Surfactant composition and cleaning agent

Abstract

The present invention pertains to a surfactant composition containing (A) an alkyl hydroxy ether acetic acid (salt) represented by general formula (1) and (B) an alkyl hydroxy ether acetic acid (salt) represented by general formula (2), the total weight ratio of the alkyl hydroxy ether acetic acid and the salt (B) thereof being 0.05-1 wt% with respect to the total weight of the alkyl hydroxy ether acetic acid and the salt (A) thereof. R1-CH (OH)-CH2-OCH2COOM1 (1) [In the formula, R1 represents an alkyl group having 8 to 12 carbon atoms, and M1 represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolamine. ] R2-O-CH (X1) CH (X2)-OCH2COOM2 (2) [In the formula, either X1 or X2 is a hydrogen atom, the other is an alkyl group having 8-12 carbon atoms, R2 is a hydroxyalkyl group in which any one hydrogen atom bonded to a carbon atom bonded to a carbon atom having a position number of 1 in an alkyl group having 10-14 carbon atoms is substituted with a hydroxyl group, and n is the number of carbon atoms in the alkyl group having 8-12 carbon atoms represented by X1 or X2. The number of carbon atoms in R2 is n + 2, and M2 represents a hydrogen atom, a sodium atom, a potassium atom or triethanolamine. ].

Description

Technical Field

[0001] The present invention relates to surfactant compositions and cleaning agents. Background Art

[0002] Cleansing agents for human skin and hair use surfactants such as anionic surfactants, and a cleansing agent containing sodium dodecanediol acetate is known as a cleansing agent that exhibits moderate viscosity and generates foam with excellent foaming power, foam stability, and moisturizing power (Patent Document 1).

[0003] However, although conventional cleansing agents containing sodium monoacetate of dodecanediol have a strong cleansing power against sebum, they remove the natural moisturizing factors present in the skin at the same time as the sebum, and thus have problems with moisturizing properties after cleansing.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: Japanese Patent Application Publication No. 2017-197732 Summary of the invention

[0007] Problems to be solved by the invention

[0008] An object of the present invention is to provide a surfactant composition capable of obtaining a cleansing agent having excellent cleansing power against sebum and moisturizing properties after cleansing.

[0009] Means for solving problems

[0010] The present inventors have conducted intensive studies to achieve the above-mentioned object, and as a result, have accomplished the present invention.

[0011] That is, the present invention relates to a surfactant composition and a cleaning agent containing the surfactant composition, wherein the surfactant composition contains an alkyl hydroxy ether acetic acid (salt) (A) represented by the following general formula (1) and an alkyl hydroxy ether acetic acid (salt) (B) represented by the following general formula (2), wherein the total weight ratio of the alkyl hydroxy ether acetic acid and the salt (B) is 0.05% by weight to 1% by weight relative to the total weight of the alkyl hydroxy ether acetic acid and the salt (A).

[0012] R 1 -CH(OH)-CH 2 -OCH 2 COOM 1 (1)

[0013] [Where R 1 represents an alkyl group having 8 to 12 carbon atoms, M 1 represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolammonium.]

[0014] R 2 -O-CH(X 1 )CH(X 2 )-OCH 2 COOM 2 (2)

[0015] [Wherein, X 1 and X 2 One of them is a hydrogen atom, and the other is an alkyl group having 8 to 12 carbon atoms,

[0016] R 2 A hydroxyalkyl group is a group in which any one of the hydrogen atoms bonded to the carbon atom at position number 1 in an alkyl group having 10 to 14 carbon atoms is replaced by a hydroxyl group,

[0017] X 1 or X 2 When the number of carbon atoms of the alkyl group having 8 to 12 carbon atoms represented by is n, R 2 The number of carbon atoms is n+2.

[0018] M 2 represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolammonium.]

[0019] Effects of the Invention

[0020] The cleansing agent containing the surfactant composition of the present invention has excellent cleaning power against sebum, so there is less stickiness after cleaning. In addition, since the natural moisturizing factor present in the skin is not washed away, the moisturizing property of the skin after cleaning is high. DETAILED DESCRIPTION

[0021] The present invention is described in detail below.

[0022] <Alkyl hydroxy ether acetic acid (salt) (A)>

[0023] The surfactant composition of the first invention of the present application contains, as the alkyl hydroxy ether acetic acid (salt) (A), an alkyl hydroxy ether acetic acid (salt) (A) represented by the general formula (1).

[0024] R 1 -CH(OH)-CH 2 -OCH 2 COOM 1 (1)

[0025] [Where R 1 represents an alkyl group having 8 to 12 carbon atoms, M 1 represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolammonium.]

[0026] It should be noted that, in the present specification, alkyl hydroxy ether acetic acid (salt) means alkyl hydroxy ether acetic acid and / or alkyl hydroxy ether acetic acid salt.

[0027] In the general formula (1), R 1 It represents an alkyl group having 8 to 12 carbon atoms.

[0028] Examples of the alkyl group having 8 to 12 carbon atoms include n-octyl, isooctyl, 2-ethylhexyl, n-nonyl, isononyl, n-decyl, isodecyl, undecyl, n-dodecyl, and isododecyl.

[0029] R 1 Among them, from the viewpoint of the detergency against sebum, an alkyl group having 8 to 10 carbon atoms is preferred, an alkyl group having 10 carbon atoms is more preferred, and an n-decyl group is particularly preferred. In addition, a linear alkyl group is preferred.

[0030] In the general formula (1), M 1 It is a hydrogen atom, a sodium atom, a potassium atom or triethanolammonium.

[0031] M 1 Among them, from the viewpoint of the cleansing power against sebum, a sodium atom or triethanolammonium is preferred, and a sodium atom is more preferred.

[0032] Specific examples of the alkyl hydroxyether acetic acid (A) represented by the general formula (1) include decyl hydroxyether acetic acid (2-hydroxydecyl acetate), isodecyl hydroxyether acetic acid (2-hydroxyisodecyl acetate), ethyloctyl hydroxyether acetic acid (2-hydroxyethyloctyl acetate), undecyl hydroxyether acetic acid (2-hydroxyundecyl acetate), isoundecyl hydroxyether acetic acid (2-hydroxyisoundecyl acetate), dodecyl hydroxyether acetic acid (2-hydroxydodecyl acetate), isododecyl hydroxyether acetic acid (2-hydroxyisododecyl acetate), tridecyl hydroxyether acetic acid (2-hydroxytridecyl acetate), tetradecyl hydroxyether acetic acid (2-hydroxytetradecyl acetate) and isotetradecyl hydroxyether acetic acid (2-hydroxyisotetradecyl acetate).

[0033] Specific examples of the alkyl hydroxyether acetate (A) represented by the general formula (1) include decyl hydroxyether sodium acetate, isodecyl hydroxyether sodium acetate, ethyl octyl hydroxyether sodium acetate, undecyl hydroxyether sodium acetate, isoundecyl hydroxyether sodium acetate, dodecyl hydroxyether sodium acetate, isododecyl hydroxyether sodium acetate, tridecyl hydroxyether sodium acetate, tetradecyl hydroxyether sodium acetate, isotetradecyl hydroxyether sodium acetate, decyl hydroxyether potassium acetate, isodecyl hydroxyether potassium acetate, ethyl octyl hydroxyether potassium acetate, undecyl hydroxyether potassium acetate, isoundecyl hydroxyether potassium ... tridecyl hydroxyether sodium acetate, tetradecyl hydroxyether sodium acetate, isotetradecyl hydroxyether sodium acetate, tridecyl hydroxyether sodium acetate, tetradecyl hydroxyether sodium acetate, isotetradecyl hydroxyether sodium acetate, tridecyl hydroxyether sodium acetate, tetradecyl hydroxyether sodium acetate, isodecyl hydroxyether potassium acetate, tridecyl hydroxyether sodium acetate, tetradecyl hydroxyether sodium acetate, isododecyl hydroxyether potassium acetate, tridecyl hydroxyether sodium acetate, tetradecyl hydroxyether sodium acetate, isododecyl hydroxyether potassium acetate, tridecyl hydroxyether sodium acetate, tetradecyl hydroxyether sodium acetate, iso decyl hydroxyether triethanolammonium acetate, isodecyl hydroxyether triethanolammonium acetate, ethyloctyl hydroxyether triethanolammonium acetate, undecyl hydroxyether triethanolammonium acetate, isodecyl hydroxyether triethanolammonium acetate, dodecyl hydroxyether triethanolammonium acetate, isododecyl hydroxyether triethanolammonium acetate, tridecyl hydroxyether triethanolammonium acetate, tetradecyl hydroxyether triethanolammonium acetate and isotetradecyl hydroxyether triethanolammonium acetate, etc.

[0034] Among these, one type may be used alone, or two or more types may be used in combination.

[0035] As the alkyl hydroxyether acetic acid represented by the general formula (1) and its salt (A), from the viewpoint of the cleansing power against sebum, the alkyl hydroxyether acetate represented by the general formula (1) is preferred, and sodium decyl hydroxyether acetate, sodium dodecyl hydroxyether acetate, sodium tetradecyl hydroxyether acetate, decyl hydroxyether acetate triethanolammonium, dodecyl hydroxyether acetate triethanolammonium and tetradecyl hydroxyether acetate triethanolammonium are more preferred, sodium decyl hydroxyether acetate and sodium dodecyl hydroxyether acetate are particularly preferred, and sodium dodecyl hydroxyether acetate is most preferred.

[0036] The alkyl hydroxy ether acetic acid represented by the general formula (1) and a salt thereof (A) can be obtained by a known method described in JP-A-2017-197732 and the like.

[0037] Specifically, 1.04 mol of sodium monochloroacetate is added to 1 mol of 1,2-diol having 10 to 14 carbon atoms, and an aqueous solution containing crude alkyl hydroxy ether sodium acetate is obtained by SN2 reaction at preferably 30 to 80° C., more preferably 50 to 70° C., and then hydrochloric acid is added to obtain an aqueous surfactant solution containing alkyl hydroxy ether acetic acid (A).

[0038] The obtained surfactant aqueous solution containing the alkyl hydroxy ether acetic acid (A) can be further neutralized with a basic compound such as sodium hydroxide, potassium hydroxide and triethanolamine to obtain an aqueous surfactant solution containing the alkyl hydroxy ether acetate (A).

[0039] The surfactant aqueous solution containing alkyl hydroxy ether acetic acid or its salt (A) can be used directly in the preparation of the surfactant composition of the present invention; the surfactant aqueous solution can also be desolvated by a known method such as an evaporator, and the obtained powder containing alkyl hydroxy ether acetic acid or its salt (A) can be used for the preparation of the surfactant composition; the surfactant aqueous solution containing alkyl hydroxy ether acetic acid or its salt (A) can also be mixed with the powder containing alkyl hydroxy ether acetic acid or its salt (A) and used for the preparation of the surfactant composition.

[0040] The molecular structure of the alkyl hydroxy ether acetic acid can be determined by nuclear magnetic resonance (NMR) spectroscopy, and the type of cation constituting the alkyl hydroxy ether acetate can be determined by high-frequency inductively coupled plasma spectroscopy (ICP) analysis and nuclear magnetic resonance (NMR) spectroscopy.

[0041] <Method for determining the type of cation constituting alkyl hydroxy ether acetate by ICP analysis>

[0042] A sodium standard solution [1,000 ppm {Fujifilm Wako Pure Chemical Industries, Ltd.}] was diluted with ultrapure water to 50, 100, 200, 500, and 1,000 ppm to prepare a calibration curve solution. A surfactant aqueous solution or a powder containing a surfactant was further diluted 200,000 times with ultrapure water.

[0043] The sodium concentration contained in the surfactant aqueous solution or the powder containing the surfactant was calculated based on the measurement results of ICP-OES [product name: ICP-OES5900 {manufactured by Agilent Technologies, Inc.}].

[0044] If the sodium concentration contained in the obtained aqueous surfactant solution or powder containing the surfactant is 0.8 to 1.2 in terms of molar ratio relative to the content of the alkyl hydroxy ether acetate contained in the aqueous surfactant solution or powder containing the surfactant, it can be said that the alkyl hydroxy ether acetate contained in the obtained aqueous surfactant solution or powder containing the surfactant is a sodium salt.

[0045] The potassium concentration contained in the surfactant aqueous solution or the powder containing the surfactant is measured by the same method as the sodium salt using a potassium standard solution [1,000 ppm {manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.}]. If the potassium concentration contained in the obtained surfactant aqueous solution or the powder containing the surfactant is 0.8 to 1.2 in terms of molar ratio relative to the content of the alkyl hydroxy ether acetate contained in the surfactant aqueous solution or the powder containing the surfactant, it can be said that the alkyl hydroxy ether acetate contained in the obtained surfactant aqueous solution or the powder containing the surfactant is a potassium salt.

[0046] <Method for Identifying the Type of Cation Constituting Alkyl Hydroxyether Acetate by NMR Spectroscopy>

[0047] A sample of 10 mg of an aqueous surfactant solution or a powder containing a surfactant homogenized with deuterated acetone was subjected to H-NMR measurement using a nuclear magnetic resonance spectrometer [product name: AVANCE III 400HD {manufactured by BRUKER}].

[0048] If the peak area ratio of the peak of the α-position methylene in the carboxylic acid group of the alkyl hydroxy ether acetate appearing at 3.0 to 3.2 ppm and the peak of the triethanolammonium of the alkyl hydroxy ether acetate appearing at 3.6 to 3.7 ppm in the obtained H-NMR spectrum is 1:2.4 to 1:3.6, it can be said that the alkyl hydroxy ether acetate contained in the surfactant aqueous solution or the powder containing the surfactant is a triethanolammonium salt.

[0049] In addition, the content of the alkyl hydroxy ether acetic acid and its salt (A) contained in the surfactant aqueous solution or the surfactant can be measured using high performance liquid chromatography (hereinafter sometimes abbreviated as HPLC) by the method described in the later-described <Quantitative analysis method of alkyl hydroxy ether acetic acid (salt) (A) by HPLC>.

[0050] <Quantitative Analysis Method of Alkyl Hydroxyether Acetic Acid (Salt) (A) by HPLC>

[0051] Alkyl hydroxy ether acetate (salt) (A) R 1 In the case of an alkyl group having 10 carbon atoms, a calibration curve solution 1 having a 1,2-dodecanediol concentration of 0.0002 g / L and an undecanoic acid concentration of 1.2 g / L is prepared; a calibration curve solution 2 having a 1,2-dodecanediol concentration of 0.0004 g / L and an undecanoic acid concentration of 1.2 g / L is prepared; a calibration curve solution 3 having a 1,2-dodecanediol concentration of 0.0006 g / L and an undecanoic acid concentration of 1.2 g / L is prepared; and a sample solution having a surfactant aqueous solution or a powder containing a surfactant at a concentration of 9.0 g / L and an undecanoic acid concentration of 1.2 g / L is prepared.

