surfactant

Abstract

To provide a surfactant free of fluorocarbon chains or polydimethylsiloxane chains, which can be used at room temperature and offers a significant surface tension reduction rate.SOLUTION: A surfactant comprises a compound represented by the general formula (1). [In the general formula (1), R1 and R2 independently represent a hydrogen atom, a C1-3 hydrocarbon group or a C1-3 heterohydrocarbon group, where R1 and R2 may together form a hydrocarbon ring or a heterocycle. A represents -SO3- or -OSO3-, M represents alkali metal, alkaline earth metal, or -N(R10)4 (R10 independently represent a hydrogen atom, a C1-3 alkyl group, or a C1-3 hydroxyl alkyl group), n represents an integer of 1-17, and m represents an integer of 1-17. l represents 0 or 1, q is 1 when M is alkali metal or -N(R10)4, and q is 2 when M is alkaline earth metal.]SELECTED DRAWING: None

Description

[Technical Field]

[0001] This invention relates to surfactants. [Background technology]

[0002] Surfactants are amphiphilic molecules that possess both hydrophilic and hydrophobic parts within their molecule, and are used as components in detergents, antistatic agents, cosmetics, surface treatment agents, etc. (for example, Non-Patent Document 1).

[0003] Surfactants adsorb to the surface of water or the water / oil interface, reducing the surface tension of water and the water / oil interface tension, thereby exhibiting effects such as emulsification, solubilization, foaming, and wetting. When the adsorption rate of surfactants is high, it becomes possible to quickly stabilize the new surface / interface state created by emulsification, solubilization, foaming, and wetting. [Prior art documents] [Non-patent literature]

[0004] [Non-Patent Document 1] Tokiyuki Yoshida, "New Edition: Surfactants," Engineering Books Co., Ltd., 2nd edition. [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] According to our findings, the adsorption rate of a surfactant, i.e., the rate at which surface tension (interfacial tension) is reduced, can be achieved by increasing the hydrophobicity of the surfactant, for example, by lengthening the hydrophobic chain, or by changing it to a fluorinated carbon chain or polydimethylsiloxane chain, which is more hydrophobic than hydrocarbon groups. Another method is to introduce many methyl branches into the hydrophobic group, thereby lowering the surface energy and increasing hydrophobicity while maintaining water solubility.

[0006] However, when increasing the hydrocarbon chain length, or when using fluorinated carbon chains or polydimethylsiloxane chains, the strong hydrophobicity leads to a loss of solubility in water, resulting in a higher Krafft point (the lower limit temperature at which ionic surfactants form micelles and begin to dissolve) or a lower cloud point (the upper limit temperature at which nonionic surfactants begin to precipitate). Therefore, it may not be possible to use these products at room temperature.

[0007] Fluorine carbon does not normally exist in nature, making it difficult to decompose and resulting in a significant environmental burden. Furthermore, there are concerns about its potential health effects, such as bioaccumulation. On the other hand, polydimethylsiloxane chains are easily hydrolyzed in water, meaning their effects are not sustained for long after dissolution, making long-term storage difficult.

[0008] Therefore, the object of the present invention is to provide a surfactant that does not have a fluorinated carbon chain or a polydimethylsiloxane chain, can be used at room temperature, and has a high rate of surface tension reduction. [Means for solving the problem]

[0009] The present invention provides the following [1] to

[10] . [1] A surfactant comprising a compound represented by the following general formula (1). [ka] [In general formula (1), R 1 and R 2 Each of these independently represents a hydrogen atom, a hydrocarbon group having 1 to 3 carbon atoms, or a heterohydrocarbon group having 1 to 3 carbon atoms. 1 and R 2 These may together form a hydrocarbon ring or heterocycle. A is -SO3- or -OSO3-, M is an alkali metal, alkaline earth metal or -N(R 10 )4(R 10Each independently represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a hydroxylalkyl group having 1 to 3 carbon atoms. ), n represents an integer from 1 to 17, and m represents an integer from 1 to 17. l is 0 or 1, and when M is an alkali metal or -N(R 10 )4, q is 1, and when M is an alkaline earth metal, q is 2. Note that the surfactant composed of the compound represented by the general formula (1) may be a mixture of those having different m, n, l, q, or isomers (those having different bonding positions of -A). [2]R 1 and R 2 are both hydrogen atoms, the surfactant according to [1]. [3] The sum of m and n is 2 to 18, the surfactant according to [1] or [2]. [4] The difference between m and n is 0 to 3, the surfactant according to any one of [1] to [3]. [5] A is -SO3-, the surfactant according to any one of [1] to [4]. [6] M is sodium, calcium or magnesium, the surfactant according to any one of [1] to [5]. [7] A compound represented by the following general formula (100a). [Chemical formula] [8] A compound represented by the following general formula (100b). [Chemical formula] [9] A compound represented by the following general formula (100c). [Chemical formula]

[10] A method for improving the surface tension reduction rate of water, which includes adding a surfactant according to any one of [1] to [6] to water.

[0010] The surfactant represented by general formula (1) is a surfactant that hybridizes alkyl chains having trimethylsilyl groups with other alkyl chains, and exhibits a rate of decrease in the surface tension of water (adsorption rate) that is about 10 times greater than that of symmetrical double-chain surfactants having two identical hydrophobic chains.

[0011] Normally, increasing the adsorption rate requires increasing the hydrophobicity of the surfactant, but this method reduces water solubility, making it difficult to use. However, according to the present invention, the adsorption rate can be greatly increased without significantly changing the hydrophobicity or reducing water solubility. Furthermore, the molecular features include a "hybrid hydrophobic chain structure" having a "trimethylsilyl group," a structure in which two or more hydrophobic chains with poor compatibility coexist within the molecule. [Effects of the Invention]

[0012] According to the present invention, a surfactant is provided that does not have a fluorinated carbon chain or a polydimethylsiloxane chain, can be used at room temperature (e.g., 25°C), and has a high rate of surface tension reduction. [Brief explanation of the drawing]

