Surfactant

Abstract

To provide a surfactant without fluorocarbon or polydimethylsiloxane chains, usable at a room temperature, and exhibiting a rapid rate of surface tension reduction.SOLUTION: The present invention provides a surfactant composed of a monovalent or polyvalent metal salt of a succinate diester sulfonic acid. All succinate diester backbones have one ester moiety bonded to a linear hydrocarbon group and the other bonded to a hydrocarbon group terminating in a trimethylsilyl group. A total number of carbon atoms in the linear hydrocarbon group and the hydrocarbon group terminating in the trimethylsilyl group is 5-15.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a surfactant. [Background technology]

[0002] Surfactants are amphiphilic molecules that have both hydrophilic and hydrophobic parts in the molecule, and are used as ingredients 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, lowering the surface tension of water and the interfacial tension of water / oil, and are effective in emulsification, solubilization, foaming, wetting, etc. If the surfactant has a high adsorption rate, it becomes possible to quickly stabilize the new surface / interface state that arises from emulsification, solubilization, foaming, wetting, etc. [Prior art documents] [Non-patent literature]

[0004] [Non-Patent Document 1] Tokiyuki Yoshida, "New Edition: Surfactants", Kogaku Tosho Publishing Co., Ltd., 2nd Edition Summary of the Invention [Problem to be solved by the invention]

[0005] According to the findings of the present inventors, the adsorption rate of the surfactant, i.e., the rate at which the 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 to a fluorocarbon chain or polydimethylsiloxane chain, which has a stronger hydrophobicity than a hydrocarbon group. There is also a method of introducing many methyl branches into the hydrophobic group, which increases the hydrophobicity while lowering the surface energy and also maintains water solubility.

[0006] However, when the hydrocarbon chain length is increased or when a fluorocarbon chain or polydimethylsiloxane chain is used, the hydrophobicity is strong, so the solubility in water is lost, the Krafft point (the minimum temperature at which an ionic surfactant forms micelles and begins to dissolve) becomes high, or the cloud point (the maximum temperature at which a nonionic surfactant begins to precipitate) becomes low. Therefore, it may not be possible to use the surfactant at room temperature.

[0007] Fluorocarbons do not normally exist in nature, so they are difficult to decompose and have a large environmental impact. There are also concerns about their impact on health, such as their bioaccumulation. On the other hand, polydimethylsiloxane chains are easily hydrolyzed in water, so their effectiveness does not last long after dissolving in water, making long-term storage difficult.

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

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

[19] . [1] A surfactant comprising a monovalent or polyvalent metal salt of succinic acid diester sulfonic acid (a surfactant comprising a sulfosuccinate diester), In all of the succinic acid diester skeletons, a linear hydrocarbon group is bonded to one of the ester groups in the skeleton, and a hydrocarbon group having a trimethylsilyl group terminal is bonded to the other ester group in the skeleton, The surfactant has a total of 5 to 15 carbon atoms contained in the linear hydrocarbon group and the hydrocarbon group having a trimethylsilyl group terminal. [2] The surfactant of [1], which is a sodium salt, a magnesium salt, or a calcium salt. [3] The surfactant according to [1] or [2], wherein, in each of the succinic acid diester skeletons, the difference between the number of carbon atoms contained in the linear hydrocarbon group and the number of carbon atoms contained in the hydrocarbon group having a trimethylsilyl group terminal is 0 to 5. [4] A compound represented by the following general formula (100a): [ka] [5] A compound represented by the following general formula (100b): [ka] [6] A compound represented by the following general formula (100c): [ka] [7] A compound represented by the following general formula (100d): [ka] [8] A compound represented by the following general formula (100e): [ka] [9] A compound represented by the following general formula (110a): [ka]

[10] A compound represented by the following general formula (110b): [ka]

[11] A compound represented by the following general formula (110c): [ka]

[12] A compound represented by the following general formula (110d): [ka]

[13] A compound represented by the following general formula (110e): [ka]

[14] A compound represented by the following general formula (111a): [ka]

[15] A compound represented by the following general formula (111b). [ka]

[16] A compound represented by the following general formula (111c): [ka]

[17] A compound represented by the following general formula (111d): [ka]

[18] A compound represented by the following general formula (111e): [ka]

[19] A method for improving the rate of reduction of the surface tension of water, comprising adding any one of the surfactants [1] to [3] to water. The compounds [4] to

[18] can be used as the surfactant described in [1].

[0010] The above surfactant is a surfactant in which a hydrocarbon group having a trimethylsilyl group and a straight-chain hydrocarbon group are hybridized, and has a high rate of reduction in the surface tension of water (adsorption rate).

[0011] Usually, in order to increase the adsorption rate, it is necessary to increase the hydrophobicity of the surfactant, but this method reduces the water solubility and makes it difficult to use. However, according to the present invention, the adsorption rate can be greatly increased without significantly changing the hydrophobicity or reducing the water solubility. The molecule is characterized by a "hybrid hydrophobic chain structure" with a "trimethylsilyl group," and has a structure in which two or more hydrophobic chains with poor compatibility coexist within the molecule. Effect of the Invention

[0012] According to the present invention, it is possible to provide a surfactant that does not have a fluorocarbon chain or a polydimethylsiloxane chain, can be used at room temperature (e.g., 25° C.), and has a high rate of surface tension reduction. In addition, since this surfactant can be produced using relatively inexpensive raw materials, it is easy to use as an industrial product and is highly useful. [Brief description of the drawings]

[0013] [Figure 1] FIG. 2 is a graph showing the relationship between surface tension and surfactant concentration when the surfactants of Examples 1 to 5 and Reference Example 1 were used. [Diagram 2] FIG. 1 is a graph showing the relationship between surface tension and surfactant concentration when the surfactants of Examples 6 to 10 were used. [Diagram 3] FIG. 1 is a graph showing the relationship between surface tension and surfactant concentration when the surfactants of Examples 11 to 15 were used. [Figure 4] FIG. 1 shows the relationship between the natural logarithm of the critical micelle concentration (CMC) and the carbon number of the linear hydrocarbon group of the surfactant and the total number of carbon atoms and silicon atoms (NC+Si) contained in the hydrocarbon group having a trimethylsilyl group terminal in Examples 1 to 15. [Diagram 5] FIG. 1 shows the relationship between the value of πCMC / Log(CMC×1010) and the carbon number of the linear hydrocarbon group of the surfactant and the total number of carbon atoms and silicon atoms (NC+Si) contained in the hydrocarbon group having a trimethylsilyl group terminal in Examples 1 to 15. [Figure 6]FIG. 1 is a graph showing the relationship between surface tension and surface life when the surfactant [SC5-SiPSS] of Example 1 is used. [Figure 7] FIG. 13 is a graph showing the relationship between surface tension and surface life when the surfactant [SC6-SiPSS] of Example 2 is used. [Figure 8] FIG. 13 is a graph showing the relationship between surface tension and surface life when the surfactant [SC7-SiPSS] of Example 3 is used. [Figure 9] FIG. 13 is a graph showing the relationship between surface tension and surface life when the surfactant [SC8-SiPSS] of Example 4 is used. [Figure 10] FIG. 13 is a graph showing the relationship between surface tension and surface life when the surfactant [SC9-SiPSS] of Example 5 is used. [Figure 11] FIG. 13 is a diagram showing the relationship between surface tension and surface life when the surfactant [Mg(SC5-SiPSS)2] of Example 6 is used. [Figure 12] FIG. 13 is a diagram showing the relationship between surface tension and surface life when the surfactant [Mg(SC6-SiPSS)2] of Example 7 is used. [Figure 13] FIG. 13 is a diagram showing the relationship between surface tension and surface life when the surfactant [Mg(SC7-SiPSS)2] of Example 8 is used. [Figure 14] FIG. 13 is a diagram showing the relationship between surface tension and surface life when the surfactant [Mg(SC8-SiPSS)2] of Example 9 is used. [Figure 15] FIG. 13 is a graph showing the relationship between surface tension and surface life when the surfactant [Mg(SC9-SiPSS)2] of Example 10 is used. [Figure 16] FIG. 13 is a graph showing the relationship between surface tension and surface life when the surfactant [Ca(SC5-SiPSS)2] of Example 11 is used. [Figure 17] FIG. 13 is a graph showing the relationship between surface tension and surface life when the surfactant [Ca(SC6-SiPSS)2] of Example 12 is used. [Figure 18]FIG. 13 is a graph showing the relationship between surface tension and surface life when the surfactant [Ca(SC7-SiPSS)2] of Example 13 is used. [Figure 19] FIG. 13 is a graph showing the relationship between surface tension and surface life when the surfactant [Ca(SC8-SiPSS)2] of Example 14 is used. [Figure 20] FIG. 13 is a graph showing the relationship between surface tension and surface life when the surfactant [Ca(SC9-SiPSS)2] of Example 15 is used. [Figure 21] FIG. 2 is a graph showing the relationship between the characteristic time τ and the concentration of a surfactant when the surfactants of Examples 1 to 5 and Reference Example 1 were used. [Figure 22] FIG. 1 is a graph showing the relationship between the characteristic time τ and the converted concentration obtained by correcting the surfactant concentration based on the critical micelle concentration (CMC) of the surfactant when the surfactants of Examples 1 to 5 and Reference Example 1 were used. [Diagram 23] FIG. 1 is a graph showing the relationship between the surface tension reduction rate R1 / 2 and the concentration of the surfactant when the surfactants of Examples 1 to 5 and Reference Example 1 were used. [Figure 24] FIG. 1 is a graph showing the relationship between the surface tension reduction rate R1 / 2 and the converted concentration obtained by correcting the surfactant concentration based on the critical micelle concentration (CMC) of the surfactant when the surfactants of Examples 1 to 5 and Reference Example 1 were used. [Diagram 25] FIG. 1 is a graph showing the relationship between the characteristic time τ and the concentration of the surfactant when the surfactants of Examples 6 to 10 were used. [Figure 26] FIG. 1 is a graph showing the relationship between the characteristic time τ and the converted concentration obtained by correcting the surfactant concentration based on the critical micelle concentration (CMC) of the surfactant when the surfactants of Examples 6 to 10 were used. [Figure 27] FIG. 1 is a graph showing the relationship between the surface tension reduction rate R1 / 2 and the surfactant concentration when the surfactants of Examples 6 to 10 were used. [Figure 28] FIG. 1 is a graph showing the relationship between the surface tension reduction rate R1 / 2 and the converted concentration obtained by correcting the surfactant concentration based on the critical micelle concentration (CMC) of the surfactant when the surfactants of Examples 6 to 10 were used. [Figure 29]FIG. 1 is a graph showing the relationship between the characteristic time τ and the concentration of the surfactant when the surfactants of Examples 11 to 15 were used. [Diagram 30] FIG. 1 is a graph showing the relationship between the characteristic time τ and the converted concentration obtained by correcting the surfactant concentration based on the critical micelle concentration (CMC) of the surfactant when the surfactants of Examples 11 to 15 were used. [Diagram 31] FIG. 1 is a graph showing the relationship between the surface tension reduction rate R1 / 2 and the surfactant concentration when the surfactants of Examples 11 to 15 were used. [Diagram 32] FIG. 1 shows the relationship between the surface tension reduction rate R1 / 2 and the converted concentration obtained by correcting the surfactant concentration based on the critical micelle concentration (CMC) of the surfactant when the surfactants of Examples 11 to 15 were used. [Diagram 33] These are photographs taken with a high-speed fluid behavior visualization system, showing the wetting behavior of a droplet on a hydrophobic solid surface. [Diagram 34] 1 is a graph showing the change over time in the spreading diameter Dt / D0 after the aqueous solutions containing the surfactants of Examples 1 to 5 and pure water collide with a hydrophobic solid surface. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] The surfactant according to the embodiment is a monovalent or polyvalent metal salt of succinic acid diester sulfonic acid, and is a compound in which, in all of the succinic acid diester skeletons, a straight-chain hydrocarbon group is bonded to one ester group in the skeleton and a hydrocarbon group having a trimethylsilyl group terminal is bonded to the other ester group, and the total number of carbon atoms contained in the straight-chain hydrocarbon group (hereinafter sometimes referred to as the "first hydrocarbon group") and the hydrocarbon group having a trimethylsilyl group terminal (hereinafter sometimes referred to as the "second hydrocarbon group") is 5 to 15.

