Surfactant Compositions and Cleaning Agents

Abstract

This invention relates to a surfactant composition comprising an alkyl hydroxy ether acetic acid (salt) (A) represented by general formula (1) and an alkyl hydroxy ether acetic acid (salt) (B) represented by general formula (2), wherein the total weight percentage of the alkyl hydroxy ether acetic acid and its salt (B) is 0.05 to 1% by weight relative to the total weight of the alkyl hydroxy ether acetic acid and its salt (A). 1 -CH(OH)-CH2-OCH2COOM 1 (1) [where R is the formula] 1 M represents an alkyl group with 8 to 12 carbon atoms. 1 This represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolamine. 2 -O-CH(X) 1 )CH(X 2 )-OCH2COOM 2 (2) [where X] 1 and X 2 One of them is a hydrogen atom, and the other is an alkyl group with 8 to 12 carbon atoms, R 2 A hydroxyalkyl group is formed by replacing any one hydrogen atom bonded to the carbon atom at position 1 of an alkyl group with 10 to 14 carbon atoms with a hydroxyl group. 1 or X 2 When the alkyl group representing 8 to 12 carbon atoms has n carbon atoms, R 2 The number of carbon atoms is n+2, M 2 This represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolamine.

Description

Technical Field

[0001] This invention relates to surfactant compositions and cleaning agents. Background Technology

[0002] In cleansing agents for human skin and hair, surfactants such as anionic surfactants are used to produce foams that exhibit moderate viscosity and excellent foaming power, foam stability, and moisturizing power. Cleansing agents containing sodium dodecanediol acetate are known (Patent Document 1).

[0003] However, while existing cleansers containing sodium monoacetate of dodecanediol are effective at removing sebum, they also remove the skin's natural moisturizing factors along with the sebum, thus causing problems with post-cleansing hydration.

[0004] Existing technical documents

[0005] Patent documents

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

[0007] The problem that the invention aims to solve

[0008] The purpose of this invention is to provide a surfactant composition that provides a cleanser with excellent cleansing power against sebum and excellent moisturizing properties after cleansing.

[0009] Methods for solving problems

[0010] In order to achieve the above objectives, the inventors conducted in-depth research and, as a result, realized the present invention.

[0011] That is, the present invention relates to a surfactant composition and a cleaning agent containing the above 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 its salt (B) is 0.05% to 1% by weight relative to the total weight of the alkyl hydroxy ether acetic acid and its salt (A).

[0012] R 1 -CH(OH)-CH2-OCH2COOM 1 (1)

[0013] [In the formula, R] 1 M represents an alkyl group with 8 to 12 carbon atoms. 1 This represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolamine.

[0014] R 2-O-CH(X 1 )CH(X 2 )-OCH2COOM 2 (2)

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

[0016] R 2 A hydroxyalkyl group is formed by replacing any one hydrogen atom bonded to the carbon atom at position 1 of an alkyl group with 10 to 14 carbon atoms with a hydroxyl group.

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

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

[0019] The effects of the invention

[0020] Cleansing agents containing the surfactant compositions of the present invention have excellent sebum-removing power, resulting in less stickiness after washing. Furthermore, since they do not wash away the natural moisturizing factors present in the skin, the skin remains highly moisturized after washing. Detailed Implementation

[0021] The present invention will be described in detail below.

[0022] <Alkyl Hydroxyether Acetic Acid (Salt) (A)>

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

[0024] R 1 -CH(OH)-CH2-OCH2COOM 1 (1)

[0025] [In the formula, R] 1 M represents an alkyl group with 8 to 12 carbon atoms. 1 This represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolamine.

[0026] It should be noted that in this specification, alkyl hydroxy ether acetic acid (salt) refers to alkyl hydroxy ether acetic acid and / or alkyl hydroxy ether acetic acid salts.

[0027] In general formula (1), R1 It refers to alkyl groups with 8 to 12 carbon atoms.

[0028] Examples of alkyl groups with 8 to 12 carbon atoms include n-octyl, isooctyl, 2-ethylhexyl, n-nonyl, isonyl, n-decyl, isodel, undecyl, n-dodecyl, and isododecyl.

[0029] R 1 From the perspective of cleansing power against sebum, alkyl groups with 8 to 10 carbon atoms are preferred, alkyl groups with 10 carbon atoms are more preferred, and n-decyl groups are particularly preferred. Furthermore, straight-chain alkyl groups are preferred.