[0013] [Figure 1] This figure shows the relationship between surface tension and surface life when using the surfactant [BC4P-SiPSS] from Example 1. [Figure 2] This figure shows the relationship between surface tension and surface life when using the surfactant [BC18-SiPSS] of Comparative Example 1. [Figure 3] This figure shows the relationship between surface tension and surface life when using the surfactant [di-BC4PSS] of Comparative Example 2. [Figure 4] This figure shows the relationship between surface tension and surface life when using the surfactant [di-SiPSS] of Comparative Example 3. [Figure 5] This figure shows the relationship between surface tension and surface life when using the surfactant [BC18-BC4ESS] of Comparative Example 4. [Figure 6]This figure shows the relationship between the characteristic time τ of the surfactant in the examples and comparative examples and the concentration of the surfactant. [Figure 7] This figure shows the surface tension of aqueous solutions of Examples 1 to 3 at various concentrations. [Figure 8] This figure shows the relationship between surface tension and surface life when using the surfactant [Mg(BC4P-SiPSS)2] from Example 2. [Figure 9] This figure shows the relationship between surface tension and surface life when using the surfactant [Cu(BC4P-SiPSS)2] from Example 3. [Figure 10] This figure shows the relationship between the characteristic time τ of the surfactants in Examples 1-3 and the concentration of the surfactants. [Figure 11] This figure shows the relationship between the characteristic time τ of the surfactants in Examples 1-3 and the value when the surfactant concentration is corrected by the critical micelle concentration (CMC). [Modes for carrying out the invention]

[0014] The surfactant according to this embodiment consists of a compound represented by the following general formula (1). [ka] In general formula (1), R 1 and R 2 Each of these independently represents a hydrogen atom, a hydrocarbon group having 1 to 3 carbon atoms, or a heterohydrocarbon group having 1 to 3 carbon atoms. 1 and R 2 R may be a hydrogen atom, a hydrocarbon group having 1 to 2 carbon atoms, or a heterohydrocarbon group having 1 to 2 carbon atoms, or a hydrogen atom, a hydrocarbon group having 1 carbon atom, or a heterohydrocarbon group having 1 carbon atom. 1 and R 2 Both can be hydrogen atoms. Examples of hydrocarbon groups with 1 to 3 carbon atoms include the methyl group, ethyl group, and propyl group (n-propyl group, i-propyl group), while examples of heterohydrocarbon groups with 1 to 3 carbon atoms include the methoxy group, ethoxy group, and propoxy group.

[0015] R 1 and R 2 These may together form a hydrocarbon ring or a heterocycle. Examples of hydrocarbon rings include cyclopentane rings, cyclohexane rings, cycloheptane rings, cyclooctane rings, benzene rings, and naphthalene rings. Examples of heterocycles include pyrrolidine rings, tetrahydrofuran rings, tetrahydrothiophene rings, piperazine rings, pyrrole rings, furan rings, thiophene rings, pyridine rings, and indole rings.

[0016] As can be seen from the fact that l in general formula (1) is 0 or 1, R 1 The carbon and R that are bonded together 2 The carbon atoms to which the group is bonded are either directly bonded or bonded via a single carbon atom. This structure allows the hydrophobic chain with the t-butyl group and the hydrophobic chain with the trimethylsilyl (TMS) group to exist in close proximity. As a result, both when dissolved as a monomer in water and when forming micelles, the two hydrophobic chains tend to align in the same direction, and the repulsive interaction between the hydrophobic chains becomes stronger. This reduces the stability of the dissolved state of the surfactant in water and can increase the adsorption rate of the surfactant, i.e., the rate at which the surface tension decreases.

[0017] R 1 and R 2 When these elements combine to form a hydrocarbon ring or heterocycle, l can be 0 or 1. However, when the hydrocarbon ring or heterocycle is an aromatic ring such as a benzene ring, naphthalene ring, pyrrole ring, furan ring, thiophene ring, pyridine ring, or indole ring, it is preferable that l be 0.

[0018] In general formula (1), n ​​is an integer between 1 and 17, and m is an integer between 1 and 17. n may also be between 1 and 12, 1 and 10, 1 and 8, 1 and 6, or 1 and 3, and m may also be between 1 and 12, 1 and 10, 1 and 8, 1 and 6, or 1 and 3.

[0019] The values ​​of m and n can be any combination as long as m is an integer from 1 to 17 and n is an integer from 1 to 17. However, compounds in which the sum of m and n is 2 to 18 are preferred because they exhibit superior hydrophobicity of the hydrophobic groups and are superior in terms of the rate at which surface tension is reduced. Furthermore, the difference between m and n is preferably 0 to 3, but may also be 0 to 2, 0 to 1, or even 0, meaning the number of m and n are the same. Note that the sum of m and n may be 2 to 18 and the difference between m and n may be 0 to 3.

[0020] In general formula (1), M is an alkali metal, an alkaline earth metal, or -N(R 10 )4(R 10 These independently represent a hydrogen atom, a C1-C3 alkyl group, and a C1-C3 hydroxylalkyl group.

[0021] If M is an alkali metal, examples of M include sodium, potassium, and lithium, with sodium being the most representative. If M is an alkaline earth metal, examples of M include magnesium, calcium, and barium, with magnesium and calcium being the most representative.

[0022] M is -N(R 10 If it is represented by )4, R 10 This is a hydrogen atom, a C1-C3 alkyl group (methyl group, ethyl group, propyl group), or a C1-C3 hydroxylalkyl group (hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, etc.). -N(R 10 An example of )4 is -NH4(R 10 (All hydrogen atoms), -NH(C2H4OH)3(R 10 (One of them is a hydrogen atom and the other three are hydroxyethyl groups), -N(C2H4OH)4(R 10 (All of these are hydroxyethyl groups.)

[0023] A is -SO3- or -OSO3-, and when employing a synthesis route using an unsaturated dicarboxylic acid, -SO3- is preferred for A.