[0015] The above surfactant does not have a fluorocarbon chain or a polydimethylsiloxane chain, can be used at room temperature, and has the characteristics of a high rate of surface tension reduction. Here, a high rate of surface tension reduction means, for example, a rate of surface tension reduction of 30 mN·m when the surfactant concentration is 0.1 mM to 2.0 mM. -1 s -1 This means that there exists a concentration where the rate of surface tension reduction is 30 mN m -1 s -1 The concentration of the surfactant at or above this level may be 0.5 mM to 2.0 mM, 0.7 mM to 2.0 mM, 0.7 mM to 1.5 mM, 0.8 mM to 1.2 mM, or 1.0 mM.

[0016] The surfactant according to the embodiment has a surface tension reduction rate of 50 mN·m in the above concentration range. -1 s -1 A surfactant with a concentration of 70 mN m or more and a surface tension reduction rate of 70 mN m -1 s -1 The surfactant has a concentration of 100 mN m or more, or the rate of surface tension reduction is 100 mN m -1 s -1 The surfactant may be present at a concentration equal to or greater than this.

[0017] The surfactant according to the embodiment has a surface tension reduction rate of 30 mN m when the ratio of the surfactant concentration to the CMC of the surfactant is 0.1 to 10. -1 s -1 The surfactant may be a surfactant having a surface tension reduction rate of 30 mN m when the ratio of the surfactant concentration to the CMC of the surfactant is 0.1 to 1. -1 s -1 It is preferable that the surfactant exists at a concentration equal to or higher than this.

[0018] The surfactant according to this embodiment can be represented, for example, by the following general formula (1). [ka]

[0019] The surfactant of the above general formula (1) can also be represented by the following general formula (1'). [ka]

[0020] In the above general formulas (1) and (1'), M is a q-valent metal atom, and q is an integer of 1 to 4. q may be 1 to 3 or 1 to 2. The surfactants represented by the above general formulas (1) and (1') have q succinic acid diester skeletons, and the total number of carbon atoms contained in the first hydrocarbon group and the second hydrocarbon group of each succinic acid diester skeleton is 5 to 15. The total number of carbon atoms contained in the first hydrocarbon group and the second hydrocarbon group of each succinic acid diester skeleton may be 6 to 15, 7 to 15, 8 to 15, 9 to 15, 10 to 15, or 11 to 15, and among these, the total number of carbon atoms contained in the first hydrocarbon group and the second hydrocarbon group is preferably 11 to 15. By setting the carbon number in this range, a faster surface tension reduction rate can be obtained.

[0021] In particular, when the total number of carbon atoms contained in the first hydrocarbon group and the second hydrocarbon group of each succinic acid diester skeleton is 11 to 13, a fast rate of surface tension reduction can be obtained before the surfactant forms micelles, and when the total number of carbon atoms contained in the first hydrocarbon group and the second hydrocarbon group of each succinic acid diester skeleton is 13 to 15, an especially fast rate of surface tension reduction can be obtained.

[0022] In general formula (1), m is an integer from 1 to 11, n is an integer from 1 to 10, and as long as the total number of carbon atoms contained in the first hydrocarbon group and the second hydrocarbon group is 5 to 15, m and n may be in any combination, m may be 2 to 6, 2 to 5, 2 to 4, 3 to 6, 3 to 5, or 3 to 4, and n may be 2 to 10, 3 to 10, 4 to 10, 5 to 9, 5 to 7, or 7 to 9.

[0023] When the total number of carbon atoms contained in the first hydrocarbon group and the second hydrocarbon group of each succinic acid diester skeleton is 5 to 15, the combination of (m,n) is (1,1), (2,1), (3,1), (4,1), (5,1), (6,1), (7,1), (8,1), (9,1), (10,1), (11,1), (1,2), (2,2), (3,2), (4,2), (5,2), (6,2), (7,2), (8,2), (9,2), (10,2), (1,3), (2,3), (3,3), (4,3), (5,3), (6,3), (7, 3), (8,3), (9,3), (1,4), (2,4), (3,4), (4,4), (5,4), (6,4), (7,4), (8,4), (1,5), (2,5), (3,5), (4,5), (5,5), (6,5), (7,5), (1,6), (2,6), (3,6), (4,6), (5,6), (6,6), (1,7), (2,7), (3,7), (4,7), (5,7), (1,8), (2,8), (3,8), (4,8), (1,9), (2,9), (3,9), (1,10), (2,10), and (1,11).

[0024] The difference between the number of carbon atoms contained in the first hydrocarbon group and the second hydrocarbon group of each succinic acid diester skeleton is preferably 0 to 5. In this case, m is an integer of 1 to 7, and n is an integer of 1 to 9. With such a configuration, the lengths of the two hydrophobic groups in one molecule become close to each other, and they are easily oriented as hydrophobic groups, resulting in an excellent speed of reducing the surface tension.

[0025] The pairs of (m,n) satisfying that the difference in the number of carbon atoms contained in the first hydrocarbon group and the second hydrocarbon group of each succinic acid diester skeleton is 0 to 5 are (1,1), (2,1), (3,1), (1,2), (2,2), (3,2), (4,2), (1,3), (2,3), (3,3), (4,3), (5,3), (1,4), (2,4), (3,4), (4,4), and (5,4). , (6,4), (1,5), (2,5), (3,5), (4,5), (5,5), (6,5), (7,5), (1,6), (2,6), (3,6), (4,6), (5,6), (6,6), (1,7), (2,7), (3,7), (4,7), (5,7), (1,8), (2,8), (3,8), (4,8), (1,9), (2,9), (3,9), and (2,10).

[0026] In general formula (1), when q is 1, M is an alkali metal, and when q is 2, M is an alkaline earth metal.

[0027] When M is an alkali metal, examples of M include sodium, potassium, and lithium, and sodium is typical. When M is an alkaline earth metal, examples of M include magnesium, calcium, and barium, and magnesium and calcium are typical.

[0028] One embodiment of the compound represented by general formula (1) is a compound represented by the following general formula (10), in which q is 1 and M is an alkali metal. Note that m and n, including preferred examples, are as defined above. [ka]

[0029] The compound represented by general formula (10) may have the following two types of isomers depending on the bonding position of -SO3-, but the compound represented by general formula (10) may be either isomer or a mixture of isomers. [ka]

[0030] One embodiment of the compound represented by general formula (1) is a compound represented by the following general formula (11), in which q is 2 and M is an alkaline earth metal. Note that m and n, including preferred examples, are as defined above. [ka]

[0031] The compound represented by general formula (11) may have the following three isomers depending on the bonding position of -SO3-, and the compound represented by general formula (11) may be any isomer or a mixture of isomers. [ka]

[0032] A preferred embodiment of the compound represented by the general formula (10) is, for example, a compound represented by the following formula (100a) in which m is 3, n is 5, and M is sodium. The compound represented by the formula (100a) may have the following two isomers depending on the bonding position of -SO3-, but the compound represented by the formula (100a) may be either isomer or a mixture of isomers. [ka] [ka]

[0033] A preferred embodiment of the compound represented by general formula (10) is, for example, a compound represented by the following formula (100b) in which m is 3, n is 6, and M is sodium. The compound represented by formula (100b) may have the following two isomers depending on the bonding position of -SO3-, but the compound represented by formula (100b) may be either isomer or a mixture of isomers. [ka] [ka]

[0034] A preferred embodiment of the compound represented by general formula (10) is, for example, a compound represented by the following formula (100c) in which m is 3, n is 7, and M is sodium. The compound represented by formula (100c) may have the following two isomers depending on the bonding position of -SO3-, but the compound represented by formula (100c) may be either isomer or a mixture of isomers. [ka] [ka]

[0035] A preferred embodiment of the compound represented by general formula (10) is, for example, a compound represented by the following formula (100d) in which m is 3, n is 8, and M is sodium. The compound represented by formula (100d) may have the following two isomers depending on the bonding position of -SO3-, but the compound represented by formula (100d) may be either isomer or a mixture of isomers. [ka] [ka]

[0036] A preferred embodiment of the compound represented by general formula (10) is, for example, a compound represented by the following formula (100e) in which m is 3, n is 9, and M is sodium. The compound represented by formula (100e) may have the following two isomers depending on the bonding position of -SO3-, but the compound represented by formula (100e) may be either isomer or a mixture of isomers. [ka] [ka]

[0037] A preferred embodiment of the compound represented by the general formula (11) is, for example, a compound represented by the following formula (110a) in which m is 3, n is 5, and M is magnesium. Note that the handling of isomers in all the preferred embodiments of the compound represented by the general formula (11) described below is as described above. [ka]

[0038] A preferred embodiment of the compound represented by general formula (11) is, for example, a compound represented by the following formula (110b) in which m is 3, n is 6, and M is magnesium. [ka]

[0039] A preferred embodiment of the compound represented by general formula (11) is, for example, a compound represented by the following formula (110c) in which m is 3, n is 7, and M is magnesium. [ka]

[0040] A preferred embodiment of the compound represented by general formula (11) is, for example, a compound represented by the following formula (110d) in which m is 3, n is 8, and M is magnesium. [ka]

[0041] A preferred embodiment of the compound represented by general formula (11) is, for example, a compound represented by the following formula (110e) in which m is 3, n is 9, and M is magnesium. [ka]

[0042] A preferred embodiment of the compound represented by general formula (11) is, for example, a compound represented by the following formula (111a) in which m is 3, n is 5, and M is calcium. [ka]

[0043] A preferred embodiment of the compound represented by general formula (11) is, for example, a compound represented by the following formula (111b) in which m is 3, n is 6, and M is calcium. [ka]

[0044] A preferred embodiment of the compound represented by general formula (11) is, for example, a compound represented by the following formula (111c) in which m is 3, n is 7, and M is calcium. [ka]

[0045] A preferred embodiment of the compound represented by general formula (11) is, for example, a compound represented by the following formula (111d) in which m is 3, n is 8, and M is calcium. [ka]

[0046] A preferred embodiment of the compound represented by general formula (11) is, for example, a compound represented by the following formula (111e) in which m is 3, n is 9, and M is calcium. [ka]

[0047] Among the compounds represented by general formula (1), a compound represented by general formula (10) in which q is 1 and M is an alkali metal can be synthesized, for example, by the following reaction scheme. [ka]

[0048] Of the compounds represented by general formula (1), compounds in which M is magnesium or calcium and q is 2 can be prepared by adding a saturated Mg(NO3)2 or saturated Ca(NO3)2 solution to the above product and reacting them.

