Compound, surfactant, and surfactant composition

Abstract

The present invention provides a non-fluorine compound, a non-fluorine surfactant, and a non-fluorine surfactant composition that have excellent surface tension reduction ability on the same level as fluorine surfactants. The compound is represented by [R1-O-CpH2p-CR2(OH)-CqH2q-NR3-CrH2r-(O)n-SO3]zM (formula (1)). The symbols in formula (1) indicate the following. R1 is a C9–18 branched alkyl group, R2 is a hydrogen atom or a C1–6 alkyl group, p, q, and r are independently an integer from 1 to 6, inclusive, M is a hydrogen atom or a mono- or divalent cation, n is 0 or 1, and R3 is a hydrogen atom, a C1–12 alkyl group, or a group represented by R4-O-CxH2x-CR5(OH)-CyH2y- (formula (2)), in which R4 is a C9–18 branched alkyl group, R5 is a hydrogen atom or a C1–6 alkyl group, x and y are independently an integer from 1 to 6, inclusive, and z is 1 or 2.

Description

Compounds, surfactants and surfactant compositions

[0001] The present invention relates to compounds, surfactants and surfactant compositions.

[0002] It has been known that fluorosurfactants having a perfluoroalkyl group have excellent surface tension reducing ability (ability to reduce surface tension). However, in recent years, concerns have arisen about the environmental impact of compounds having perfluoroalkyl groups, and alternatives to fluorosurfactants are being sought. On the other hand, it has been known that branched alkyl sulfosuccinate esters having branched alkyl groups can be used as surfactants (for example, Patent Document 1).

[0003] Japanese Patent Application Laid-Open No. 2021-147618

[0004] The present inventors have studied the sulfosuccinic acid branched alkyl esters disclosed in Patent Document 1 and have found that the surface tension reducing ability of the above-mentioned sulfosuccinic acid branched alkyl esters is lower than the surface tension reducing ability of fluorosurfactants having a perfluoroalkyl group.

[0005] Therefore, an object of the present invention is to provide a non-fluorine-containing compound having excellent surface tension reducing ability at the same level as that of a fluorine-containing surfactant. Another object of the present invention is to provide a surfactant and a surfactant composition.

[0006] As a result of extensive research into solving the above problems, the present inventors have found that the problems can be solved by the following configuration.

[0007] [1] A compound represented by the formula (1) described below. [2] The compound according to [1], wherein n is 0 in the formula (1). [3] In the formula (1), R ２ [4] The compound according to [1] or [2], wherein R ３ is a group represented by formula (2) described below, and R in formula (1) １ and R in formula (2) ４are each independently a branched alkyl group selected from the groups represented by formulas (3) to (5) described below. [5] A surfactant containing the compound according to any one of [1] to [4]. [6] A surfactant composition containing the surfactant according to [5] and an aqueous medium.

[0008] In this specification, a compound represented by formula (1) may be simply referred to as "compound (1)" or "(1)". The same applies to a compound represented by formula (6) and the like. In this specification, a group represented by formula (2) may be simply referred to as "group (2)" or "(2)". The same applies to a group represented by formula (3) and the like.

[0009] According to the present invention, it is possible to provide a non-fluorine-containing compound having excellent surface tension reducing ability equivalent to that of a fluorine-containing surfactant. The present invention can also provide a surfactant and a surfactant composition.

[0010] FIG. 1 is a chart of the FT-IR analysis of the reaction product obtained by reacting the compound represented by formula (10) with taurine in Example 1.

[0011] The present invention will be described in detail below. The following description of the constituent elements may be based on a representative embodiment of the present invention, but the present invention is not limited to such an embodiment. In this specification, a numerical range expressed using "to" means a range including the numerical values ​​before and after "to" as the lower and upper limits. In this specification, each component can be used alone or in combination of two or more. In this specification, when two or more components are used in combination, the "content" of the component refers to the total content of those two or more components, unless otherwise specified. In this specification, the manufacturing method of each component is not particularly limited unless otherwise specified. For example, a conventionally known method can be used. The compound of the present invention will be described below.

[0012] [Compound] The compound of the present invention is a compound represented by the following formula (1): １ -O-C ｐ H２ｐ -CR ２ (OH)-C ｑ H ２ｑ -NR ３ -C ｒ H ２ｒ -(O) ｎ -SO ３ ] ｚ M (1) The symbols in formula (1) have the following meanings: R １ R: a branched alkyl group having 9 to 18 carbon atoms ２ p, q, and r are each independently an integer of 1 to 6; M is a hydrogen atom or a monovalent or divalent cation; n is 0 or 1; R is an alkyl group having 1 to 6 carbon atoms; ３ R: a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a group represented by the following formula (2): ４ -O-C ｘ H ２ｘ -CR ５ (OH)-C ｙ H ２ｙ - (2) R ４ R: a branched alkyl group having 9 to 18 carbon atoms ５ x and y are each independently an integer from 1 to 6; z is 1 or 2;

[0013] The reason why the compound of the present invention having the above-mentioned structure can solve the problem of the present invention is not necessarily clear, but the present inventors speculate as follows. Note that the following speculation does not limit the mechanism by which the effect is obtained. In other words, even if the effect is obtained by a mechanism other than the one described below, it is still within the scope of the present invention. The compound of the present invention is a compound of formula (1) in which R represents a branched alkyl group having 9 to 18 carbon atoms. １ In addition to [...-O-C ｐ H ２ｐ -CR ２ (OH)-C ｑ H ２ｑ -NR ３ -C ｒ H ２ｒ -(O) ｎ -SO ３ ] ｚIt is believed that the compound of the present invention has an excellent surface tension reducing ability equivalent to that of a fluorosurfactant due to the presence of the structure M. Furthermore, since the compound of the present invention does not have a carboxylic acid ester bond but has an ether bond which is more difficult to decompose than a carboxylic acid ester bond, it is believed that the compound can stably exhibit an excellent surface tension reducing ability equivalent to that of a fluorosurfactant.