[0024] A preferred embodiment of the compound represented by general formula (1) is, for example, in general formula (1), R 1 and R 2 Examples of compounds represented by the following general formula (10) include those in which the atom is a hydrogen atom. [ka]

[0025] A specific example of the general formula (10) is when l is 0 and q is 1 (M is an alkali metal or -N(R 10 Examples of compounds are those in the case of (4), and such compounds can be represented by the following general formula (10a). Note that m, n, l, A, and M have the same meaning as above, including in the preferred examples (the same applies hereinafter). [ka]

[0026] Other specific examples of general formula (10) include compounds where l is 0 and q is 2 (when M is an alkaline earth metal), and such compounds can be represented by the following general formula (10b). [ka]

[0027] Another specific example of general formula (10) is when l is 1 and q is 1 (M is an alkali metal or -N(R 10 Examples of compounds in the case of )4) include such compounds, and such compounds can be represented by the following general formula (11a). [ka]

[0028] Another specific example of general formula (10) is a compound in which l is 1 and q is 2 (when M is an alkaline earth metal), and such a compound can be represented by the following general formula (11b). [ka]

[0029] A preferred embodiment of the compound represented by general formula (10a) is, for example, the compound represented by the following formula (100a), in which m and n are 3, A is -SO3-, and M is sodium. Note that the compound represented by formula (100a) can have two isomers depending on the bond position of -SO3-, but either isomer or a mixture of isomers may be used. [ka] [ka]

[0030] A preferred embodiment of the compound represented by general formula (10b) is, for example, the compound represented by the following formula (100b), in which m and n are each 3, A is -SO3-, and M is calcium. [ka]

[0031] A preferred embodiment of the compound represented by general formula (10b) is, for example, the compound represented by the following formula (100c), in which m and n are each 3, A is -SO3-, and M is magnesium. [ka]

[0032] The compound represented by formula (100b) or formula (100c) can have three isomers depending on the position of the -SO3- bond, as follows, but any of the isomers or a mixture of the isomers may be used. In the following formulas, M 0 This represents calcium or magnesium.

[0033] [ka]

[0034] A preferred embodiment of the compound represented by general formula (11a) is, for example, the compound represented by the following formula (110a), in which m and n are 3, A is -SO3-, and M is sodium. Note that the compound represented by formula (110a) can have three isomers depending on the bond position of -SO3-, but any of these isomers or a mixture of isomers may also be considered. [ka] [ka]

[0035] A preferred embodiment of the compound represented by general formula (11b) is, for example, the compound represented by the following formula (110b), in which m and n are each 3, A is -SO3-, and M is calcium. [ka]

[0036] A preferred embodiment of the compound represented by general formula (11b) is, for example, the compound represented by the following formula (110c), in which m and n are each 3, A is -SO3-, and M is magnesium. [ka]

[0037] The compound represented by formula (110b) or formula (110c) can have six different isomers depending on the position of the -SO3- bond, as follows, but any of these isomers or a mixture of isomers may be used. In the following formulas, M 0 This represents calcium or magnesium.

[0038] [ka]

[0039] Among the compounds represented by general formula (1), R 1 and R 2 A compound in which is a hydrogen atom, A is -SO3-, l is 0, and q is 1 can be synthesized, for example, by the following reaction scheme. [ka]

[0040] Among the compounds represented by general formula (1), R 1 and R 2 A compound in which is a hydrogen atom, A is -SO3-, l is 1, and q is 1 can be synthesized, for example, by the following reaction scheme. [ka]

[0041] Among the compounds represented by general formula (1), R 1 and R 2 Compounds in which A is a hydrogen atom, A is -SO3-, q is 2, and M is magnesium or sodium can be reacted by adding saturated Mg(NO3)2 solution or saturated Ca(NO3)2 solution, respectively, to the above product.

[0042] Among the compounds represented by general formula (1), R 1 and R 2 A compound in which is a hydrogen atom, A is -OSO3-, and q is 1 can be synthesized, for example, in the following steps. [ka]

[0043] Among the compounds represented by general formula (1), R 1 and R 2Compounds in which A is -SO3- and q is 1, formed by the combination of these atoms to create a hydrocarbon ring or heterocycle, can be synthesized, for example, by the following reaction scheme. Note that X is a carbon atom or a heteroatom (oxygen atom, nitrogen atom, etc.), and when X is a carbon atom, p is an integer from 1 to 4, and when X is a heteroatom, p is an integer from 1 to 5. [ka]

[0044] The compound represented by general formula (1) may be used in combination with other surfactants (such as non-fluorinated surfactants), and may contain water, ethanol, isopropanol, methanol, acetone, toluene, tetrahydrofuran, acetonitrile, chloroform, saturated and unsaturated hydrocarbon oils, supercritical carbon dioxide, ionic liquids, etc. as a solvent. In addition, other additives (for example, cosolvents and cosurfactants such as organic fine particles, inorganic fine particles, polymers, hydrotropes, dyes, and higher alcohols) may be added. Applications of surfactants consisting of the compound represented by general formula (1) include fire extinguishing agents, leveling agents, crude oil recovery agents, pesticides, pharmaceuticals, cosmetics, detergents, water-repellent agents, hydrophilic agents, emulsifiers, dispersants, and foaming agents. [Examples]

[0045] The present invention will be described more specifically below based on examples. However, the present invention is not limited to the following examples.

[0046] The compounds were synthesized using the methods described in Examples 1-3 and Comparative Examples 1-4. The following samples were used for synthesis and measurement.

[0047] [Samples for synthesis and measurement] ·2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctan-1-ol C 18 H 38 O = 270.49 Nissan Chemical Corporation ·4,4-dimethylpentan-1-ol C7H 15O=115.19 ChemBridge Co., Ltd., purity 95.0% ·3-(trimethylsilyl)propan-1-ol C6H 16 OSi=132.28SIGMA-ALDRICH Co., Ltd., purity 97.0% • Fumaric acid C4H4O4 116.07 Kanto Chemical Co., Ltd. Purity 99.0% Maleic anhydride C4H2O3 = 98.06, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., purity 99.0% ·4-Dimethylaminopyridine C7H 10 N2 = 122.17, Kanto Chemical Co., Ltd., Purity 99.0% ·1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride C8H 17 N3·HCl = 191.71, Watanabe Chemical Industry Co., Ltd., purity 98.0% • Sodium bisulfite NaHSO3 = 104.06, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., purity 64.0-67% [mixture of sodium bisulfite (NaHSO3) and sodium metabisulfite (Na2S2O5)] p-toluenesulfonic acid monohydrate C7H8O3S·H2O=190.22 Fujifilm Wako Pure Chemical Industries, Ltd., purity 99.0%

[0048] The synthesized compounds were purified by column chromatography using silica gel (63-210 μm) (KANTOCHEMICAL Co. INK.). The structure was then confirmed by nuclear magnetic resonance (NMR) spectroscopy and infrared (IR) spectroscopy, and the purity was confirmed by organic trace element analysis. Measurements were performed under the following conditions.

[0049] [Measurement conditions] NMR spectra were measured using either the JEOL (JEOL Ltd.) product name "JMN-GX400" or "JMN-ECZ400". Chemical shifts are expressed in parts per million (ppm). Tetramethylsilane (TMS) was used as the internal standard. Coupling constants (J) are shown in Hertz, with abbreviations s, d, t, q, and m representing singlet, doublet, triplet, quartet, and multiplet, respectively. IR spectra were measured using the BIO-RAD product name "FTS-30". Purity was confirmed by organic trace element analysis (EA1110, CE Instrumental (ACOM Co., Ltd.)).