[0049] The compound of the present invention may be used together 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, organic fine particles, inorganic fine particles, polymers, hydrotropes, dyes, cosolvents such as higher alcohols, cosurfactants, etc.) can also be added. Applications of the surfactants made of the compounds represented by general formula (1) include fire extinguishing agents, leveling agents, agents for enhanced crude oil recovery, agricultural chemicals, pharmaceuticals, cosmetics, cleaning agents, water repellent agents, hydrophilic agents, emulsifiers, dispersants, foaming agents, etc.

[0050] The method for improving the rate of reduction of the surface tension of water of the present invention includes adding the surfactant of the present invention. By adding the surfactant of the present invention, the surfactant can be used at room temperature even though it does not have a fluorocarbon chain or a polydimethylsiloxane chain, and the rate of reduction of the surface tension of water is improved due to the presence of the surfactant of the present invention. EXAMPLES

[0051] The present invention will be described in more detail below with reference to examples, although the present invention is not limited to the following examples.

[0052] The compounds were synthesized by the methods described in Examples 1 to 15 and Reference Example 1. The following samples were used for synthesis and measurement. [Samples for synthesis and measurement] 1-pentanol C5H 12 O = 88.15 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., purity 98.0% or more) 1-Hexanol C6H 14 O = 102.17 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., purity 97.0% or more) 1-heptanol C7H 16 O = 116.20 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., purity 98.0% or more) 1-octanol C8H 18 O = 130.23 (Tokyo Chemical Industry Co., Ltd., purity 99.0% or more) 1-nonanol C9H 20 O = 144.26 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., purity 95.0% or more) ·3-(trimethylsilyl)propan-1-olC6H 16 OSi=132.28SIGMA-ALDRICH Co., Ltd., purity 97.0% Maleic anhydride C4H2O3 = 98.06 Fujifilm Wako Pure Chemical Industries, Ltd., purity 99.0% 4-DimethylaminopyridineC7H 10 N2=122.17 Kanto Chemical Co., Ltd., purity 99.0% ·1-(3-Dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride C8H 17 N3·HCl=191.71 Watanabe Chemical Industry Co., Ltd., purity 98.0% Sodium bisulfite NaHSO3 = 104.06 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% Magnesium nitrate Mg(NO3)2=148.30 Fujifilm Wako Pure Chemical Industries, Ltd. Calcium nitrate Ca(NO3)2=164.088 Fujifilm Wako Pure Chemical Industries, Ltd.

[0053] The synthesized compounds were purified by column chromatography using silica gel (63-210 μm) (KANTOCHEMICAL Co. INK.). The structures were then confirmed by nuclear magnetic resonance (NMR) spectroscopy and infrared (IR) spectroscopy, and the purity was confirmed by organic microanalysis. The measurements were performed under the following conditions.

[0054] [Measurement conditions] NMR spectra were measured using a JEOL (Japan Electron Corporation) instrument under the trade name "JMN-GX400" or the same company's trade name "JMN-ECZ400". Chemical shifts are expressed in parts per million (ppm). Tetramethylsilane (TMS) was used as an internal standard. Coupling constants (J) are shown in Hertz, and the abbreviations s, d, t, q, and m stand for singlet, doublet, triplet, quartet, and multiplet, respectively. IR spectra were measured using a BIO-RAD instrument under the trade name "FTS-30". Purity was confirmed by organic trace element analysis (EA1110, CE Instrumental Acom Co., Ltd.).

[0055] [Surfactant SC n -Synthesis of SiPSS] Surfactant SCn Each of the -SiPSS (n=5 to 9) was synthesized according to the following scheme: The synthesis procedures for the surfactants of Examples 1, 2, 3, 4, and 5 are described in detail below. [ka]

[0056] Example 1: Synthesis of SC5-SiPSS SC5-SiPSS was synthesized by a method including the following three steps.

[0057] [Step 1] Synthesis of 1-pentylhydrogen maleate (SC5M) 1-pentanol (3.09g, 35.0mmol) and maleic anhydride (4.90g, 50.0mmol) were added to 30mL of hexane and stirred and refluxed at 90℃ for 24 hours. After the reaction, unreacted maleic anhydride was extracted from the reaction solution using a separatory funnel with diethyl ether and a saturated aqueous solution of NaCl adjusted to pH 2. Anhydrous magnesium sulfate was added to the organic layer to dehydrate it, and then it was filtered and concentrated under reduced pressure. The resulting solution was purified by column chromatography using a developing solvent of hexane:ethyl acetate = 2:1 to obtain a colorless, transparent liquid SC5M (4.37g, yield 67.1%).

[0058] SC5M 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:6.45(dd,2H,-C H =C H -,J=13.2Hz,J=12.6Hz),4.32(t,2H,-OC H 2-,J=6.9Hz),1.78-1.72(m,2H,-O-CH2-C H 2-),1.40-1.37(m,4H,-O-CH2-CH2-(C H 2)2-CH3),0.96-0.90(m,3H,-O-(CH2)4-C H 3) Elemental analysis (C9H14 O4) C / 56.83%, H / 7.11% (theoretical values: C / 58.05%, H / 7.58%)

[0059] [Step 2] Synthesis of 1-(3-(trimethylsilyl)-1-propyl)-4-(1-pentyl)maleate (SC5-SiPM) The synthesized SC5M (3.00g, 16.1mmol), 3-(trimethylsilyl)propanol (2.65g, 20.0mmol), and p-toluenesulfonic acid (1.31g, 7.36mmol) were dissolved in 100mL of toluene and stirred at 120℃ for 24 hours using a Dean-Stark apparatus. Unreacted p-toluenesulfonic acid was extracted from the reaction solution using a saturated aqueous solution of NaCl, and the organic layer was dehydrated by adding anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The resulting solution was purified by column chromatography using a developing solvent of hexane:ethyl acetate = 4:1 to obtain a colorless, transparent liquid SC5-SiPM (3.33g, yield 68.8%).

[0060] SC5-SiPM 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:6.87(s,2H,-C H =C H -), 4.23-4.16(m,4H,-OC H 2-CH2-CH2-Si(CH3)3,-OC H 2-(CH2)3-CH3),1.72-1.66(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)2-CH3),1.40-1.37(m,4H,-O-CH2-CH2-(C H 2)2-CH3),0.95-0.93(m,3H,-O-(CH2)4-C H 3),0.55-0.52(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H3)3)

[0061] [Step 3] Synthesis of sodium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-pentyl) sulfosuccinate (SC5-SiPSS) The synthesized SC5-SiPM (2.85 g, 9.32 mmol) was dissolved in 100 mL of ethanol, mixed with NaHSO3 / water (9.70 g / 100 mL), and stirred and refluxed at 110°C for 16 hours. The reaction solution was concentrated under reduced pressure, dried in vacuum, and then filtered using hexane to remove unreacted NaHSO3. The filtrate was concentrated and the unreacted intermediate product was removed from the compound obtained by column chromatography using a 1:1 mixture of hexane and ethyl acetate as the developing solvent. The developing solvent was then changed to methanol for purification, yielding a white solid SC5-SiPSS (1.84 g, 85.8% yield).

[0062] SC5-SiPSS 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.34(m,1H,-CH2-C H (SO3Na)-), 4.17-4.13(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.05-4.01(m,2H,-OC H 2-(CH2)3-CH3),3.23-3.13(m,2H,-CH(SO3Na)-C H 2-), 1.61-1.60(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)2-CH3),1.33-1.32(m,4H,-O-CH2-CH2-(C H 2)2-CH3),0.93-0.89(m,3H,-O-(CH2)4-C H 3),0.49-0.45(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) IR(KBr)ν max / cm-1 :2954(-CH3),2873(-CH2),1734(C=O,-COO-),1247(O=S=O),1051(O=S=O) Elemental analysis (C 15 H 29 NaO7SSi) C / 43.30%, H / 6.96%, S / 7.88% (theoretical values: C / 44.53%, H / 7.23%, S / 7.93%)

[0063] (Example 2) Synthesis of SC6-SiPSS SC6-SiPSS was synthesized by a method including the following three steps.

[0064] [Step 1] Synthesis of 1-hexylhydrogen maleate (SC6M) 1-Hexanol (3.72g, 36.4mmol) and maleic anhydride (5.14g, 52.4mmol) were added to 30mL of hexane and stirred and refluxed at 90℃ for 24 hours. After the reaction, unreacted maleic anhydride was extracted from the reaction solution using a separatory funnel with diethyl ether and a saturated aqueous solution of NaCl adjusted to pH 2. Anhydrous magnesium sulfate was added to the organic layer to dehydrate it, and then it was filtered and concentrated under reduced pressure. The resulting solution was purified by column chromatography using a developing solvent of hexane:ethyl acetate = 2:1 to obtain a colorless, transparent liquid SC6M (5.09g, yield 69.9%).

[0065] SC6M 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:6.44(dd,2H,-C H =C H -,J=12.6Hz,J=13.2Hz),4.30(t,2H,-OC H 2-,J=6.9Hz)1.76-1.71(m,2H,-O-CH2-C H 2-),1.43-1.32(m,6H,-O-CH2-CH2-(C H 2)3-CH3),0.93-0.90(m,3H,-O-(CH2)5-C H3) Elemental analysis (C 10 H 16 O4) C / 58.33%, H / 7.30% (theoretical values: C / 59.98%, H / 8.05%)

[0066] [Step 2] Synthesis of 1-(3-(trimethylsilyl)-1-propyl)-4-(1-hexyl)maleate (SC6-SiPM) The synthesized SC6M (3.82 g, 19.8 mmol), 3-(trimethylsilyl)propanol (2.65 g, 20.0 mmol), and p-toluenesulfonic acid (1.81 g, 9.5 mmol) were dissolved in 100 mL of toluene and stirred for 24 hours at 120°C using a Dean-Stark apparatus. Unreacted p-toluenesulfonic acid was extracted from the reaction solution using a saturated aqueous solution of NaCl. Anhydrous magnesium sulfate was added to the organic layer to dehydrate it, and then it was filtered and concentrated under reduced pressure. The resulting solution was purified by column chromatography using a developing solvent of hexane:ethyl acetate = 4:1 to obtain a colorless transparent liquid SC6-SiPM (2.18 g, yield 36.5%).

[0067] SC6-SiPM 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:6.87(s,2H,-C H =C H -), 4.22-4.16(m,4H,-OC H 2-CH2-CH2-Si(CH3)3,-OC H 2-(CH2)4-CH3),1.71-1.65(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)3-CH3),1.38-1.32(m,6H,-O-CH2-CH2-(C H 2)3-CH3),0.92-0.89(m,3H,-O-(CH2)5-C H 3),0.55-0.51(m,2H,-O-CH2-CH2-C H2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) Elemental analysis (C 16 H 30 O4Si) C / 60.89%, H / 9.65% (theoretical values: C / 61.10%, H / 9.62%)

[0068] [Step 3] Synthesis of sodium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-hexyl) sulfosuccinate (SC6-SiPSS) The synthesized SC6-SiPM (2.18 g, 6.9 mmol) was dissolved in 100 mL of ethanol, mixed with NaHSO3 / water (7.20 g / 100 mL), and stirred and refluxed at 110°C for 16 hours. The reaction solution was concentrated under reduced pressure, vacuum dried, and then filtered using hexane to remove unreacted NaHSO3. The filtrate was concentrated and the unreacted intermediate product was removed from the compound obtained by column chromatography using a hexane:ethyl acetate = 1:1 developing solvent. The developing solvent was then changed to methanol and the product was purified to obtain a white solid SC6-SiPSS (2.66 g, 91.9% yield).

