Compounds, surfactants, and surfactant compositions

Abstract

The present invention provides a low-foaming anionic compound, a surfactant, and a surfactant composition having excellent surface tension reducing ability. 【Solution】Formula (1): R 1 -O-C p H 2p -CR 2 (OH)-C q H 2q -S-C r H 2r -CHR 3 -COO - M + A compound represented by. In formula (1), R 1 is a branched alkyl group having 9 to 18 carbon atoms, R 2 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, p and q are each independently an integer of 1 to 6, r is an integer of 0 to 6, R 3 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, -CH2COO - M + or -NHCOCH3, M + are each independently H + , a monovalent metal cation, or an ammonium cation represented by formula (2): N(R 4 )4 + , R 4 each independently represent a hydrogen atom or an optionally substituted alkyl group having 1 to 6 carbon atoms.

Description

[Technical Field]

[0001] This invention relates to compounds, surfactants, and surfactant compositions. [Background technology]

[0002] Traditionally, anionic surfactants have been widely used in laundry detergents and other applications due to their excellent foaming ability. On the other hand, when surfactants are used in cleaning agents for electronic materials, wetting agents for water-based paints and inks, dispersants for pigments and resins, and metal plating chemicals, foaming often causes problems, and low-foaming surfactants (surfactants that suppress foam generation) are required. Examples of low-foaming surfactants include polyalkylene oxide adducts of aliphatic alcohols (for example, Patent Document 1). [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Patent No. 2800164 [Overview of the project] [Problems that the invention aims to solve]

[0004] However, the mainstream low-foaming surfactants described in Patent Document 1, etc., are nonionic surfactants, which do not have sufficient surface tension reduction ability, penetration power, wettability, etc. Furthermore, when used as an additive to paints, metal plating chemicals, etc., their compatibility or stability is insufficient, and there is a possibility that the nonionic surfactant may precipitate or decompose.

[0005] Therefore, the object of the present invention is to provide a low-foaming anionic compound that has excellent surface tension reduction ability. Furthermore, the present invention aims to provide surfactants and surfactant compositions. [Means for solving the problem]

[0006] As a result of intensive studies conducted by the present inventors to solve the above problems, they have found that the problems can be solved by the following constitution.

[0007] [1] A compound represented by the following formula (1). R 1 -O-C p H 2p -CR 2 (OH)-C q H 2q -S-C r H 2r -CHR 3 -COO - M + (1) The symbols in formula (1) have the following meanings. R 1 : a branched alkyl group having 9 to 18 carbon atoms R 2 : a hydrogen atom or an alkyl group having 1 to 6 carbon atoms p and q are each independently an integer of 1 to 6 r is an integer of 0 to 6 R 3 : a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, -CH2COO - M + or -NHCOCH3 M + are each independently H + , a monovalent metal cation, or an ammonium cation represented by the following formula (2) N(R 4 )4 + (2) R 4 each independently represent a hydrogen atom or an optionally substituted alkyl group having 1 to 6 carbon atoms. [2] The compound according to [1], wherein R 2 in the above formula (1) is a hydrogen atom. [3] The compound according to [1] to [2], wherein R 3 in the above formula (1) is a hydrogen atom. [4] The compound according to any one of [1] to [3], wherein R 1 in the above formula (1) is any branched alkyl group selected from the groups represented by the following formulas (3) to (5). Formula (3): [ka] Formula (4): [ka] Formula (5): [ka] [5] A surfactant containing one of the compounds described in [1] to [4]. A surfactant composition comprising the surfactant described in [6] [5] and an aqueous medium.

[0008] In this specification, the compound represented by formula (1) may be simply referred to as "compound (1)" or "(1)". In this specification, the group represented by formula (2) may be simply referred to as "group (2)" or "(2)". The same applies to the groups represented by formulas (3) to (5), etc. [Effects of the Invention]

[0009] According to the present invention, it is possible to provide a low-foaming anionic compound that has excellent surface tension reduction ability. Furthermore, the present invention can also provide surfactants and surfactant compositions. [Modes for carrying out the invention]

[0010] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments of the present invention, but the present invention is not limited to such embodiments. In this specification, a numerical range represented by "~" means a range that includes the numbers written before and after "~" as the lower and upper limits, respectively. In this specification, each component may be used individually or in combination of two or more. In this specification, when two or more ingredients are used in combination, the "content" of those ingredients means the total content of those two or more ingredients unless otherwise specified. In this specification, the method for producing each component is not particularly limited unless otherwise specified. For example, conventionally known methods may be used. In this specification, "the effects of the present invention are superior" also refers to a situation where one or both of the surface tension reduction ability and low foaming properties are superior.