[0050] (Example 1) Synthesis of BC4P-SiPSS BC4P-SiPSS was synthesized by a three-step method following the reaction scheme described below. [ka]

[0051] [Step 1] Synthesis of 3-(trimethylsilyl)-1-propyl hydrogen maleate (SiPM) 3-(trimethylsilyl)propan-1-ol (5.05 g, 38.18 mmol) and maleic anhydride (5.02 g, 75.57 mmol) were stirred and refluxed at 90°C for 24 hours. After the reaction, unreacted maleic anhydride was extracted from the reaction solution using a separatory funnel with saturated NaCl aqueous solution adjusted to pH 1 and diethyl ether. Anhydrous sodium sulfate was added to the organic layer, dehydrated, filtered, and concentrated. The solution was then purified by HPLC to obtain a colorless, transparent liquid SiPM (3-(trimethylsilyl)-1-propylhydrogen maleate) (3.18 g, yield 36.1%).

[0052] SiPM 1H NMR (500MHz, CDCl3,TMS): δH / ppm: 6.41 (dd, 2H, -CH=CH-, J = 39.5 Hz, J =12.6Hz), 4.23 (t, 2H, -O-CH2-, J=7.2 Hz), 1.72-1.66 (m,2H, -O-CH2-CH2-),0.52-0.49(m, 2H, -CH2-C(CH3)3), 0.00 (s, 9H, -Si(CH3)3) IR (KBr) νmax / cm -1 : 3192 (-OH), 2954 (CH), 1734 (C=O,-COO-), 1631 (C=C)

[0053] [Step 2] Synthesis of 1-(3-(trimethylsilyl)-1-propyl)-4-(4,4-dimethylpent-1-yl) fumarate (BC4P-SiPF) Next, the synthesized 3-(trimethylsilyl)-1-propyl hydrogen maleate (3.18 g, 13.80 mmol), 4,4-dimethylpentan-1-ol (1.61 g, 13.86 mmol), 4-Dimethylaminopyridine (DMAP) (1.69 g, 13.83 mmol), and 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (EDC) (3.34 g, 17.42 mmol) were stirred at room temperature for 24 hours. After concentrating the reaction solution, it was vacuum-dried at 50°C for 24 hours, and the precipitated solid was removed by filtration using toluene. After concentrating the filtrate, it was purified by column chromatography using toluene as the developing solvent to obtain a colorless, transparent liquid BC4P-SiPF(1-(3-(trimethylsilyl)-1-propyl)-4-(4,4-dimethylpent-1-yl)fumarate) (4.53 g, yield 42.2%).

[0054] BC4P-SiPF 1H NMR (500 MHz, CDCl3,TMS) : δH / ppm : 6.85 (s, 2H, -CH=CH-), 4.17 (t, 2H,-O-CH2-CH2-CH2-Si(CH3)3,J=6.9 Hz), 4.15 (t, 2H, -O-CH2-CH2-CH2-C(CH3)3,J=6.9 Hz), 1.68-1.63(m, 4H, -O-CH2-CH2-), 1.25-1.22 (m,2H, -CH2-C(CH3)3), 0.89 (s, 9H, -C(CH3)3),0.53-0.49(m, 2H, -CH2-C(CH3)3), 0.00 (s, 9H,-Si(CH3)3) IR (KBr) νmax / cm -1 : 2955 (CH), 1724 (C=O, -COO-), 1646(C=C)

[0055] [Step 3] Synthesis of Sodium 1-(3-(trimethylsilyl)-1-propyl)-4-(4,4-dimethylpent-1-yl)sulfosuccinate (BC4P-SiPSS) Next, the synthesized 1-(3-(trimethylsilyl)-1-propyl)-4-(4,4-dimethylpent-1-yl) fumarate (3.04 g, 4.89 mmol) was dissolved in 1,4-dioxane (75 mL) and 2-propanol (75 mL). After adding NaHSO3 / water (7.59 g, 49.1 mmol / 75 mL), the mixture was stirred and refluxed at 110°C for 24 hours. The reaction solution was concentrated and then vacuum-dried at 50°C for 24 hours. Unreacted NaHSO3 was removed by filtration using dichloromethane. After concentrating the filtrate, unreacted intermediate products were removed by column chromatography using toluene as the developing solvent, and then a white solid was obtained using methanol as the developing solvent. The resulting compound was concentrated and dried in a vacuum oven for 24 hours to obtain a white solid sodium 1-(3-(trimethylsilyl)-1-propyl)-4-(4,4-dimethylpent-1-yl)sulfosuccinate (0.97 g, yield 38.5%).

[0056] BC4P-SiPSS 1 H NMR (500 MHz, CDCl3,TMS): δH / ppm: 4.36-4.33 (m, 1H, -CH2-CH(SO3Na)-), 4.18-4.13 (m, 2H, -O-CH2-CH2-CH2-Si(CH3)3), 4.05-4.00 (m, 2H, -O-CH2-CH2-CH2-C(CH3)3),3.24-3.12 (m, 2H, -CH(SO3Na)-CH2-), 1.65-1.55 (m, 4H,-O-CH2-CH2-), 1.22-1.17 (m, 2H, -CH2-C(CH3)3),0.89 (s, 9H, -C(CH3)3), 0.50-0.45 (m, 2H, -CH2-Si(CH3)3),0.00 (s, 9H, -Si(CH3)3) IR (KBr) νmax / cm -1 : 2952 (CH), 1736 (C=O, -COO-), 1248 (O=S=O), 1055 (O=S=O) Elemental analysis (C 17 H 33 NaO7SSi) C / 47.70%, H / 7.46%, S / 7.72% (Theoretical value C / 47.20%, H / 7.69%, S / 7.41%)

[0057] (Example 2) Synthesis of Mg(BC4P-SiPSS)2 Mg(BC4P-SiPSS)2は, the following reaction method is synthesized.

change

[0058] (Example 3) Synthesis of Ca(BC4P-SiPSS)2 Ca(BC4P-SiPSS)2 was synthesized according to the following reaction scheme. [ka] BC4P-SiPSS was synthesized by the method described in Example 1. BC4P-SiPSS (0.5004 g, 1.16 mmol) was dissolved in the minimum amount of ethanol (EtOH) (5 mL) and added to 5 mL of saturated Ca(NO3)2 solution, and stirred for 24 hours. The target product was then extracted into toluene using a separatory funnel, and after removing the aqueous layer, saturated CaCl2 solution was added to extract and remove unreacted BC4P-SiPSS into the aqueous layer. Anhydrous magnesium sulfate was added to the organic layer to dehydrate it, and then filtration and vacuum concentration were performed to obtain a white solid, Calcium 1-(3-(trimethylsilyl)-1-propyl)-4-(4,4-dimethylpent-1-yl)sulfosuccinate (Ca(BC4P-SiPSS)2) (0.3694 g, yield 74.3%).