[0069] SC6-SiPSS 1 HNMR (500MHz, CDCl3, TMS) H / ppm:4.33(m,1H,-CH2-C H (SO3Na)-), 4.19-4.13(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.06-4.01(m,2H,-OC H 2-(CH2)4-CH3),3.23-3.12(m,2H,-CH(SO3Na)-C H 2-), 1.61-1.60(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)3-CH3),1.33-1.32(m,6H,-O-CH2-CH2-(C H2)3-CH3),0.90-0.89(m,3H,-O-(CH2)5-C H 3),0.49-0.47(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) IR(KBr)ν max / cm -1 :2954(-CH3),2859(-CH2),1736(C=O,-COO-),1248(O=S=O),1054(O=S=O) Elemental analysis (C 16 H 31 NaO7SSi) C / 45.92%, H / 6.97%, S / 7.53% (theoretical values: C / 45.91%, H / 7.47%, S / 7.66%)

[0070] (Example 3) Synthesis of SC7-SiPSS SC7-SiPSS was synthesized by a method including the following three steps.

[0071] [Step 1] Synthesis of 1-heptylhydrogen maleate (SC7M) 1-heptanol (6.04 g, 52.0 mmol) and maleic anhydride (5.10 g, 52.0 mmol) were added to 30 mL of hexane, and the mixture was 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 diethyl ether and a saturated aqueous solution of NaCl adjusted to pH 2. Anhydrous magnesium sulfate was added to the organic layer to dehydrate it, and then it was filtered and concentrated under reduced pressure. The resulting solution was purified by column chromatography using a developing solvent of hexane:ethyl acetate = 2:1 to obtain a white solid SC7M (8.18 g, yield 73.4%).

[0072] SC7M 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:6.45(dd,2H,-C H =C H-,J=12.6Hz,J=12.6Hz),4.30(t,2H,-OC H 2-,J=6.9Hz),1.76-1.71(m,2H,-O-CH2-C H 2-),1.38-1.31(m,8H,-O-CH2-CH2-(C H 2)4-CH3),0.92-0.89(m,3H,-O-(CH2)6-C H 3) Elemental analysis (C 11 H 18 O4) C / 61.61%, H / 8.36% (theoretical value: C / 61.66%, H / 8.47%)

[0073] [Step 2] Synthesis of 1-(3-(trimethylsilyl)-1-propyl)-4-(1-heptyl)maleate (SC7-SiPM) The synthesized SC7M (3.07 g, 14.3 mmol), 3-(trimethylsilyl)propanol (1.90 g, 14.3 mmol), and p-toluenesulfonic acid (1.31 g, 6.9 mmol) were dissolved in 100 mL of toluene and stirred for 24 hours at 120°C using a Dean-Stark apparatus. Unreacted p-toluenesulfonic acid was extracted from the reaction solution using a saturated aqueous solution of NaCl. Anhydrous magnesium sulfate was added to the organic layer to dehydrate it, and then it was filtered and concentrated under reduced pressure. The resulting solution was purified by column chromatography using a developing solvent of hexane:ethyl acetate = 4:1 to obtain a colorless transparent liquid SC7-SiPM (3.24 g, yield 68.9%).

[0074] SC7-SiPM 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:6.87(s,2H,-C H =C H -), 4.22-4.15(m,4H,-OC H 2-CH2-CH2-Si(CH3)3,-OC H 2-(CH2)5-CH3),1.71-1.65(m,4H,-O-CH2-CH 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)4-CH3),1.38-1.28(m,8H,-O-CH2-CH2-(C H 2)4-CH3),0.91-0.88(m,3H,-O-(CH2)6-C H 3),0.55-0.51(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) Elemental analysis (C 17 H 32 O4Si) C / 62.96%, H / 9.14% (theoretical value: C / 62.15%, H / 9.82%)

[0075] [Step 3] Synthesis of sodium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-heptyl) sulfosuccinate (SC7-SiPSS) The synthesized SC7-SiPM (3.24 g, 9.87 mmol) was dissolved in 100 mL of ethanol, mixed with NaHSO3 / water (10.27 g / 100 mL), and stirred and refluxed at 110°C for 20 hours. The reaction solution was concentrated under reduced pressure, dried in vacuum, and then filtered using hexane to remove unreacted NaHSO3. The filtrate was concentrated and the unreacted intermediate product was removed from the compound obtained by column chromatography using a 1:1 mixture of hexane and ethyl acetate as the developing solvent. The developing solvent was then changed to methanol and the product was purified to obtain a white solid SC7-SiPSS (1.84 g, 43.2% yield).

[0076] SC7-SiPSS 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.32(m,1H,-CH2-C H (SO3Na)-), 4.15-4.11(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.00-4.05(m,2H,-OC H2-(CH2)5-CH3),3.22-3.11(m,2H,-CH(SO3Na)-C H 2-), 1.59-1.61(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)4-CH3),1.29-1.28(m,8H,-O-CH2-CH2-(C H 2)4-CH3),0.91-0.87(m,3H,-O-(CH2)6-C H 3),0.48-0.45(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) IR(KBr)ν max / cm -1 :2954(-CH3),2929,2857(-CH2),1735(C=O,-COO-),1247(O=S=O),1052(O=S=O) Elemental analysis (C 17 H 33 NaO7SSi) C / 45.34%, H / 7.48%, S / 7.23% (theoretical values: C / 47.20%, H / 7.69%, S / 7.41%)

[0077] Example 4: Synthesis of SC8-SiPSS SC8-SiPSS was synthesized by a method including the following three steps.

[0078] [Step 1] Synthesis of 1-octylhydrogen maleate (SC8M) 1-octanol (5.10g, 52.0mmol) and maleic anhydride (6.80g, 52.0mmol) were added to 30mL of hexane, and the mixture was stirred and refluxed at 90℃ for 24 hours. After the reaction, unreacted maleic anhydride was extracted from the reaction solution using a separatory funnel with diethyl ether and a saturated aqueous solution of NaCl adjusted to pH 2. Anhydrous magnesium sulfate was added to the organic layer to dehydrate it, and then it was filtered and concentrated under reduced pressure. The resulting solution was purified by column chromatography using a developing solvent of hexane:ethyl acetate = 2:1 to obtain a white solid SC8M (9.60g, yield 80.2%).

[0079] SC8M 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:6.45(dd,2H,-C H =C H -,J=13.6Hz,J=13.6Hz),4.31(t,2H,-OC H 2-,J=6.6Hz),1.77-1.71(m,2H,-O-CH2-C H 2-),1.39-1.29(m,10H,-O-CH2-CH2-(C H 2)5-CH3),0.92-0.89(m,3H,-O-(CH2)7-C H 3)

[0080] [Step 2] Synthesis of 1-(3-(trimethylsilyl)-1-propyl)-4-(1-octyl)maleate (SC8-SiPM) The synthesized SC8M (3.14 g, 13.6 mmol), 3-(trimethylsilyl)propanol (1.85 g, 14.0 mmol), and p-toluenesulfonic acid (1.30 g, 6.9 mmol) were dissolved in 100 mL of toluene and stirred at 120 °C for 24 hours using a Dean-Stark apparatus. Unreacted p-toluenesulfonic acid was extracted from the reaction solution using a saturated aqueous solution of NaCl. Anhydrous magnesium sulfate was added to the organic layer to dehydrate it, and then it was filtered and concentrated under reduced pressure. The resulting solution was purified by column chromatography using a developing solvent of hexane:ethyl acetate = 4:1 to obtain a colorless transparent liquid SC8-SiPM (1.10 g, yield 23.6%).

[0081] SC8-SiPM 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:6.87(s,2H,-C H =C H -), 4.22-4.15(m,4H,-OC H 2-CH2-CH2-Si(CH3)3,-OC H 2-(CH2)6-CH3),1.70-1.65(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)5-CH3),1.36-1.30(m,10H,-O-CH2-CH2-(C H 2)5-CH3),0.91-0.88(m,3H,-O-(CH2)7-C H 3),0.54-0.51(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3)

[0082] [Step 3] Synthesis of sodium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-octyl) sulfosuccinate (SC8-SiPSS) The synthesized SC8-SiPM (1.10 g, 3.22 mmol) was dissolved in 100 mL of ethanol, mixed with NaHSO3 / water (3.10 g / 100 mL), and stirred and refluxed at 110°C for 24 hours. The reaction solution was concentrated under reduced pressure, vacuum dried, and then filtered using hexane to remove unreacted NaHSO3. The filtrate was concentrated and the unreacted intermediate product was removed from the compound obtained by column chromatography using a developing solvent of hexane:ethyl acetate = 1:1. The developing solvent was then changed to methanol and the product was purified to obtain a white solid SC8-SiPSS (0.50 g, yield 34.7%).

[0083] SC8-SiPSS 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.33(m,1H,-CH2-C H (SO3Na)-), 4.15-4.11(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.05-4.00(m,2H,-OC H 2-(CH2)6-CH3),3.20-3.11(m,2H,-CH(SO3Na)-C H 2-), 1.61-1.60(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)5-CH3),1.29-1.28(m,10H,-O-CH2-CH2-(C H 2)5-CH3),0.91-0.88(m,3H,-O-(CH2)7-C H 3),0.48-0.45(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) IR(KBr)ν max / cm -1 :2925(-CH3),2856(-CH2),1733(C=O,-COO-),1245(O=S=O),1052(O=S=O) Elemental analysis (C 18 H 35 NaO7SSi) C / 46.14%, H / 7.89%, S / 7.32% (theoretical values: C / 48.41%, H / 7.90%, S / 7.18%)

[0084] (Example 5) Synthesis of SC9-SiPSS SC9-SiPSS was synthesized by a method including the following three steps.

[0085] [Step 1] Synthesis of 1-nonylhydrogen maleate (SC9M) 1-nonanol (5.95g, 41.2mmol) and maleic anhydride (4.05g, 41.2mmol) were added to 30mL of hexane, and the mixture was stirred and refluxed at 90℃ for 24 hours. After the reaction, the unreacted maleic anhydride was extracted from the reaction solution using a separatory funnel with diethyl ether and a saturated aqueous solution of NaCl adjusted to pH 2. The organic layer was dehydrated by adding anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The resulting solution was purified by column chromatography using a developing solvent of hexane:ethyl acetate = 2:1 to obtain a white solid SC9M (6.68g, yield 67.0%).

[0086] SC9M 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:6.45(dd,2H,-C H =C H -,J=12.6Hz,J=13.6Hz),4.31(t,2H,-OC H 2-,J=6.6Hz),1.77-1.71(m,2H,-O-CH2-C H 2-),1.39-1.29(m,12H,-O-CH2-CH2-(C H 2)6-CH3),0.91-0.88(m,3H,-O-(CH2)8-C H 3)

[0087] [Step 2] Synthesis of 1-(3-(trimethylsilyl)-1-propyl)-4-(1-nonyl)maleate (SC9-SiPM) The synthesized SC9M (3.00g, 12.4mmol), 3-(trimethylsilyl)propanol (1.64g, 12.4mmol), and p-toluenesulfonic acid (1.17g, 6.2mmol) were dissolved in 100mL of toluene and stirred at 120℃ for 24 hours using a Dean-Stark apparatus. Unreacted p-toluenesulfonic acid was extracted from the reaction solution using a saturated aqueous solution of NaCl. Anhydrous magnesium sulfate was added to the organic layer to dehydrate it, and then it was filtered and concentrated under reduced pressure. The resulting solution was purified by column chromatography using a developing solvent of hexane:ethyl acetate = 4:1 to obtain a colorless transparent liquid SC9-SiPM (2.52g, yield 57.0%).