[0052] Under the HPLC measurement conditions described below, the sample solution and calibration curve solutions 1 to 3 are analyzed. Based on the peak area ratios of the peak of 1,2-dodecanediol appearing at a retention time of 11.7 to 12.2 minutes, the peak of alkyl hydroxy ether acetate (A) appearing at a retention time of 13.4 to 14.7 minutes, and the peak of undecanoic acid appearing at a retention time of 12.1 to 19.6 minutes in the obtained HPLC chromatogram, the content of alkyl hydroxy ether acetate (A) contained in the surfactant aqueous solution or the powder containing the surfactant is calculated based on the content of undecanoic acid contained in the sampled surfactant aqueous solution or the powder containing the surfactant.

[0053] It should be noted that when R of alkyl hydroxy ether acetate (A) 1 is an alkyl other than an alkyl having 10 carbon atoms, quantification can be carried out by using the corresponding 1,2-diol instead of 1,2-dodecanediol.

[0054] <HPLC Measurement Conditions>

[0055] Apparatus: Liquid chromatography (manufactured by Shimadzu Corporation)

[0056] Detector: Differential refractive index meter

[0057] Column: Capcell Pak C18 SG 120A (inner diameter 4.6 nm, length 25 cm, manufactured by Osaka Soda Co., Ltd.)

[0058] Column temperature: 40 °C

[0059] Eluent: A mixed solution of 0.02 mol / L phosphoric acid, 0.01 mol / L sodium dihydrogen phosphate solution, and acetonitrile [47:53 (volume ratio)]

[0060] Sample injection volume: 40 μL

[0061] <Alkyl Hydroxy Ether Acetate (B)>

[0062] The surfactant composition of the first invention of the present application contains alkyl hydroxy ether acetate (B) represented by the general formula (2).

[0063] R 2 -O-CH(X 1 )CH(X 2 )-OCH 2 COOM 2 (2)

[0064] [In the formula, any one of X 1 and X 2 is a hydrogen atom, and the other is an alkyl having 8 to 12 carbon atoms,

[0065] R 2 A hydroxyalkyl group is a group in which any one of the hydrogen atoms bonded to the carbon atom at position number 1 in an alkyl group having 10 to 14 carbon atoms is replaced by a hydroxyl group,

[0066] X 1 or X 2 When the number of carbon atoms of the alkyl group having 8 to 12 carbon atoms represented by is n, R 2 The number of carbon atoms is n+2.

[0067] M 2 represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolammonium.]

[0068] In the general formula (2), X 1 and X 2 One of them is a hydrogen atom, and the other is an alkyl group having 8 to 12 carbon atoms.

[0069] Examples of the alkyl group having 8 to 12 carbon atoms include n-octyl, isooctyl, 2-ethylhexyl, n-nonyl, isononyl, n-decyl, isodecyl, undecyl, n-dodecyl, and isododecyl.

[0070] The alkyl group having 8 to 12 carbon atoms is preferably an alkyl group having 8 to 10 carbon atoms, more preferably an alkyl group having 10 carbon atoms, and particularly preferably an n-decyl group, from the viewpoint of moisturizing properties of the skin after washing. A linear alkyl group is also preferred.

[0071] In the general formula (2), R 2 It is a hydroxyalkyl group in which the hydrogen atom bonded to the carbon atom at position number 1 in an alkyl group having 10 to 14 carbon atoms is substituted with a hydroxyl group.

[0072] The hydroxyalkyl group refers to an alkyl group substituted with one or more hydroxy groups.

[0073] R 2 The carbon atom numbered 1 in the alkyl group having 10 to 14 carbon atoms represented by means of R 2 The carbon atom to which the oxygen atom of the ether bond is bonded is bonded.

[0074] Examples of the hydroxyalkyl group having 10 to 14 carbon atoms include hydroxydecyl, hydroxyundecyl, hydroxydodecyl, hydroxytridecyl, and hydroxytetradecyl.

[0075] R 2 Among them, from the viewpoint of moisturizing properties of the skin after washing, a hydroxyalkyl group having 10 to 12 carbon atoms is preferred, a hydroxyalkyl group having 10 carbon atoms is more preferred, and a hydroxydecyl group is particularly preferred.

[0076] In the general formula (2), M 2 It is a hydrogen atom, a sodium atom, a potassium atom or triethanolammonium.

[0077] M 2 Among them, from the viewpoint of moisturizing properties of the skin after washing, a sodium atom or triethanolammonium is preferred, and a sodium atom is more preferred.

[0078] Specific examples of the alkyl hydroxyether acetic acid (B) represented by the general formula (2) include 2-((1-((2-hydroxydecyl)oxy)decyl-2-yl)oxy)acetic acid, 2-((1-((2-hydroxyisodecyl)oxy)isodecyl-2-yl)oxy)acetic acid, 2-((1-((2-hydroxyundecyl)oxy)undecyl-2-yl)oxy)acetic acid, 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetic acid, 2-((1-((2-hydroxyisododecyl)oxy)isododecyl-2-yl)oxy)acetic acid, 2-((1-((2-hydroxytridecyl)oxy)tridecyl-2-yl)oxy)acetic acid, 2-((1-((2-hydroxytridecyl)oxy)tridecyl-2-yl)oxy)acetic acid, 2-((2-hydroxyisotridecyl)oxy)isotridecyl-2-yl)oxy)acetic acid, 2-((1-((2-hydroxytetradecyl)oxy)tetradecyl-2-yl)oxy)acetic acid, 2-((1-((2-hydroxyisotetradecyl)oxy)isotetradecyl-2-yl)oxy)acetic acid, 2-((2-((2-hydroxydecyl)oxy)decyl)oxy)acetic acid, 2-((2-((2-hydroxyisodecyl)oxy)isodecyl)oxy)acetic acid, 2-((2-((2-hydroxyundecyl)oxy)undecyl)oxy)acetic acid, 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetic acid, 2-((2-((2-hydroxyisododecyl)oxy)isododecyl)oxy)acetic acid oxy)acetic acid, 2-((2-((2-hydroxytridecyl)oxy)tridecyl)oxy)acetic acid, 2-((2-((2-hydroxyisotridecyl)oxy)isotridecyl)oxy)acetic acid, 2-((2-((2-hydroxytetradecyl)oxy)tetradecyl)oxy)acetic acid, 2-((2-((2-hydroxyisotetradecyl)oxy)isotetradecyl)oxy)acetic acid, 2-((1-((1-hydroxydecyl-2-yl)oxy)decyl-2-yl)oxy)acetic acid, 2-((1-((1-hydroxyisodecyl-2-yl)oxy)isodecyl-2-yl)oxy)acetic acid, 2-((1-((1-hydroxyundecyl-2-yl)oxy)undecyl-2-yl)oxy )acetic acid, 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetic acid, 2-((1-((1-hydroxyisododecyl-2-yl)oxy)isododecyl-2-yl)oxy)acetic acid, 2-((1-((1-hydroxytridecyl-2-yl)oxy)tridecyl-2-yl)oxy)acetic acid, 2-((1-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl-2-yl)oxy)acetic acid, 2-((1-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl-2-yl)oxy)acetic acid, 2-((1-((1-hydroxytetradecyl-2-yl)oxy)tetradecyl-2-yl)oxy)acetic acid, 2-((1-((1-hydroxyisotetradecyl-2-yl)oxy)isotetradecyl-2-yl)oxy)acetic acid,2-((2-((1-hydroxydecyl-2-yl)oxy)decyl)oxy)acetic acid, 2-((2-((1-hydroxyisodecyl-2-yl)oxy)isodecyl)oxy)acetic acid, 2-((2-((1-hydroxyundecyl-2-yl)oxy)undecyl)oxy)acetic acid, 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetic acid, 2-((2-((1-hydroxyisododecyl-2-yl)oxy) )isododecyl)oxy)acetic acid, 2-((2-((1-hydroxytridecyl-2-yl)oxy)tridecyl)oxy)acetic acid, 2-((2-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl)oxy)acetic acid, 2-((2-((1-hydroxytetradecyl-2-yl)oxy)tetradecyl)oxy)acetic acid and 2-((2-((1-hydroxyisotetradecyl-2-yl)oxy)isotetradecyl)oxy)acetic acid, etc.

[0079] Specific examples of the sodium salt of the alkyl hydroxy ether acetate (B) represented by the general formula (2) include sodium 2-((1-((2-hydroxydecyl)oxy)decyl-2-yl)oxy)acetate, sodium 2-((1-((2-hydroxyisodecyl)oxy)isodecyl-2-yl)oxy)acetate, sodium 2-((1-((2-hydroxyundecyl)oxy)undecyl-2-yl)oxy)acetate, sodium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate, sodium 2-((1-((2-hydroxyisododecyl)oxy)isododecyl-2-yl)oxy)acetate, sodium 2-((1-((2-hydroxytridecyl)oxy)tridecyl-2-yl)oxy)acetate sodium acetate, sodium 2-((1-((2-hydroxyisotridecyl)oxy)isotridecyl-2-yl)oxy)acetate, sodium 2-((1-((2-hydroxytetradecyl)oxy)tetradecyl-2-yl)oxy)acetate, sodium 2-((1-((2-hydroxyisotetradecyl)oxy)isotetradecyl-2-yl)oxy)acetate, sodium 2-((2-((2-hydroxydecyl)oxy)decyl)oxy)acetate, sodium 2-((2-((2-hydroxyisodecyl)oxy)isodecyl)oxy)acetate, sodium 2-((2-((2-hydroxyundecyl)oxy)undecyl)oxy)acetate, sodium 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetate, sodium 2-( Sodium (2-((2-hydroxyisododecyl)oxy)isododecyl)oxy)acetate, sodium 2-((2-((2-hydroxytridecyl)oxy)tridecyl)oxy)acetate, sodium 2-((2-((2-hydroxyisotridecyl)oxy)isotridecyl)oxy)acetate, sodium 2-((2-((2-hydroxyisotridecyl)oxy)isotridecyl)oxy)acetate, sodium 2-((2-((2-hydroxytetradecyl)oxy)tetradecyl)oxy)acetate, sodium 2-((2-((2-hydroxyisotetradecyl)oxy)isotetradecyl)oxy)acetate, sodium 2-((1-((1-hydroxydecyl-2-yl)oxy)decyl-2-yl)oxy)acetate, sodium 2-((1-((1-hydroxyisodecyl-2-yl)oxy)isodecyl-2-yl)oxy)acetate, sodium 2-((1-((1-hydroxyisodecyl-2-yl)oxy)isodecyl-2-yl)oxy)acetate, sodium 2-( Sodium (1-((1-hydroxyundecyl-2-yl)oxy)undecyl-2-yl)oxy)acetate, sodium 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetate, sodium 2-((1-((1-hydroxyisododecyl-2-yl)oxy)isododecyl-2-yl)oxy)acetate, sodium 2-((1-((1-hydroxytridecyl-2-yl)oxy)tridecyl-2-yl)oxy)acetate, sodium 2-((1-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl-2-yl)oxy)acetate, sodium 2-((1-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl-2-yl)oxy)acetate, sodium 2-((1-((1-hydroxytetradecyl-2-yl)oxy)tetradecyl-2-yl)oxy)acetate,Sodium 2-((1-((1-hydroxyisotetradecyl-2-yl)oxy)isotetradecyl-2-yl)oxy)acetate, sodium 2-((2-((1-hydroxydecyl-2-yl)oxy)decyl)oxy)acetate, sodium 2-((2-((1-hydroxyisodecyl-2-yl)oxy)isodecyl)oxy)acetate, sodium 2-((2-((1-hydroxyisodecyl-2-yl)oxy)isodecyl)oxy)acetate, sodium 2-((2-((1-hydroxyundecyl-2-yl)oxy)undecyl)oxy)acetate, sodium 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetate, sodium 2-( Sodium (2-((1-hydroxyisododecyl-2-yl)oxy)isododecyl)oxy)acetate, sodium 2-((2-((1-hydroxytridecyl-2-yl)oxy)tridecyl)oxy)acetate, sodium 2-((2-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl)oxy)acetate, sodium 2-((2-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl)oxy)acetate, sodium 2-((2-((1-hydroxytetradecyl-2-yl)oxy)tetradecyl)oxy)acetate, sodium 2-((2-((1-hydroxyisotetradecyl-2-yl)oxy)isotetradecyl)oxy)acetate, etc.

[0080] Specific examples of the alkyl hydroxy ether acetate (B) represented by the general formula (2) as a potassium salt include potassium 2-((1-((2-hydroxydecyl)oxy)decyl-2-yl)oxy)acetate, potassium 2-((1-((2-hydroxyisodecyl)oxy)isodecyl-2-yl)oxy)acetate, potassium 2-((1-((2-hydroxyundecyl)oxy)undecyl-2-yl)oxy)acetate, potassium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate, potassium 2-((1-((2-hydroxyisododecyl)oxy)isododecyl-2-yl)oxy)acetate, potassium 2-((1-((2-hydroxytridecyl)oxy)tridecyl-2-yl)oxy)acetate Potassium acetate, potassium 2-((1-((2-hydroxyisotridecyl)oxy)isotridecyl-2-yl)oxy)acetate, potassium 2-((1-((2-hydroxytetradecyl)oxy)tetradecyl-2-yl)oxy)acetate, potassium 2-((1-((2-hydroxyisotetradecyl)oxy)isotetradecyl-2-yl)oxy)acetate, potassium 2-((2-((2-hydroxydecyl)oxy)decyl)oxy)acetate, potassium 2-((2-((2-hydroxyisodecyl)oxy)isodecyl)oxy)acetate, potassium 2-((2-((2-hydroxyundecyl)oxy)undecyl)oxy)acetate, potassium 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetate, potassium 2-( Potassium (2-((2-hydroxyisododecyl)oxy)isododecyl)oxy)acetate, potassium 2-((2-((2-hydroxytridecyl)oxy)tridecyl)oxy)acetate, potassium 2-((2-((2-hydroxyisotridecyl)oxy)isotridecyl)oxy)acetate, potassium 2-((2-((2-hydroxyisotridecyl)oxy)isotridecyl)oxy)acetate, potassium 2-((2-((2-hydroxytetradecyl)oxy)tetradecyl)oxy)acetate, potassium 2-((2-((2-hydroxyisotetradecyl)oxy)isotetradecyl)oxy)acetate, potassium 2-((1-((1-hydroxydecyl-2-yl)oxy)decyl-2-yl)oxy)acetate, potassium 2-((1-((1-hydroxyisodecyl-2-yl)oxy)isodecyl-2-yl)oxy)acetate, potassium 2-( Potassium (1-((1-hydroxyundecyl-2-yl)oxy)undecyl-2-yl)oxy)acetate, potassium 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetate, potassium 2-((1-((1-hydroxyisododecyl-2-yl)oxy)isododecyl-2-yl)oxy)acetate, potassium 2-((1-((1-hydroxytridecyl-2-yl)oxy)tridecyl-2-yl)oxy)acetate, potassium 2-((1-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl-2-yl)oxy)acetate, potassium 2-((1-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl-2-yl)oxy)acetate, potassium 2-((1-((1-hydroxytetradecyl-2-yl)oxy)tetradecyl-2-yl)oxy)acetate,Potassium 2-((1-((1-hydroxyisotetradecyl-2-yl)oxy)isotetradecyl-2-yl)oxy)acetate, potassium 2-((2-((1-hydroxydecyl-2-yl)oxy)decyl)oxy)acetate, potassium 2-((2-((1-hydroxyisodecyl-2-yl)oxy)isodecyl)oxy)acetate, potassium 2-((2-((1-hydroxyisodecyl-2-yl)oxy)isodecyl)oxy)acetate, potassium 2-((2-((1-hydroxyundecyl-2-yl)oxy)undecyl)oxy)acetate, potassium 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetate, potassium 2-( Potassium (2-((1-hydroxyisododecyl-2-yl)oxy)isododecyl)oxy)acetate, potassium 2-((2-((1-hydroxytridecyl-2-yl)oxy)tridecyl)oxy)acetate, potassium 2-((2-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl)oxy)acetate, potassium 2-((2-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl)oxy)acetate, potassium 2-((2-((1-hydroxytetradecyl-2-yl)oxy)tetradecyl)oxy)acetate, potassium 2-((2-((1-hydroxyisotetradecyl-2-yl)oxy)isotetradecyl)oxy)acetate, and the like.