[0014] Each symbol in formula (1) will be explained below. １ ] In formula (1), R １ is a branched alkyl group having 9 to 18 carbon atoms. １ Examples of the branched alkyl group having 9 to 18 carbon atoms as R include groups represented by the following formulas (3) to (5), an isodecyl group, an isododecyl group, an isotridecyl group, an isostearyl group, a 2-hexyl-1-dodecyl group, a 2,6,8-trimethyl-4-nonyl group, and an 8-methyl-2-(4-methylhexyl)decyl group. １ From the viewpoint of achieving a more excellent effect of the present invention, the branched alkyl group having 9 to 18 carbon atoms as R １ is preferably any branched alkyl group selected from groups represented by the following formulas (3) to (5). The wavy line in formula (3) represents the letter "CH ２ " represents the end of a bond of the carbon atom of R １ is bonded to an oxygen atom, R １ The group represented by formula (3) is bonded to the oxygen atom via the bond. The wavy lines in formulas (4) and (5) have the same meaning.

[0015] In formula (1), “R １ " and "-C ｐ H ２ｐ Regarding the "-O-" located between "-", the "-O-" is "R １ The above "-O-" can be bonded to any of the carbon atoms of -C ｐ H ２ｐ It is sufficient that the bond is made to any of the carbon atoms having the -.

[0016] [R ２ ] In formula (1), R ２ is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ２ Examples of the alkyl group having 1 to 6 carbon atoms as the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a heptyl group. The alkyl group having 1 to 6 carbon atoms may be linear, and when it has 3 to 6 carbon atoms, it may be linear, branched, or cyclic.

[0017] R ２ is preferably a hydrogen atom from the viewpoint of easy availability and reactivity of the raw materials constituting the compound of the present invention.

[0018] [p, q and r] In formula (1), p, q and r are each independently an integer of 1 to 6. ｐ H ２ｐ The divalent linking group represented by - may be linear, and when p is an integer of 3 to 6, it may be either linear or branched. ｒ H ２ｒ - is also the same.

[0019] [p] In formula (1), p is preferably an integer of 1 to 3, and more preferably 1, from the viewpoint of easy availability and reactivity of the raw materials constituting the compound of the present invention.

[0020] [q] In formula (1), q is preferably an integer of 1 to 3, more preferably 1, from the viewpoint of easy availability and reactivity of the raw materials constituting the compound of the present invention. ｑ H ２ｑ The divalent linking group represented by - may be linear, and when q is an integer of 3 to 6, it may be either linear or branched.

[0021] [r] In formula (1), from the viewpoint of easy availability and reactivity of the raw materials constituting the compound of the present invention, r is preferably an integer of 1 to 3, and more preferably an integer of 2 or 3. In formula (1), from the viewpoint of more excellent effects of the present invention, r is preferably an integer of 1 to 3, more preferably an integer of 2 or 3, and even more preferably 3.

[0022] [-CR ２ (OH)-] in formula (1) ２ (OH)-" is -C ｐ H ２ｐ The "-CR" in formula (1) may be bonded to any of the carbon atoms of the "-CR" ２ (OH)-" is -C ｑ H ２ｑ It is sufficient that the bond is made to any of the carbon atoms having the -.

[0023] [-NR ３ -] "-NR" in formula (1) ３ -" is -C ｑ H ２ｑ The "-NR" in formula (1) may be bonded to any of the carbon atoms of the "-NR" ３ -" is -C ｒ H ２ｒ It is sufficient that the bond is made to any of the carbon atoms having the -.

[0024] [M] In formula (1), M is a hydrogen atom or a monovalent or divalent cation.

[0025] (Monovalent or divalent cation) When M is a monovalent or divalent cation, —SO ３ is -SO ３ － That is, when M is a monovalent or divalent cation, the compound represented by formula (1) is a sulfonate (n=0) or sulfate (n=1). When M is a monovalent cation, examples of the monovalent cation include alkali metal ions and ammonium ions (NH ４ ＋ ), and organic ammonium ions. Examples of alkali metal ions include lithium ions, sodium ions, and potassium ions. Examples of organic ammonium ions include ammonium ions (NH ４ ＋) in which some or all of the hydrogen atoms have been substituted with alkyl groups or hydroxyalkyl groups (the alkyl groups or hydroxyalkyl groups have 1 or 2 carbon atoms), and specific examples thereof include triethylammonium ions and diethanolammonium ions.

[0026] When M is a divalent cation, examples of the divalent cation include alkaline earth metal ions, such as magnesium ions and calcium ions.

[0027] From the viewpoints of achieving better effects of the present invention, producing fewer by-products when synthesizing the compound of the present invention, and facilitating dissolution of the compound of the present invention in a solvent, M is preferably a hydrogen atom or an alkali metal ion, and more preferably a sodium ion.

[0028] [n] In formula (1), n ​​is 0 or 1. When n is 1, "-(O)" in formula (1) １ -" is -C ｒ H ２ｒ When n is 0, the "-SO ３ " is -C ｒ H ２ｒ It is sufficient that the bond is made to any of the carbon atoms having the -.

[0029] From the viewpoint of achieving better effects of the present invention and having excellent stability under acidic conditions (for example, being less susceptible to hydrolysis), n is preferably 0.

[0030] [R ３ ] In formula (1), R ３ is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a group represented by the following formula (2): ４ -O-C ｘ H ２ｘ -CR ５ (OH)-C ｙ H ２ｙ - (2) In formula (1), R ３ is preferably a group represented by formula (2) from the viewpoint of achieving better effects of the present invention.

[0031] (C1-12 alkyl group) R ３ is an alkyl group having 1 to 12 carbon atoms, examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a heptyl group, an octyl group, a decyl group, and a dodecyl group. The alkyl group having 1 to 12 carbon atoms may be linear, and when it has 3 to 12 carbon atoms, it may be linear, branched, cyclic, or a combination thereof.

[0032] (Group represented by formula (2)) R ３ When is a group represented by formula (2), each symbol in formula (2) will be explained below.

[0033] (R ４ ) In formula (2), R ４ is a branched alkyl group having 9 to 18 carbon atoms. ４ The branched alkyl group having 9 to 18 carbon atoms as R １ The same applies to the branched alkyl group having 9 to 18 carbon atoms as R ４ From the viewpoint of achieving a more excellent effect of the present invention, the branched alkyl group having 9 to 18 carbon atoms as R ４ is preferably any branched alkyl group selected from the groups represented by the above formulas (3) to (5).