[0059] (Comparative example 1) BC 18 -SiPSS synthesis BC 18-SiPSS was synthesized by a two-step method following the reaction scheme described below. 18 -SiPSS was a mixture of two structural isomers as described below. [ka]

[0060] [Step 1] 1-(3-(trimethylsilyl)-1-propyl)-4-(2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctyl) fumarate (BC 18 Synthesis of -SiPF) 2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctan-1-ol (11.68 g, 43.17 mmol), 3-(trimethylsilyl)propan-1-ol (5.82 g, 44.02 mmol), and fumaric acid (5.02 g, 43.28 mmol) were dissolved in 200 mL of toluene. p-toluenesulfonic acid monohydrate (1.29 g, 6.79 mmol) was added, and the mixture was stirred and refluxed at 130°C for 69 hours using a Dean-Stark apparatus. After the reaction, p-toluenesulfonic acid monohydrate was extracted from the reaction solution with saturated NaCl aqueous solution using a separatory funnel. Anhydrous sodium sulfate was added to the organic layer, and after dehydration, the mixture was filtered and concentrated. Subsequently, the mixture was purified by column chromatography using a toluene:hexane = 1:1 solution as the developing solvent, and a yellow liquid BC was obtained. 18 SiPF(1-(3-(trimethylsilyl)-1-propyl)-4-(2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctyl)fumarate) (7.61 g, yield 36.4%) was obtained.

[0061] BC 18 -SiPF 11H NMR (500 MHz, CDCl3, TMS): δH / ppm: 6.85 (s, 2H, -HC=CH-), 4.15 (t, 2H, -O-CH2-CH2-, J = 6.9 Hz), 4.12 - 4.08 (m, 2H, -O-CH2-CH-), 1.70 - 1.00 (m, 13H, -O-CH2-CH2-, -O-CH2-CH-, -CH2-CH2-CH(CH3)-, -CH2-CH2-CH(CH3)-, -CH-CH3, -CH2-C(CH3)3), 0.91 - 0.88 (m, 24H, -C(CH3), -CH3-CH-), 0.53 - 0.49 (m, 2H, -CH2-Si(CH3)3), 0.00 (s, 9H, -Si(CH3)3) IR (KBr) νmax / cm -1 : 2954 (C-H), 1724 (C=O, -COO-), 1646 (C=C)

[0062] [Step 2] Synthesis of Sodium 1-(3-(trimethylsilyl)-1-propyl)-4-(2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctyl)sulfosuccinate (BC 18 -SiPSS) Next, the synthesized 1-(3-(trimethylsilyl)-1-propyl)-4-(2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctyl)fumarate (3.52 g, 7.29 mmol) was dissolved in 1,4-dioxane (85 mL) and 2-propanol (85 mL). After adding NaHSO3 / water (7.59 g, 72.9 mmol / 85 mL), the mixture was stirred and refluxed at 110°C for 41 hours. The reaction solution was concentrated and then vacuum-dried at 50°C for 24 hours. Unreacted NaHSO3 was removed by filtration using dichloromethane. After concentrating the filtrate, unreacted intermediate products were removed by column chromatography using toluene as the developing solvent, and then a white solid was obtained using methanol as the developing solvent. The resulting compound was concentrated and dried in a vacuum oven for 24 hours to obtain a white solid sodium 1-(3-(trimethylsilyl)-1-propyl)-4-(2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctyl)sulfosuccinate (3.28 g, yield 76.7%).

[0063] BC 18 -SiPSS 1 H NMR (500 MHz, CDCl3,TMS): δH / ppm: 4.36-4.30 (m, 1H, -CH2-CH(SO3Na)-),4.19-4.08 (m, 2H, -O-CH2-CH2-), 4.00- 3.96 (m, 2H, -O-CH2-CH-),3.17 (s, 2H, -S-CH-CH2-), 1.71-1.01 (m, 13H, -O-CH2-CH2-,-O-CH2-CH-, -CH2-CH2-CH(CH3)-, -CH2-CH2-CH(CH3)-,-CHCH3, -CH2-C(CH3)3), 0.91-0.87(m, 24H, -C(CH3), -CH3-CH-), 0.49-0.45 (m, 2H, -CH2-Si(CH3)3),0.00 (s, 9H, -Si(CH3)3) IR (KBr) νmax / cm -1:2955 (CH), 1738 (C=O, -COO-), 1250 (O=S=O), 1053 (O=S=O) Elemental analysis (C 28 H 55 NaO7SSi)C / 56.37%,H / 9.58%,S / 6.10%(Theoretical value C / 57.30%, H / 9.45%, S / 5.46%)

[0064] (Comparative Example 2) Synthesis of di-BC4PSS di-BC4PSS was synthesized by a two-step method according to the following reaction scheme. Note that di-BC4PSS was a mixture of two structural isomers as described below. [ka] [Step 1] Synthesis of Bis(4,4-dimethylpent-1-yl) fumarate (di-BC4PF) 4,4-dimethylpentan-1-ol (3.03 g, 26.10 mmol) and fumaricasid (1.51 g, 13.00 mmol) were dissolved in 150 mL of toluene, and p-toluenesulfonic acid monohydrate (0.76 g, 4.01 mmol) was added. The mixture was stirred at 130°C for 24 hours under reflux using a Dean-Stark apparatus. After the reaction, p-toluenesulfonic acid monohydrate was extracted from the reaction solution with saturated NaCl aqueous solution using a separatory funnel. Anhydrous sodium sulfate was added to the organic layer, and after dehydration, the solution was filtered and concentrated. Subsequently, the solution was purified by column chromatography using toluene as the developing solvent to obtain a colorless, transparent liquid di-BC4PF (bis(4,4-dimethylpent-1-yl)fumarate) (3.46 g, yield 85.3%).