[0030] In general formula (1), M 1 It can be a hydrogen atom, a sodium atom, a potassium atom, or triethanolamine.

[0031] M 1 In terms of its ability to cleanse sebum, sodium atoms or triethanolamine are preferred, and sodium atoms are even more preferred.

[0032] Specific examples of alkyl hydroxy ether acetic acid (A) represented by general formula (1) include decyl hydroxy ether acetic acid (2-hydroxydecyl acetate), isodecyl hydroxy ether acetic acid (2-hydroxyisodecyl acetate), ethyl octyl hydroxy ether acetic acid (2-hydroxyethyl octyl acetate), undecyl hydroxy ether acetic acid (2-hydroxyundecyl acetate), isoundecyl hydroxy ether acetic acid (2-hydroxyisoundecyl acetate), dodecyl hydroxy ether acetic acid (2-hydroxydodecyl acetate), isododecyl hydroxy ether acetic acid (2-hydroxyisododecyl acetate), tridecyl hydroxy ether acetic acid (2-hydroxytetrazyl acetate), tetradecyl hydroxy ether acetic acid (2-hydroxytetradecyl acetate), and isotetradecyl hydroxy ether acetic acid (2-hydroxyisotetradecyl acetate).

[0033] Specific examples of alkyl hydroxy ether acetates (A) represented by general formula (1) include sodium decyl hydroxy ether acetate, sodium isodecayl hydroxy ether acetate, sodium ethyl octyl hydroxy ether acetate, sodium undecyl hydroxy ether acetate, sodium isoundecyl hydroxy ether acetate, sodium dodecyl hydroxy ether acetate, sodium isododecyl hydroxy ether acetate, sodium tridecyl hydroxy ether acetate, sodium tetradecyl hydroxy ether acetate, sodium isotetradecyl hydroxy ether acetate, potassium decyl hydroxy ether acetate, potassium isodecayl hydroxy ether acetate, potassium ethyl octyl hydroxy ether acetate, potassium undecyl hydroxy ether acetate, potassium isoundecyl hydroxy ether acetate, potassium dodecyl hydroxy ether acetate, and sodium dodecyl hydroxy ether acetate. Potassium hydroxy ether acetate, potassium isododecyl hydroxy ether acetate, potassium tridecyl hydroxy ether acetate, potassium tetradecyl hydroxy ether acetate, potassium isotetradecyl hydroxy ether acetate, decyl hydroxy ether acetate triethanolamine, isodecyl hydroxy ether acetate triethanolamine, ethyl octyl hydroxy ether acetate triethanolamine, undecyl hydroxy ether acetate triethanolamine, isoundecyl hydroxy ether acetate triethanolamine, dodecyl hydroxy ether acetate triethanolamine, isododecyl hydroxy ether acetate triethanolamine, tridecyl hydroxy ether acetate triethanolamine, tetradecyl hydroxy ether acetate triethanolamine, and isotetradecyl hydroxy ether acetate triethanolamine, etc.

[0034] Of these, one can be used alone, or two or more can be used together.

[0035] As for the alkyl hydroxy ether acetic acid and its salt (A) represented by general formula (1), from the perspective of the cleansing power against sebum, the alkyl hydroxy ether acetic acid salt represented by general formula (1) is preferred, further preferred are sodium decyl hydroxy ether acetic acid, sodium dodecyl hydroxy ether acetic acid, sodium tetradecyl hydroxy ether acetic acid, triethanolamine decyl hydroxy ether acetic acid, triethanolamine dodecyl hydroxy ether acetic acid, and triethanolamine tetradecyl hydroxy ether acetic acid, particularly preferred are sodium decyl hydroxy ether acetic acid and sodium dodecyl hydroxy ether acetic acid, and most preferred are sodium dodecyl hydroxy ether acetic acid.

[0036] The alkyl hydroxy ether acetic acid represented by general formula (1) and its salt (A) can be obtained by known methods as described in Japanese Patent Application Publication No. 2017-197732, etc.

[0037] Specifically, relative to 1 mole of 1,2-diol with 10 to 14 carbon atoms, 1.04 moles of sodium monochloroacetate are added, and an aqueous solution containing crude alkyl hydroxy ether acetate is obtained by SN2 reaction at a preferred temperature of 30 to 80°C, more preferably 50 to 70°C. Then, hydrochloric acid is added, thereby obtaining an aqueous solution of surfactant containing alkyl hydroxy ether acetate (A).