[0011] The compounds of the present invention will be described below. [Compound] The compound of the present invention is a compound represented by the following formula (1). R 1 -OC p H 2p -CR 2 (OH)-C q H 2q -SC r H 2r -CHR 3 -COO - M + (1) The symbols in equation (1) have the following meanings: R 1 : Branched alkyl groups with 9 to 18 carbon atoms R 2 : Hydrogen atom or alkyl group having 1 to 6 carbon atoms p, q: mutually independent integers from 1 to 6 r: an integer from 0 to 6 R 3 : Hydrogen atom, alkyl group with 1-6 carbon atoms, -CH2COO - M + or -NHCOCH3 M + : Mutually independent, H + , a monovalent metal cation, or an ammonium cation represented by the following formula (2) N(R 4 )4 + (2) R 4 : Represents a C1-C6 alkyl group that may have a hydrogen atom or substituents, independently of each other. Note that in equation (1), -C q H 2q - and -C r H 2r The "S" between the dashes represents sulfur.

[0012] The symbols in equation (1) are explained below. [R 1 ] In formula (1), R 1 It is a branched alkyl group having 9 to 18 carbon atoms. R 1 Examples of branched alkyl groups having 9 to 18 carbon atoms include the group represented by formulas (3) to (5) below, isodecyl group, isododecyl group, isotridecyl group, isostearyl group, 2-hexyl-1-dodecyl group, 2,6,8-trimethyl-4-nonyl group, and 8-methyl-2-(4-methylhexyl)decyl group.

[0013] R 1 From the viewpoint of achieving superior effects of the present invention, the branched alkyl group having 9 to 18 carbon atoms is preferably one of the branched alkyl groups selected from the groups represented by the following formulas (3) to (5). Note that the wavy lines in equation (3) represent the ends of the bonds of the carbon atoms in the "CH2" group represented by letters in equation (3). As shown in equation (1) above, R 1 Where it bonds with the oxygen atom, R 1 The group represented by formula (3) is bonded to the oxygen atom by the above bond. The wavy lines in formulas (4) and (5) have the same meaning.

[0014] Formula (3): [ka]

[0015] Formula (4): [ka]

[0016] Formula (5): [ka]

[0017] In formula (1), “R 1 " and "-C p H 2p Regarding the "-O-" located between "-", the above "-O-" is "R 1 It just needs to bond to any of the carbon atoms that " " possesses. The above "-O-" is -C p H 2p - It can bond to any of the carbon atoms it possesses.

[0018] [R 2 ] In formula (1), R 2 This is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 2 Examples of C1-C6 alkyl groups include methyl, ethyl, propyl, butyl, pentyl, and hexyl groups. C1-C6 alkyl groups may be linear, and if they have 3-C6 atoms, they may be linear, branched, or cyclic.

[0019] R 2 From the viewpoint of ease of obtaining and reactivity of the raw materials constituting the compound of the present invention, it is preferable that the atom is a hydrogen atom.

[0020] [p, q] In equation (1), p and q are mutually independent integers between 1 and 6.

[0021] [p] In formula (1), p is preferably an integer from 1 to 3, and more preferably 1, from the viewpoint of the availability and reactivity of the raw materials constituting the compound of the present invention. -C p H 2p The divalent linking group represented by - may be linear, and when p is an integer between 3 and 6, it may be linear, branched, or a combination of these.

[0022] [q] In formula (1), q is preferably an integer from 1 to 3, and more preferably 1, from the viewpoint of the availability and reactivity of the raw materials constituting the compound of the present invention. -C q H 2q The divalent linking group represented by - may be linear, and when q is an integer between 3 and 6, it may be linear or branched.

[0023] [r] In equation (1), r is an integer between 0 and 6. In formula (1), r is preferably an integer between 0 and 3, and more preferably an integer between 0 and 2, from the viewpoint of the availability and reactivity of the raw materials constituting the compound of the present invention. -C r H 2r -A divalent linking group represented by - becomes a single bond when r is 0. -C r H 2r The divalent linking group represented by - may be linear when r is an integer from 1 to 6, and may be either linear or branched when r is an integer from 3 to 6.