[0081] Specific examples of the alkyl hydroxy ether acetate salt (B) represented by the general formula (2) as the triethanolammonium salt include 2-((1-((2-hydroxydecyl)oxy)decyl-2-yl)oxy)acetate triethanolammonium, 2-((1-((2-hydroxyisodecyl)oxy)isodecyl-2-yl)oxy)acetate triethanolammonium, 2-((1-((2-hydroxyundecyl)oxy)undecyl-2-yl)oxy)acetate triethanolammonium, 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate triethanolammonium, 2-((1-((2-hydroxyisododecyl)oxy)isododecyl-2-yl)oxy)acetate triethanolammonium, 2-((1-((2-hydroxytridecyl)oxy)tridecyl -2-yl)oxy)acetic acid triethanolammonium, 2-((1-((2-hydroxyisotridecyl)oxy)isotridecyl-2-yl)oxy)acetic acid triethanolammonium, 2-((1-((2-hydroxytetradecyl)oxy)tetradecyl-2-yl)oxy)acetic acid triethanolammonium, 2-((1-((2-hydroxyisotetradecyl)oxy)isotetradecyl-2-yl)oxy)acetic acid triethanolammonium, 2-((2-((2-hydroxydecyl)oxy)decyl)oxy)acetic acid triethanolammonium, 2-((2-((2-hydroxyisodecyl)oxy)isodecyl)oxy)acetic acid triethanolammonium, 2-((2-((2-hydroxyundecyl)oxy)undecyl)oxy)acetic acid triethanolammonium, 2-((2-((2-hydroxydodecyl)oxy) triethanolammonium 2-((2-((2-hydroxyisododecyl)oxy)isododecyl)oxy)acetate, triethanolammonium 2-((2-((2-hydroxytridecyl)oxy)tridecyl)oxy)acetate, triethanolammonium 2-((2-((2-hydroxyisotridecyl)oxy)isotridecyl)oxy)acetate, triethanolammonium 2-((2-((2-hydroxyisotridecyl)oxy)isotridecyl)oxy)acetate, triethanolammonium 2-((2-((2-hydroxyisotetradecyl)oxy)tetradecyl)oxy)acetate, triethanolammonium 2-((2-((2-hydroxyisotetradecyl)oxy)isotetradecyl)oxy)acetate, triethanolammonium 2-((1-((1-hydroxydecyl-2-yl)oxy)decyl-2-yl)oxy)acetate, triethanolammonium 2-((1-((1-hydroxydecyl-2-yl)oxy)decyl-2-yl)oxy)acetate, triethanolammonium 2-((1-((1-hydroxyundecyl-2-yl)oxy)undecyl-2-yl)oxy)acetate, triethanolammonium 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetate, triethanolammonium 2-((1-((1-hydroxyisododecyl-2-yl)oxy)isododecyl-2-yl)oxy)acetate, triethanolammonium 2-((1-((1-hydroxytridecyl-2-yl)oxy)tridecyl-2-yl)oxy)acetate, triethanolammonium 2-((1-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl-2-yl)oxy)acetate,2-((1-((1-hydroxytetradecyl-2-yl)oxy)tetradecyl-2-yl)oxy)acetic acid triethanolammonium, 2-((1-((1-hydroxyisotetradecyl-2-yl)oxy)isotetradecyl-2-yl)oxy)acetic acid triethanolammonium, 2-((2-((1-hydroxydecyl-2-yl)oxy)decyl)oxy)acetic acid triethanolammonium, 2-((2-((1-hydroxyisodecyl-2-yl)oxy)isodecyl)oxy)acetic acid triethanolammonium, 2-((2-((1-hydroxyundecyl-2-yl)oxy)undecyl)oxy)acetic acid triethanolammonium, 2-((2-((1-hydroxydodecyl-2-yl)oxy) triethanolammonium 2-((2-((1-hydroxyisododecyl-2-yl)oxy)isododecyl)oxy)acetate, triethanolammonium 2-((2-((1-hydroxytridecyl-2-yl)oxy)tridecyl)oxy)acetate, triethanolammonium 2-((2-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl)oxy)acetate, triethanolammonium 2-((2-((1-hydroxyisotridecyl-2-yl)oxy)isotridecyl)oxy)acetate, triethanolammonium 2-((2-((1-hydroxytetradecyl-2-yl)oxy)tetradecyl)oxy)acetate, and triethanolammonium 2-((2-((1-hydroxyisotetradecyl-2-yl)oxy)isotetradecyl)oxy)acetate.

[0082] Among these, one type may be used alone or two or more types may be used in combination.

[0083] As the alkyl hydroxy ether acetic acid represented by the general formula (2) and its salt (B), from the viewpoint of moisturizing properties of the skin after washing, preferably the alkyl hydroxy ether acetate salt represented by the general formula (2), more preferably sodium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate, sodium 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetate, sodium 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetate, Sodium 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetate, potassium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate, potassium 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetate, potassium 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetate, potassium 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetate, Potassium acetate, 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetic acid triethanolammonium, 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetic acid triethanolammonium and 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetic acid triethanolammonium and 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetic acid triethanolammonium, particularly preferably 2-((1-((2 Preferably, the present invention comprises sodium 2-((2-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate, sodium 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetate and sodium 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetate, and sodium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate is most preferably sodium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate.

[0084] The relationship between the compound name of the alkyl hydroxy ether acetic acid and its salt (B) and the structure in the general formula (2) will be described below by way of example.

[0085] For sodium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate, in the general formula (2), R 2 is 2-hydroxydodecyl, X 1 is a hydrogen atom, X 2 is decyl, M 2 is a sodium atom. 2 This is a structure in which the hydrogen atom bonded to the carbon atom at position 1 of 2-dodecanol is substituted by bonding to the oxygen atom of the ether bond.

[0086] For sodium 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetate, in the general formula (2), R 2 is 2-hydroxydodecyl, X 1 is decyl, X 2 is a hydrogen atom, M 2 is a sodium atom. 2 This is a structure in which the hydrogen atom bonded to the carbon atom at position 1 of 2-dodecanol is substituted by bonding to the oxygen atom of the ether bond.

[0087] For sodium 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetate, in the general formula (2), R 2 is hydroxydodecyl, X 1 is a hydrogen atom, X 2 is decyl, M 2 is a sodium atom. 2 The structure is formed by substitution in such a way that the hydrogen atom bonded to the carbon atom at position 2 of 1-dodecanol is bonded to the oxygen atom of the ether bond. 2 The compound name is described as "1-hydroxydodecyl-2-yl", but R in the present invention is 2 The carbon atom numbered 1 in the position of the compound is not the carbon atom at position 1 in the compound name, but refers to the carbon atom at position 1 in the compound name. 2 That is, the carbon atom corresponding to the carbon atom at position 2 of 1-dodecanol becomes R in the present invention. 2 The carbon atom at position number 1.

[0088] For sodium 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetate, in the general formula (2), R 2 is hydroxydodecyl, X 1 is decyl, X 2 is a hydrogen atom, M 2 is a sodium atom. 2 The structure is formed by substitution in such a way that the hydrogen atom bonded to the carbon atom at position 2 of 1-dodecanol is bonded to the oxygen atom of the ether bond. 2 The compound name is described as "1-hydroxydodecyl-2-yl", but in the present invention, R 2 The carbon atom numbered 1 in the position of R is not the carbon atom at position 1 in the above compound name, but refers to the carbon atom at position 1 in the compound name. 2 That is, the carbon atom corresponding to the carbon atom at position 2 of 1-dodecanol becomes R in the present invention. 2 The carbon atom at position number 1.

[0089] The method for producing the alkylhydroxyether acetic acid represented by the general formula (2) and its salt (B) is as follows.

[0090] First, a 1,2-diol having 10 to 14 carbon atoms is subjected to dehydration condensation between two molecules to obtain a dimer of the 1,2-diol. 1.04 mol of sodium monochloroacetate is added to 1 mol of the obtained dimer of the 1,2-diol, and an aqueous solution containing crude alkyl hydroxy ether sodium acetate is obtained by SN2 reaction at preferably 30 to 80° C., more preferably 50 to 80° C., and then hydrochloric acid is added to obtain an aqueous surfactant solution containing alkyl hydroxy ether acetic acid (B).

[0091] Next, the obtained surfactant aqueous solution containing the alkyl ether glycolic acid (B) is neutralized with a basic compound such as sodium hydroxide, potassium hydroxide, and triethanolamine, thereby obtaining an aqueous surfactant solution containing the alkyl hydroxy ether acetate (B).

[0092] The surfactant aqueous solution containing alkyl hydroxy ether acetic acid or its salt (B) can be used directly in the preparation of the surfactant composition of the present invention; the surfactant aqueous solution can also be desolvated by a known method such as an evaporator, and the obtained powder containing alkyl hydroxy ether acetic acid or its salt (B) can be used for the preparation of the surfactant composition; the surfactant aqueous solution containing alkyl hydroxy ether acetic acid or its salt (B) can also be mixed with the powder containing alkyl hydroxy ether acetic acid or its salt (B) and used for the preparation of the surfactant composition.

[0093] The molecular structure of the alkyl hydroxy ether acetic acid (B) can be determined by NMR spectroscopy, and the type of cations constituting the alkyl hydroxy ether acetate (B) can be determined by ICP analysis and NMR spectroscopy. The ICP analysis and NMR spectroscopy are the same as the above-mentioned <Method for determining the type of cations constituting the alkyl hydroxy ether acetate by ICP analysis> and <Method for determining the type of cations constituting the alkyl hydroxy ether acetate by NMR spectroscopy>.

[0094] The contents of the alkyl hydroxy ether acetic acid and its salt (B) can be measured using HPLC by the method described in <Quantitative analysis method of alkyl hydroxy ether acetic acid (salt) (B) by HPLC> described later.

[0095] <Quantitative Analysis Method of Alkyl Hydroxyether Acetic Acid (Salt) (B) by HPLC>

[0096] Alkyl hydroxy ether acetate (salt) (B) R 2 is an alkyl group having 12 carbon atoms, X 1 or X 2When any one of them is an alkyl group having 10 carbon atoms, a calibration curve solution 4 with a concentration of 0.0002 g / L of the dimer of 1,2-dodecanediol and a concentration of 1.2 g / L of undecanoic acid; a calibration curve solution 5 with a concentration of 0.0004 g / L of the dimer of 1,2-dodecanediol and a concentration of 1.2 g / L of undecanoic acid; a calibration curve solution 6 with a concentration of 0.0006 g / L of the dimer of 1,2-dodecanediol and a concentration of 1.2 g / L of undecanoic acid; and a sample solution with a concentration of 9.0 g / L of an aqueous surfactant solution or a powder containing a surfactant and a concentration of 1.2 g / L of undecanoic acid are prepared.

[0097] The sample solution and calibration curve solutions 4 to 6 are analyzed under the HPLC measurement conditions described below. Based on the peak area ratios of the peak of the mixture of the dimer of 1,2-dodecanediol appearing at a retention time of 9.0 to 9.5 minutes, the peak of alkyl hydroxy ether acetate (salt) (B) appearing at a retention time of 12.5 to 13.0, and the peak of undecanoic acid appearing at a retention time of 12.1 to 19.6 in the obtained HPLC spectrum, the content of alkyl hydroxy ether acetate (salt) (B) contained in the aqueous surfactant solution or the powder containing a surfactant is calculated based on the content of undecanoic acid contained in the sampled aqueous surfactant solution or the powder containing a surfactant.

[0098] It should be noted that for alkyl hydroxy ether acetate (salt) (B), R 2 is an alkyl group other than having 12 carbon atoms, X 1 or X 2 When any one of them is an alkyl group other than an alkyl group having 10 carbon atoms, quantification can be performed by using the corresponding 1,2-diol instead of 1,2-dodecanediol.

[0099] <HPLC Measurement Conditions>

[0100] Apparatus: Liquid chromatography (manufactured by Shimadzu Corporation)

[0101] Detector: Differential refractive index detector

[0102] Column: Capcell Pak C18 SG 120A (inner diameter 4.6 nm, length 25 cm, manufactured by Osaka Soda Co., Ltd.)

[0103] Column temperature: 40 °C

[0104] Eluent: A mixed solution of 0.02 M phosphoric acid, 0.01 M sodium dihydrogen phosphate solution, and acetonitrile [47:53 (volume ratio)]

[0105] Sample injection volume: 40 μL

[0106] <Surfactant Composition>

[0107] The surfactant composition of the first invention of the present application contains alkyl hydroxy ether acetic acid (salt) (A) and alkyl hydroxy ether acetic acid (salt) (B), and the total weight ratio of the alkyl hydroxy ether acetic acid and the salt (B) is 0.05 to 1% by weight relative to the total weight of the alkyl hydroxy ether acetic acid and the salt (A).

[0108] In the surfactant composition, if the total weight ratio of the alkyl hydroxy ether acetic acid and its salt (B) relative to the total weight of the alkyl hydroxy ether acetic acid and its salt (A) is less than 0.05% by weight, the moisturizing property of the skin after washing is insufficient. If the total weight ratio of the alkyl hydroxy ether acetic acid and its salt (B) relative to the total weight of the alkyl hydroxy ether acetic acid and its salt (A) is more than 1% by weight, the foam quality during washing is insufficient.