[0034] (R ５ ) In formula (2), R ５ is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ５ The alkyl group having 1 to 6 carbon atoms as R ２ The alkyl group having 1 to 6 carbon atoms is the same as the alkyl group having 1 to 6 carbon atoms. ５ is preferably a hydrogen atom from the viewpoint of easy availability and reactivity of the raw materials constituting the compound of the present invention.

[0035] (x and y) In formula (2), x and y are each independently an integer of 1 to 6. x in formula (2) is the same as p in formula (1) described above. In formula (2), p is preferably an integer of 1 to 3, more preferably 1, from the viewpoint of easy availability and reactivity of the raw materials constituting the compound of the present invention. y in formula (2) is the same as q in formula (1) described above. In formula (2), q is preferably an integer of 1 to 3, more preferably 1, from the viewpoint of easy availability and reactivity of the raw materials constituting the compound of the present invention.

[0036] —O—, —C in formula (2) ｘ H ２ｘ -, CR ５ (OH), -C ｙ H ２ｙ - represents -O-, -C in formula (1). ｐ H ２ｐ -, -CR ２ (OH)-, -C ｑ H ２ｑ - and the same respectively.

[0037] [z] In formula (1), z is 1 or 2. When M is a hydrogen atom or a monovalent cation, z is 1. When M is a divalent cation, z is 2. In a preferred embodiment, M is 1. When z is 2, two [R １ -O-C ｐ H ２ｐ -CR ２ (OH)-C ｑ H ２ｑ -NR ３ -C ｒ H ２ｒ -(O) ｎ -SO ３ ] may be the same or different.

[0038] (Preferred embodiment of the compound represented by formula (1)) In view of the superior effect of the present invention, the compound represented by formula (1) is ３ is a group represented by formula (2), and R in formula (1) １ and R in formula (2) ４are each independently a branched alkyl group selected from the groups represented by the above formulas (3) to (5), and z is 1.

[0039] Examples of the compound represented by formula (1) include the following compounds: ３ is a group represented by formula (2), and R in formula (1) １ and R in formula (2) ４ are all groups represented by the above formula (3), and R ２ and R in formula (2) ５ When R is a hydrogen atom and z is 1, examples of the compound include the following compounds. １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ -SO ３ H and R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ -SO ３ Li, and R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ -SO ３ Na, R ３ is R ４ -O-CH ２ -CH(OH)-CH２ - and R １ and R ４ are all groups represented by the above formula (3). The above compound is represented by the following formula (6). R １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ -SO ３ K and R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ -SO ３ NH ４ and R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ CH ２ -SO ３ H and R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH２ CH ２ -SO ３ Li, and R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ CH ２ -SO ３ Na, R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４ are all groups represented by the above formula (3). The compound is represented by the following formula (9). R １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ CH ２ -SO ３ K and R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ CH ２ -SO ３ NH ４ and R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １and R ４ are both groups represented by the above formula (3).

[0040] ・R ３ is a group represented by formula (2), and R in formula (1) １ and R in formula (2) ４ are all groups represented by the above formula (3), and R ２ and R in formula (2) ５ When R is a methyl group and z is 1, examples of the compound include the following: １ -O-CH ２ -C(CH ３ )(OH)—CH ２ -NR ３ -CH ２ CH ２ -SO ３ H and R ３ is R ４ -O-CH ２ -C(CH ３ )(OH)—CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -C(CH ３ )(OH)—CH ２ -NR ３ -CH ２ CH ２ -SO ３ Li, and R ３ is R ４ -O-CH ２ -C(CH ３ )(OH)—CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -C(CH ３ )(OH)—CH ２ -NR ３ -CH ２ CH ２ -SO ３ Na, R ３ is R ４-O-CH ２ -C(CH ３ )(OH)—CH ２ - and R １ and R ４ are all groups represented by the above formula (3). The compound is represented by the following formula (8). R １ -O-CH ２ -C(CH ３ )(OH)—CH ２ -NR ３ -CH ２ CH ２ -SO ３ K and R ３ is R ４ -O-CH ２ -C(CH ３ )(OH)—CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -C(CH ３ )(OH)—CH ２ -NR ３ -CH ２ CH ２ -SO ３ NH ４ and R ３ is R ４ -O-CH ２ -C(CH ３ )(OH)—CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -C(CH ３ )(OH)—CH ２ -NR ３ -CH ２ CH ２ CH ２ -SO ３ H and R ３ is R ４ -O-CH ２ -C(CH ３ )(OH)—CH ２ - and R１ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -C(CH ３ )(OH)—CH ２ -NR ３ -CH ２ CH ２ CH ２ -SO ３ Li, and R ３ is R ４ -O-CH ２ -C(CH ３ )(OH)—CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -C(CH ３ )(OH)—CH ２ -NR ３ -CH ２ CH ２ CH ２ -SO ３ Na, R ３ is R ４ -O-CH ２ -C(CH ３ )(OH)—CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH ２ -C(CH ３ )(OH)—CH ２ -NR ３ -CH ２ CH ２ CH ２ -SO ３ K and R ３ is R ４ -O-CH ２ -C(CH ３ )(OH)—CH ２ - and R １ and R ４ are all groups represented by the above formula (3). １ -O-CH２ -C(CH ３ )(OH)—CH ２ -NR ３ -CH ２ CH ２ CH ２ -SO ３ NH ４ and R ３ is R ４ -O-CH ２ -C(CH ３ )(OH)—CH ２ - and R １ and R ４ are both groups represented by the above formula (3).

[0041] ・R ３ is a group represented by formula (2), and R in formula (1) １ and R in formula (2) ４ are all groups represented by the above formula (4), and R ２ and R in formula (2) ５ When all of R are hydrogen atoms and z is 1, examples of the compounds include the following: １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ -SO ３ H and R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４ are all groups represented by the above formula (4). １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ -SO ３ Li, and R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４are all groups represented by the above formula (4). １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ -SO ３ Na, R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４ are all groups represented by the above formula (4). １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ -SO ３ K and R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４ are all groups represented by the above formula (4). １ -O-CH ２ -CH(OH)-CH ２ -NR ３ -CH ２ CH ２ -SO ３ NH ４ and R ３ is R ４ -O-CH ２ -CH(OH)-CH ２ - and R １ and R ４ are both groups represented by the above formula (4).