[0024] [-CR 2 (OH)-] In equation (1), "-CR 2 (OH)-" is -C p H 2p - It can bond to any of the carbon atoms it possesses. In equation (1), "-CR 2 (OH)-" is -C q H 2q - It can bond to any of the carbon atoms it possesses.

[0025] [M + ] In formula (1), M + H + This represents a monovalent metal cation, or an ammonium cation represented by formula (2) described later. Note that the -CHR expressed in equation (1) 3 - Joint COO - M +“M in + ” and R represented in formula (1) 3 is -CH2COO - M + , “M in the case where + ” each independently represent H + , a monovalent metal cation, or an ammonium cation represented by formula (2). R 3 will be described later.

[0026] (Monovalent metal cation) M + When M is a monovalent metal cation, examples of the monovalent metal cation include alkali metal ions, and examples thereof include potassium ions and sodium ions.

[0027] (Ammonium cation represented by formula (2)) The ammonium cation represented by formula (2) is as follows. N(R 4 )4 + (2) In formula (2), R 4 each independently represent a hydrogen atom or an optionally substituted alkyl group having 1 to 6 carbon atoms.

[0028] (R 4 ) In formula (2), R 4 each independently represent a hydrogen atom or an optionally substituted alkyl group having 1 to 6 carbon atoms.

[0029] (Optionally substituted alkyl group having 1 to 6 carbon atoms) R 4If the alkyl group is a C1-C6 alkyl group which may have substituents, examples of C1-C6 alkyl groups include methyl, ethyl, propyl, butyl, pentyl, and hexyl groups. The C1-C6 alkyl group may be linear, and if it has 3-C6 atoms, it may be linear, branched, cyclic, or a combination thereof. Examples of substituents which the above C1-C6 alkyl group may have include hydroxyl, aryl, and heteroaryl groups. As an ammonium cation represented by formula (2), NH4 is preferred in terms of the superior effects of the present invention. + It is preferable.

[0030] In the present invention, M + Preferably, the ammonium cation represented by formula (2) is preferable in terms of the superior effects of the present invention, and NH4 + This is preferable.

[0031] [R 3 ] In formula (1), R 3 It consists of a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, and -CH2COO - M + Alternatively, it is -NHCOCH3.

[0032] (Alkyl alkyl groups with 1 to 6 carbon atoms) R 3 When the alkyl group has 1 to 6 carbon atoms, examples of alkyl groups with 1 to 6 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, and hexyl groups. The alkyl group with 1 to 6 carbon atoms may be linear, and if it has 3 to 6 carbon atoms, it may be linear, branched, cyclic, or a combination of these.

[0033] (-CH2COO - M + ) R 3 ga-CH2COO - M + In that case, the above M + H +This represents a monovalent metal cation, or an ammonium cation represented by the following formula (2). N(R 4 )4 + (2) In equation (2) above, R 4 Each of these independently represents a C1-C6 alkyl group that may have a hydrogen atom or a substituent. R 3 ga-CH2COO - M + In the case of M + As a monovalent metal cation, the ammonium cation represented by formula (2) is -CHR as expressed in formula (1) above. 3 -COO - M + M in + This is similar to a monovalent metal cation, or an ammonium cation represented by formula (2).

[0034] In equation (1), R 3 From the viewpoint of having superior effects in the present invention, hydrogen atoms or -CH2COO - M + It is preferable that it be a hydrogen atom, and more preferably a hydrogen atom.

[0035] (Preferred embodiments of the compound represented by formula (1)) The compound represented by formula (1) is, from the viewpoint of having superior effects in the present invention, R in formula (1). 3 It has a hydrogen atom, and R in formula (1) 1 However, compounds with a group represented by the above formula (3) are preferred.

[0036] Examples of compounds represented by formula (1) include the following compounds. [ka] JPEG2026148232000008.jpg2091JPEG2026148232000009.jpg3495JPEG2026148232 000010.jpg4593JPEG2026148232000011.jpg3591JPEG2026148232000012.jpg3383 JPEG2026148232000013.jpg3174JPEG2026148232000014.jpg3090JPEG2026148232 000015.jpg2299JPEG2026148232000016.jpg2979JPEG2026148232000017.jpg4082