[0088] SC9-SiPM 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:6.88(s,2H,-C H =C H -), 4.22-4.16(m,4H,-OC H 2-CH2-CH2-Si(CH3)3,-OC H 2-(CH2)7-CH3),1.72-1.66(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)6-CH3),1.39-1.29(m,12H,-O-CH2-CH2-(C H 2)6-CH3),0.91-0.89(m,3H,-O-(CH2)8-C H 3),0.55-0.52(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) Elemental analysis (C 19 H 37 NaO7SSi) C / 47.00%, H / 8.08%, S / 7.08% (theoretical values: C / 49.54%, H / 8.10%, S / 6.96%)

[0089] [Step 3] Synthesis of sodium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-octyl) sulfosuccinate (SC9-SiPSS) The synthesized SC9-SiPM (2.52 g, 7.06 mmol) was dissolved in 100 mL of ethanol, mixed with NaHSO3 / water (7.35 g / 100 mL), and stirred and refluxed at 110°C for 24 hours. The reaction solution was concentrated under reduced pressure, dried in vacuum, and then filtered using hexane to remove unreacted NaHSO3. The filtrate was concentrated and the unreacted intermediate product was removed from the compound obtained by column chromatography using a 1:1 mixture of hexane and ethyl acetate as the developing solvent. The developing solvent was then changed to methanol and the product was purified to obtain a white solid SC9-SiPSS (2.17 g, 66.8% yield).

[0090] SC9-SiPSS 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.33(m,1H,-CH2-C H (SO3Na)-), 4.19-4.13(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.05-3.99(m,2H,-OC H 2-(CH2)7-CH3),3.23-3.12(m,2H,-CH(SO3Na)-C H 2-), 1.62-1.60(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)6-CH3),1.30-1.28(m,12H,-O-CH2-CH2-(C H 2)6-CH3),0.91-0.88(m,3H,-O-(CH2)8-C H 3),0.49-0.45(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) IR(KBr)ν max / cm -1:2923(-CH3),2854(-CH2),1734(C=O,-COO-),1246(O=S=O),1053(O=S=O)

[0091] (Reference Example 1) Synthesis of BC4P-SiPSS BC4P-SiPSS was synthesized by a three-step method according to the following reaction scheme. [ka]

[0092] [Step 1] Synthesis of 3-(trimethylsilyl)-1-propylhydrogenmaleate (SiPM) 3-(trimethylsilyl)propan-1-ol (5.05g, 38.18mmol) and maleic anhydride (5.02g, 75.57mmol) were stirred and refluxed at 90℃ for 24 hours. After the reaction, the unreacted maleic anhydride was extracted from the reaction solution using a separatory funnel with a saturated NaCl aqueous solution adjusted to pH 1 and diethyl ether. Anhydrous sodium sulfate was added to the organic layer, which was then dehydrated, filtered, and concentrated. The product was then purified using HPLC to obtain SiPM (3-(trimethylsilyl)-1-propylhydrogenmaleate) (3.18g, yield 36.1%) as a colorless, transparent liquid.

[0093] SiPM 1 HNMR(500MHz,CDCl3,TMS):δH / ppm:6.41(dd,2H,-C H =C H -,J=39.5Hz,J=12.6Hz),4.23(t,2H,-OC H 2-,J=7.2Hz),1.72-1.66(m,2H,-O-CH2-C H 2-), 0.52-0.49(m, 2H, -C H 2-C(CH3)3), 0.00(s, 9H, -Si(C H 3)3) IR(KBr)νmax / cm -1:3192(-OH),2954(CH),1734(C=O,-COO-),1631(C=C)

[0094] [Step 2] Synthesis of 1-(3-(trimethylsilyl)-1-propyl)-4-(4,4-dimethylpent-1-yl)fumarate (BC4P-SiPF) Next, the synthesized 3-(trimethylsilyl)-1-propylhydrogenmaleate (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-ethylcarbodiimide hydrochloride (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. The filtrate was concentrated and then purified by column chromatography using toluene as a developing solvent to obtain BC4P-SiPF(1-(3-(trimethylsilyl)-1-propyl)-4-(4,4-dimethylpent-1-yl)fumarate) (4.53 g, yield 42.2%) as a colorless, transparent liquid.

[0095] BC4P-SiPF 1 HNMR(500MHz,CDCl3,TMS):δH / ppm:6.85(s,2H,-C H =C H -), 4.17(t,2H,-OC H 2-CH2-CH2-Si(CH3)3,J=6.9Hz),4.15(t,2H,-OC H 2-CH2-CH2-C(CH3)3,J=6.9Hz),1.68-1.63(m,4H,-O-CH2-C H 2-), 1.25-1.22(m,2H,-C H 2-C(CH3)3), 0.89(s, 9H, -C(C H3)3),0.53-0.49(m,2H,-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) IR(KBr)νmax / cm -1 :2955(CH),1724(C=O,-COO-),1646(C=C)

[0096] [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), and NaHSO3 / water (7.59 g, 49.1 mmol / 75 mL) was added, followed by stirring and refluxing at 110°C for 24 hours. The reaction solution was concentrated and then vacuum dried at 50°C for 24 hours, and unreacted NaHSO3 was removed by filtration using dichloromethane. After concentrating the filtrate, the unreacted intermediate product was removed by column chromatography using toluene as a developing solvent, and then methanol was used as a developing solvent to obtain a white solid. 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%).

[0097] BC4P-SiPSS 1 HNMR(500MHz,CDCl3,TMS):δH / ppm:4.36-4.33(m,1H,-CH2-C H (SO3Na)-), 4.18-4.13(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.05-4.00(m,2H,-OC H2-CH2-CH2-C(CH3)3),3.24-3.12(m,2H,-CH(SO3Na)-C H 2-), 1.65-1.55(m,4H,-O-CH2-C H 2-), 1.22-1.17(m,2H,-C H 2-C(CH3)3), 0.89(s, 9H, -C(C H 3)3),0.50-0.45(m,2H,-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) IR(KBr)νmax / cm -1 :2952(CH),1736(C=O,-COO-),1248(O=S=O),1055(O=S=O)

[0098] [Surfactant Mg(SC n Synthesis of -SiPSS2 Surfactant Mg(SC n Each of the surfactants, SiPSS)2 (n=5 to 9), was synthesized according to the following scheme. The synthesis procedures for the surfactants in Examples 6, 7, 8, 9, and 10 are shown in detail below. [ka]

[0099] (Example 6) Synthesis of Mg(SC5-SiPSS)2 SC5-SiPSS was synthesized by the method described in Example 1. SC5-SiPSS (0.7300 g, 1.80 mmol) was dissolved in a minimum amount of ethanol (5 mL), added to 5 mL of saturated Mg(NO3)2 solution, and stirred for 24 hours. The target substance was then extracted into toluene using a separatory funnel, and after removing the aqueous layer, saturated MgCl2 solution was added to extract and remove unreacted SC5-SiPSS into the aqueous layer. Anhydrous magnesium sulfate was added to the organic layer for dehydration, followed by filtration and concentration under reduced pressure to obtain white solid magnesium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-pentyl) sulfosuccinate (Mg(SC5-SiPSS)2) (0.6195 g, yield 87.2%).

[0100] Mg(SC5-SiPSS)2 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.34(m,1H,-CH2-C H (SO3Mg)-), 4.17-4.13(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.05-4.01(m,2H,-OC H 2-(CH2)3-CH3),3.23-3.13(m,2H,-CH(SO3Mg)-C H 2-), 1.61-1.60(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)2-CH3),1.33-1.32(m,4H,-O-CH2-CH2-(C H 2)2-CH3),0.93-0.89(m,3H,-O-(CH2)4-C H 3),0.49-0.45(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) Elemental analysis (C 30 H 58 O 14 S2Si2Mg) C / 45.54%, H / 7.28%, S / 8.00% (theoretical values: C / 45.76%, H / 7.43%, S / 8.15%)

[0101] (Example 7) Synthesis of Mg(SC6-SiPSS)2 SC6-SiPSS was synthesized by the method described in Example 2. SC6-SiPSS (0.7522 g, 1.80 mmol) was dissolved in a minimum amount of ethanol (5 mL), added to 5 mL of saturated Mg(NO3)2 solution, and stirred for 24 hours. The target substance was then extracted into toluene using a separatory funnel, and after removing the aqueous layer, saturated MgCl2 solution was added to extract and remove unreacted SC6-SiPSS into the aqueous layer. Anhydrous magnesium sulfate was added to the organic layer for dehydration, followed by filtration and concentration under reduced pressure to obtain white solid Magnesium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-hexyl) sulfosuccinate (Mg(SC6-SiPSS)2) (0.5217 g, 71.2% yield).

[0102] Mg(SC6-SiPSS)2 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.33(m,1H,-CH2-C H (SO3Mg)-), 4.19-4.13(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.06-4.01(m,2H,-OC H 2-(CH2)4-CH3),3.23-3.12(m,2H,-CH(SO3Mg)-C H 2-), 1.61-1.60(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)3-CH3),1.33-1.32(m,6H,-O-CH2-CH2-(C H 2)3-CH3),0.90-0.89(m,3H,-O-(CH2)5-C H 3),0.49-0.47(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(CH 3)3) Elemental analysis (C 32 H 62 O 14 S2Si2Mg) C / 45.92%, H / 7.56%, S / 6.40% (theoretical values: C / 47.13%, H / 7.66%, S / 7.86%)

[0103] (Example 8) Synthesis of Mg(SC7-SiPSS) SC7-SiPSS was synthesized by the method described in Example 3. SC7-SiPSS (2.0230 g, 4.68 mmol) was dissolved in a minimum amount of ethanol (5 mL), added to 5 mL of saturated Mg(NO3)2 solution, and stirred for 24 hours. The target substance was then extracted into toluene using a separatory funnel, and after removing the aqueous layer, saturated MgCl2 solution was added to extract and remove unreacted SC7-SiPSS into the aqueous layer. Anhydrous magnesium sulfate was added to the organic layer for dehydration, followed by filtration and concentration under reduced pressure to obtain white solid Magnesium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-heptyl)sulfosuccinate (Mg(SC7-SiPSS)2) (1.2369 g, yield 62.7%).

[0104] Mg(SC7-SiPSS)2 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.32(m,1H,-CH2-C H (SO3Mg)-), 4.15-4.11(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.00-4.05(m,2H,-OC H 2-(CH2)5-CH3),3.22-3.11(m,2H,-CH(SO3Mg)-C H 2-), 1.59-1.61(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)4-CH3),1.29-1.28(m,8H,-O-CH2-CH2-(C H2)4-CH3),0.91-0.87(m,3H,-O-(CH2)6-C H 3),0.48-0.45(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) IR(KBr)ν max / cm -1 :2954(-CH3),2857(-CH2),1737(C=O,-COO-),1467(O=S=O),1062(O=S=O) Elemental analysis (C 34 H 66 O 14 S2Si2Mg) C / 45.92%, H / 7.56%, S / 6.40% (theoretical values: C / 48.41%, H / 7.88%, S / 7.60%)

[0105] (Example 9) Synthesis of Mg(SC8-SiPSS)2 SC8-SiPSS was synthesized by the method described in Example 4. SC8-SiPSS (0.6669 g, 1.49 mmol) was dissolved in a minimum amount of ethanol (5 mL), added to 5 mL of saturated Mg(NO3)2 solution, and stirred for 24 hours. The target substance was then extracted into toluene using a separatory funnel, and after removing the aqueous layer, saturated MgCl2 solution was added to extract and remove unreacted SC8-SiPSS into the aqueous layer. Anhydrous magnesium sulfate was added to the organic layer to dehydrate it, and then filtered and concentrated under reduced pressure to obtain white solid Magnesium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-octyl)sulfosuccinate (Mg(SC8-SiPSS)2) (0.4265 g, yield 65.5%).