[0109] In the surfactant composition of the first invention of the present application, the total weight ratio of the alkyl hydroxy ether acetic acid and its salt (B) relative to the total weight of the alkyl hydroxy ether acetic acid and its salt (A) is preferably 0.1 to 0.8% by weight, more preferably 0.2 to 0.6% by weight, from the viewpoint of moisture retention.

[0110] In the surfactant composition of the first invention of the present application, the total weight ratio of the alkyl hydroxy ether acetic acid and the salt thereof (A) is preferably 10 to 20% by weight, more preferably 15 to 18% by weight, based on the total weight of the surfactant composition, from the viewpoint of storage stability.

[0111] In the surfactant composition of the first invention of the present application, from the viewpoint of storage stability, the total weight ratio of the alkyl hydroxy ether acetic acid and the salt thereof (B) is preferably 0.01 to 0.9% by weight, more preferably 0.01 to 0.2% by weight, and particularly preferably 0.01 to 0.05% by weight relative to the total weight of the surfactant composition.

[0112] The surfactant composition of the first invention of the present application can be obtained by mixing an aqueous surfactant solution containing alkyl hydroxy ether acetic acid or its salt (A) or a powder containing a surfactant, and an aqueous surfactant solution containing alkyl hydroxy ether acetic acid or its salt (B) or a powder containing a surfactant so that the contents of the alkyl hydroxy ether acetic acid or its salt (A) and the alkyl hydroxy ether acetic acid or its salt (B) are at a predetermined ratio.

[0113] The surfactant composition of the present invention may further comprise optional other ingredients, preferably water.

[0114] When the surfactant composition of the first invention of the present application contains water, the content of water is preferably 60 to 90% by weight, more preferably 65 to 85% by weight, based on the total weight of the surfactant composition from the viewpoint of storage stability.

[0115] The water contained in the surfactant composition may be water used as a reaction solvent when producing the alkyl hydroxy ether acetic acid or its salt (A) and the alkyl hydroxy ether acetic acid or its salt (B), or may be mixed with the alkyl hydroxy ether acetic acid or its salt (A) and the alkyl hydroxy ether acetic acid or its salt (B) using ordinary water, purified water, hard water, soft water, natural water, deep sea water, hot spring water, electrolyzed alkaline ion water, electrolyzed acidic ion water, ion exchange water, cluster water, etc., in a predetermined weight ratio.

[0116] The surfactant composition of the first invention of the present application may also contain a part of the amphoteric surfactant contained in the cleaning agent described later, anionic surfactants other than alkyl hydroxy ether acetic acid and its salt (A) and alkyl hydroxy ether acetic acid and its salt (B) (hereinafter referred to as other anionic surfactants), cationic surfactants, nonionic surfactants, water, oily components, solvents, moisturizers, chelating agents, conditioners, thickeners, whitening agents, pH adjusters, cooling agents, colorants, ultraviolet scattering agents, ultraviolet absorbers, preservatives, and antioxidants.

[0117] The surfactant composition may contain unreacted products and reaction catalyst residues when synthesizing the alkyl hydroxy ether acetic acid or its salt (A) and the alkyl hydroxy ether acetic acid or its salt (B).

[0118] The surfactant composition of the first invention of the present application can be obtained by mixing alkyl hydroxy ether acetic acid and its salt (A), alkyl hydroxy ether acetic acid and its salt (B), and water used as needed so that a predetermined ratio is achieved using a known mixing device equipped with a stirring device such as a paddle-type stirring blade or a spiral stirring blade.

[0119] The content of the alkyl hydroxy ether acetic acid and its salt (A) contained in the surfactant composition can be measured by HPLC. The HPLC measurement method and conditions are the same as the quantitative analysis method of the alkyl hydroxy ether acetic acid (salt) (A) based on HPLC.

[0120] The content of the alkyl hydroxy ether acetic acid and its salt (B) contained in the surfactant composition can be measured by HPLC. The HPLC measurement method and conditions are the same as the above-mentioned quantitative analysis method of the alkyl hydroxy ether acetic acid (salt) (B) based on HPLC.

[0121] The surfactant composition of the first invention of the present application is excellent in foaming properties and storage stability and can therefore be preferably used as a raw material for a cleaning agent.

[0122] <Cleaning agent>

[0123] The cleaning agent of the second invention of the present application is a cleaning agent containing the surfactant composition of the first invention of the present application, and is a cleaning agent containing alkylhydroxyetheracetic acid (salt) (A) and alkylhydroxyetheracetic acid (salt) (B) as essential components of the surfactant composition.

[0124] It should be noted that the cleaning agent in the present application refers to a cleaning agent for hair or skin cleaning (shampoo, facial cleanser, body wash, bar soap, skin cleanser, liquid soap, etc.).

[0125] In view of the cleaning power against sebum and the moisturizing property after cleaning, the cleaning agent of the second invention of the present application preferably contains 0.1 to 10.0 wt %, more preferably 1.0 to 3.0 wt % of the surfactant composition of the first invention of the present application relative to the total weight of the cleaning agent.

[0126] In the cleaning agent of the second invention of the present application, from the viewpoint of moisture retention, the total weight ratio of the alkyl hydroxy ether acetic acid and its salt (B) relative to the total weight of the alkyl hydroxy ether acetic acid and its salt (A) is preferably 0.05 to 1% by weight, more preferably 0.1 to 0.8% by weight, and particularly preferably 0.2 to 0.6% by weight.

[0127] From the viewpoint of cleaning power, the total weight ratio of the alkyl hydroxy ether acetic acid and its salt (A) and the alkyl hydroxy ether acetic acid and its salt (B) contained in the cleaning agent of the second invention of the present application is preferably 0.00175 to 1.75 wt %, more preferably 0.175 to 1.05 wt %.

[0128] The content of the alkyl hydroxy ether acetic acid and its salt (A) contained in the cleaning agent can be measured by HPLC. The HPLC measurement method and conditions are the same as the quantitative analysis method of the alkyl hydroxy ether acetic acid (salt) (A) by HPLC.

[0129] In the cleaning agent of the second invention of the present application, the total weight ratio of the alkyl hydroxy ether acetic acid and its salt (A) is preferably 0.01 to 1.75 wt %, more preferably 0.10 to 1.25 wt % based on the total weight of the cleaning agent from the viewpoint of cleaning power.

[0130] The content of the alkyl hydroxy ether acetic acid and its salt (B) contained in the cleaning agent can be measured by HPLC. The HPLC measurement method and conditions are the same as the quantitative analysis method of the alkyl hydroxy ether acetic acid (salt) (B) by HPLC described above.

[0131] In the cleaning agent of the second invention of the present application, the total weight ratio of the alkyl hydroxy ether acetic acid and its salt (B) is preferably 0.000006 to 0.003 wt %, more preferably 0.001 to 0.002 wt % based on the total weight of the cleaning agent from the viewpoint of cleaning power.

[0132] The cleaning agent of the second invention of the present application may contain other optional ingredients. As other optional ingredients, well-known cosmetic ingredients such as amphoteric surfactants, other anionic surfactants, cationic surfactants, nonionic surfactants, water, oily components, solvents, moisturizers, chelating agents, conditioners, thickeners, whitening agents, pH adjusters, cooling agents, colorants, ultraviolet scattering agents, ultraviolet absorbers, preservatives and antioxidants can be cited.

[0133] Examples of the amphoteric surfactant include alkyl dimethylacetic acid betaine, fatty amide propyl betaine, alkyl imidazolinium betaine, sulfobetaine-type amphoteric surfactants, and amphoteric amino acid-based surfactants.

[0134] Examples of the alkyl dimethyl acetate betaine include lauryl dimethylamino acetate betaine [another name: lauryl betaine], myristyl dimethylamino acetate betaine [another name: myristyl betaine], and stearyl dimethylamino acetate betaine [another name: stearyl betaine].

[0135] Examples of fatty amidopropyl betaine include lauric acid amidopropyl betaine [also known as lauryl amidopropyl betaine], myristic acid amidopropyl betaine [also known as myristic acid amidopropyl betaine], isostearic acid amidopropyl betaine, and coconut fatty acid amidopropyl betaine [also known as cocoamidopropyl betaine].

[0136] Examples of the alkyl imidazolinium betaine include 2-coconut fatty acid-N-hydroxyethyl-N-hydroxyethyl imidazolinium betaine, sodium N-lauroyl-N'-carboxymethyl-N'-hydroxyethylethylenediamine [also known as sodium lauroylamphoacetate], and sodium N-coconut fatty acid acyl-N'-carboxymethyl-N'-hydroxyethylethylenediamine [also known as sodium cocoamphoacetate].

[0137] Examples of the sulfobetaine-type amphoteric surfactant include lauramidopropyl hydroxysulfobetaine and cocamidopropyl hydroxysulfobetaine.

[0138] Examples of the amphoteric amino acid-based surfactant include sodium lauryl aspartate, sodium myristyl aspartate, sodium lauryl-β-alanine, and sodium lauroyl methyl-β-alanine [also known as sodium lauroyl methyl alanine].

[0139] Examples of other anionic surfactants include ether carboxylic acids or salts thereof (hereinafter referred to as ether carboxylate salts or salts thereof), sulfate ester salts, sulfonate salts, phosphate ester salts, fatty acid salts, and acylated amino acid salts, except for alkyl hydroxy ether acetic acid and salts thereof (A) and alkyl hydroxy ether acetic acid and salts thereof (B).

[0140] Examples of the ether carboxylates or their salts include sodium polyoxyethylene (average degree of polymerization 4) lauryl ether carboxylate [also known as sodium polyoxyethylene (average degree of polymerization 4) lauryl ether acetate, sodium laureth-4 carboxylate], sodium polyoxyethylene (average degree of polymerization 6) lauryl ether carboxylate [also known as sodium laureth-6 carboxylate], sodium polyoxyethylene (average degree of polymerization 4) tridecyl ether carboxylate [also known as sodium trideceth-4 carboxylate], and sodium polyoxyethylene (average degree of polymerization 7) tridecyl ether carboxylate [also known as sodium trideceth-7 carboxylate].

[0141] Examples of the sulfate ester salts include sodium lauryl sulfate [also known as sodium lauryl sulfate], sodium polyoxyethylene (average degree of polymerization 2) lauryl ether sulfate [also known as sodium laureth-2 sulfate], sodium polyoxyethylene (average degree of polymerization 3) lauryl ether sulfate [also known as sodium laureth-3 sulfate], triethanolamine polyoxyethylene (average degree of polymerization 3) lauryl ether sulfate [also known as TEA laureth-3 sulfate], sodium polyoxyethylene (average degree of polymerization 3) coconut fatty acid monoethanolamide sulfate [also known as PEG-3 coconut fatty acid amide MEA sulfate Na], and sodium polyoxyethylene (average degree of polymerization 3) alkyl (carbon number 12-13) ether sulfate [also known as (C12, C13) pareth-3 sulfate Na].

[0142] Examples of the sulfonates include sodium olefin (C14-16) sulfonate [also known as Na olefin (C14-16) sulfonate], sodium dodecylbenzene sulfonate [also known as Na dodecylbenzene sulfonate], polyoxyethylene (average degree of polymerization 2) lauryl sulfonated succinate disodium salt [also known as sulfonated succinic acid lauryl alcohol polyether 2Na], lauryl sulfonated succinate disodium salt [also known as sulfonated succinic acid lauryl 2Na], and polyoxyethylene (average degree of polymerization 5) sulfonated succinic acid lauroylethanolamide disodium salt.

[0143] Examples of the phosphoric acid ester salt include sodium lauryl phosphate [another name: sodium lauryl phosphate] and sodium polyoxyethylene lauryl ether phosphate [another name: tri(laureth-4)phosphate].

[0144] Examples of fatty acid salts include salts of myristic acid (sodium myristic acid [also known as Na myristic acid], potassium myristic acid [also known as K myristic acid], triethanolamine myristic acid [also known as TEA myristic acid], etc.), salts of lauric acid (sodium laurate [also known as Na laurate], potassium laurate [also known as K laurate], triethanolamine laurate [also known as TEA laurate], etc.), salts of stearic acid (sodium stearate [also known as Na stearate], triethanolamine stearate [also known as TEA stearate], etc.), and salts of palmitic acid (sodium palmitate [also known as Na palmitate] and triethanolamine palmitate [also known as TEA palmitate]).

[0145] Examples of the acylated amino acid salts include potassium N-coconut fatty acid acyl glycinate [also known as coconut oil acyl glycine K], sodium N-coconut fatty acid methyl taurate [also known as coconut oil acyl methyl taurate Na], sodium N-coconut fatty acid sarcosinate [also known as coconut oil acyl sarcosinate Na], sodium N-lauroyl sarcosinate [also known as lauroyl sarcosinate Na], triethanolamine N-coconut fatty acid sarcosinate [also known as acyl glutamic acid TEA], triethanolamine N-coconut fatty acid acyl-L-glutamate [also known as coconut oil acyl glutamate TEA], sodium N-coconut fatty acid acyl-L-glutamate [also known as coconut oil acyl glutamate Na], and triethanolamine lauroyl-L-glutamate [also known as lauroyl glutamate TEA].

[0146] Examples of the cationic surfactant include quaternary ammonium salts and amine salts.

[0147] Examples of the quaternary ammonium salt include stearyl trimethyl ammonium chloride [also known as stearyl triammonium chloride], behenyl trimethyl ammonium chloride [also known as behenyl triammonium chloride], distearyl dimethyl ammonium chloride [also known as distearyl diammonium chloride], and ethylsulfate lanolin fatty acid aminopropyl ethyl dimethyl ammonium [also known as Quaternium-33].

[0148] Examples of the amine salt include stearic acid diethylaminoethylamide lactate [another name: stearamidoethyldiethylamine lactate] and behenic acid dimethylaminoethylamide lactate [another name: behenamidopropyldimethylamine lactate].

[0149] Examples of the nonionic surfactant include alkylene oxide (carbon number 2 to 8) adducts of alcohols having 4 to 24 carbon atoms, esters or ethers of fatty acids having 8 to 24 carbon atoms and alcohols or alkylene oxide (carbon number 2 to 8) polymers, alkylene oxide adducts of higher fatty acid esters of polyvalent (2-10 valent) alcohols, glycerol fatty acid esters, polyglycerol fatty acid esters, and fatty acid alkanolamides.

[0150] Examples of the alkylene oxide (carbon number 2 to 8) adducts of alcohols having 4 to 24 carbon atoms include polyoxyethylene (average degree of polymerization 10) polyoxypropylene (average degree of polymerization 7) butyl ether [alias: PPG-7 butyl ether-10], polyoxyethylene (average degree of polymerization 20) lauryl ether [alias: laureth-20], polyoxyethylene (average degree of polymerization 20) oleyl ether [alias: oleth-20], polyoxyethylene (average degree of polymerization 12) polyoxypropylene (average degree of polymerization 2) cetyl ether [alias: PPG-2 cetyl ether-12], and a mixture of polyoxyethylene cetearyl ether and polyoxyethylene oleyl ether [alias: cetoleth-5], etc.