[0037] (Method for producing the compound of the present invention) The method for producing the compound of the present invention is not particularly limited. One method for producing the compound of the present invention is to heat a mixture containing a mercaptocarboxylic acid compound represented by the following formula (7) and an alkali metal hydroxide, ammonia, or amine to 30-80°C, and then dropwise add an epoxy compound represented by the following formula (6) to the mixture and allow it to react. In the above reaction, a water-soluble organic solvent such as 2-propanol or water can be used as a solvent to suppress the heat of reaction and dissolve the raw materials and products. Formula (6): [ka]

[0038] SH-C r H 2r -CHR 3 -COOH (7)

[0039] • Epoxy compounds The epoxy compound used in the above manufacturing method is the compound represented by formula (6) above. R in equation (6) 1 , R 2 p and q are R in equation (1). 1 , R 2 It is the same as p and q. Examples of compounds represented by formula (6) include 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane (structure represented by formula (8) below), compounds represented by formula (9) below, compounds in which a glycidyloxy group is bonded to the bond of the group represented by formula (4) above, and compounds in which a glycidyloxy group is bonded to the bond of the group represented by formula (5) above.

[0040] Formula (8): [ka]

[0041] Formula (9): [ka]

[0042] The compound represented by formula (6) can be used in an amount of 0.9 to 1.2 molar equivalents relative to the mercaptocarboxylic acid compound represented by formula (7).

[0043] • Mercaptocarboxylic acid compounds The mercaptocarboxylic acid compound used in the above manufacturing method is a compound represented by the following formula (7). SH-C r H 2r -CHR 3 -COOH (7) R in equation (7) 3 , r is R in equation (1) 3 It is the same as r.

[0044] Examples of mercaptocarboxylic acid compounds represented by formula (7) include 3-mercaptopropionic acid, 2-mercaptopropionic acid, thioglycolic acid, thiomalic acid, and N-acetyl-L-cysteine.

[0045] • Alkali metal hydroxides or ammonia or amines Examples of alkali metal hydroxides that can be used in the above manufacturing method include lithium hydroxide, sodium hydroxide, and potassium hydroxide. Examples of amines that can be used in the above manufacturing method include ammonia, and compounds in which some or all of the hydrogen atoms of ammonia are substituted with alkyl groups (the alkyl groups have 1 to 6 carbon atoms) or hydroxyalkyl groups (the hydroxyalkyl groups have 1 to 6 carbon atoms). Specifically, examples include ammonia, triethylamine, and diethanolamine. For the mercaptocarboxylic acid compound represented by formula (7), an alkali metal hydroxide, ammonia, or amine can be used in amounts of 1 to 3 molar equivalents.

[0046] • Water-soluble organic solvents Examples of water-soluble organic solvents that can be used in the above-mentioned method for producing the compound of the present invention include alcohols such as methanol, ethanol, isopropanol (isopropyl alcohol), 1-propanol, and tert-butanol; ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, sulfolane, and N-methylpyrrolidone; glycol ethers such as diethylene glycol monomethyl ether and propylene glycol monomethyl ether acetate; and glycols such as ethylene glycol and propylene glycol.

[0047] • Amount of water and water-soluble organic solvents used The amount of water used in the above manufacturing method is not particularly limited. The same applies to the amount of water-soluble organic solvents used.

[0048] (use) When using the compound of the present invention, examples of the compound of the present invention include the compound alone and a mixture of the compound of the present invention and an aqueous medium.

[0049] ·Aqueous medium Examples of the aqueous media mentioned above include water, water-soluble organic solvents, or mixtures of water and water-soluble organic solvents. Examples of water-soluble organic solvents include alcohols such as methanol, ethanol, isopropanol, 1-propanol, and tert-butanol; ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, sulfolane, and N-methylpyrrolidone; glycol ethers such as diethylene glycol monomethyl ether and propylene glycol monomethyl ether acetate; and glycols such as ethylene glycol and propylene glycol. If the compound of the present invention is a mixture with an aqueous medium, the aqueous medium contained in the mixture may include water and a water-soluble organic solvent used in the production of the compound of the present invention.

[0050] • Content of aqueous media When the compound of the present invention is in the form of a mixture with an aqueous medium, the content of the aqueous medium is not particularly limited.

[0051] (Application) The compounds of the present invention can be used, for example, as surfactants (anionic surfactants).