[0042] ・R ２ , R ３ is a hydrogen atom, and R in formula (1) １ is a group represented by the above formula (5) and z is 1, examples of the compound include the following: １ -O-CH ２ -CH(OH)-CH ２-NH-CH ２ CH ２ -SO ３ H and R １ is a group represented by the above formula (5). The compound is represented by the following formula (7): R １ -O-CH ２ -CH(OH)-CH ２ -NH-CH ２ CH ２ -SO ３ Li, and R １ is a group represented by the above formula (5). １ -O-CH ２ -CH(OH)-CH ２ -NH-CH ２ CH ２ -SO ３ Na, R １ is a group represented by the above formula (5). １ -O-CH ２ -CH(OH)-CH ２ -NH-CH ２ CH ２ -SO ３ K and R １ is a group represented by the above formula (5). １ -O-CH ２ -CH(OH)-CH ２ -NH-CH ２ CH ２ -SO ３ NH ４ and R １ is a group represented by the above formula (5).

[0043] (Production Method) The compound of the present invention can be produced, for example, by a method comprising: reacting a compound represented by the formula (15): NHR with a hydroxide of an alkali metal or alkaline earth metal, or ammonia or an amine; water such as ion-exchanged water; ６ -C ｒ H ２ｒ -(O) ｎ -SO ３One example of a method for producing the compound of the present invention is to heat a mixed solution containing an aminosulfonic acid (n=0) or aminosulfuric acid ester (n=1) represented by H and a water-soluble organic solvent to 60 to 80°C, add dropwise an epoxy compound represented by the following formula (16) to the mixture while stirring, and then react the aminosulfonic acid or aminosulfuric acid ester represented by the above formula (15) with the epoxy compound represented by formula (16) at room temperature after the dropwise addition. The aminosulfonic acid or aminosulfuric acid ester represented by the above formula (15) will hereinafter also be referred to as "aminosulfonic acid, etc. represented by formula (15)". In the above formula (15), R ６ is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and r in formula (15) is the same as r in formula (1). ６ The alkyl group having 1 to 12 carbon atoms as R ３ The alkyl group is the same as the alkyl group having 1 to 12 carbon atoms. R in formula (16) １ , R ２ , p, and q are R in formula (1). １ , R ２ , p, q.

[0044] When formula (15) and formula (16) are reacted in the presence of an alkali metal hydroxide or the like as described above, M in the resulting formula (1) can be converted to a cation. Furthermore, after reacting formula (15) and formula (16) in the presence of an alkali metal hydroxide or the like as described above, M (cation) in the resulting formula (1) can be converted to a hydrogen atom by creating an acidic condition in the reaction system using a strong acid. After the above reaction, the resulting compound of the present invention may be purified as needed. The purification method is not particularly limited.

[0045] - Hydroxides of alkali metals or alkaline earth metals, or ammonia or amines. Examples of hydroxides of alkali metals or alkaline earth metals used in the above production method include lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, and magnesium hydroxide. Examples of amines include compounds in which some or all of the hydrogen atoms of ammonia are substituted with alkyl groups or hydroxyalkyl groups (the alkyl groups or hydroxyalkyl groups have 1 or 2 carbon atoms), and specific examples include triethylamine and diethanolamine. Aminosulfonic acids represented by formula (15) are water-soluble (e.g., taurine), and the NHR ６ - is N in water ＋ H ２ R ６ - (when formula (15) is taurine (R ６ is a hydrogen atom), and the amino group of taurine is N ＋ H ３ -), and by making the reaction system alkaline using hydroxides of the above-mentioned alkali metals as a base, N ＋ H ２ R ６ -NHR ６ It is preferable to return it to the negative state and react the aminosulfonic acid or the like represented by the above formula (15) with the epoxy compound represented by the formula (16).

[0046] Amount of hydroxide, etc. used relative to aminosulfonic acid, etc. The amount of alkali metal hydroxide, etc. used relative to the aminosulfonic acid, etc. represented by formula (15) can be, for example, 1 to 3 molar equivalents of the alkali metal hydroxide per 1 molar equivalent of the aminosulfone, etc. The amount of alkaline earth metal hydroxide, etc. used relative to the aminosulfonic acid, etc. represented by formula (15) can be, for example, 0.5 to 3 molar equivalents of the alkaline earth metal hydroxide per 1 molar equivalent of the aminosulfone, etc. The amount of ammonia or amine used relative to the aminosulfone, etc. represented by formula (15) can be, for example, 1 to 3 molar equivalents of the ammonia or amine per 1 molar equivalent of the aminosulfone, etc.

[0047] Aminosulfonic acid represented by formula (17) (compound in the above formula (15) where n=0) In the above production method, the aminosulfonic acid represented by formula (15) (where n=0) may be, for example, a compound represented by formula (17): NHR ６ -C ｒ H ２ｒ -SO ３ A compound represented by R in formula (17) is used. ６ is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and r in formula (17) is the same as r in formula (1). ６ The alkyl group having 1 to 12 carbon atoms as R ３ The alkyl group having 1 to 12 carbon atoms is the same as the alkyl group having 1 to 12 carbon atoms as the compound represented by formula (17). ２ -CH ２ CH ２ -SO ３ H), aminomethanesulfonic acid (NH ２ -CH ２ -SO ３ H), 3-aminopropanesulfonic acid (NH ２ -CH ２ CH ２ CH ２ -SO ３ H. Homotaurine), N-methyltaurine (CH ３ NH-CH２ CH ２ -SO ３ H).

[0048] Aminosulfate ester represented by formula (18) (compound in the above formula (15) where n=1) In the above production method, the aminosulfate ester represented by formula (15) (where n=1) may be, for example, a compound represented by formula (18): NHR ６ -C ｒ H ２ｒ -O-SO ３ A compound represented by R in formula (18) is used. ６ is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and r in formula (18) is the same as r in formula (1). ６ The alkyl group having 1 to 12 carbon atoms as R ３ The compound represented by formula (18) is, for example, 2-aminoethyl hydrogen sulfate (NH ２ -CH ２ CH ２ -O-SO ３ H).