[0065] di-BC4PF 1H NMR (500 MHz, CDCl3,TMS): δH / ppm: 6.86 (s, 2H, -CH=CH-), 4.18 (t, 4H,-O-CH2-, J= 6.9 Hz), 1.68-1.63 (m, 4H, -O-CH2-CH2-),1.26-1.22 (m, 4H, -CH2-C(CH3)3), 0.90 (s, 18H,-C(CH3)3) IR (KBr) νmax / cm -1 : 2956 (CH), 1725 (C=O, -COO-),1645 (C=C)

[0066] [Step 2] Synthesis of Sodium bis(4,4-dimethylpent-1-yl) sulfosuccinate (di-BC4PSS) Next, the synthesized bis(4,4-dimethylpent-1-yl) fumarate (3.46 g, 11.08 mmol) was dissolved in 2-propanol (85 mL), and NaHSO3 / water (11.53 g, 110.8 mmol / 85 mL) was added. The mixture was then stirred at 110°C for 21 hours under reflux. The reaction solution was concentrated and vacuum-dried at 50°C for 24 hours. Unreacted NaHSO3 was removed by filtration using dichloromethane. After concentrating the filtrate, unreacted intermediate products were removed by column chromatography using toluene as the developing solvent, and then a white solid was obtained using methanol as the developing solvent. The obtained compound was concentrated and dried in a vacuum oven for 24 hours to obtain a white solid sodium bis (4,4-dimethylpent-1-yl)sulfosuccinate (3.30 g, yield 71.6%).

[0067] di-BC4PSS 1H NMR (500 MHz, CDCl3,TMS) : δH / ppm : 4.33-4.30 (m, 1H, -CH2-CH(SO3Na)-),4.16 (t, 2H, -CH2-COO-CH2-, J = 6.6 Hz), 4.02 (t, 2H,-CH(SO3Na)-COO-CH2-, J = 6.9 Hz), 3.22-3.11(m, 2H, -CH(SO3Na)-CH2-),1.64-1.55 (m, 4H, -O-CH2-CH2-), 1.21-1.16 (m, 4H, -CH2-C(CH3)3),0.88 (s, 18H, -C(CH3)3) IR (KBr) νmax / cm -1 : 2955 (CH), 1736 (C=O, -COO-), 1246(O=S=O), 1048 (O=S=O) Elemental analysis (C 18 H 33 NaO7S) C / 51.23%, H / 7.68%, S / 7.75% (Theoretical values: C / 51.90%, H / 7.99%, S / 7.70%)

[0068] (Comparative Example 3) Synthesis of di-SiPSS di-SiPSS was synthesized by a two-step method according to the following reaction scheme. Note that di-SiPSS was a mixture of two structural isomers as described below. [ka]

[0069] [Step 1] Synthesis of Bis(3-(trimethylsilyl)-1-propyl) fumarate (di-SiPF) 3-(trimethylsilyl)-1-propanol (8.00 g, 60.5 mmol) and fumaric acid (3.51 g, 30.2 mmol) were dissolved in toluene (150 mL), and p-toluenesulfonic acid monohydrate (1.45 g, 7.66 mmol) was added. The mixture was stirred at 130°C for 3.5 hours under reflux using a Dean-Stark apparatus. After removing the precipitated starting materials from the reaction solution by filtration, p-toluenesulfonic acid monohydrate was extracted from the reaction solution with saturated NaCl aqueous solution using a separatory funnel. Anhydrous magnesium sulfate was added to the organic layer, and after dehydration, the solution was filtered and concentrated. Subsequently, the solution was purified by column chromatography (toluene as the developing solvent) to obtain bis(3-(trimethylsilyl)-1-propyl) fumarate (7.68 g, yield 73.8%) as a yellow transparent liquid.

[0070] di-SiPF 1H NMR (500 MHz, CDCl3, TMS) δH / ppm : 6.85 (s, 2H, -CH=CH-), 4.14 (t, 4H, -O-CH2-, J = 7.5 Hz),1.69-1.63 (m, 4H, -O-CH2-CH2-), 0.52-0.49 (m, 4H, -CH2-Si(CH3)3),0.00 (s, 18H, -Si(CH3)3) IR (liquid film method) νmax / cm -1 : 2953, 2895 (CH), 1723 (C=O, -COO-), 1463(C=C), 839, 753 (C-Si)

[0071] [Step 2] Synthesis of Sodium bis(3-(trimethylsilyl)-1-propyl) sulfosuccinate (di-SiPSS) Next, the synthesized bis(3-(trimethylsilyl)-1-propyl) fumarate (2.96 g, 8.59 mmol) was dissolved in ethanol (60 mL), and NaHSO3 / water (8.33 g (80.0 mmol) / 45 mL) was added. The mixture was then stirred at 110°C for 3 hours under reflux. The reaction solution was concentrated and then vacuum-dried at 50°C. Unreacted NaHSO3 was removed by filtration using dichloromethane. After concentrating the filtrate, unreacted intermediate products were removed by column chromatography using ethyl acetate as the developing solvent, and then a white solid was obtained using methanol as the developing solvent. The solution was then further purified by column chromatography using ethyl acetate and 1,4-dioxane to obtain a white solid sodiumbis(3-(trimethylsilyl)-1-propyl) sulfosuccinate (3.24 g, yield 84.1%).

[0072] di-SiPSS 1H NMR (500 MHz, CDCl3, TMS) δH / ppm : 4.31 (q, 1H, -CH2-CH(SO3Na)-, J = 5.0 Hz), 4.12 (t,2H, -CH2-COO-CH2-, J = 7.5 Hz), 4.00-3.96 (m, 2H, -CH(SO3Na)-COO-CH2-),3.21-3.09 (m, 2H, -CH2-CH(SO3Na)-), 1.62-1.54 (m, 4H,-O-CH2-CH2-), 0.47-0.43 (m, 4H, -CH2-Si(CH3)3),-0.01, -0.02 (s, 18H, -Si(CH3)3) IR (KBr) νmax / cm -1 : 2954, 2896 (CH), 1735 (C=O, -COO-), 1248 (O=S=O), 1054 (O=S=O), 861, 751(C-Si) Elemental analysis (C 16 H 33 NaO7SSi2) C / 42.37 % H / 7.14 % S / 6.59 % (Theoretical values: C / 42.83 % H / 7.41 % S / 7.15 %)