[0106] Mg(SC8-SiPSS)2 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.33(m,1H,-CH2-C H (SO3Mg)-), 4.15-4.11(m,2H,-OC H2-CH2-CH2-Si(CH3)3),4.05-4.00(m,2H,-OC H 2-(CH2)6-CH3),3.20-3.11(m,2H,-CH(SO3Mg)-C H 2-),1.61-1.60(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)5-CH3),1.29-1.28(m,10H,-O-CH2-CH2-(C H 2)5-CH3),0.91-0.88(m,3H,-O-(CH2)8-C H 3),0.48-0.45(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) IR(KBr)ν max / cm -1 :2925(-CH3),2856(-CH2),1733(C=O,COO-),1467(O=S=O),1332(O=S=O) Elemental analysis (C 36 H 70 O 14 S2Si2Mg) C / 46.75%, H / 8.47%, S / 6.20% (theoretical value C / 49.61%, H / 8.10%, S / 7.35%)

[0107] (Example 10) Synthesis of Mg(SC9-SiPSS)2 SC9-SiPSS was synthesized by the method described in Example 5. SC9-SiPSS (0.4982 g, 1.08 mmol) was dissolved in a minimum amount of ethanol (5 mL), added to 5 mL of saturated Mg(NO3)2 solution, and stirred for 24 hours. The target substance was then extracted into toluene using a separatory funnel, and after removing the aqueous layer, saturated MgCl2 solution was added to extract and remove unreacted SC9-SiPSS into the aqueous layer. Anhydrous magnesium sulfate was added to the organic layer for dehydration, followed by filtration and concentration under reduced pressure to obtain white solid Magnesium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-nonyl)sulfosuccinate (Mg(SC9-SiPSS)2) (0.3244 g, yield 66.7%).

[0108] Mg(SC9-SiPSS)2 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.33(m,1H,-CH2-C H (SO3Mg)-), 4.19-4.13(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.05-3.99(m,2H,-OC H 2-(CH2)7-CH3),3.23-3.12(m,2H,-CH(SO3Mg)-C H 2-), 1.62-1.60(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)6-CH3),1.30-1.28(m,12H,-O-CH2-CH2-(C H 2)6-CH3),0.91-0.88(m,3H,-O-(CH2)8-C H 3),0.49-0.45(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) IR(KBr)ν max / cm -1 :2925(-CH3),2866(-CH2),1737(C=O,COO-),1467(O=S=O),1332(O=S=O) Elemental analysis (C 38 H 74 O 14 S2Si2Mg) C / 50.86%, H / 8.41%, S / 5.94% (theoretical values: C / 50.74%, H / 8.29%, S / 7.13%)

[0109] [Surfactant Ca(SC n Synthesis of -SiPSS2 Surfactant Ca(SC n Each of the surfactants, SiPSS)2 (n=5 to 9), was synthesized according to the following scheme. The synthesis procedures for the surfactants in Examples 11, 12, 13, 14, and 15 are shown in detail below. [ka]

[0110] (Example 11) Synthesis of Ca(SC5-SiPSS)2 SC5-SiPSS was synthesized by the method described in Example 1. SC5-SiPSS (0.8301 g, 2.05 mmol) was dissolved in a minimum amount of ethanol (5 mL), added to 5 mL of saturated Ca(NO3)2 solution, and stirred for 24 hours. The target substance 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 SC5-SiPSS into the aqueous layer. Anhydrous magnesium sulfate was added to the organic layer for dehydration, followed by filtration and concentration under reduced pressure to obtain a white solid, Calcium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-pentyl) sulfosuccinate (Ca(SC5-SiPSS)2) (0.2041 g, yield 24.8%).

[0111] Ca(SC5-SiPSS)2 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.40m,1H,-CH2-C H (SO3Ca)-), 4.17-4.13(m,2H,-OC H2-CH2-CH2-Si(CH3)3),4.05-4.01(m,2H,-OC H 2-(CH2)3-CH3),3.23-3.13(m,2H,-CH(SO3Ca)-C H 2-), 1.61-1.60(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)2-CH3),1.33-1.32(m,4H,-O-CH2-CH2-(C H 2)2-CH3),0.93-0.89(m,3H,-O-(CH2)4-C H 3),0.49-0.45(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) Elemental analysis (C 30 H 58 O 14 S2Si2Ca) C / 45.92%, H / 7.56%, S / 6.40% (theoretical values: C / 44.86%, H / 7.28%, S / 7.98%)

[0112] (Example 12) Synthesis of Ca(SC6-SiPSS)2 SC6-SiPSS was synthesized by the method described in Example 2. SC6-SiPSS (0.7046 g, 1.68 mmol) was dissolved in a minimum amount of ethanol (5 mL), added to 5 mL of saturated Ca(NO3)2 solution, and stirred for 24 hours. The target substance 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 SC6-SiPSS into the aqueous layer. Anhydrous magnesium sulfate was added to the organic layer for dehydration, followed by filtration and concentration under reduced pressure to obtain a white solid, Calcium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-hexyl)sulfosuccinate (Ca(SC6-SiPSS)2) (0.3450 g, yield 49.3%).

[0113] Ca(SC6-SiPSS)2 1HNMR (500MHz, CDCl3, TMS)δ H / ppm:4.33(m,1H,-CH2-C H (SO3Ca)-),4.19-4.13(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.06-4.01(m,2H,-OC H 2-(CH2)4-CH3),3.23-3.12(m,2H,-CH(SO3Ca)-C H 2-),1.61-1.60(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)3-CH3),1.33-1.32(m,6H,-O-CH2-CH2-(C H 2)3-CH3),0.90-0.89(m,3H,-O-(CH2)5-C H 3),0.49-0.47(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) Elemental analysis (C 32 H 62 O 14 S2Si2Ca) C / 45.33%, H / 7.34%, S / 7.02% (theoretical value C / 46.24%, H / 7.51%, S / 7.72%)

[0114] (Example 13) Synthesis of Ca(SC7-SiPSS)2 SC7-SiPSS was synthesized by the method described in Example 3. SC7-SiPSS (0.7128 g, 1.65 mmol) was dissolved in a minimum amount of ethanol (5 mL), added to 5 mL of saturated Ca(NO3)2 solution, and stirred for 24 hours. The target substance 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 SC7-SiPSS into the aqueous layer. Anhydrous magnesium sulfate was added to the organic layer for dehydration, followed by filtration and concentration under reduced pressure to obtain a white solid, Calcium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-heptyl) sulfosuccinate (Ca(SC7-SiPSS)2) (0.3240 g, yield 45.8%).

[0115] Ca(SC7-SiPSS)2 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.34(m,1H,-CH2-C H (SO3Ca)-), 4.16-4.12(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.00-4.05(m,2H,-OC H 2-(CH2)5-CH3),3.22-3.11(m,2H,-CH(SO3Ca)-C H 2-), 1.59-1.61(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)4-CH3),1.29-1.28(m,8H,-O-CH2-CH2-(C H 2)4-CH3),0.91-0.87(m,3H,-O-(CH2)6-C H 3),0.48-0.45(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) Elemental analysis (C 34 H 66 O 14 S2Si2Ca) C / 45.92%, H / 7.56%, S / 6.80% (theoretical values: C / 47.52%, H / 7.74%, S / 7.46%)

[0116] (Example 14) Synthesis of Ca(SC8-SiPSS)2 SC8-SiPSS was synthesized by the method described in Example 4. SC8-SiPSS (0.7711 g, 1.73 mmol) was dissolved in a minimum amount of ethanol (5 mL), added to 5 mL of saturated Ca(NO3)2 solution, and stirred for 24 hours. The target substance 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 SC8-SiPSS into the aqueous layer. Anhydrous magnesium sulfate was added to the organic layer for dehydration, followed by filtration and concentration under reduced pressure to obtain a white solid, Calcium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-octyl) sulfosuccinate (Ca(SC8-SiPSS)2) (0.4884 g, yield 63.8%).

[0117] Ca(SC8-SiPSS)2 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.33(m,1H,-CH2-C H (SO3Ca)-), 4.15-4.11(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.05-4.00(m,2H,-OC H 2-(CH2)6-CH3),3.20-3.11(m,2H,-CH(SO3Ca)-C H 2-), 1.61-1.60(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)5-CH3),1.29-1.28(m,10H,-O-CH2-CH2-(C H 2)5-CH3),0.91-0.88(m,3H,-O-(CH2)7-C H 3),0.48-0.45(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(CH 3)3) Elemental analysis (C 36 H 70 O 14 S2Si2Ca) C / 47.83%, H / 7.530%, S / 6.45% (theoretical values: C / 48.73%, H / 7.95%, S / 7.23%)

[0118] (Example 15) Synthesis of Ca(SC9-SiPSS)2 SC9-SiPSS was synthesized by the method described in Example 5. SC9-SiPSS (1.2218 g, 2.65 mmol) was dissolved in a minimum amount of ethanol (5 mL), added to 5 mL of saturated Ca(NO3)2 solution, and stirred for 24 hours. The target substance 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 SC9-SiPSS into the aqueous layer. Anhydrous magnesium sulfate was added to the organic layer for dehydration, followed by filtration and concentration under reduced pressure to obtain a white solid, Calcium 1-(3-(trimethylsilyl)-1-propyl)-4-(1-nonyl)sulfosuccinate (Ca(SC9-SiPSS)2) (0.6576 g, yield 54.2%).

[0119] Ca(SC9-SiPSS)2 1 HNMR(500MHz,CDCl3,TMS)δ H / ppm:4.36(m,1H,-CH2-C H (SO3Ca)-), 4.19-4.13(m,2H,-OC H 2-CH2-CH2-Si(CH3)3),4.05-3.99(m,2H,-OC H 2-(CH2)7-CH3),3.23-3.12(m,2H,-CH(SO3Ca)-C H 2-), 1.62-1.60(m,4H,-O-CH2-C H 2-CH2-Si(CH3)3,-O-CH2-C H 2-(CH2)6-CH3),1.30-1.28(m,12H,-O-CH2-CH2-(C H2)6-CH3),0.91-0.88(m,3H,-O-(CH2)8-C H 3),0.49-0.45(m,2H,-O-CH2-CH2-C H 2-Si(CH3)3),0.00(s,9H,-Si(C H 3)3) Elemental analysis (C 38 H 74 O 14 S2Si2Ca) C / 50.86%, H / 8.41%, S / 5.94% (theoretical values: C / 49.86%, H / 8.15%, S / 7.01%)

[0120] [Usability of surfactants at room temperature (25℃)] In Examples 1 to 15, the final products (surfactants) were obtained as white solids, which were dissolved in water at 25°C to evaluate their usability at room temperature. Specifically, when the compounds obtained in Examples 1 to 15 were added in an amount twice the CMC to distilled water at 25°C and stirred, they dissolved in the distilled water and no insoluble matter was observed. Therefore, it was found that the surfactants of Examples 1 to 15 were usable at room temperature.