[0151] Examples of the esters or ethers of the polymers of fatty acids having 8 to 24 carbon atoms and alcohols or alkylene oxides (having 2 to 8 carbon atoms) include glyceryl monostearate [also known as stearic acid glyceryl], glyceryl monocaprylate [also known as caprylic acid glyceryl], glyceryl monomyristate [also known as myristic acid glyceryl], glyceryl monooleate [also known as oleic acid glyceryl], ethylene glycol monostearate [also known as stearic acid ethylene glycol ester (Glycol stearate)], sorbitan monolaurate [alias: sorbitan laurate], sorbitan monopalmitate [alias: sorbitan palmitate], sorbitan monostearate [alias: sorbitan stearate], sorbitan monooleate [alias: sorbitan oleate], coconut fatty acid sorbitan ester, polyoxyethylene monooleate (average degree of polymerization 6) sorbitan ester [alias: PEG-6 sorbitan oleate], polyoxyethylene (average degree of polymerization 20) stearyl ether [alias: stearyl alcohol Polyether-20], polyethylene glycol monostearate (average degree of polymerization 23) ester [alias: PEG-23 stearate], polyethylene glycol distearate (average degree of polymerization 3) ester [alias: PEG-3 distearate], polyethylene glycol distearate (average degree of polymerization 150) ester [alias: PEG-150 distearate], polyethylene glycol distearate (average degree of polymerization 190) ester [alias: PEG-190 distearate] and polyoxyethylene (average degree of polymerization 60) hydrogenated castor oil [alias: PEG-60 hydrogenated castor oil], etc.

[0152] Examples of the alkylene oxide adducts of higher fatty acid esters of polyvalent (2-10 valent) alcohols include polyethylene oxide (average degree of polymerization 6) addition polymers of glyceryl esters of caprylic acid and capric acid [alias: PEG-6 (caprylic acid / capric acid) glycerides], polyoxyethylene monolaurate (average degree of polymerization 10) sorbitan ester [alias: PEG-10 sorbitan laurate], polyoxyethylene monolaurate (average degree of polymerization 80) sorbitan ester [alias: PEG-80 sorbitan laurate], polyoxyethylene monooleate (average degree of polymerization 6) sorbitan ester [alias: PEG-6 sorbitan oleate], polyoxyethylene monooleate (average degree of polymerization 3) sorbitan ester [alias: PEG- : PEG-3 sorbitan oleate], monooleic acid polyoxyethylene (average degree of polymerization 40) sorbitan ester [alias: PEG-40 sorbitan oleate], monostearic acid polyoxyethylene (average degree of polymerization 6) sorbitan ester [alias: PEG-6 sorbitan stearate], monostearic acid polyoxyethylene (average degree of polymerization 40) sorbitan ester [alias: PEG-40 sorbitan stearate], triisostearic acid polyoxyethylene (average degree of polymerization 160) sorbitan ester [alias: PEG-160 sorbitan triisostearate] and polyoxyethylene (degree of polymerization 120) dioleic acid methyl glucoside [alias: PEG-120 dioleic acid methyl glucose], etc.

[0153] Examples of the polyglyceryl fatty acid esters include decaglyceryl monooleate [also known as polyglyceryl oleate-10], decaglyceryl monolaurate [also known as polyglyceryl laurate-10], decaglyceryl isostearate [also known as polyglyceryl isostearate-10], polyglyceryl distearate [also known as polyglyceryl distearate-10], polyglyceryl stearate [also known as polyglyceryl stearate-10], hexaglyceryl polyricinoleate [also known as polyglyceryl polyricinoleate-6], and diglyceryl monoisostearate [also known as polyglyceryl isostearate-2].

[0154] Examples of fatty acid alkanolamides include coconut fatty acid monoethanolamide [also known as cocamide MEA], coconut fatty acid N-methylethanolamide [also known as cocamide methyl MEA], and coconut fatty acid diethanolamide [also known as cocamide DEA].

[0155] Examples of water include normal water, purified water, hard water, soft water, natural water, deep sea water, hot spring water, electrolyzed alkaline ion water, electrolyzed acidic ion water, ion exchange water, and cluster water.

[0156] Examples of the oily component include liquid oils, solid oils, hydrocarbon oils, synthetic ester oils, silicone oils, and essential oils.

[0157] Examples of the liquid oil include avocado oil, camellia oil, tortoise oil, macadamia seed oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, camellia oil, castor oil, linseed oil, safflower oil, cottonseed oil, soybean oil, peanut oil, tea seed oil, citronella oil, rice bran oil, jojoba oil, rice germ oil, tri(2-ethylhexanoin)glyceryl [also known as tri(ethylhexanoin) ester], and triisopalmitin [also known as triisopalmitin].

[0158] Examples of the solid fats and oils include cocoa butter, coconut oil, candelilla wax, beeswax, shea butter, horse oil, hydrogenated coconut oil, palm oil, beef tallow, lanolin, hydrogenated beef tallow, palm kernel oil, hydrogenated palm oil, lard, wood wax, and hydrogenated castor oil.

[0159] Examples of the hydrocarbon oil include 2,2,4,6,6-pentamethylheptane [also known as isododecane], 2,2,4,4,6,8,8-heptamethylnonane [also known as isohexadecane], hexamethyltetracosane [also known as squalane], 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene [also known as squalene], vaseline, paraffin, hydrogenated polyisobutene, ozokerite, 2,6,10,14-tetramethylpentadecane, ceresin, and microcrystalline wax.

[0160] Examples of the synthetic ester oil include isopropyl myristate, cetyl ethylhexanoate, octyldodecyl myristate, cetyl palmitate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyldecyl ethylhexanoate, cetyl lactate, myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesteryl hydroxystearate, glycol diethylhexanoate, Neopentyl glycol dicaprate, caprylic acid and capric acid triester with glycerol [alias: tri(caprylic acid / capric acid) glyceryl], hydroxystearic acid, hydroxystearic acid, stearic acid and rosin acid hexaester with dipentaerythritol [alias: hexa(hydroxystearic acid / stearic acid / rosin acid) dipentaerythritol ester], diisostearyl malate, diisostearate glyceryl, trimethylolpropane tri(2-ethylhexanoate), trimethylolpropane triethylhexanoate, pentaerythritol Tetraethylhexanoate, Trimethylolpropane Triisostearate, Ethylhexyl Palmitate, Trimyristyl Glyceryl [Also known as Trimyristin], Methyl Ricinoleate, Oleyl Oleate, Diisobutyl Adipate, Lauroyl Glutamic Acid Esters with Phytosterols and Octyldodecanol [Also known as Di(Phytosteryl / Octyldodecyl) Lauroyl Glutamate], Diheptyl Undecyl Adipate, Ethyl Laurate Esters, diethylhexyl sebacate, isocetyl myristate, hexyldecyl palmitate, dihexyldecyl adipate, diisopropyl sebacate, diethylhexyl succinate, triethyl citrate, polyoxyethylene (average degree of polymerization 3) trimethylolpropane triisostearate [alias: PEG-3 trimethylolpropane triisostearate], diglyceryl triisostearate [alias: polyglyceryl-2 triisostearate] and sucrose tetraisostearate, etc.

[0161] Examples of the silicone oil include chain polysiloxane, cyclic polysiloxane, and modified polysiloxane (amino-modified polysiloxane, polyether-modified silicone, alkyl-modified polysiloxane, and fluorine-modified polysiloxane).

[0162] Examples of the chain polysiloxane include methylphenyl polysiloxane [also known as diphenyl polydimethicone], octyl polymethicone, polydimethylsiloxane, dimethyl polysiloxane, dimethyl polysiloxane cross-linked with divinyl dimethyl polysiloxane [also known as (dimethyl polysiloxane / vinyl dimethicone) cross-linked polymer], and dimethyl polysiloxane copolymer cross-linked with phenyl vinyl dimethyl polysiloxane [also known as (dimethyl polysiloxane / phenyl vinyl dimethicone) cross-linked polymer].

[0163] Examples of the cyclic polysiloxane include decamethylcyclopentasiloxane [another name: cyclopentasiloxane] and dodecamethylcyclohexasiloxane [another name: cyclohexasiloxane].

[0164] Examples of the modified polysiloxane include aminopropyl dimethicone, alkyl (C26-28) dimethicone, alkyl (C30-45) dimethicone, polyoxyethylene (average degree of polymerization 10)-methyl polysiloxane copolymer [alias: PEG-10 dimethicone], polyoxyethylene (average degree of polymerization 12)-methyl polysiloxane copolymer [alias: PEG-12 dimethicone], and polyoxyethylene (average degree of polymerization 9) dimethylsiloxyethyl dimethicone [alias: PEG-9 polydimethylsiloxyethyl dimethicone].

[0165] Examples of the solvent include ethanol, isoprene glycol [also known as isopentyl glycol], modified alcohol, dipropylene glycol [also known as DPG], 1,2-hexanediol [also known as 1,2-hexanediol], isododecane, isopropyl alcohol, butyl acetate, diethylene glycol monoethyl ether [also known as ethoxydiglycol], and propylene glycol [also known as PG].

[0166] Examples of the moisturizing agent include glycerin, 1,3-butylene glycol [also known as BG], hardened rapeseed alcohol [also known as hydrogenated rapeseed alcohol], sorbitol, sodium acetate [also known as sodium lactate], sodium pyrrolidone carboxylate [also known as PCN-Na], sodium hyaluronate [also known as sodium hyaluronate], and sodium chondroitin sulfate [also known as sodium chondroitin sulfate].

[0167] Examples of the chelating agent include ethylenediaminetetraacetic acid [also known as EDTA], disodium salt of ethylenediaminetetraacetic acid [also known as EDTA-2Na], sodium polyphosphate [also known as sodium polyphosphate], disodium pyrophosphate [also known as 2Na pyrophosphate], gluconic acid, sodium gluconate [also known as sodium gluconate], and ascorbic acid.

[0168] Examples of conditioning agents include quaternary ammonium salt polymers obtained by adding glycidyltrimethylammonium chloride to hydroxyethylcellulose [alias: Polyquaternium-10], quaternary ammonium salt polymers obtained from acrylamide and dimethyldiallylammonium chloride [alias: Polyquaternium-7], copolymers of dimethyldiallylammonium chloride and acrylic acid [alias: Polyquaternium-22], copolymers of vinyl acetate and vinylpyrrolidone [alias: (VP / VA) copolymer], quaternary ammonium salts obtained by adding glycidyltrimethylammonium chloride to guar gum [alias: Guar Hydroxypropyltrimonium Chloride], polyethylene glycol 20000 [alias: PEG-400], sodium polyacrylate [alias: Polyacrylic Acid Na], hydroxyethylcellulose and D-panthenol [alias: Panthenol], and the like.

[0169] Examples of the thickener include guar gum, xanthan gum, starch, behenyl alcohol, stearyl alcohol, cetearyl alcohol, cetyl alcohol, myristyl alcohol, carboxyvinyl polymer [also known as carbomer], hydroxypropyl methylcellulose, polyvinyl alcohol, sodium polyacrylate [also known as polyacrylate Na], sodium salt of a substance obtained by grafting acrylic acid onto starch [also known as sodium acrylate grafted starch], dimethyl distearyl ammonium hectorite [also known as distearyl dimethyl ammonium hectorite], talc, coconut fatty acid N-methylethanolamide [also known as cocoamidomethyl MEA], and ethylene glycol distearate and acrylic acid / methacrylate alkyl ester (carbon number 10 to 30) copolymer [also known as (acrylate / alkyl acrylate (C10-30)) crosslinked polymer], etc.

[0170] Examples of the whitening agent include tranexamic acid, arbutin, and hydroquinone.

[0171] Examples of the pH adjuster include lactic acid, citric acid, phosphoric acid, malic acid, tartaric acid, hydrochloric acid, acetic acid, sodium hydroxide, potassium hydroxide, and triethanolamine.

[0172] Examples of the cooling agent include menthol, peppermint oil, thymol, methyl salicylate, and camphor.

[0173] Examples of the coloring material include Blue No. 1, Blue No. 2, Green No. 3, and Red No. 1.

[0174] Examples of the ultraviolet scattering agent include titanium oxide and zinc oxide.

[0175] Examples of the ultraviolet absorber include ethylhexyl methoxycinnamate, ester of dimethyl p-aminobenzoic acid and 2-ethylhexanol [another name: dimethyl PABA ethylhexyl ester], and tert-butyl methoxydibenzoylmethane.

[0176] Examples of the preservative include phenoxyethanol, o-cymene-5-ol, methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, and isobutylparaben.

[0177] Examples of the antioxidant include vitamin E [also known as tocopherol], butylated hydroxytoluene [also known as BHT], butylated hydroxyanisole [also known as BHA], dipotassium glycyrrhizinate [also known as glycyrrhizic acid 2K], ascorbyl palmitate, and rosemary leaf extract.

[0178] The types and contents of known cosmetic ingredients that can be used as needed in the cleaning agent of the second invention of the present application are as follows.

[0179] Based on the total weight of the cleaning agent, the amphoteric surfactant, other anionic surfactant, cationic surfactant, nonionic surfactant, water, oily component, solvent and moisturizer are preferably 50% by weight or less, more preferably 10% by weight or less.

[0180] The chelating agent, conditioning agent, thickener and whitening agent are each preferably 30% by weight or less, more preferably 10% by weight or less, based on the total weight of the cleaning agent.

[0181] The pH adjuster, the cooling agent, the colorant, the ultraviolet scattering agent, the ultraviolet absorber, the preservative and the antioxidant are each preferably 10% by weight or less, more preferably 5% by weight or less, based on the total weight of the cleaning agent.

[0182] As a method for producing the cleaning agent of the second invention of the present application, the cleaning agent can be produced by mixing the surfactant composition and any other components using a known stirrer.

[0183] Examples of agitators used in the production of the cleaning agent of the second invention of the present application include Henschel mixers, ball mills, jet mills, kneaders, planetary mixers, sand mills, attritors, ribbon mixers, dispersers, and homomixers, and preferably dispersers can be used.

[0184] The cleaning agent of the second invention of the present application is preferably in a solid, liquid or paste state at 25° C., and is more preferably in a liquid state from the viewpoint of ease of handling.

[0185] When the cleaning agent of the present invention is a shampoo, the shampoo preferably contains the following components, for example.

[0186] In the following description, the active ingredient refers to the component obtained by removing water from the raw materials of each component.

[0187] As other anionic surfactants, at least one selected from the group consisting of polyoxyethylene (average degree of polymerization 2) lauryl ether sodium sulfate, polyoxyethylene (average degree of polymerization 4) lauryl ether sodium acetate, N-coconut fatty acid acyl-L-glutamate sodium, N-lauroyl sarcosine sodium and olefin (C14-16) sulfonate sodium is preferred.