[0049] Epoxy Compound In the above production method, for example, a compound represented by the following formula (16) is used as the epoxy compound. R in formula (16) １ , R ２ , p, and q are R in formula (1). １ , R ２ , p, and q are the same. Examples of the compound represented by formula (16) include 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane (structure represented by formula (10) below), a compound represented by formula (19) below, a compound in which a glycidyloxy group is bonded to a bond of the group represented by formula (4) above, and a compound in which a glycidyloxy group is bonded to a bond of the group represented by formula (5) above.

[0050] Amount of epoxy compound used relative to aminosulfonic acid, etc. The amount of epoxy compound used relative to the aminosulfonic acid, etc., represented by formula (15) can be, for example, 1 to 3 molar equivalents of the epoxy compound per 1 molar equivalent of the aminosulfonic acid, etc. In formula (1), R ３ When synthesizing a compound in which R is a group represented by formula (2), for example, ６ The epoxy compound may be reacted in an amount of 2 molar equivalents or more with 1 molar equivalent of an aminosulfonic acid or the like in which R is a hydrogen atom. ６ When R is a hydrogen atom, the epoxy compound is reacted with 1 molar equivalent of the aminosulfonic acid in a theoretical amount of 2 molar equivalents to form the compound represented by the formula (1). ３ is a group represented by formula (2). ３ When synthesizing a compound in which R is the hydrogen atom or the alkyl group, for example, a compound represented by the above formula (15) is used. ６ Theoretically, 1 molar equivalent of the epoxy compound may be reacted with 1 molar equivalent of aminosulfonic acid or the like, in which R is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.

[0051] Water-soluble organic solvent: Examples of the water-soluble organic solvent used in the production method include alcohols such as methanol, ethanol, isopropanol (isopropyl alcohol), and tertiary 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.

[0052] Amount of Water and Water-Soluble Organic Solvent Used There are no particular restrictions on the amount of water used in the above production method, and the same applies to the amount of water-soluble organic solvent used.

[0053] (Use) When the compound of the present invention is used, the compound of the present invention may be in the form of the compound of the present invention alone or a mixture of the compound of the present invention with an aqueous medium.

[0054] Aqueous Medium: Examples of the aqueous medium include water, a water-soluble organic solvent, or a mixture of water and a water-soluble organic solvent. Examples of water-soluble organic solvents include alcohols such as methanol, ethanol, isopropanol, and tertiary 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 compound of the present invention is a mixture with an aqueous medium, the aqueous medium contained in the mixture may contain the water and water-soluble organic solvent used in producing the compound of the present invention.

[0055] Content of Aqueous Medium When the compound of the present invention is in the state of a mixture with an aqueous medium, the content of the aqueous medium is not particularly limited.

[0056] (Uses) The compound of the present invention can be used, for example, as a surfactant.

[0057] [Surfactant] The surfactant of the present invention is a surfactant containing the compound of the present invention. [Compound as an essential component] 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. When the surfactant of the present invention contains two or more compounds of the present invention, the combination thereof can be, for example, R １ and a combination of compounds having different branched alkyl groups represented by R ３ is a hydrogen atom and a compound in which R ３ is a group represented by formula (2).

[0058] In the present invention, the compound of the present invention may be used as it is as the surfactant of the present invention.

[0059] [Surfactant Composition] The surfactant composition of the present invention is a surfactant composition containing the surfactant of the present invention and an aqueous medium.

[0060] [Surfactant] 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.

[0061] (Concentration of 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 is not particularly limited, but is preferably 10 to 70% by mass, and particularly preferably 15 to 60% by mass. When it is in the above range, the amount of solvent (including aqueous medium) in the surfactant composition of the present invention is small, which is preferable because it is easy to ensure that the amount of surfactant of the present invention is an appropriate amount when the surfactant composition of the present invention is used as an additive. Furthermore, when it is in the above range, the viscosity of the surfactant composition of the present invention does not become too high, which is preferable because it has good handleability and the surfactant of the present invention is less likely to precipitate during storage.

[0062] [Aqueous Medium] The aqueous medium contained as an essential component in the surfactant composition of the present invention includes water, a water-soluble organic solvent, or a mixture of water and a water-soluble organic solvent. Examples of water-soluble organic solvents include alcohols such as methanol, ethanol, isopropanol, and tertiary 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.

[0063] (Additives) The surfactant composition of the present invention may further contain, as needed, for example, other surfactants, pH adjusters, rust inhibitors, dyes, dye stabilizers, flame retardants, antifoaming agents, and antistatic agents, within the range that does not impair the effects of the present invention. The type and content of the additives may be appropriately selected.

[0064] (Other Surfactants) The surfactant composition of the present invention may further contain a surfactant (other surfactant) other than the compound of the present invention. The other surfactant is not particularly limited. For example, conventionally known surfactants may be used. The other surfactant may not be a fluorine-based surfactant.

[0065] (Production Method) Examples of the method for producing the surfactant composition of the present invention include a method for producing the surfactant composition of the present invention by mixing the surfactant of the present invention, an aqueous medium, and additives that can be used as needed.