[0121] [Evaluation of the surface tension reducing ability of surfactants] Surfactant of Example 1 [SC5-SiPSS], Surfactant of Example 2 [SC6-SiPSS], Surfactant of Example 3 [SC7-SiPSS], Surfactant of Example 4 [SC8-SiPSS], Surfactant of Example 5 [SC9-SiPSS], Surfactant of Example 6 [Mg(SC5-SiPSS)2], Surfactant of Example 7 [Mg(SC6-SiPSS)2], Surfactant of Example 8 [Mg(SC7-SiPSS)2], Surfactant of Example 9 [Mg(SC8-SiPSS)2], Surfactant of Example 10 The surface tensions of aqueous solutions of the surfactant [Mg(SC9-SiPSS)2] of Example 11, the surfactant [Ca(SC5-SiPSS)2] of Example 12, the surfactant [Ca(SC6-SiPSS)2] of Example 13, the surfactant [Ca(SC7-SiPSS)2] of Example 14, the surfactant [Ca(SC8-SiPSS)2] of Example 15, and the surfactant [BC4P-SiPSS] of Reference Example 1 were measured by the Whilhelmy method at 25°C. FIG. 1 is a diagram showing the surface tensions when the surfactants of Examples 1 to 5 and Reference Example 1 are at various concentrations. FIG. 2 is a diagram showing the surface tensions when the surfactants of Examples 6 to 10 are at various concentrations. FIG. 3 is a diagram showing the surface tensions when the surfactants of Examples 11 to 15 are at various concentrations.

[0122] The micelle formation concentration (CMC) and surface tension value at CMC (γ CMC ), molecular occupancy area at CMC (A min ) are shown in Table 1. min was calculated from the Gibbs adsorption equation and the slope in Figure 1. As can be seen from the CMC in Table 1, it was confirmed that as the carbon number of the linear hydrocarbon group of the surfactant increases, the hydrophobicity increases, the CMC drops sharply, and the minimum achievable surface tension drops slightly. In addition, compared to the physical properties of BC4-SiPSS in Reference Example 1, SC7-SiPSS and SC6-SiPSS, which have similar carbon numbers in the hydrophobic group, have the closest CMC and γ CMC showed.

[0123] [Table 1]

[0124] The micelle formation concentration (CMC) and surface tension value at CMC (γ CMC ), molecular occupancy area at CMC (A min ) are shown in Table 2. min was calculated from the Gibbs adsorption equation and the slopes in Figures 2 and 3. As can be seen from the CMC in Table 2, even for surfactants whose counter ions are magnesium or calcium, it was confirmed that the CMC rapidly decreased and the minimum achievable surface tension decreased slightly as the carbon number of the linear hydrocarbon group of the surfactant increased.

[0125] [Table 2]

[0126] Comparing the surfactants of Examples 1 to 5 in which the counter ion is sodium with the surfactants of Examples 6 to 15 in which the counter ion is magnesium or calcium, the CMC of the surfactants in which the counter ion is magnesium or calcium was smaller than the CMC of the surfactants in which the counter ion is sodium. min showed a value smaller than twice the molecular occupancy area of ​​the surfactant whose counter ion is sodium. This is because the surfactant whose counter ion is magnesium or calcium has two succinic acid diester sulfonic acid skeletons in one molecule, and the surfactant whose counter ion is magnesium or calcium has a molecular occupancy area A per succinic acid diester sulfonic acid skeleton. min is smaller than the molecular occupancy area of ​​a surfactant whose counter ion is sodium. This confirmed that by exchanging the counter ion for a divalent cation such as magnesium or calcium, the surfactant molecules can be densely packed, increasing the hydrophobic density and showing the surface tension reducing effect even with a single molecule.

[0127] The total number of carbon atoms and silicon atoms (N C+Si ) and the critical micelle concentration (CMC) were evaluated.

[0128] FIG. 4 shows the results of Examples 1 to 5 [SC n -SiPSS], Examples 6 to 10 [Mg(SC n -SiPSS)2], and Examples 11 to 15 [Ca(SC n The natural logarithm of the critical micelle concentration (CMC) of the surfactant [-SiPSS2] and the total number of carbon atoms and silicon atoms (N C+Si ) is a graph showing the relationship between the C+Si The value of N is 12-14 (the number of carbon atoms in the linear hydrocarbon group is 5-7) and C+Si Two linear relationships with different slopes were obtained for the CMC value of 14 to 16 (the number of carbon atoms in the linear hydrocarbon group is 7 to 9). Generally, the CMC of a surfactant follows the Klevens formula (1) below. Log(CMC)=AB·N C+Si (1) In formula (1), A is a constant that depends on the properties and thermodynamic contribution of the hydrophilic group of the surfactant, and B is a constant that depends on the methylene group contained in the surfactant. From the graph in Fig. 4, the constants A and B in the two linear relationships were determined for each of the surfactants of Examples 1 to 5, Examples 6 to 10, and Examples 11 to 15.

[0129] As shown in Table 3, for all surfactants, the surface active agents having a linear hydrocarbon group with 7 to 9 carbon atoms exhibited higher constant B values ​​than the surfactants having a linear hydrocarbon group with 5 to 7 carbon atoms.

[0130] [Table 3]

[0131] [Evaluation of the surface tension reduction efficiency of surfactants] The surface tension reducing efficiency of the surfactants in Examples 1 to 15 is expressed as π CMC / Log(CMC×10 10 ) was calculated as π CMC is the surface pressure at the CMC when the surfactant concentration is CMC =γ water -γ CMC , γ water : Surface tension of water, γ CMC : surface tension when the surfactant concentration is CMC), and π CMC / Log(CMC×10 10 ) is the case when the surfactant concentration is sufficiently small (10 -10 The surface pressure at a surfactant concentration of 10 -10 This means the average rate of change in surface pressure when changing from mol / L to CMC. That is, π CMC / Log(CMC×10 10 The larger the value of π) is, the better the surface tension reducing efficiency is. CMC / Log(CMC×10 10 ) was shown.

[0132] [Table 4]

[0133] As shown in Table 4, the π CMC / Log(CMC×10 10 In addition, when comparing surfactants with the same number of carbon atoms in the linear hydrocarbon group, surfactants with magnesium or calcium counter ions have a larger π CMC / Log(CMC×10 10 ) values ​​were shown.

[0134] FIG. 5 shows the results of Examples 1 to 5 [SC n -SiPSS], Examples 6 to 10 [Mg(SC n -SiPSS)2], and Examples 11 to 15 [Ca(SC n-SiPSS)2] surfactant, π CMC / Log(CMC×10 10 ) and the total number of carbon atoms and silicon atoms contained in the linear hydrocarbon group and the hydrocarbon group having a trimethylsilyl group terminal (N C+Si 5 is a graph showing the relationship between the total number of carbon and silicon atoms (N C+Si The surface tension reduction efficiency tends to increase more significantly when the total number of carbon and silicon atoms (N C+Si ) is larger for surfactants whose counter ions are magnesium or calcium than for surfactants whose counter ions are sodium. CMC / Log(CMC×10 10 ) values ​​were shown.

[0135] [Evaluation of the rate of surface tension reduction of surfactants] Surfactant of Example 1 [SC5-SiPSS], surfactant of Example 2 [SC6-SiPSS], surfactant of Example 3 [SC7-SiPSS], surfactant of Example 4 [SC8-SiPSS], surfactant of Example 5 [SC9-SiPSS], surfactant of Example 6 [Mg(SC5-SiPSS)2], surfactant of Example 7 [Mg(SC6-SiPSS)2], surfactant of Example 8 [Mg(SC7-SiPSS)2], surfactant of Example 9 [Mg(SC8-SiPSS)2], surfactant of Example 10 The dynamic surface tension of aqueous solutions prepared at various concentrations for the surfactant [Mg(SC9-SiPSS)2], the surfactant of Example 11 [Ca(SC5-SiPSS)2], the surfactant of Example 12 [Ca(SC6-SiPSS)2], the surfactant of Example 13 [Ca(SC7-SiPSS)2], the surfactant of Example 14 [Ca(SC8-SiPSS)2], the surfactant of Example 15 [Ca(SC9-SiPSS)2], and the surfactant of the reference example [BC4P-SiPSS] was measured at 25°C using the maximum bubble pressure method. The measurements were performed using a handheld dynamic surface tensiometer BP50 manufactured by KRUSS, Germany.

[0136] 6, 7, 8, 9, and 10 are diagrams showing the relationship between the surface tension and the surface life of the surfactants of Example 1, Example 2, Example 3, Example 4, and Example 5 at each concentration. The horizontal axis indicates the surface life, and the vertical axis indicates the surface tension. 11, 12, 13, 14, and 15 are diagrams showing the relationship between the surface tension and the surface life of the surfactants of Example 6, Example 7, Example 8, Example 9, and Example 10 at each concentration. The horizontal axis indicates the surface life, and the vertical axis indicates the surface tension. 16, 17, 18, 19, and 20 are diagrams showing the relationship between the surface tension and the surface life of the surfactants of Example 11, Example 12, Example 13, Example 14, and Example 15 at each concentration. The horizontal axis indicates the surface life, and the vertical axis indicates the surface tension.

[0137] Dynamic surface tension measurement by the maximum bubble pressure method is a method to obtain surface tension by introducing gas into a capillary inserted in liquid (in water) and measuring the maximum pressure when bubbles are generated. When bubbles are generated from a capillary in liquid, the pressure inside the capillary gradually changes, and the pressure reaches its maximum when the radius of curvature of the bubble is equal to 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 begins to change periodically, and the time from the minimum pressure to the maximum pressure (the time from when the gas-liquid interface begins to form until the pressure reaches its maximum) is called the surface life (also called the surface formation time, bubble life, lifetime, etc.). By keeping the surfactant concentration constant and changing the gas introduction rate, the surface tension at various surface lifes can be obtained. In addition, by changing the concentration and repeating this, the relationship between surface tension and surface life can be obtained for each surfactant concentration, which is shown in Figures 6 to 20. Note that the surface tension reaches an equilibrium value as the surface life increases.

[0138] As shown in Figures 6, 7, 8, 9, and 10, it was found that in all of the surfactants in Examples 1, 2, 3, 4, and 5, the higher the concentration, the faster the surface tension reaches the equilibrium value. As shown in Figures 11, 12, 13, 14, and 15, it was found that in all of the surfactants in Examples 6, 7, 8, 9, and 10, the higher the concentration, the faster the surface tension reaches the equilibrium value. As shown in Figures 16, 17, 18, 19, and 20, it was found that in all of the surfactants in Examples 11, 12, 13, 14, and 15, the higher the concentration, the faster the surface tension reaches the equilibrium value.

[0139] From the dynamic surface tension values ​​obtained, the half-life value γ was calculated using the following formula for each surfactant concentration. τ asked for. Gamma τ =(γ0+γ ∞ ) / 2 Here, γ0 is the initial surface tension value (surface life = 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 decreases to half of the total decrease amount. τ (characteristic time) is the time when the surface tension value decreases to γ τ For systems in which the dynamic surface tension value had dropped to its lowest point 15 ms after the start of the measurement, γ0 was calculated as the surface tension value of water (72 mN / m).

[0140] Fig. 21 is a diagram showing the relationship between the characteristic time τ of the surfactants in Examples 1 to 5 and the Reference Example and the concentration of the surfactant. The horizontal axis in Fig. 21 shows the surfactant concentration, and the vertical axis shows the characteristic time τ. Fig. 22 is a diagram showing the relationship between the characteristic time τ of the surfactants in Examples 1 to 5 and the Reference Example and the value when the surfactant concentration is corrected with the critical micelle concentration (CMC). The horizontal axis in Fig. 22 shows the converted concentration obtained by correcting the surfactant concentration with the CMC, and the vertical axis shows the characteristic time τ.