[0052] [Surfactants] The surfactant of the present invention is a surfactant that contains the compound of the present invention. [Compounds as essential components] The compound contained as an essential component in the surfactant of the present invention is not particularly limited as long as it is a compound of the present invention. The surfactant of the present invention contains one or more compounds of the present invention. The surfactant of the present invention contains two or more compounds of the present invention, and the combination thereof is not particularly limited. For example, the above combination includes R in formula (1). 1 Examples include combinations of compounds with different branched alkyl group structures represented by .

[0053] In the present invention, the compound of the present invention may be used as the surfactant of the present invention as is.

[0054] [Surfactant composition] The surfactant composition of the present invention is a surfactant composition containing the surfactant of the present invention and an aqueous medium.

[0055] [Surfactants] The surfactant contained as an essential component in the surfactant composition of the present invention is not particularly limited as long as it is the surfactant of the present invention.

[0056] (Concentration of the surfactant of the present invention) The concentration of the surfactant of the present invention (one or more compounds of the present invention) in the surfactant composition of the present invention (if there are two or more compounds of the present invention, the total concentration thereof) is not particularly limited, and the concentration of the surfactant of the present invention in the surfactant composition of the present invention may be greater than 0% by mass and less than 100% by mass of the total amount of the surfactant composition of the present invention. Furthermore, the concentration of the surfactant of the present invention in the surfactant composition of the present invention is preferably 10 to 70% by mass, and particularly preferably 15 to 60% by mass, from the following viewpoints. When the composition falls within the above range, the amount of solvent (including aqueous media) in the surfactant composition of the present invention is small, which is preferable because it makes it easier to ensure that the amount of the surfactant of the present invention is appropriate when using the surfactant composition of the present invention as an additive. Furthermore, when the viscosity is within the above range, the viscosity of the surfactant composition of the present invention does not become too high, resulting in good handling properties, and the surfactant of the present invention is less likely to precipitate during storage, which is preferable.

[0057] [Aqueous medium] Examples of aqueous media included as essential components in the surfactant composition of the present invention include water, water-soluble organic solvents, or a mixture of water and water-soluble organic solvents. Examples of water-soluble organic solvents include alcohols such as methanol, ethanol, isopropanol, 1-propanol, and tert-butanol; ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, sulfolane, and N-methylpyrrolidone; glycol ethers such as diethylene glycol monomethyl ether and propylene glycol monomethyl ether acetate; and glycols such as ethylene glycol and propylene glycol. When the aqueous medium is a mixture of water and a water-soluble organic solvent, the mass ratio of water to the water-soluble organic solvent is not particularly limited.

[0058] (Additives) The surfactant composition of the present invention may further contain, as necessary, other surfactants, pH adjusters, rust inhibitors, dyes, dye stabilizers, flame retardants, defoamers, and antistatic agents, to the extent that it does not impair the effects of the present invention. The type and amount of additives can be selected as appropriate.

[0059] (Other surfactants) The surfactant composition of the present invention may further contain surfactants other than the compound of the present invention (other surfactants). The other surfactants are not particularly limited. For example, conventionally known surfactants can be used. Fluorine-based surfactants may not be used as the other surfactants.

[0060] (Manufacturing method) One method for producing the surfactant composition of the present invention is to mix the surfactant of the present invention with an aqueous medium and additives that can be used as needed.

[0061] (Application) The surfactant composition of the present invention can exhibit sufficient surface tension reduction ability even at low concentrations, making it suitable for use as an additive in various applications. For example, the surfactant composition of the present invention can be used as a leveling agent for waxes, a foaming aid, an additive for stable foam generation and improved fire extinguishing performance for foam fire extinguishing, a cleaning agent, a mold release agent, an emulsifier, a rust inhibitor, a latex stabilizer, an antifogging agent for agricultural films, a pigment dispersant, an improver of wettability and penetration of inks, paints, and resists, a water-repellent agent for curable resins, an antifouling agent, a flotation agent, a smoothing agent, a deinking agent, and so on. Furthermore, the surfactant composition of the present invention can be used in a wide range of applications, including cleaning and gravure printing. Furthermore, the surfactants and surfactant compositions of the present invention can lower the surface tension of various liquids without being limited by the solvent composition by adding the surfactant or surfactant composition of the present invention to the liquids. The amount of the surfactant or surfactant composition of the present invention to be added is set appropriately depending on the purpose and usage conditions, but it is preferable that the mixture after adding the surfactant or surfactant composition of the present invention to the liquids contains compound (1) in an amount of 0.001 to 5% by mass, and more preferably 0.005 to 1% by mass, in the state in which it is actually used. Even if the concentration of compound (1) in the mixture in the state in which it is actually used is as low as in the above range, compound (1) can fully exhibit its excellent surface tension lowering ability and is preferable because it does not negate the functionality of the main agent (the liquid before adding the surfactant or surfactant composition of the present invention). If the surfactant or surfactant composition of the present invention contains two or more types of compound (1), it is preferable that the total amount is within the above range. In addition, due to its surface tension lowering ability, it can impart functions such as leveling, permeability, foaming, cleaning, and emulsification to the added liquid. [Examples]