[0066] (Applications) The surfactant composition of the present invention exhibits sufficient surface tension reducing ability even at low concentrations, making it suitable for use as an additive in a variety of applications. The surfactant composition of the present invention can be used, for example, as a leveling agent for waxes and the like, a foaming aid, an additive for generating stable foam and improving fire extinguishing performance in foam fire extinguishing, a detergent, a release agent, an emulsifier, a rust inhibitor, a latex stabilizer, an anti-fogging agent for agricultural films, a pigment dispersant, an agent for improving the wettability and penetration of inks, paints, resists, etc., an agent for imparting water and oil repellency to curable resins, an anti-fogging agent for agricultural films, an antifouling agent, a flotation agent, a leveling agent, a deinking agent, and the like. The surfactant composition of the present invention can also be used in a wide range of applications, including cleaning and gravure printing. The surfactant and surfactant composition of the present invention can also be used in various liquids by adding the surfactant or surfactant composition of the present invention to the liquid to reduce the surface tension of the liquid without being limited by the solvent composition. The amount of the surfactant or surfactant composition of the present invention added is determined appropriately depending on the purpose and conditions of use. However, in the state of actual use (in the mixture after adding the surfactant or surfactant composition of the present invention to various liquids), compound (1) is preferably contained in an amount of 0.001 to 5% by mass, and more preferably 0.005 to 1% by mass. A content within the above range is preferred because it fully exhibits the surface tension-reducing ability and does not negate the functionality of the main component (the liquid before adding the surfactant or surfactant composition of the present invention). When the surfactant or surfactant composition of the present invention contains two or more types of compound (1), the total amount thereof is preferably within the above range. Furthermore, due to its surface tension-reducing ability, it can impart functions such as leveling, penetration, foaming, cleansing, and emulsifying properties to the liquid to which it is added.

[0067] The present invention will be described in more detail below based on examples. The materials, amounts used, ratios, processing details, processing procedures, etc. shown in the following examples can be changed 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 examples shown below. In the following, unless otherwise specified, "parts" and "%" mean "parts by mass" and "% by mass".

[0068] Example 1 Production of Specific Compound 1 (Synthesis of 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane) Epichlorohydrin (384.81 g, 4159 mmol), 3,5,5-trimethyl-1-hexanol (400.00 g, 2773 mmol) represented by the following formula (12), sodium hydroxide (166.40 g, 4160 mmol), and tetrabutylammonium bromide (44.69 g, 139 mmol) were placed in a 2000 ml glass flask, and the temperature was raised to 30° C., and the reaction was carried out at that temperature for 11 hours. Gas chromatography analysis of the reaction solution indicated that the reaction rate of 3,5,5-trimethyl-1-hexanol was 88% or higher. The reaction solution was transferred to a separatory funnel, and ion-exchanged water and ethyl acetate were added thereto. The mixture was separated and filtered, after which the ethyl acetate was removed using an evaporator. The removed solution was distilled to obtain 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane (356.96 g, purity 98%, yield 63%, structure represented by the following formula (10)).

[0069] (Synthesis of sodium 2-(bis(2-hydroxy-3-((3,5,5-trimethylhexyl)oxy)propyl)amino)ethane-1-sulfonate (Specific Compound 1)) Sodium hydroxide (6.57 g, 164 mmol), ion-exchanged water (87.31 g, 4845 mmol), and taurine (20.56 g, 164 mmol) were placed in a 300 ml glass flask and stirred for 30 minutes. Isopropyl alcohol (87.19 g, 1451 mmol) was then placed in the solution and heated to 76.5°C. 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane (66.68 g, 329 mmol) synthesized as above was added dropwise over 2 hours, and the reaction was carried out at that temperature for 13 hours. Gas chromatography analysis of the reaction solution revealed that the conversion of 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane was 99% or more. As a result of the above synthesis, a water / isopropyl alcohol solution containing 35% of the reaction product (299.62 g, yield 99.87%) was obtained.

[0070] <Gas Chromatography Analysis> The measurement conditions for the gas chromatography analysis are as follows: Apparatus: GC-2014 (Shimadzu Corporation) Column: DB-5msUI (Agilent Technologies Inc.) (inner diameter 0.25 mm, length 30 m, film thickness 0.25 μm) Injection port temperature: 250°C Injection method: split split ratio: 50 Column temperature program: temperature program of holding at 50°C for 5 minutes, increasing the temperature to 250°C at 10°C / min, and holding at 250°C for 10 minutes

[0071] (Analysis) A part of the obtained solution was dried, and the solid content was analyzed by FT-IR (ATR method) using FT / IR-4600 (manufactured by JASCO Corporation) and NMR analysis ( １ H-NMR, １３ C-NMR) was performed.

[0072] FT-IR (ATR) Analysis Figure 1 is a chart of the FT-IR analysis of the reaction product obtained by reacting the compound represented by formula (10) with taurine in Example 1. As shown in Figure 1, the peaks at 3417, 2950, ​​1647, 1468, 1364, 1172, 1120, 1035, 739, 610, and 528 cm －１ A peak was detected at

[0073] ・NMR analysis ( １ H-NMR, １３ C-NMR) of the reaction product obtained by reacting the compound represented by formula (10) with taurine in Example 1 １ H-NMR and １３ The C-NMR spectrum data is as follows: １ H-NMR (400 MHz, solvent: acetone-d ６, standard material: TMS), δ (ppm): 0.94 (s, 18H), 0.97 (d, J = 6.8Hz, 6H), 1.10 (dd, J = 14.4Hz, 6.8Hz, 2H), 1.30 (dd, J = 14.4Hz, 4.0Hz, 2H), 1.40-1.50 (m, 2H), 1.57-1.71 (m, 4H), 2.52-2.73 (m, 2H), 2.92-3.02 (m, 6H), 3.40-3.54 (m, 8H), 3.90-4.06 (m, 2H) １３ C-NMR (100 MHz, solvent: acetone-d ６ ), δ (ppm): 23.6, 27.2, 30.6, 31.8, 40.1, 52.2, 59.4, 61.4, 67.6, 69.2, 70.5, 74.4

[0074] <NMR Measurement> NMR ( １ H-NMR, １３ The measurement of the C-NMR is as follows: ６ The sample was dissolved in 100 ml of 10 ... １ H-NMR (standard: TMS), １３ C-NMR

[0075] As a result of the above analysis, it was found that the obtained reaction product was sodium 2-(bis(2-hydroxy-3-((3,5,5-trimethylhexyl)oxy)propyl)amino)ethane-1-sulfonate (a compound represented by the following formula (6)). The compound represented by the above formula (6) corresponds to the compound of the present invention and the surfactant of the present invention. In this specification, the sodium 2-(bis(2-hydroxy-3-((3,5,5-trimethylhexyl)oxy)propyl)amino)ethane-1-sulfonate obtained as described above is also referred to as "Specific Compound 1" hereinafter.