[0188] In the shampoo, based on the weight of the entire shampoo, 3.0 to 10.0% by weight of polyoxyethylene (average degree of polymerization 2) sodium lauryl ether sulfate can be contained in terms of active ingredients. In the shampoo, based on the weight of the entire shampoo, 1.0 to 5.0% by weight of polyoxyethylene (average degree of polymerization 4) sodium lauryl ether acetate can be contained in terms of active ingredients. In the shampoo, based on the weight of the entire shampoo, 3.0 to 10.0% by weight of sodium N-coconut fatty acid acyl-L-glutamate can be contained in terms of active ingredients. In the shampoo, based on the weight of the entire shampoo, 1.0 to 5.0% by weight of sodium N-lauroyl sarcosinate can be contained in terms of active ingredients. In the shampoo, based on the weight of the entire shampoo, 1.0 to 10.0% by weight of sodium olefin (C14-16) sulfonate can be contained in terms of active ingredients.

[0189] The amphoteric surfactant is preferably at least one selected from the group consisting of cocamidopropyl betaine and 2-coconut fatty acid-N-hydroxyethyl-N-hydroxyethylimidazolinium betaine.

[0190] The shampoo may contain 1.0 to 5.0% by weight of cocamidopropyl betaine in terms of active ingredients, based on the total weight of the shampoo. The shampoo may contain 1.0 to 5.0% by weight of 2-coconut fatty acid-N-hydroxyethyl-N-hydroxyethylimidazolinium betaine in terms of active ingredients, based on the total weight of the shampoo.

[0191] As the moisturizing agent, at least one selected from the group consisting of 1,3-butylene glycol and glycerin is preferred.

[0192] The shampoo may contain 1.0 to 5.0% by weight of 1,3-butylene glycol as an active ingredient based on the total weight of the shampoo. The shampoo may contain 1.0 to 5.0% by weight of glycerin as an active ingredient based on the total weight of the shampoo.

[0193] As the conditioning agent, at least one selected from the group consisting of polyquaternium-22, polyquaternium-7, and polyquaternium-10 is preferred.

[0194] In the shampoo, 0.1 to 1.0 weight % of polyquaternium-22 can be contained in the shampoo as an active ingredient, based on the weight of the entire shampoo. In the shampoo, 0.05 to 0.5 weight % of polyquaternium-7 can be contained in the shampoo as an active ingredient, based on the weight of the entire shampoo. In the shampoo, 0.1 to 1.0 weight % of polyquaternium-10 can be contained in the shampoo as an active ingredient, based on the weight of the entire shampoo.

[0195] As the oily component, polydimethylsiloxane is preferred.

[0196] The shampoo may contain 0.1 to 1.0% by weight of polydimethylsiloxane in terms of active ingredient based on the total weight of the shampoo.

[0197] As the chelating agent, EDTA-2Na is preferred.

[0198] The shampoo may contain 0.05 to 0.5% by weight of EDTA-2Na in terms of active ingredient based on the total weight of the shampoo.

[0199] As the thickener, coconut fatty acid N-methylethanolamide is preferred.

[0200] The shampoo may contain 1.0 to 5.0% by weight of coconut fatty acid N-methylethanolamide in terms of active ingredient based on the total weight of the shampoo.

[0201] As the nonionic surfactant, PEG-160 sorbitan triisostearate is preferred.

[0202] The shampoo may contain PEG-160 sorbitan triisostearate in an amount of 1.0 to 5.0% by weight as an active ingredient based on the weight of the entire shampoo.

[0203] As the cooling agent, menthol is preferred.

[0204] The shampoo may contain 0.5 to 3.0% by weight of menthol in terms of active ingredient based on the total weight of the shampoo.

[0205] As the pH adjuster, citric acid is preferred.

[0206] The shampoo may contain 0.05 to 0.5% by weight of citric acid in terms of active ingredient based on the total weight of the shampoo.

[0207] When the cleaning agent of the present invention is a shampoo, the following compositions are mentioned as preferred compositions of the components calculated as active ingredients.

[0208] Alkyl hydroxy ether acetic acid (salt) (A): 0.15-1.30 wt%

[0209] Alkyl hydroxy ether acetic acid (salt) (B): 0.00010 to 0.0040% by weight

[0210] Other anionic surfactants: 3.0-20.0 wt%

[0211] Amphoteric surfactant: 1.0-5.0% by weight

[0212] Moisturizer: 1.0-5.0% by weight

[0213] Conditioner: 0.1-1.0 wt%

[0214] Oily component: 0.1-1.0% by weight

[0215] Chelating agent: 0.05-0.5% by weight

[0216] Thickener: 1.0-5.0% by weight

[0217] Nonionic surfactant: 1.0-5.0 wt%

[0218] Cooling agent: 0.5-3.0% by weight

[0219] pH adjuster: 0.05-0.5% by weight

[0220] When the cleansing agent of the present invention is a pump foamer facial cleanser, the pump foamer facial cleanser preferably contains the following components, for example.

[0221] As the other anionic surfactant, at least one selected from the group consisting of lauroyl-L-glutamic acid triethanolamine and sodium olefin (C14-16) sulfonate is preferred.

[0222] The pump foamer facial cleanser may contain 1.0 to 10.0 wt% of lauroyl-L-glutamic acid triethanolamine based on the total weight of the pump foamer facial cleanser as an active ingredient. The pump foamer facial cleanser may contain 0.5 to 3.0 wt% of sodium olefin (C14-16) sulfonate based on the total weight of the pump foamer facial cleanser as an active ingredient.

[0223] As the amphoteric surfactant, cocamidopropyl betaine is preferred.

[0224] The pump foamer facial cleanser may contain 0.5 to 3.0% by weight of cocamidopropyl betaine in terms of active ingredient based on the total weight of the pump foamer facial cleanser.

[0225] As the conditioning agent, polyquaternium-7 is preferred.

[0226] The pump foamer facial cleanser may contain 0.05 to 0.5% by weight of polyquaternium-7 in terms of active ingredient based on the total weight of the pump foamer facial cleanser.

[0227] When the cleansing agent of the present invention is a facial cleanser for a pump foamer, the following compositions can be cited as preferred compositions of the components calculated as active ingredients.

[0228] Alkyl hydroxy ether acetic acid (salt) (A): 0.20-1.00 wt%

[0229] Alkyl hydroxy ether acetic acid (salt) (B): 0.00020 to 0.00100% by weight

[0230] Other anionic surfactants: 1.0-10.0% by weight

[0231] Amphoteric surfactant: 0.5-3.0 wt%

[0232] Conditioner: 0.05-0.5% by weight

[0233] When the cleansing agent of the present invention is a cream-type facial cleanser, the cream-type facial cleanser preferably contains the following components, for example.

[0234] As other anionic surfactants, at least one selected from the group consisting of sodium N-coconut fatty acid acyl-L-glutamate, potassium N-coconut fatty acid acyl glycinate, salts of lauric acid, salts of stearic acid, and salts of palmitic acid is preferred.

[0235] In the cream-like facial cleanser, 1.0 to 3.0 weight % of sodium N-coconut fatty acid acyl-L-glutamate can be contained in terms of active ingredients, based on the total weight of the cream-like facial cleanser. In the cream-like facial cleanser, 5.0 to 20.0 weight % of potassium N-coconut fatty acid acyl glycinate can be contained in terms of active ingredients, based on the total weight of the cream-like facial cleanser. In the cream-like facial cleanser, 0.5 to 5.0 weight % of lauric acid salt can be contained in terms of active ingredients, based on the total weight of the cream-like facial cleanser. In the cream-like facial cleanser, 0.5 to 20.0 weight % of stearic acid salt can be contained in terms of active ingredients, based on the total weight of the cream-like facial cleanser. In the cream-like facial cleanser, 5.0 to 20.0 weight % of palmitic acid salt can be contained in terms of active ingredients, based on the total weight of the cream-like facial cleanser.

[0236] In addition, in this specification, when other anionic surfactants contain fatty acid salts, it is assumed that all fatty acids are in the form of potassium salts, and the weight of the potassium salt of the fatty acid is regarded as the weight of the fatty acid salt.

[0237] As the amphoteric surfactant, cocamidopropyl betaine is preferred.

[0238] The creamy facial cleanser may contain 0.5 to 3.0% by weight of cocamidopropyl betaine in terms of active ingredient based on the total weight of the creamy facial cleanser.

[0239] As the moisturizing agent, glycerin is preferred.

[0240] The creamy facial cleanser may contain 5.0 to 20.0% by weight of glycerin in terms of active ingredient based on the total weight of the creamy facial cleanser.

[0241] As the conditioning agent, polyquaternium-7 is preferred.

[0242] The creamy facial cleanser may contain 0.01 to 0.10% by weight of polyquaternium-7 in terms of active ingredient based on the total weight of the creamy facial cleanser.

[0243] As the antioxidant, vitamin E is preferred.

[0244] The creamy facial cleanser may contain 0.05 to 0.30% by weight of vitamin E in terms of active ingredient based on the total weight of the creamy facial cleanser.

[0245] As the thickener, at least one selected from the group consisting of coconut fatty acid N-methylethanolamide and glycol distearate is preferred.

[0246] The cream-like facial cleanser may contain 1.0 to 3.0 wt% of coconut fatty acid N-methylethanolamide as an active ingredient based on the total weight of the cream-like facial cleanser. The cream-like facial cleanser may contain 1.0 to 3.0 wt% of ethylene glycol distearate as an active ingredient based on the total weight of the cream-like facial cleanser.

[0247] As the nonionic surfactant, PEG-190 distearate is preferred.

[0248] The creamy facial cleanser may contain 3.0 to 10.0% by weight of PEG-190 distearate in terms of active ingredient based on the total weight of the creamy facial cleanser.

[0249] As the pH adjuster, potassium hydroxide is preferred.

[0250] The cream-like facial cleanser may contain 3.0 to 10.0% by weight of potassium hydroxide in terms of active ingredient based on the total weight of the cream-like facial cleanser.

[0251] When the cleansing agent of the present invention is a cream-like facial cleanser, the following compositions can be mentioned as preferred compositions of the components calculated as active ingredients.

[0252] Alkyl hydroxy ether acetic acid (salt) (A): 0.015-1.5 wt%

[0253] Alkyl hydroxy ether acetic acid (salt) (B): 0.000005-0.003 wt%

[0254] Other anionic surfactants: 10.0-40.0% by weight

[0255] Amphoteric surfactant: 0.5-3.0 wt%

[0256] Moisturizer: 5.0-20.0% by weight

[0257] Conditioner: 0.01-0.10 wt%

[0258] Antioxidant: 0.05-0.30 wt%

[0259] Thickener: 1.0-10.0% by weight

[0260] Nonionic surfactant: 3.0-10.0 wt%

[0261] pH adjuster: 3.0 to 10.0% by weight

[0262] The following matters are disclosed in this specification.

[0263] The present disclosure (1) is a surfactant composition comprising an alkyl hydroxy ether acetate (salt) (A) represented by the following general formula (1) and an alkyl hydroxy ether acetate (salt) (B) represented by the following general formula (2),

[0264] The total weight ratio of the alkyl hydroxy ether acetic acid and the salt thereof (B) is 0.05 to 1% by weight based on the total weight of the alkyl hydroxy ether acetic acid and the salt thereof (A).

[0265] R 1 -CH(OH)-CH 2 -OCH 2 COOM 1 (1)

[0266] [Where R 1 represents an alkyl group having 8 to 12 carbon atoms, M 1 represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolammonium.]

[0267] R 2 -O-CH(X 1 )CH(X 2 )-OCH 2 COOM 2 (2)

[0268] [Wherein, X 1 and X 2 One of them is a hydrogen atom, and the other is an alkyl group having 8 to 12 carbon atoms,

[0269] R 2 A hydroxyalkyl group is a group in which any one of the hydrogen atoms bonded to the carbon atom at position number 1 in an alkyl group having 10 to 14 carbon atoms is replaced by a hydroxyl group,

[0270] X 1 or X 2 When the number of carbon atoms of the alkyl group having 8 to 12 carbon atoms represented by is n, R 2 The number of carbon atoms is n+2.

[0271] M 2 represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolammonium.]

[0272] The present disclosure (2) is a cleaning agent containing the surfactant composition described in the present disclosure (1).

[0273] Example

[0274] The present invention will be further described below with reference to Examples and Comparative Examples, but the present invention is not limited thereto.

[0275] <Production Example 1>

[0276] In a 1 L four-necked flask equipped with a stirrer, a reflux cooler, a dropping funnel and a thermometer, 50 g of 1,2-dodecanediol [manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.], 10 g of toluene [manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.] and 30 g of sodium monochloroacetate [manufactured by Denak Corporation] were added, the atmosphere was replaced with nitrogen, the temperature was raised to 50° C., 10 g of granular sodium hydroxide [manufactured by Tosoh Corporation] was slowly added over 5 hours with stirring, and then the mixture was aged for 3 hours.

[0277] 25 g of ion exchange water was added to the solution after the reaction at 50°C, the temperature was raised to 70°C, 32 g of 38% hydrochloric acid aqueous solution [manufactured by Toagosei Co., Ltd.] was added, and the mixture was stirred for 30 minutes. The solution was then transferred to a separatory funnel, allowed to stand for 30 minutes, and then separated to remove the lower layer of the solution. 10 g of sodium hydroxide was added to the remaining supernatant solution, and the pressure was reduced to 2.7 kPa at 75°C using a rotary evaporator. The volatile components were removed by maintaining the temperature and pressure for 7 hours, and a powder 1 containing a surfactant was obtained.

[0278] 1 g of sample is collected from powder 1 containing a surfactant, and the molecular structure of the surfactant contained in the powder 1 containing a surfactant and the type of cations constituting the surfactant are determined by ICP and NMR, and the content of the surfactant in the powder 1 containing a surfactant is further determined by the quantitative analysis method based on HPLC described later.

[0279] The surfactant-containing powder 1 is a powder containing 40% by weight of sodium decyl hydroxyether acetate as the alkyl hydroxyether acetic acid (salt) (A).

[0280] <Quantitative Analysis Method of Alkyl Hydroxyether Acetic Acid (Salt) (A) Content by HPLC>

[0281] Prepare calibration curve solution 1 with a concentration of 0.0002 g / L of 1,2-dodecanediol and a concentration of 1.2 g / L of undecanoic acid; calibration curve solution 2 with a concentration of 0.0004 g / L of 1,2-dodecanediol and a concentration of 1.2 g / L of undecanoic acid; calibration curve solution 3 with a concentration of 0.0006 g / L of 1,2-dodecanediol and a concentration of 1.2 g / L of undecanoic acid; and a sample solution with a concentration of 9.0 g / L of surfactant-containing powder 1 and a concentration of 1.2 g / L of undecanoic acid.