[0141] The results in Figure 21 show that, although there are large differences in the critical micelle concentrations (CMC) of the surfactants in Examples 1 to 5, there is no large difference in the characteristic time τ for surfactants with a linear hydrocarbon chain having 7 or more carbon atoms, and all of them exhibited very short characteristic times, i.e., very fast adsorption behavior.

[0142] On the other hand, as shown in Figure 22, when the surfactant concentration is re-expressed in terms of the converted concentration based on the critical micelle concentration (CMC) of each surfactant and the effects of increased hydrophobicity and micelle formation are excluded, the characteristic time τ becomes smaller as the linear hydrocarbon chain length becomes shorter, and when the carbon number of the linear hydrocarbon chain is 5 to 7, a very short characteristic time, that is, very fast adsorption behavior is observed even under the conditions before micelle formation (the region where the converted concentration value is smaller than 1).

[0143] Fig. 25 is a diagram showing the relationship between the characteristic time τ of the surfactants in Examples 6 to 10 and the concentration of the surfactant. The horizontal axis in Fig. 25 shows the surfactant concentration, and the vertical axis shows the characteristic time τ. Fig. 26 is a diagram showing the relationship between the characteristic time τ of the surfactants in Examples 6 to 10 and the value when the surfactant concentration is corrected with the critical micelle concentration (CMC). The horizontal axis in Fig. 26 shows the converted concentration obtained by correcting the surfactant concentration with the CMC, and the vertical axis shows the characteristic time τ.

[0144] Fig. 29 is a diagram showing the relationship between the characteristic time τ of the surfactants in Examples 11 to 15 and the concentration of the surfactant. The horizontal axis in Fig. 29 shows the surfactant concentration, and the vertical axis shows the characteristic time τ. Fig. 30 is a diagram showing the relationship between the characteristic time τ of the surfactants in Examples 11 to 15 and the value when the surfactant concentration is corrected with the critical micelle concentration (CMC). The horizontal axis in Fig. 30 shows the converted concentration obtained by correcting the surfactant concentration with the CMC, and the vertical axis shows the characteristic time τ.

[0145] The results in FIGS. 25 and 29 show that the characteristic time also becomes shorter as the surfactant concentration increases in the case of surfactants whose counter ions are magnesium or calcium.

[0146] Comparing the results of Figures 21, 25, and 29, it was confirmed that the characteristic time τ of the surfactant whose counter ion is magnesium or calcium is smaller than the characteristic time of the surfactant whose counter ion is sodium, particularly at a surfactant concentration of around 0.1 mM, and the adsorption rate is increased.

[0147] On the other hand, when the surfactant concentration was expressed in terms of a converted concentration based on the critical micelle concentration (CMC) of each surfactant and the effects of increased hydrophobicity and micelle formation were excluded, the results in Figures 22, 26, and 30 showed that, when the critical micelle concentration was used as the standard, the difference in characteristic time depending on the type of counterion was small, and the adsorption rate was not affected by the valence of the counterion.

[0148] Next, from the obtained characteristic time τ, the surface tension reduction rate R 1 / 2 was calculated using the following formula: R 1 / 2 =(γ0-γ ∞ ) / (2τ) FIG. 23 shows the surface tension reduction rate R 1 / 2 23 is a graph showing the relationship between the surface tension reduction rate R and the surfactant concentration. 1 / 2 FIG. 24 shows the surface tension reduction rate R of the surfactants in Examples 1 to 5 and the Reference Example. 1 / 2 The horizontal axis in FIG. 24 represents the converted concentration of the surfactant corrected by the CMC, and the vertical axis represents the surface tension reduction rate R 1 / 2 Shows.

[0149] From the results in Figure 23, the surface tension reduction rate R 1 / 2 When compared at the same concentration, the surfactants of Examples 3, 4, and 5, which have linear hydrocarbon chains with 7 or more carbon chains, have large R 1 / 2, i.e., a very fast surface tension reduction rate was obtained. On the other hand, as shown in FIG. 24, when the surfactant concentration is re-expressed as a converted concentration based on the critical micelle concentration (CMC) of each surfactant and the effects of increased hydrophobicity and micelle formation are excluded, the surfactants in Examples 1, 2, and 3, which have a short linear hydrocarbon chain carbon number, show a surface tension reduction rate of R 1 / 2 It was confirmed that a very fast surface tension reduction rate was obtained even under the conditions before micelle formation (the region where the reduced concentration value is smaller than 1).

[0150] FIG. 27 shows the surface tension reduction rate R 1 / 2 2 is a graph showing the relationship between the surface tension reduction rate R and the surfactant concentration. 1 / 2 FIG. 28 shows the surface tension reduction rate R 1 / 2 The horizontal axis in FIG. 28 represents the converted concentration of the surfactant corrected by the CMC, and the vertical axis represents the surface tension reduction rate R 1 / 2 Shows.

[0151] FIG. 31 shows the surface tension reduction rate R 1 / 2 The horizontal axis in FIG. 31 represents the surfactant concentration, and the vertical axis represents the surface tension reduction rate R 1 / 2 FIG. 32 shows the surface tension reduction rate R of the surfactants in Examples 11 to 15. 1 / 2 This is a graph showing the relationship between the surfactant concentration and the value when the surfactant concentration is corrected by the critical micelle concentration (CMC). The horizontal axis in FIG. 32 shows the converted concentration when the surfactant concentration is corrected by the CMC, and the vertical axis shows the surface tension reduction rate R 1 / 2 Shows.

[0152] From the results of Figures 27 and 31, even if the counter ion is magnesium or calcium, the surfactants of Examples 8, 9, 10, 13, 14, and 15, in which the carbon chain number of the linear hydrocarbon chain is 7 or more, have a large R 1 / 2, i.e., a very fast surface tension reduction rate was obtained. On the other hand, as shown in Figures 28 and 32, when the concentration is converted based on the critical micelle concentration (CMC) of each surfactant and the effects of increased hydrophobicity and micelle formation are excluded, the surfactants of Examples 6, 7, 8, 11, 12, and 13, which have a short linear hydrocarbon chain carbon number, have a surface tension reduction rate of R 1 / 2 It was confirmed that a very fast surface tension reduction rate was obtained even under the conditions before micelle formation (the region where the reduced concentration value is smaller than 1).

[0153] From the above, it was shown that when the carbon number of the linear hydrocarbon chain is 6 or less, a fast adsorption rate and a fast rate of reduction in surface tension are observed before micelle formation, and when the carbon number is 8 or more, a particularly fast adsorption rate and a fast rate of reduction in surface tension are observed at the actual concentration, and when the carbon number of the linear hydrocarbon chain is 7, a fast adsorption rate and a fast rate of reduction in surface tension are observed before micelle formation, and also a fast adsorption rate and a fast surface tension are observed even at the actual concentration.

[0154] Furthermore, when the valence of the counter ion of the surfactant is taken into consideration, surfactants whose counter ion is magnesium or calcium have a much larger R than surfactants whose counter ion is Na, when the surfactant concentration is the same. 1 / 2 , i.e., a very fast surface tension reduction rate was obtained.

[0155] A small characteristic time τ leads to a short time until the equilibrium surface tension value is reached, and is useful in applications such as fire extinguishing agents, leveling agents, agricultural chemicals, pharmaceuticals, cosmetics, enhanced oil recovery, and cleaning agents.

[0156] [Observation of droplet wetting behavior of aqueous solutions containing surfactants on hydrophobic solid surfaces] Using a high-speed fluid behavior visualization system (Photron, FASTCAM SA-Z), the wetting behavior of droplets of aqueous solutions containing the surfactants of Examples 1 to 5 dropped onto a hydrophobic solid surface at 25°C was observed.

[0157] FIG. 33 is a photograph of the wetting behavior of a droplet on a hydrophobic solid surface taken with a high-speed fluid behavior visualization system. In observing the wetting behavior of a droplet on a hydrophobic solid surface, an aqueous solution was dropped from a needle with a tip diameter of 18 G at a position 30 cm above the hydrophobic solid surface (Teflon (registered trademark) plate). Before colliding with the hydrophobic solid, the dropped aqueous solution falls to the hydrophobic solid surface as a spherical droplet with a radius D0. The droplet then collides with the hydrophobic solid surface at time t = 0 (ms), and after the collision, it spreads on the hydrophobic solid surface. The position where the droplet collides with the hydrophobic solid surface is set as the origin, and the distance between the periphery of the droplet that has spread and wetted after t (ms) after the collision and the origin is defined as D. t As the spreading diameter D t / D0 was calculated and evaluated.

[0158] FIG. 34 shows the spreading diameter D of the aqueous solutions containing the surfactants of Examples 1 to 5 and pure water after they collide with a hydrophobic solid surface. t 34 shows the change in / D0 over time. The results in Fig. 34 indicate that, in the case of pure water, the droplet wets and spreads on the surface of a hydrophobic solid 5 ms after collision, and then the wet and spread pure water shrinks 10 ms after collision. On the other hand, in the case of the aqueous solutions containing the surfactants of Examples 1, 2, 3, and 4, the aqueous solutions wet and spread on the surface of a hydrophobic solid after collision, but the aqueous solutions did not shrink after wet and spread.

[0159] Furthermore, the wetting and spreading speeds S ( / s) of the aqueous solutions containing the surfactants of Examples 1 to 5 and pure water on a hydrophobic solid surface were calculated from the plots in Figure 34. The wetting and spreading speed S is the spreading diameter D tThe wetting speed S was calculated as the slope of / D0, and the larger the value of the wetting speed S, the faster the droplets wet onto the hydrophobic surface. As shown in Table 5, the aqueous solutions containing the surfactants of Examples 1, 2, 3, 4, and 5 showed a higher wetting speed S than pure water, indicating that they wet onto the hydrophobic surface at a higher speed. In particular, the surfactants of Examples 1, 2, and 3 showed particularly high wetting speeds. Furthermore, the surfactant of Example 3 not only showed the highest wetting speed S, but also had a CMC that was about half that of the surfactant of Example 2, which showed the same wetting speed as Example 3, indicating that the surfactant wets onto the hydrophobic surface at a high speed even at a lower concentration.

[0160] [Table 5]

Claims

1. A surfactant comprising a monovalent or polyvalent metal salt of succinic acid diester sulfonic acid, In all of the succinic acid diester skeletons, a linear hydrocarbon group is bonded to one of the ester groups in the skeleton, and a hydrocarbon group having a trimethylsilyl group terminal is bonded to the other ester group in the skeleton, The surfactant has a total of 5 to 15 carbon atoms contained in the linear hydrocarbon group and the hydrocarbon group having a trimethylsilyl group terminal.

2. The surfactant of claim 1 which is a sodium salt, a magnesium salt, or a calcium salt.

3. The surfactant according to claim 1, wherein, in each of the succinic acid diester skeletons, the difference between the number of carbon atoms contained in the linear hydrocarbon group and the number of carbon atoms contained in the hydrocarbon group having a trimethylsilyl group terminal is 0 to 5.

4. A compound represented by any one of the following general formulas (100a), (100b), (100c), (100d), (100e), (110a), (110b), (110c), (110d), (110e), (111a), (111b), (111c), (111d), or (111e). 【Chemistry 1】 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】

5. A method for improving the rate of surface tension reduction of water, comprising adding a surfactant according to any one of claims 1 to 3 to water.

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