[0076] Example 3 Production of Specific Compound 2 Synthesis of Sodium 3-(bis(2-hydroxy-3-((3,5,5-trimethylhexyl)oxy)propyl)amino)propane-1-sulfonate Caustic soda (0.64 g, 16 mmol), homotaurine (2.23 g, 16 mmol), isopropyl alcohol (9.00 g, 150 mmol), and ion-exchanged water (9.00 g, 500 mmol) were placed in a 100 ml glass flask and heated to 75°C. Then, 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane (6.43 g, 32 mmol) synthesized in Example 1 was added dropwise over 2 hours, and the reaction was carried out at that temperature for 12 hours. Gas chromatography analysis of the reaction solution showed that the conversion of 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane was 99% or more. As a result of the above synthesis, a water / isopropyl alcohol solution containing 30% of the reaction product (26.63 g, yield 89%) was obtained.

[0077] In Example 3, the reaction product obtained by reacting the compound represented by formula (10) with homotaurine was １ H-NMR and １３ The C-NMR spectrum data is as follows: １ H-NMR (400 MHz, solvent: acetone-d ６ , standard material: TMS), δ (ppm): 0.94 (s, 18H), 0.97 (d, J = 6.4Hz, 6H), 1.08 (dd, J = 14.0Hz, 6.0Hz, 2H), 1.29 (dd, J = 14.0H) z, 3.2Hz, 2H), 1.43-1.48 (m, 2H), 1.58-1.72 (m, 4H), 2.36-3.20 (m, 10H), 3.42-3.53 (m, 8H), 3.91-3.94 (m, 2H) １３ C-NMR (100 MHz, solvent: acetone-d ６ ), δ (ppm): 23.4, 26.9, 30.3, 31.6, 40.0, 52.0, 55.1, 56.0, 59.4, 60.9, 69.1, 70.3, 74.3

[0078] As a result of the above analysis, it was found that the obtained reaction product was sodium 3-(bis(2-hydroxy-3-((3,5,5-trimethylhexyl)oxy)propyl)amino)propane-1-sulfonate (a compound represented by the following formula (9)). The compound represented by the above formula (9) corresponds to the compound of the present invention and the surfactant of the present invention. In this specification, sodium 3-(bis(2-hydroxy-3-((3,5,5-trimethylhexyl)oxy)propyl)amino)propane-1-sulfonate obtained as described above is also referred to as "Specific Compound 2" hereinafter.

[0079] Example 4 Production of Specific Compound 3 Synthesis of Sodium 2-((2-hydroxy-3-((3,5,5-trimethylhexyl)oxy)propyl)amino)ethane-1-sulfonate Caustic soda (1.04 g, 26 mmol), taurine (3.24 g, 26 mmol), isopropyl alcohol (9.00 g, 150 mmol), and ion-exchanged water (9.00 g, 500 mmol) were placed in a 50 ml glass flask and heated to 75°C. Then, 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane (5.36 g, 26 mmol) synthesized in Example 1 was added dropwise over 2 hours, and the reaction was carried out at that temperature for 12 hours. Gas chromatography analysis of the reaction liquid showed that the conversion of 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane was 99% or more. As a result of the above synthesis, a water / isopropyl alcohol solution containing 30% of the reaction product (26.38 g, yield 88%) was obtained.

[0080] In Example 4, the reaction product obtained by reacting the compound represented by formula (10) with taurine was １ H-NMR and １３ The C-NMR spectrum data is as follows: １ H-NMR (400 MHz, solvent: acetone-d ６, standard material: TMS), δ (ppm): 0.94 (s, 9H), 0.97 (d, J = 4.0Hz, 3H), 1.07 (dd, J = 13.6Hz, 6.4Hz, 1H), 1.28 (dd, J = 14.4H) z, 3.2Hz, 1H), 1.41-1.47 (m, 1H), 1.55-1.71 (m, 2H), 2.55-3.33 (m, 6H), 3.42-3.52 (m, 4H), 3.97-4.05 (m, 1H) １３ C-NMR (100 MHz, solvent: acetone-d ６ ), δ (ppm): 23.4, 27.0, 30.3, 31.6, 40.0, 52.0, 53.3, 59.3, 61.4, 68.9, 70.3, 74.3

[0081] As a result of the above analysis, it was found that the obtained reaction product was sodium 2-((2-hydroxy-3-((3,5,5-trimethylhexyl)oxy)propyl)amino)ethane-1-sulfonate (a compound represented by the following formula (20)). The compound represented by the above formula (20) corresponds to the compound of the present invention and the surfactant of the present invention. In this specification, sodium 2-((2-hydroxy-3-((3,5,5-trimethylhexyl)oxy)propyl)amino)ethane-1-sulfonate obtained as described above is also referred to as "Specific Compound 3" hereinafter.

[0082] [Preparation of Surfactant Composition] Subsequently, ion-exchanged water was added to the water / isopropyl alcohol solution containing Specific Compound 1 obtained as described above, to obtain a water / isopropyl alcohol solution containing 30% Specific Compound 1. The water / isopropyl alcohol solution containing 30% Specific Compound 1 corresponds to the surfactant composition of the present invention. Hereinafter, the water / isopropyl alcohol solution as the surfactant composition of the present invention will also be referred to as "water / isopropyl alcohol solution 1." The water / isopropyl alcohol solution obtained in Example 3 containing 30% Specific Compound 2 corresponds to the surfactant composition of the present invention. Hereinafter, the water / isopropyl alcohol solution of Example 3 as the surfactant composition of the present invention will also be referred to as "water / isopropyl alcohol solution 2." The water / isopropyl alcohol solution obtained in Example 4 containing 30% Specific Compound 3 corresponds to the surfactant composition of the present invention. Hereinafter, the water / isopropyl alcohol solution of Example 4 as the surfactant composition of the present invention will also be referred to as "water / isopropyl alcohol solution 3."