[0282] Analyze the sample solution and calibration curve solutions 1-3 by HPLC under the following conditions. Based on the peak area ratios of the peak of 1,2-dodecanediol appearing at a retention time of 11.7 - 12.2 minutes, the peak of alkyl hydroxy ether acetate (salt) (A) appearing at a retention time of 13.4 - 14.7 minutes, and the peak of undecanoic acid appearing at a retention time of 12.1 - 19.6 minutes in the obtained HPLC spectrum, calculate the content of alkyl hydroxy ether acetate (salt) (A) contained in the surfactant-containing powder 1 based on the content of undecanoic acid contained in the sampled surfactant-containing powder 1.

[0283] <HPLC measurement conditions>

[0284] Apparatus: Liquid chromatography (manufactured by Shimadzu Corporation)

[0285] Detector: Differential refractive index meter

[0286] Column: Capcell Pak C18 SG 120A (inner diameter 4.6 nm, length 25 cm, manufactured by Osaka Soda Co., Ltd.)

[0287] Column temperature: 40 °C

[0288] Eluent: A mixed solution of 0.02 M phosphoric acid, 0.01 M sodium dihydrogen phosphate solution, and acetonitrile [47:53 (volume ratio)]

[0289] Sample injection volume: 40 μL

[0290] <Production Example 2>

[0291] Add 100 g of the surfactant-containing powder 1 produced in Production Example 1, 2 g of ion-exchanged water, and 21.8 g of 35% aqueous hydrochloric acid solution [manufactured by Kishida Chemical Co., Ltd.] to a 300 mL beaker, heat to 70 °C, and stir for 60 minutes to obtain 124 g of surfactant aqueous solution 1.

[0292] Sampling is performed from the surfactant aqueous solution 1, and the molecular structure of the surfactant contained in the surfactant aqueous solution 1 and the type of cations constituting the surfactant are determined using the same method as in Manufacturing Example 1, and the content of the surfactant contained in the surfactant aqueous solution 1 is further determined using the same method as in Manufacturing Example 1.

[0293] The surfactant aqueous solution 1 is an aqueous solution containing 30% by weight of decylhydroxyetheracetic acid as the alkylhydroxyetheracetic acid (salt) (A).

[0294] <Production Example 3>

[0295] 33.3 g of the surfactant aqueous solution 1 prepared in Preparation Example 2, 16.5 g of ion exchange water and 6 g of triethanolamine [manufactured by Tokyo Chemical Industry Co., Ltd.] were added to a 50 mL beaker, heated to 70° C. and stirred for 60 minutes to obtain 55.8 g of the surfactant aqueous solution 2.

[0296] Sampling is performed from the surfactant aqueous solution 2, and the molecular structure of the surfactant contained in the surfactant aqueous solution 2 and the type of cations constituting the surfactant are determined using the same method as in Manufacturing Example 1, and the content of the surfactant contained in the surfactant aqueous solution 2 is further determined using the same method as in Manufacturing Example 1.

[0297] The surfactant aqueous solution 2 is an aqueous solution containing 27.3% by weight of decylhydroxyether triethanolammonium acetate as the alkylhydroxyether acetic acid (salt) (A).

[0298] <Production Example 4>

[0299] 33.3 g of the surfactant aqueous solution 1 prepared in Preparation Example 2, 17.5 g of ion exchange water, and potassium hydroxide [manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.] were added to a 50 mL beaker, heated to 70° C. and stirred for 60 minutes to obtain 52.8 g of the surfactant aqueous solution 3.

[0300] Sampling is performed from the surfactant aqueous solution 3, and the molecular structure of the surfactant contained in the surfactant aqueous solution 3 and the type of cations constituting the surfactant are determined using the same method as in Manufacturing Example 1, and the content of the surfactant contained in the surfactant aqueous solution 3 is further determined using the same method as in Manufacturing Example 1.

[0301] The surfactant aqueous solution 3 is an aqueous solution containing 28.9% by weight of decylhydroxyether potassium acetate as the alkylhydroxyether acetic acid (salt) (A).

[0302] <Production Example 5>

[0303] Into a 1-L four-necked flask equipped with a stirring device, a reflux condenser, and a thermometer, 200 g of 1,2-dodecanediol [manufactured by Tokyo Chemical Industry Co., Ltd.], 300 g of toluene [manufactured by Fujifilm Wako Pure Chemical Corporation], and 4 g of 97% sulfuric acid [special grade, manufactured by Kishida Chemical Co., Ltd.] were charged. After purging with nitrogen, the temperature was raised to 90 °C, and at this temperature, the pressure was reduced to a gauge pressure of 2.7 kPa, and a dehydration condensation reaction was carried out for 7 hours.

[0304] Subsequently, the temperature was raised to 120 °C, and the solvent toluene was removed, thereby obtaining 380 g of Intermediate 1 containing a dehydration condensate of 1,2-dodecanediol.

[0305] A sample was taken from Intermediate 1, and the structure and content of the dehydration condensate of 1,2-dodecanediol contained in the sampled Intermediate 1 were measured by NMR and gas chromatography (GC) described below.

[0306] All of Intermediate 1 was a dimer of 1,2-dodecanediol.

[0307] <Analytical method for the content of the dehydration condensate of 1,2-dodecanediol based on GC>

[0308] A sample solution with a concentration of Intermediate 1 of 50 g / L was prepared, and GC-based analysis was carried out under the conditions described below.

[0309] Based on the obtained GC chromatogram, the peak of the dimer of 1,2-dodecanediol appearing at a retention time of 18 - 20 minutes was confirmed, and it was confirmed that Intermediate 1 contained the dimer of 1,2-dodecanediol.

[0310] Furthermore, based on the obtained GC chromatogram, the content of the dimer of 1,2-dodecanediol contained in Intermediate 1 was calculated using the following calculation formula.

[0311] Content of the dimer of 1,2-dodecanediol contained in Intermediate 1 (wt%) = (Total area value of the peak of the dimer of 1,2-dodecanediol appearing at a retention time of 18 - 20 minutes) / (Total area value of the peaks appearing at a retention time of 2 - 20 minutes)

[0312] <GC measurement conditions>

[0313] Apparatus: GC-2014 (manufactured by Shimadzu Corporation)

[0314] Detector: FID

[0315] GC capillary column: Ultra2 (inner diameter 0.2 mm, length 25 m, film thickness 0.11 μm, manufactured by Agilent J&W)

[0316] Column temperature: 100℃→300℃ (heating rate: 10℃ / min)

[0317] Sample injection volume: 2 μL

[0318] <Production Example 6>

[0319] Into a 1L four-necked flask equipped with a stirring device, a reflux cooler, a dropping funnel and a thermometer, 386 g of the intermediate 1, 77 g of toluene [manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.] and 121.2 g of sodium monochloroacetate [manufactured by Denak Corporation] were added, and after nitrogen substitution, the temperature was raised to 50°C, and 40.4 g of granular sodium hydroxide [manufactured by Tosoh Corporation] was slowly added over 5 hours under stirring, followed by aging for 3 hours.

[0320] Add 211 g of ion exchange water to the solution after the reaction at 50°C, heat to 75°C, add 110 g of 38% hydrochloric acid aqueous solution [manufactured by Toagosei Co., Ltd.], stir for 30 minutes, then transfer the solution to a separatory funnel, let it stand for 30 minutes and then separate the liquids, and remove the lower layer of the solution. The remaining supernatant solution was transferred to a 1L four-necked flask equipped with a stirring device, a reflux cooler and a thermometer, 86 g of ion exchange water was added, and mixed for 30 minutes. After mixing, it was transferred to a separatory funnel, and the lower layer of the solution was removed after standing for 30 minutes. 10 g of sodium hydroxide was added to the remaining supernatant solution, and a rotary evaporator was used to reduce the pressure at 75°C to a gauge pressure of 2.7 kPa. The volatile components were removed by maintaining the temperature and pressure for 7 hours to obtain 400 g of powder 2 containing a surfactant.

[0321] 1 g of sample is taken from the powder 2 containing the surfactant, and the molecular structure of the surfactant contained in the powder 2 containing the surfactant and the type of cations constituting the surfactant are determined by ICP and NMR, and the content of the surfactant contained in the powder 2 containing the surfactant is further determined by the quantitative analysis method based on HPLC described later.

[0322] The surfactant-containing powder 2 is a powder containing a total of 40 weight % of sodium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate, sodium 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetate, sodium 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetate and sodium 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetate as alkyl hydroxy ether acetic acid (salt) (B).

[0323] <Quantitative Analysis Method of Alkyl Hydroxyether Acetic Acid (Salt) (B) Content by HPLC>

[0324] Prepare calibration curve solution 4 with a concentration of 0.0002 g / L of the dimer of 1,2-dodecanediol and a concentration of 1.2 g / L of undecanoic acid; calibration curve solution 5 with a concentration of 0.0004 g / L of the dimer of 1,2-dodecanediol and a concentration of 1.2 g / L of undecanoic acid; calibration curve solution 6 with a concentration of 0.0006 g / L of the dimer of 1,2-dodecanediol and a concentration of 1.2 g / L of undecanoic acid; and a sample solution with a concentration of 9.0 g / L of powder 2 containing a surfactant and a concentration of 1.2 g / L of undecanoic acid.

[0325] Analyze the sample solution and calibration curve solutions 4 - 6 by HPLC. Based on the peak area ratios of the peak of the dimer of 1,2-dodecanediol appearing at a retention time of 9.0 - 9.52 minutes, the peak of alkyl hydroxy ether acetate (B) appearing at a retention time of 12.5 - 13.0 minutes, and the peak of undecanoic acid appearing at a retention time of 12.1 - 19.6 minutes in the obtained HPLC spectra, calculate the content of alkyl hydroxy ether acetate (B) contained in powder 2 containing a surfactant based on the content of undecanoic acid contained in the sampled powder 2 containing a surfactant.

[0326] <HPLC measurement conditions>

[0327] Apparatus: Liquid chromatography (manufactured by Shimadzu Corporation)

[0328] Detector: Differential refractive index meter

[0329] Column: Capcell Pak C18 SG 120A (inner diameter 4.6 nm, length 25 cm, manufactured by Osaka Soda Co., Ltd.)

[0330] Column temperature: 40 °C

[0331] Eluent: A mixed solution of 0.02 M phosphoric acid, 0.01 M sodium dihydrogen phosphate solution, and acetonitrile [47:53 (volume ratio)]

[0332] Sample injection volume: 40 μL

[0333] <Production Example 7>

[0334] Add 100 g of powder 2 containing a surfactant produced in Production Example 6, 4.3 g of ion-exchanged water, and 21.8 g of 35% aqueous hydrochloric acid solution [manufactured by Kishida Chemical Co., Ltd.] to a 300 mL beaker, heat to 70 °C, and stir for 60 minutes to obtain 126 g of surfactant aqueous solution 4.

[0335] Sampling is performed from the surfactant aqueous solution 4, and the molecular structure of the surfactant contained in the surfactant aqueous solution 4 and the type of cations constituting the surfactant are determined using the same method as in Manufacturing Example 6, and the content of the surfactant contained in the surfactant aqueous solution 4 is further determined using the same method as in Manufacturing Example 6.

[0336] Surfactant aqueous solution 4 is an aqueous solution containing 30 weight % in total of 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetic acid, 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetic acid, 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetic acid and 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetic acid as alkyl hydroxy ether acetic acid (salt) (B).

[0337] <Production Example 8>

[0338] 33.3 g of the surfactant aqueous solution 4 prepared in Preparation Example 7, 13.5 g of ion exchange water, and 3.9 g of triethanolamine [manufactured by Tokyo Chemical Industry Co., Ltd.] were added to a 50 mL beaker, heated to 70° C. and stirred for 60 minutes to obtain 50.7 g of the surfactant aqueous solution 5.

[0339] Sampling is performed from the surfactant aqueous solution 5, and the molecular structure of the surfactant contained in the surfactant aqueous solution 5 and the type of cations constituting the surfactant are determined using the same method as in Manufacturing Example 6, and the content of the surfactant contained in the surfactant aqueous solution 5 is further determined using the same method as in Manufacturing Example 6.

[0340] Surfactant aqueous solution 5 is an aqueous solution containing 2-((1-((2-hydroxydodecyl)oxy)dodec-2-yl)oxy)triethanolammonium acetate, 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)triethanolammonium acetate, 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)triethanolammonium acetate and 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)triethanolammonium acetate as alkylhydroxyether acetic acid (salt) (B) in a total of 27.3 weight %.

[0341] <Production Example 9>

[0342] 33.3 g of the surfactant aqueous solution 4 prepared in Preparation Example 7 and 1.3 g of potassium hydroxide [manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.] were placed in a 50 mL beaker, heated to 70° C. and stirred for 60 minutes to obtain 24.6 g of the surfactant aqueous solution 6.

[0343] Sampling is performed from the surfactant aqueous solution 6, and the molecular structure of the surfactant contained in the surfactant aqueous solution 6 and the type of cations constituting the surfactant are determined using the same method as in Manufacturing Example 6, and the content of the surfactant contained in the surfactant aqueous solution 6 is further determined using the same method as in Manufacturing Example 6.

[0344] Surfactant aqueous solution 6 is an aqueous solution containing a total of 28.9 weight % of potassium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate, potassium 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetate, potassium 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetate and potassium 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetate.

[0345] <Examples 1 to 5 and Comparative Examples 1 to 3>

[0346] The surfactant-containing powders 1 and 2 obtained in Preparation Examples 1 and 6 and the surfactant aqueous solutions 1 to 6 obtained in Preparation Examples 2 to 4 and 7 to 9 were mixed in the ratios shown in Table 1 to prepare surfactant compositions 1 to 5 of the present invention and comparative surfactant compositions 1' to 3'.

[0347] <Foaming properties>

[0348] The surfactant compositions 1 to 5 of the present invention and the comparative surfactant compositions 1' to 3' were diluted with soft water converted to 15 ppm of calcium oxide to prepare 200 mL of a 1 wt% (active ingredient concentration) aqueous solution of the surfactant composition. The mixture was stirred at 25°C for 30 seconds using a fiber mixer (National MX-V200). The foaming properties were evaluated based on the height (mm) of the foam at this time. The results are shown in Table 1.

[0349] <Storage stability>

[0350] For the surfactant compositions 1 to 5 of the present invention and the comparative surfactant compositions 1' to 3', 30 g of each surfactant composition was prepared in a light-shielded 25°C screw-cap tube No. 7 (manufactured by Maruemu Co., Ltd.), and stored immediately after preparation. The appearance on the 90th day after the start of storage was visually confirmed, and the storage stability was evaluated according to the following criteria. The results are shown in Table 1.

[0351] (Evaluation criteria for storage stability)

[0352] ○: The appearance on the 90th day was transparent, and no turbidity or separation was observed

[0353] ×: White turbidity or separation was observed in the appearance on the 90th day

[0354]

[0355] <Examples 6 to 14 and Comparative Examples 4 to 5>

[0356] Surfactant compositions 1 to 5 and comparative surfactant compositions 1' to 3' were mixed with other optional components described below in the proportions shown in Tables 2 to 5 to prepare the cleaning agents (shampoos, pump foamer facial cleansers, and creamy facial cleansers) of the present invention in Examples 6 to 14 and the comparative cleaning agents (shampoos) in Comparative Examples 4 to 5.

