and NP-10. This indicates that the nonionic surfactants prepared using root bark esters, ferulic acid esters, and hydrogenated ferulic acid esters possess good surface activity, similar to OP-10 and NP-10.

[0109] The applicant declares that the present invention illustrates the surfactant, its preparation method, and its application through the above embodiments, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials used in the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A surfactant, characterized in that, The surfactant has the formula ( The structure shown is as follows: ； Wherein, R1 is an alkyl group with 4 to 16 carbon atoms, R2 is hydrogen or methoxy, X is a carbon-carbon single bond or carbon-carbon double bond, and n is a natural number from 3 to 30. Furthermore, the surfactant is not a compound of the following type: 。 2. The surfactant according to claim 1, characterized in that, The surfactant is any one of the following compounds: 。 3. The method for preparing the surfactant according to claim 1 or 2, characterized in that, The preparation method includes the following steps: (1) Compound A reacts with compound B to give compound C. The reaction equation is as follows: ； (2) Compound C reacts with ethylene oxide to obtain formula ( The surfactant shown in the figure has the following reaction formula: ； R1, R2, X, and n are defined as in claim 1.

4. The preparation method according to claim 3, characterized in that, Compound A is any one of phloroglucinic acid, ferulic acid, or hydrogenated ferulic acid.

5. The preparation method according to claim 3, characterized in that, The molar ratio of compound A to compound B is 1:(0.85-2.0).

6. The preparation method according to claim 3, characterized in that, The reaction temperature in step (1) is 80-180℃, and the reaction time is 8-28 hours.

7. The preparation method according to claim 3, characterized in that, In step (2), the molar ratio of compound C to ethylene oxide is 1:3-30.

8. The preparation method according to claim 3, characterized in that, The reaction described in step (2) is carried out in the presence of a catalyst.

9. The preparation method according to claim 8, characterized in that, The catalyst is selected from at least one of sodium hydroxide, potassium hydroxide, boron trifluoride, or boron trifluoride diethyl ether.

10. The preparation method according to claim 3, characterized in that, The reaction temperature in step (2) is 50-80℃, and the reaction time is 3-8 hours.

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