[0038] Further neutralization of the obtained aqueous surfactant containing alkyl hydroxy ether acetate (A) using alkaline compounds such as sodium hydroxide, potassium hydroxide, and triethanolamine can yield an aqueous surfactant containing alkyl hydroxy ether acetate (A).

[0039] An aqueous solution of a surfactant containing alkyl hydroxy ether acetic acid or its salt (A) can be used directly in the manufacture of the surfactant composition of the present invention; the aqueous solution of the surfactant can also be desolventized using known methods such as an evaporator, and the resulting powder containing alkyl hydroxy ether acetic acid or its salt (A) can be used in the manufacture of the surfactant composition; or the aqueous solution of the surfactant containing alkyl hydroxy ether acetic acid or its salt (A) can be mixed with the powder containing alkyl hydroxy ether acetic acid or its salt (A) for the manufacture of the surfactant composition.

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

[0041] <Method for determining the types of cations constituting alkyl hydroxy ether acetates using ICP analysis>

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

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

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

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

[0046] <Method for determining the types of cations constituting alkyl hydroxy ether acetates using NMR spectroscopy>

[0047] For samples prepared by homogenizing an aqueous solution of surfactant or 10 mg of surfactant-containing powder with deuterated acetone, H-NMR was performed using a nuclear magnetic resonance spectrometer [product name: AVANCE III 400HD {manufactured by BRUKER}].

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

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

[0050] <HPLC-based quantitative analysis method for alkyl hydroxy ether acetic acid (salt) (A)>

[0051] R of alkyl hydroxy ether acetic acid (salt) (A) 1 In the case of an alkyl group having 10 carbon atoms, a 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 undecaneic acid was prepared; a 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 undecaneic acid was prepared; a 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 undecaneic acid was prepared; and a sample solution with a concentration of 9.0 g / L of an aqueous solution of surfactant or a powder containing surfactant and a concentration of 1.2 g / L of undecaneic acid was 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 )-OCH2COOM 2 (2)

[0064] [In the formula, either 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 formed by replacing any one hydrogen atom bonded to the carbon atom at position 1 of an alkyl group with 10 to 14 carbon atoms with a hydroxyl group.

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

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

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

[0069] Examples of alkyl groups with 8 to 12 carbon atoms include n-octyl, isooctyl, 2-ethylhexyl, n-nonyl, isonyl, n-decyl, isodel, undecyl, n-dodecyl, and isododecyl.

[0070] From the perspective of skin moisturizing after cleansing, alkyl groups with 8 to 12 carbon atoms are preferred, alkyl groups with 8 to 10 carbon atoms are more preferred, alkyl groups with 10 carbon atoms are more particularly preferred, and n-decyl groups are especially preferred. In addition, straight-chain alkyl groups are preferred.

[0071] In general formula (2), R 2 A hydroxyalkyl group is formed by replacing the hydrogen atom bonded to the carbon atom at position 1 of an alkyl group with 10 to 14 carbon atoms with a hydroxyl group.

[0072] Hydroxyalkyl refers to an alkyl group that is replaced by one or more hydroxyl groups.

[0073] R 2 The carbon atom at position 1 in the alkyl group with 10 to 14 carbon atoms refers to the carbon atom that is associated with R. 2 The oxygen atom of the bonded ether bond is bonded to the carbon atom.

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

[0075] R 2 From the perspective of skin moisturizing after cleansing, a hydroxyalkyl group with 10 to 12 carbon atoms is preferred, a hydroxyalkyl group with 10 carbon atoms is more preferred, and a hydroxydecyl group is particularly preferred.

[0076] In general formula (2), M2 It can be a hydrogen atom, a sodium atom, a potassium atom, or triethanolamine.

[0077] M 2 From the perspective of skin moisturizing after cleansing, sodium atoms or triethanolamine are preferred, and sodium atoms are even more preferred.