[0357] In addition, the numbers written in parentheses in Tables 2 to 5 are values ​​converted into the ratio of the components (sometimes also referred to as effective components) remaining after removing water from each raw material.

[0358] <Amount of sebum remaining after shampooing>

[0359] Ten male and female panelists wetted their hair thoroughly with hot water at 40°C, then used 5 g of the cleansing agent (shampoo) of Example 6 to wash the hair, rinsed with hot water at 40°C, and then wiped five random spots of the scalp with a paper towel (1 cm×1 cm) soaked in ethanol one hour later.

[0360] The wiped paper towel was immersed in a screw-cap tube (Screw-cap tube No. 6, manufactured by Maruemu Co., Ltd.) containing 1 mL of methanol, and the mixture was shaken manually for 5 minutes to extract the components wiped with the paper towel into methanol to prepare a sample solution.

[0361] Methanol solutions in which triolein was dissolved at concentrations of 5, 15, 30, and 50 ppm were prepared as calibration curve solutions.

[0362] The sample solution and the calibration curve solution were analyzed by GC under the conditions described below.

[0363] A calibration curve was prepared by the least squares method based on the relationship between the concentration of triolein in the calibration curve sample and the peak area of ​​the GC spectrum obtained using triolein, and the amount of triolein in methanol was quantified based on the calibration curve and the peak area of ​​the GC spectrum of the component extracted into methanol.

[0364] Triolein is one of the main components of sebum. The lower the concentration of triolein extracted into methanol, the lower the amount of sebum remaining after shampooing. Therefore, the quantified concentration of triolein in methanol was taken as the sebum residual amount (ppm).

[0365] For the cleaning agents (shampoos) of Examples 7 to 11 and Comparative Examples 4 to 5, evaluation was also carried out using the same method, and the results are shown in Tables 2 to 4.

[0366] <GC measurement conditions>

[0367] Apparatus: GC-1700 (manufactured by Shimadzu Corporation)

[0368] Column: Zebron ZB-5 (length: 15 m, inner diameter: 0.25 mm, film thickness: 0.25 μm, manufactured by Shimadzu GLC Co., Ltd.)

[0369] Vaporization chamber: 310 °C

[0370] Detector: FID (temperature: 320 °C)

[0371] Column temperature: 80 °C → 300 °C (heating rate 10 °C / min)

[0372] 300 °C (held for 10 minutes)

[0373] Total flow rate: 115 ml / min

[0374] Column flow rate: 2.2 ml / min

[0375] Split ratio: 50

[0376] Pressure: 100 kPa

[0377] Sample injection volume: 1 μL

[0378] <Residual sebum amount after using the facial wash for pump type foaming device and cream type facial wash>

[0379] A total of 10 male and female panelists fully wetted their faces with 40 °C hot water, then used 5 g of the cleaning agent (facial wash for pump type foaming device) of Example 12 to wash their faces, rinsed with 40 °C hot water, and randomly wiped 5 places on the forehead with a kitchen paper towel (1 cm × 1 cm) impregnated with ethanol after 1 hour.

[0380] The wiped kitchen paper towel was immersed in a screw cap tube (Screw cap tube No. 6, manufactured by Maruemu Co., Ltd.) containing 1 mL of methanol, and shaken by hand for 5 minutes to extract the components wiped with the kitchen paper towel into methanol to prepare a test sample solution.

[0381] Methanol solutions dissolved with triolein at respective concentrations of 5, 15, 30, and 50 ppm were prepared as calibration curve solutions.

[0382] The test sample solution and the calibration curve solutions were analyzed by GC. The analysis conditions were the same as those for the residual sebum amount (shampoo).

[0383] The cleansing agents (creamy facial cleansers) of Examples 13 to 14 were also evaluated by the same method. The results are shown in Table 5.

[0384] <Oily skin after using shampoo>

[0385] Ten male and female panelists wetted their hair with 40°C hot water, washed their hair with 5 g of the cleanser (shampoo) of Example 6, rinsed with 40°C hot water, dried with a hair dryer, and left the hair for 2 hours at 25°C and 40% relative humidity. Then, the gloss of the hairline at five random locations was measured using a gloss meter [trade name: MJ-GM26 Gloss Checker Satotech {manufactured by Sato Tech Co., Ltd.}]. The lower the gloss value, the more oily the skin can be.

[0386] The cleaning agents (shampoos) of Examples 7 to 11 and Comparative Examples 4 to 5 were also evaluated by the same method. The results are shown in Tables 2 to 4.

[0387] <Oily skin after using pump-type foaming cleansers and cream-type cleansers>

[0388] Ten male and female panelists moistened their faces with 40°C hot water, washed their faces with 1 g of the cleanser (pump foamer facial cleanser) of Example 12, rinsed with 40°C hot water, wiped the water droplets with a towel for 10 seconds, and spent 2 hours quietly under the conditions of temperature 25°C and relative humidity 40%. Then, the gloss of the forehead was measured at five random places using a gloss meter [trade name: MJ-GM26 Gloss Checker Satotech {manufactured by Satotech Co., Ltd.}]. The lower the gloss value, the more oily the skin can be suppressed.

[0389] The cleansing agents (creamy facial cleansers) of Examples 13 to 14 were also evaluated by the same method. The results are shown in Table 5.

[0390] <Maintaining the volume of hair after shampooing>

[0391] 20 female panelists with hair length of 30 cm or more fully wetted their hair with 40°C hot water, then washed their hair with 5 g of the cleaning agent (shampoo) of Example 6, rinsed with 40°C hot water, and dried with a hair dryer. After drying with a hair dryer, the hair was immediately placed in a room with a temperature of 25°C and a relative humidity of 40%. After 10 minutes and 2 hours of drying with a hair dryer, the vertical height of the highest part of the hair from the root of the top of the head was measured, and the difference between 10 minutes and 2 hours was taken as the hair volume retention. The smaller the difference between 10 minutes and 2 hours, the more the hair volume can be retained.

[0392] The cleaning agents (shampoos) of Examples 7 to 11 and Comparative Examples 4 to 5 were also evaluated by the same method. The results are shown in Tables 2 to 4.

[0393] <Moisturizing properties of skin after shampooing>

[0394] A total of 20 Japanese men and women aged 20 to 50 years old fully moistened their hair with 40°C hot water, cleaned their scalp with 1 g of the cleansing agent (shampoo) of Example 6, rinsed thoroughly with 40°C hot water, and then dried their hair with a hair dryer for 5 minutes. This operation was repeated once a day.

[0395] On the 14th day after the start of use, 2 hours after scalp washing, the keratin water content of three random spots on the scalp was measured using a skin moisture tester [product name: Corneometer CM825 {manufactured by Courage+Khazaka}], and the average value was calculated.

[0396] The cleaning agents (shampoos) of Examples 7 to 11 and Comparative Examples 4 to 5 were also evaluated by the same method. The results are shown in Tables 2 to 4.

[0397] <Moisturizing properties of the skin after using pump-type foaming cleansers and cream-type cleansers>

[0398] A total of 20 Japanese men and women aged 20 to 50 years old moistened their faces with 40°C hot water, cleaned their faces with 1 g of the cleanser of Example 12 (facial cleanser for a pump foamer), rinsed thoroughly with 40°C hot water, wiped off water droplets with a towel for 10 seconds, and repeated this operation once a day.

[0399] On the 14th day after the start of use, 2 hours after washing the face, the keratin water content of three random places on the forehead was measured using a skin moisture tester [product name: Corneometer CM825 {manufactured by Courage+Khazaka}], and the average value was calculated.

[0400] The cleansing agents (creamy facial cleansers) of Examples 13 to 14 were also evaluated by the same method. The results are shown in Table 5.

[0401] [Table 2]

[0402]

[0403] [Table 3]

[0404]

[0405] [Table 4]

[0406]

[0407] [Table 5]

[0408]

[0409] In addition, as other optional components described in Tables 2 to 5, the following components were used.

[0410] <Optional Other Ingredients>

[0411] · 26 wt% aqueous solution of sodium polyoxyethylene (average degree of polymerization 2) lauryl ether sulfate [trade name: Beaulight NA-25S {manufactured by Sanyo Chemical Industries, Ltd. (Beaulight is a registered trademark of Sanyo Chemical Industries, Ltd.)}]

[0412] · 28 wt% aqueous solution of sodium polyoxyethylene (average degree of polymerization 4) lauryl ether acetate [trade name: Beaulight LCA-25N {manufactured by Sanyo Chemical Industries, Ltd.}]

[0413] · A 29 wt% aqueous solution of sodium N-coconut fatty acid acyl-L-glutamate [trade name: Plantapon AminoSCG-L {manufactured by BASF (Plantapon is a registered trademark of Cognis IP Management GmbH)}]

[0414] · A 30 wt% aqueous solution of lauroyl-L-glutamic acid triethanolamine [trade name: Amisoft LT-12 {manufactured by Ajinomoto Healthy Supply Co., Ltd. (Amisoft is a registered trademark of Ajinomoto Co., Ltd.)}]

[0415] · 30 wt% aqueous solution of sodium N-lauroyl sarcosinate [trade name: Soypon SLE {manufactured by Kawaken Fine Chemicals Co., Ltd. (Soypon is a registered trademark of Kawaken Fine Chemicals Co., Ltd.)}]

[0416] Potassium N-coconut fatty acid acyl glycinate [Trade name: Amilite GCK-11 {manufactured by Ajinomoto Healthy Supply Co., Ltd. (Amilite is a registered trademark of Ajinomoto Co., Ltd.)}]

[0417] · A 37 wt% aqueous solution of sodium olefin (C14-16)sulfonate [trade name: Lipolan LJ-441 {manufactured by Lion Corporation (Lipolan is a registered trademark of Lion Specialty Chemicals Co., Ltd.)}]

[0418] · A 30 wt% aqueous solution of cocamidopropyl betaine [trade name: Lebon HC-30W {manufactured by Sanyo Chemical Industries, Ltd.}]

[0419] 43 wt% aqueous solution of 2-coconut fatty acid-N-hydroxyethyl-N-hydroxyethylimidazolinium betaine [trade name: Lebon CIB {manufactured by Sanyo Chemical Industries, Ltd.}]

[0420] ·Lauric acid [Trade name: NAA-122 {manufactured by NOF Corporation (NAA is a registered trademark of NOF Corporation)}]

[0421] · Stearic acid [trade name: NAA-172 {manufactured by NOF Corporation}]

[0422] Palmitic acid [trade name: NAA-160 {manufactured by NOF Corporation}]

[0423] ·1,3-Butanediol [manufactured by Nacalai Tesque Co., Ltd.]

[0424] · Glycerin [Trade name: Concentrated Glycerin for Cosmetics {manufactured by Kao Corporation}]

[0425] Polyquaternium-22 (40 wt% aqueous solution) [Trade name: MERQUAT 280 {manufactured by Lubrizol (MERQUAT is a registered trademark of Lubrizol Advanced Materials Incorporated)}]

[0426] · Polyquaternium-7 (9 wt% aqueous solution) [Trade name: MERQUAT 550 (manufactured by Lubrizol)]

[0427] Polyquaternium-10 [Trade name: Sensomer 10M Polymer (manufactured by Lubrizol)]

[0428] · Polydimethylsiloxane [trade name: KF-96A-2CS {manufactured by Shin-Etsu Chemical Co., Ltd.}]

[0429] Vitamin E [trade name: D-α-tocopherol {manufactured by Tokyo Chemical Industry Co., Ltd.}]

[0430] EDTA-2Na [Trade name: 2NA (EDTA·2Na) {manufactured by Dojin Chemical Laboratories Co., Ltd.}]

[0431] Coconut fatty acid N-methylethanolamide [Trade name: Aminon C-11S {manufactured by Kao Corporation (Aminon is a registered trademark of Kao Corporation)}]

[0432] PEG-160 sorbitan triisostearate [Trade name: Rheodol TW-IS399C {manufactured by Kao Corporation (Rheodol is a registered trademark of Kao Corporation)}]

[0433] PEG-190 distearate [trade name: Emulmin 862 {manufactured by Sanyo Chemical Industries, Ltd. (Emulmin is a registered trademark of Sanyo Chemical Industries, Ltd.)}]

[0434] · Ethylene glycol distearate [trade name: EMALEX EG-di-S {manufactured by Nihon Emulsion Co., Ltd. (EMALEX is a registered trademark of Nihon Emulsion Co., Ltd.)}]

[0435] ·Menthol [Trade name: l-Menthol {manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.}]

[0436] ・Citric acid [manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.]

[0437] Potassium hydroxide [manufactured by Nacalai Tesque Co., Ltd.]

[0438] As can be seen from Tables 2 to 5, the cleansing agents of Examples 6 to 14 have less residual sebum and less oiliness on the skin, and are superior in terms of hair volume and skin moisturizing properties, compared to the cleansing agents of Comparative Examples 4 to 5.

[0439] Industrial Applicability

[0440] The detergent using the surfactant composition of the present application is suitable for shampoo, facial cleanser, etc. due to the low amount of sebum residue and oil secretion of the skin, the fluffy feeling of hair and the excellent moisturizing property of the skin. In addition, it is possible to be used as a household detergent (laundry detergent, tableware detergent, etc.) and an industrial detergent (cleaning agent for metal, precision parts, etc.).

Claims

1. A surfactant composition comprising: Alkyl hydroxy ether acetate (salt) (A) represented by the following general formula (1), and Alkyl hydroxy ether acetic acid (salt) (B) represented by the following general formula (2), The total weight ratio of the alkyl hydroxy ether acetic acid and its salt (B) is 0.05 wt% to 1 wt% relative to the total weight of the alkyl hydroxy ether acetic acid and its salt (A). R 1 -CH(OH)-CH2-OCH2COOM 1 (1) In formula (1), R 1 represents an alkyl group having 8 to 12 carbon atoms, M 1 represents a hydrogen atom, a sodium atom, a potassium atom or triethanolammonium, R 2 -O-CH(X 1 )CH(X 2 )-OCH2COOM 2 (2) In formula (2), X 1 and X 2 One of them is a hydrogen atom, and the other is an alkyl group having 8 to 12 carbon atoms, R 2 A hydroxyalkyl group is a group in which any one of the hydrogen atoms bonded to the carbon atom at position number 1 in an alkyl group having 10 to 14 carbon atoms is replaced by a hydroxyl group, X 1 or X 2 When the number of carbon atoms of the alkyl group having 8 to 12 carbon atoms represented by is n, R 2 The number of carbon atoms is n+2. M 2 represents a hydrogen atom, a sodium atom, a potassium atom or triethanolammonium.

2. A cleaning agent comprising the surfactant composition according to claim 1.

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