[0073] (Comparative example 4) BC 18 - BC4ESS synthesis The di-SiPSS represented by the chemical formula below was synthesized in the following three steps. 18 -BC4ESS was a mixture of two structural isomers as described below. [ka]

[0074] [Step 1] 1-(3,3-dimethylbutyl)-4-(2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctyl) fumarate (BC 18 Synthesis of -BC4EF) 2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctan-1-ol (11.92 g, 44.07 mmol), 3,3-dimethylbutan-1-ol (4.53 g, 44.36 mmol), and fumaric acid (5.02 g, 43.21 mmol) were dissolved in 200 mL of toluene. p-toluenesulfonic acid monohydrate (1.28 g, 6.73 mmol) was added, and the mixture was stirred and refluxed at 130°C for 25.5 hours using a Dean-Stark apparatus. After the reaction, p-toluenesulfonic acid monohydrate was extracted from the reaction solution with saturated NaCl aqueous solution using a separatory funnel. Anhydrous sodium sulfate was added to the organic layer, dehydrated, filtered, and concentrated. Subsequently, the solution was purified using column chromatography (toluene:hexane = 1:1 as the developing solvent) to obtain a colorless, transparent liquid 1-(3,3-dimethylbutyl)-4-(2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctyl)fumarate (yield 4.93 g, yield 25.2%).

[0075] BC18 -BC4EF 1H NMR (500 MHz, CDCl3, TMS): δH / ppm: 6.96 (s, 2H, -HC=CH-), 4.39 (t, 2H, -O-CH2-CH2-, J = 7.4 Hz), 4.26 - 4.22 (m, 2H, -O-CH2-CH-), 1.85 (m, 1H, -O-CH2-CH-), 1.74 (t, 2H, -CH2-C(CH3)3, J = 7.5 Hz), 1.69 (m, 2H, -CH-CH2-CH2-), 1.55 (m, 1H, CH3-CH-), 1.43 (m, 1H, -CH2-CH(CH3)-CH2-), 1.40 - 1.38 (m, 2H, -CH2-CH2-CH(CH3)-), 1.34 - 1.31 (m, 2H, -CH-CH(CH3)-CH2-C(CH3)3), 1.18 - 1.12 (m, -CH2-CH(CH3)-CH2-C(CH3)3), 1.04 - 0.95 (m, 33H, -CH3)

[0076] [Step 2] Synthesis of Sodium 1-(3,3-dimethylbutyl)-4-(2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctyl)sulfosuccinate (BC 18 -BC4ESS) Next, the synthesized 1-(3,3-dimethylbutyl)-4-(2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctyl)fumarate (4.93 g, 10.9 mmol) was dissolved in 1,4-dioxane (85 mL) and 2-propanol (85 mL). After adding NaHSO3 / water (11.35 g, 109.1 mmol / 85 mL), the mixture was stirred and refluxed at 110 °C for 70 hours. The reaction solution was concentrated and then dried under vacuum at 50 °C. Unreacted NaHSO3 was removed by filtration using dichloromethane. After concentrating the filtrate, the unreacted intermediate product was removed by column chromatography using ethyl acetate as the developing solvent, and then a white solid was obtained using methanol as the developing solvent. The obtained white solid was concentrated and then dried in a vacuum oven for 7 hours to obtain white solid Sodium 1-(3,3-dimethylbutyl)-4-(2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctyl)sulfosuccinate (3.64 g, yield 60.0 %).

[0077] BC 18 -BC4ESS 1H NMR (500 MHz, CDCl3, TMS) : δH / ppm : 4.36 (m, 2H, -O-CH2-CH2-C(CH3)3), 4.25 (m, 1H, -CH(SO3Na)-), 4.08 (m, 2H, -O-CH2-CH-), 3.26 (d, 2H, -CH(SO3Na)-CH2-, J = 6.0), 1.70 - 1.17 (m, 13H, aliphatic-H), 1.05 - 1.01 (m, 33H, -CH3) IR (KBr) νmax / cm -1 : 2954, 2868 (C-H), 1737 (C=O, -COO-), 1245 (O=S=O), 1050 (O=S=O) Elemental analysis (C 28 H 53 NaO7S) C / 59.32%, H / 9.20%, S / 5.22% (Theoretical values: C / 60.40%, H / 9.59%, S / 5.76%)

[0078] [Usability of surfactants at room temperature (25°C)] In Examples 1, 2, and 3, the final product (surfactant) was obtained as a white solid. Its usability at room temperature was evaluated by dissolving it in water at 25°C. Specifically, when twice the CMC amount of the compounds obtained in Examples 1, 2, and 3 was added to distilled water at 25°C and stirred, it dissolved in the distilled water, and no insoluble matter was observed. Therefore, it was found that the surfactants of Examples 1, 2, and 3 are usable at room temperature.

[0079] [Evaluation of the surface tension reduction ability of surfactants] Surfactant of Example 1 (BC4P-SiPSS), Surfactant of Comparative Example 1 (BC 18 -SiPSS), surfactant of Comparative Example 2 (di-BC4PSS), surfactant of Comparative Example 3 (di-SiPSS), surfactant of Comparative Example 4 (BC 18 For -BC4ESS), dynamic surface tension measurements were performed at 25°C using the maximum bubble pressure method for aqueous solutions prepared at various concentrations. The measurements were performed using a handheld dynamic surface tensimeter BP50 manufactured by KRUSS GmbH, Germany.

[0080] Figures 1, 2, 3, 4, and 5 show the relationship between the surface tension and surface life of the surfactants in Example 1, Comparative Example 1, Comparative Example 2, Comparative Example 3, and Comparative Example 4 at various concentrations, respectively. The horizontal axis represents surface life, and the vertical axis represents surface tension.

[0081] The measurement of dynamic surface tension by the maximum bubble pressure method is a method of obtaining the surface tension by measuring the maximum pressure when gas is introduced into a capillary inserted in a liquid (in water) to generate bubbles. When bubbles are generated from the capillary in the liquid, the pressure inside the capillary gradually changes, and the pressure reaches its maximum when the radius of curvature of the bubble equals the radius of the capillary. When gas is continuously introduced, the size of the bubble itself increases while the pressure decreases. When gas is continuously introduced, the pressure changes periodically, and the time from the minimum value of the pressure to the maximum value of the pressure (the time from when the gas-liquid interface starts to form until the pressure reaches its maximum) is called the surface lifetime (also called the surface formation time, the lifetime of the bubble, the lifetime, etc.). By keeping the concentration of the surfactant constant and changing the gas introduction rate, the surface tension at various surface lifetimes can be obtained. Also, by changing the concentration and repeating this, the relationship between the surface tension and the surface lifetime can be obtained for each concentration of the surfactant, and Figures 1 to 5 show this. Note that the surface tension reaches the equilibrium value as the surface lifetime increases.