[0062] The present invention will be described in more detail below based on examples. The materials, quantities, proportions, processing details, and processing procedures shown in the following examples can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the following examples. In the following, unless otherwise specified, "parts" and "%" refer to "parts by mass" and "% by mass," respectively.

[0063] (Synthesis of 2-(((3,5,5-trimethylhexyl)oxymethyl)oxirane) Epichlorohydrin (384.81g, 4159 mmol), 3,5,5-trimethyl-1-hexanol (400.00g, 2773 mmol), sodium hydroxide (166.40g, 4160 mmol), and tetrabutylammonium bromide (44.69g, 139 mmol) were charged into a 2000 ml glass flask. The mixture was heated to 30°C and the reaction was carried out at that temperature for 11 hours to react epichlorohydrin with 3,5,5-trimethyl-1-hexanol. Gas chromatography analysis of the reaction solution revealed that the reaction rate of 3,5,5-trimethyl-1-hexanol was over 88%. The reaction mixture was transferred to a separatory funnel, deionized water and ethyl acetate were added, and after separation and filtration, the ethyl acetate was removed by distillation using an evaporator. By distillation of this distillate, 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane (356.96 g, purity 98%, yield 63%; structure represented by formula (8) below) was obtained.

[0064] Formula (8): [ka]

[0065] <Gas chromatography analysis> The measurement conditions for the gas chromatography analysis described above are as follows: Equipment: GC-2014 (manufactured by Shimadzu Corporation) Column: DB-5msUI (manufactured by Agilent Technologies, Inc.) (inner diameter 0.25 mm, length 30 m, film thickness 0.25 μm) Inlet temperature: 250℃ Injection method: Split Split ratio: 50 Column temperature program: Hold at 50°C for 5 minutes, increase the temperature at 10°C / min to 250°C, and hold at 250°C for 10 minutes.

[0066] [Example 1] Synthesis of compound (a) Mercaptopropionic acid (164.2 g, 646 mmol) and isopropanol (167.5 g, 359 mmol) were charged into a 1000 ml glass flask, and then 25% aqueous ammonia (115.9 g, 525 mmol) was added dropwise. Next, the temperature was raised in a water bath to 52°C, and the 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane (310.79 g, 646 mmol) synthesized as described above was added dropwise over 4 hours, after which the reaction was carried out at the same temperature for 2 hours. Post-reaction gas chromatography analysis revealed that the reaction rate of 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane was over 99%. As a result of the above synthesis, a water / isopropanol solution containing 50% of the reaction product (957.3 g, yield 95.7%) was obtained.

[0067] The compound synthesized as described above 1 H-NMR and 13 The 1C-NMR spectral data was as follows: 1 H-NMR (400MHz, solvent: acetone-d6, standard material: TMS), δ (ppm): 0.91(s, 9H), 0.92(d, J=6.8Hz, 3H), 1.03(dd, J=14.0Hz, 6.0Hz, 1H), 1.25(dd, J=13.6Hz, 3.6Hz, 1H)1.34-1 .42(m, 1H), 1.53-1.59(m, 1H), 1.63-1.71(m, 1H), 2.57-2.99(m, 6H), 3.42-3.52(m, 4H), 3.83-3.89(m, 1H)

[0068] 13 ¹³C-NMR (100 MHz, solvent: acetone-d6), δ (ppm): 23.2, 26.8, 28.4, 29.3, 31.6, 35.2, 36.5, 39.9, 51.9, 70.1, 70.9, 74.4, 206.2

[0069] The compound synthesized as described above 1 H-NMR and 13 From the 1C-NMR spectral data, it was confirmed that the compound obtained by the above reaction is represented by the following formula (a).

[0070] Formula (a): [ka]

[0071] The compound represented by formula (a) above is, R 1 =Formula (3) p=q=r=1 R 2 , R 3 =H M + =N(R 4 )4 + , R 4 Since =H, This corresponds to the compound of the present invention.