[0083] [Preparation of Comparative Compound 2] Maleic acid (20.0 g, 172 mmol), 3,5,5-trimethyl-1-hexanol (49.7 g, 345 mmol), p-toluenesulfonic acid monohydrate (6.56 g, 34.5 mmol), and toluene (150 g) were placed in a 500 mL four-neck flask equipped with a Dean-Stark tube capable of reflux dehydration, and a dehydration reaction was carried out over 7 hours while refluxing at an internal temperature of 120°C. The reaction solution was transferred to a separatory funnel, and 5% aqueous sodium bicarbonate was added to separate the liquids. The toluene was removed using an evaporator to obtain di(3,5,5-trimethylhexyl) maleate (56.9 g, yield 90%, structure represented by the following formula (13)). Subsequently, di(3,5,5-trimethylhexyl)maleate (20.0 g, 54.3 mmol), water (14.7 g), propylene glycol monomethyl ether (48.9 g), and sodium pyrosulfite (10.3 g, 54.3 mmol) synthesized as described above were added to a 200 mL four-neck flask equipped with a reflux condenser, and the mixture was heated with stirring at an internal temperature of 100°C for 15 hours. After the solvent was distilled off using an evaporator, isopropyl alcohol was added to obtain a suspension in which inorganic salts had precipitated. The precipitate was removed by filtering this suspension, and the filtrate was distilled off using an evaporator to obtain sodium di(3,5,5-trimethylhexyl)sulfosuccinate (22.7 g, yield 88%, structure represented by the following formula (14)). The reaction product obtained as described above (sodium di(3,5,5-trimethylhexyl) sulfosuccinate) is hereinafter also referred to as "comparative compound 2."

[0084] [Evaluation] The following evaluations were carried out using the evaluation liquids obtained as follows. The results are shown in Table 1.

[0085] [Preparation of Evaluation Solutions] Example 2 Ion-exchanged water was added to the water / isopropyl alcohol solution 1 produced as described above to prepare evaluation solution 1 containing specific compound 1. The concentration of specific compound 1 in the total amount of evaluation solution 1 was 0.01% by mass. The water content in the total amount of evaluation solution 1 was 99.98% by mass. Examples 5 and 6 Ion-exchanged water was also added to water / isopropyl alcohol solutions 2 and 3 produced as described above in the same manner as in Example 1 to prepare evaluation solution 4 containing specific compound 2 and evaluation solution 5 containing specific compound 3, respectively.

[0086] Comparative Example 1 Sodium di(2-ethylhexyl)sulfosuccinate (manufactured by Tokyo Chemical Industry Co., Ltd., structure represented by the following formula (11); also referred to as comparative compound 1) was used as a surfactant. Ion-exchanged water was added to the comparative compound 1 to prepare evaluation solution 2 containing the comparative compound 1 as a surfactant. The concentration of comparative compound 1 in the total amount of evaluation solution 2 was the same as in Example 2.

[0087] Comparative Example 2 Ion-exchanged water was added to the comparative compound 2 prepared as described above to prepare evaluation solution 3 containing comparative compound 2 as a surfactant. The concentration of comparative compound 1 in the total amount of evaluation solution 3 was the same as in Example 2.

[0088] (Method for measuring surface tension) Using a multifunctional automatic surface tensiometer K100 (manufactured by KRUSS), the static surface tension (mN / m) of each of the surfactant compositions was measured by the Wilhelmy method (platinum plate) at 25° C. In the present invention, the ability to reduce surface tension was evaluated based on the static surface tension measured as described above.

[0089] (Static Surface Tension of Fluorine-Based Surfactant) In general, the static surface tension of a fluorochemical surfactant having a perfluoroalkyl group is required to be approximately 15 to 28 mN / m at 0.01% by mass.

[0090] (Evaluation Criteria for Surface Tension-Reducing Ability in the Present Invention) In the present invention, when the static surface tension measured as described above was 28 mN / m or less, the surface tension-reducing ability of the non-fluorine-based compound contained in the surfactant composition was evaluated as being at the same level as that of a fluorine-based surfactant. The smaller the static surface tension is below 28 mN / m, the better and more preferable the surface tension-reducing ability is. On the other hand, when the static surface tension is above 28 mN / m, the surface tension-reducing ability of the non-fluorine-based compound contained in the surfactant composition was evaluated as being insufficient compared to the surface tension-reducing ability of the fluorine-based surfactant.

[0091]

[0092] From the results in Table 1, it was confirmed that the compound of the present invention exhibits the desired effects. From a comparison between Example 2 and Example 5, it was confirmed that when r in formula (1) is 3, the effect of the present invention is more excellent than when r is 2. From a comparison between Example 2 and Example 6, it was confirmed that when R in formula (1) is 3, the effect of the present invention is more excellent than when r is 2. ３ is a group represented by formula (2), R ３It was confirmed that the effect of the present invention is more excellent than when is a hydrogen atom. On the other hand, the surface tension reducing ability of Comparative Examples 1 and 2, which did not contain the compound of the present invention but contained Comparative Compound 1 or Comparative Compound 2 instead, was insufficient compared to the surface tension reducing ability of the fluorosurfactant.

Claims

1. A compound represented by the following formula (1): [R １ -O-C ｐ H ２ｐ -CR ２ (OH)-C ｑ H ２ｑ -NR ３ -C ｒ H ２ｒ -(O) ｎ -SO ３ ] ｚ M (1) The symbols in formula (1) have the following meanings: R １ R: a branched alkyl group having 9 to 18 carbon atoms ２ : hydrogen atom or alkyl group having 1 to 6 carbon atoms; p, q, and r: independently an integer of 1 to 6; M: hydrogen atom or monovalent or divalent cation; n: 0 or 1; R ３ R: a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a group represented by the following formula (2): ４ -O-C ｘ H ２ｘ -CR ５ (OH)-C ｙ H ２ｙ - (2) R ４ R: a branched alkyl group having 9 to 18 carbon atoms ５ x and y are each independently an integer from 1 to 6; z is 1 or 2; 2. The compound according to claim 1, wherein n is 0 in formula (1).

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

4. In the formula (1), R ３ is a group represented by the formula (2), and R in the formula (1) １ and R in the formula (2) ４ are each independently a branched alkyl group selected from groups represented by the following formulas (3) to (5):

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

6. A surfactant composition comprising the surfactant according to claim 5 and an aqueous medium.

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