[0082] As shown in Figures 1, 2, 3, 4, and 5, it was found that for all the surfactants in Example 1, Comparative Example 1, Comparative Example 2, Comparative Example 3, and Comparative Example 4, the higher the concentration, the faster the surface tension reaches the equilibrium value.

[0083] From the obtained values of the dynamic surface tension, for each concentration of each surfactant, the following equation was used to obtain the half-value γ τ was determined. γ τ =(γ0 + γ ∞ ) / 2 Here, γ0 is the surface tension value at the initial stage (surface lifetime = 15 ms), γ ∞ is the equilibrium surface tension value (static surface tension), and γ τ is the surface tension value when the surface tension value has decreased by half of the total decrease amount. τ (characteristic time) was determined as the surface lifetime when the surface tension value becomes γ τ . For systems where the dynamic surface tension value has completely dropped at the 15 ms time point at the start of the measurement, γ0 was calculated using the surface tension value of water (72 mN / m).

[0084] Figure 6 shows the relationship between the characteristic time τ of the surfactants in the examples and comparative examples, and the concentration of the surfactants. In Figure 6, the horizontal axis represents the concentration of the surfactant, the vertical axis represents the characteristic time τ, and the dotted line is an approximate straight line of the plot showing the relationship between the concentration of each surfactant and the characteristic time τ. From the results in Figure 6, in all concentration ranges, the characteristic time τ of the surfactant in Example 1 (BC4P-SiPSS) showed an unexpectedly remarkable characteristic, being about 1 / 10th that of the surfactant in the comparative example. A small characteristic time τ means that the time to reach the equilibrium surface tension value is short, which is useful in applications such as fire extinguishing agents, leveling agents, pesticides, pharmaceuticals, cosmetics, crude oil enhanced recovery, and cleaning agents.

[0085] The surface tension of aqueous solutions of the surfactant [BC4P-SiPSS] from Example 1, the surfactant [Mg(BC4P-SiPSS)2] from Example 2, and the surfactant [Ca(BC4P-SiPSS)2] from Example 3 was measured by the Whilhelmy method at 25°C. Figure 7 shows the surface tension of the aqueous solutions of Examples 1 to 3 at various concentrations.

[0086] Micelle formation concentration (CMC), surface tension value (γ) in CMC CMC ), molecular occupancy area in CMC (A min ) are shown in Table 1 below. Note that A min This was calculated from Gibbs' adsorption equation and the slope in Figure 7. As can be seen from Table 1, it was confirmed that exchanging a counterion for a divalent cation reduces the CMC by about 1 / 10 and increases surface activity. [Table 1]

[0087] [Evaluation of the effect of counterions on surface tension reduction ability] To investigate whether the surface tension reduction ability of the surfactant [BC4-SiPSS] in Example 1 is affected by the type of counterion, dynamic surface tension measurements were performed at 25°C using the maximum pressure method for the surfactant [Mg(BC4P-SiPSS)2] in Example 2 and the surfactant [Ca(BC4P-SiPSS)2] in Example 3. Figures 8 and 9 show the relationship between the surface tension and surface life of the surfactants in Example 2 and Example 3 at various concentrations, respectively. The horizontal axis represents surface life, and the vertical axis represents surface tension.

[0088] From Figures 1, 8, and 9, the initial surface tension value and the half-value γ from the equilibrium surface tension value are shown. τ The characteristic time τ, which is the time it takes to reach a certain state, was determined. Figure 10 shows the relationship between characteristic time τ and surfactant concentration. From Figure 10, it became clear that the characteristic time τ is reduced to less than 1 / 10 due to counterion exchange with the divalent cation.

[0089] However, as shown in Table 1, the CMC of the surfactant [Mg(BC4P-SiPSS)2] in Example 2 and the surfactant [Ca(BC4P-SiPSS)2] in Example 3 decreased by about 1 / 10, indicating an increase in the hydrophobicity of the surfactants. Therefore, this can be considered as an increase in adsorption rate due to that. So, the surfactant concentration on the horizontal axis was converted to a CMC standard and the relationship with the characteristic time was graphed. Figure 11 shows the relationship between the characteristic time τ of the surfactants in Examples 1 to 3 and the value when the surfactant concentration is corrected by the critical micelle concentration (CMC). As a result, when the surfactant concentration is reexpressed on a CMC standard and the effect of increased hydrophobicity is excluded, it was found that the characteristic time does not have much effect on counterion exchange with Ca and Mg.

Claims

1. A surfactant comprising a compound represented by the following general formula (1). 【Chemistry 1】 In general formula (1), R １０ and R ２ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 3 carbon atoms, or a heterohydrocarbon group having 1 to 3 carbon atoms. Incidentally, R １ and R ２ may together form a hydrocarbon ring or a heterocyclic ring. A is -SO ３ - or -OSO ３ -, M is an alkali metal, an alkaline earth metal or -N(R １０ )(R ４ each independently represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a hydroxylalkyl group having 1 to 3 carbon atoms.), n is an integer from 1 to 17, m is an integer from 1 to 17, respectively. l is 0 or 1, and when M is an alkali metal or -N(R １０ ), q is 1, and when M is an alkaline earth metal, q is 2.]​​​​

2. R １ and R ２ The surfactant according to claim 1, wherein both are hydrogen atoms.

3. The surfactant according to claim 1, wherein the sum of m and n is between 2 and 18.

4. The surfactant according to claim 1, wherein the difference between m and n is 0 to 3.

5. A is -SO ３ - The surfactant according to claim 1.

6. The surfactant according to claim 1, wherein M is sodium, calcium, or magnesium.

7. A compound represented by the following general formula (100a). 【Chemistry 2】

8. A compound represented by the following general formula (100b). 【Transformation 3】

9. A compound represented by the following general formula (100c). 【Chemistry 4】

10. A method for improving the rate at which the surface tension of water decreases, comprising adding a surfactant according to any one of claims 1 to 6 to water.

Images