[0072] In this specification, compound (a) prepared as described above will also be referred to as "surfactant 1". Furthermore, a water / isopropanol solution containing 50% surfactant 1, prepared as described above, was used as "surfactant composition 1".

[0073] [Example 2] Synthesis of compound (b) Thiomalic acid (20.0 g, 133 mmol) and Solmix AP-7 (40.0 g, a mixed solvent mainly composed of ethanol, manufactured by Nippon Alcohol Sales Co., Ltd.) were charged into a 200 ml glass flask, and then 28% aqueous ammonia (16.2 g, 266 mmol) was added dropwise. Next, the temperature was raised in an oil bath to 50°C, and the 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane (27.2g, 133 mmol) synthesized as described above was added dropwise over 1 hour, followed by a reaction at the same temperature for 8 hours. Post-reaction gas chromatography analysis revealed that the reaction rate of 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane was over 99%. As a result of the above synthesis, a water / Solmix AP-7 solution containing 49% of the reaction product (97.6 g, yield 93.0%) was obtained.

[0074] The compound synthesized as described above 1 H-NMR and 13 The 1C-NMR spectral data was as follows: 1 H-NMR (400MHz, solvent: methanol-d4), δ(ppm):0.94(s, 9H), 0.97(d, J=6.8Hz, 3H), 1.09(dd, J=14.0Hz, 6.0Hz, 1H), 1.29(dd, J=14.0Hz, 3.2Hz, 1 H), 1.38-1.48(m, 1H), 1.53-1.72(m, 2H), 2.48-2.54(m, 2H), 2.68-2.94(m, 3H), 3.44-3.57(m, 4H), 3.61-3.68(m, 1H), 3.90-3.98(m, 1H)

[0075] 13 ¹¹C-NMR (100 MHz, solvent: methanol-d4), δ (ppm): 23.4, 27.5, 30.6, 32.1, 36.6, 36.9, 40.3, 42.1, 52.6, 71.0, 71.5, 75.0, 179.2, 180.3

[0076] The compound synthesized as described above 1 H-NMR and 13 From the 1C-NMR spectral data, it was confirmed that the compound obtained by the above reaction is represented by the following formula (b).

[0077] Formula (b): [Chemistry]

[0078] The compound represented by the above formula (b), in the above formula (1), R 1 =Formula (3) p=q=1 r=0 R 2 =H R 3 =-CH2COO - M + , M + =N(R 4 )4 + , R 4 =H, and the two M groups of the compound + are both N(R 4 )4 + , and the R groups contained in the two M groups + are both H, therefore 4 , the compound represented by the above formula (b) falls within the scope of the compound of the present invention. The compound represented by the above formula (b) corresponds to the compound of the present invention.

[0079] In the present specification, the compound (b) produced as described above is hereinafter also referred to as "Surfactant 2". Further, a water / Solmix AP-7 solution containing 49% of Surfactant 2 produced as described above was used as "Surfactant Composition 2".

[0080] (Analysis) In the present invention, for the aforementioned 1 H-NMR, 13 C-NMR, a portion of the obtained solution was dried, and NMR analysis ( 1 H-NMR, 13 C-NMR) was performed on the solid content using JNM-ECZ400R / S1 manufactured by JEOL Ltd., with FT / IR-4600 manufactured by JASCO Corporation.

[0081] <NMR Measurement> NMR ( 1 H-NMR, 13 C-NMR) measurement is described below. The substance to be measured was dissolved in the deuterated solvent acetone-d6, and a solution was prepared to a concentration of approximately 5% by mass. The prepared solution was then transferred to an NMR measuring tube. In addition, a small amount of a reference substance was added when measuring each nuclide. The measurement conditions are shown below. Equipment: JNM-ECZ400R / S1 (manufactured by JEOL Ltd., 400MHz) radionuclides: 1 H-NMR (standard: TMS), 13 C-NMR

[0082] [evaluation] The following evaluations were performed using each of the evaluation solutions obtained as described below. The results are shown in Table 1.

[0083] [Preparation of evaluation solution] (Examples 3-4) As described above, surfactant compositions 1 and 2 were each diluted with deionized water to prepare evaluation solutions 1 and 2 (see Examples 3 and 4, Table 1). The concentration of surfactant 1 in the total volume of evaluation solution 1 was 0.01% by mass. The concentration of surfactant 2 in the total volume of evaluation solution 2 was also 0.01% by mass. In this specification, the content or concentration of the compound of the present invention or the surfactant of the present invention is defined as the total amount of the compound of the present invention (M in formula (1)). + The calculation was based on the amount including the quantity of [the missing element].

[0084] (Comparative Example 1) As a surfactant, sodium di(2-ethylhexyl)sulfosuccinate (manufactured by Tokyo Chemical Industry Co., Ltd., with a structure represented by the following formula (10); also known as comparative compound 1) was used. Deionized water was added to the above comparative compound 1 to prepare evaluation solution 3 containing the above comparative compound 1 as a surfactant. The concentration of comparative compound 1 in the total volume of evaluation solution 3 is the same as in Example 3.

[0085] Equation (10): [ka]

[0086] [Evaluation of surface tension reduction ability] (Method for measuring surface tension) The static surface tension (mN / m) of each of the above-mentioned evaluation solutions was measured using the Wilhelmy method (platinum plate) at 25°C using a multi-functional automatic surface tension meter K100 (manufactured by KRUSS). In this invention, the ability to reduce surface tension was evaluated using the static surface tension measured as described above. (Evaluation criteria for surface tension reduction ability) In this specification, a compound used as a surfactant was evaluated as having excellent surface tension reduction ability when the static surface tension measured as described above was 35 mN / m or less. The lower the static surface tension was compared to 35 mN / m, the better the surface tension reduction ability of the compound used as a surfactant was evaluated.

[0087] [Evaluation of low foaming properties] (Method for measuring foaming power) 30g of each evaluation solution was placed in a 110ml glass bottle (mouth diameter × body diameter × total length: φ20.3 × φ40 × 120mm). The glass bottle was shaken for 10 seconds under 25°C conditions, then allowed to stand, and the height of the bubbles generated inside the glass bottle (unit: mm) was measured. After the glass bottle stood, bubbles formed on top of each evaluation solution inside the glass bottle, so the height of the bubbles was defined as the distance from the top surface of the bubbles to the boundary between the bubbles and the evaluation solution (the liquid surface above the evaluation solution). The results are shown in the "Foaming Power" column of Table 1. (Evaluation criteria for low foaming properties) In this specification, if the foam height measured as described above was 10 mm or less, the compound used as a surfactant was evaluated as having excellent low-foaming properties. The lower the foam height was compared to 10 mm, the better the low-foaming properties of the compound used as a surfactant were evaluated.

[0088] [Table 1]

[0089] The results in Table 1 confirm that the compounds of the present invention (surfactants of the present invention, surfactant compositions of the present invention) exhibit the desired effects. On the other hand, Comparative Example 1, which did not contain the compound of the present invention but instead contained Comparative Compound 1, exhibited insufficient surface tension reduction ability and low foaming properties.

Claims

1. A compound represented by the following formula (1). R １ -O-C ｐ H ２ｐ -CR ２ (OH)-C ｑ H ２ｑ -S-C ｒ H ２ｒ -CHR ３ -COO － M ＋ (1) The symbols in equation (1) have the following meanings: R １ : Branched alkyl groups with 9 to 18 carbon atoms R ２ : Hydrogen atom or alkyl group having 1 to 6 carbon atoms p, q: mutually independent integers from 1 to 6 r: an integer between 0 and 6 R ３ : Hydrogen atom, alkyl group having 1 to 6 carbon atoms, -CH ２ COO － M ＋ or -NHCOCH ３ M ＋ : Mutually independent, H ＋ , a monovalent metal cation, or an ammonium cation represented by the following formula (2) N(R ４ ) ４ ＋ (2) R ４ : Represents a C1-C6 alkyl group that may have a hydrogen atom or substituents, independently of each other.

2. In the above formula (1), R ２ The compound according to claim 1, wherein is a hydrogen atom.

3. In the above formula (1), R ３ The compound according to claim 1, wherein is a hydrogen atom.

4. R in formula (1) １ The compound according to claim 1, wherein the group is a branched alkyl group selected from the groups represented by the following formulas (3) to (5). Formula (3): 【Chemistry 1】 Formula (4): 【Chemistry 2】 Formula (5): 【Transformation 3】

5. A surfactant containing the compound described in any one of claims 1 to 4.

6. A surfactant composition comprising the surfactant described in claim 5 and an aqueous medium.

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