[0078] Specific examples of alkyl hydroxy ether acetic acid (B) represented by 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-hydroxytetranyl)oxy)tetranyl-2-yl)oxy)acetic acid, 2-((1-((2-hydroxytetranyl)oxy)tetranyl-2-yl)oxy)acetic acid, 2-((1-(( 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)isododecane 2-((2-hydroxytetrazyl)oxy)tetrazyl)oxy)acetic acid, 2-((2-((2-hydroxyisotetrazyl)oxy)isotetrazyl)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)oxy)acetic acid, 2-((1-((1-hydroxyundecyl-2-yl)oxy)undecyl-2-yl)oxy)oxy)acetic acid 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-hydroxytetrazyl-2-yl)oxy)tetrazyl-2-yl)oxy)acetic acid, 2-((1-((1-hydroxyisotetrazyl-2-yl)oxy)isotetrazyl-2-yl)oxy)acetic acid, 2-((1-((1-hydroxyisotetrazyl-2-yl)oxy)tetrazyl-2-yl)oxy)acetic acid, 2-((1-((1-hydroxyisotetrazyl-2-yl)oxy)isotetrazyl-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) 2-((2-((1-hydroxytetrazyl-2-yl)oxy)tetrazyl)oxy)acetic acid, 2-((2-((1-hydroxyisotetrazyl-2-yl)oxy)isotetrazyl)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 alkyl hydroxy ether acetates (B) represented by the general formula (2) as sodium salts 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-hydroxytetrazyl)oxy)tetrazyl-2-yl)oxy)acetate, sodium 2-((1-((2-hydroxytetrazyl)oxy)tetrazyl-2-yl)oxy) Sodium acetate, 2-((1-((2-hydroxyisotridecyl)oxy)isotridecyl-2-yl)oxy)sodium acetate, 2-((1-((2-hydroxytetradecyl)oxy)tetradecyl-2-yl)oxy)sodium acetate, 2-((1-((2-hydroxyisotetradecyl)oxy)isotetradecyl-2-yl)oxy)sodium acetate, 2-((2-((2-hydroxydecyl)oxy)decyl)oxy)sodium acetate, 2-((2-((2-hydroxyisodecyl)oxy)isodecyl)oxy)sodium acetate, 2-((2-((2-hydroxyundecyl)oxy)undecyl)oxy)sodium acetate, 2-( Sodium (2-((2-hydroxyisododecyl)oxy)isododecyl)oxy)acetate, sodium (2-((2-hydroxytetrazyl)oxy)tetrazyl)oxy)acetate, sodium (2-((2-hydroxyisotetrazyl)oxy)isotetrazyl)oxy)acetate, sodium (2-((2-hydroxytetradecyl)oxy)tetradecyl)oxy)acetate, sodium (2-((2-hydroxyisotetradecyl)oxy)isotetradecyl)oxy)acetate, sodium (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-( Sodium (1-((1-hydroxyundecyl-2-yl)oxy)undecyl-2-yl)oxy)acetate, 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetate, 2-((1-((1-hydroxyisododecyl-2-yl)oxy)isododecyl-2-yl)oxy)acetate, 2-((1-((1-hydroxytetrazyl-2-yl)oxy)tetrazyl-2-yl)oxy)acetate, 2-((1-((1-hydroxyisotetrazyl-2-yl)oxy)isotetrazyl-2-yl)oxy)acetate, 2-((1-((1-hydroxyisotetrazyl-2-yl)oxy)tetradecyl-2-yl)oxy)acetate, 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-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-hydroxytetrazyl-2-yl)oxy)tetrazyl)oxy)acetate, sodium 2-((2-((1-hydroxyisotetrazyl-2-yl)oxy)isotetrazyl)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 alkyl hydroxy ether acetates (B) represented by the general formula (2) as potassium salts include 2-((1-((2-hydroxydecyl)oxy)decyl-2-yl)oxy)potassium acetate, 2-((1-((2-hydroxyisodecyl)oxy)isodecyl-2-yl)oxy)potassium acetate, 2-((1-((2-hydroxyundecyl)oxy)undecyl-2-yl)oxy)potassium acetate, 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)potassium acetate, 2-((1-((2-hydroxyisododecyl)oxy)isododecyl-2-yl)oxy)potassium acetate, 2-((1-((2-hydroxytetranyl)oxy)tetranyl-2-yl)oxy)potassium acetate, 2-((1-((2-hydroxytetranyl)oxy)tetranyl-2-yl)oxy) Potassium acetate, 2-((1-((2-hydroxyisotridecyl)oxy)isotridecyl-2-yl)oxy)potassium acetate, 2-((1-((2-hydroxytetradecyl)oxy)tetradecyl-2-yl)oxy)potassium acetate, 2-((1-((2-hydroxyisotetradecyl)oxy)isotetradecyl-2-yl)oxy)potassium acetate, 2-((2-((2-hydroxydecyl)oxy)decyl)oxy)potassium acetate, 2-((2-((2-hydroxyisodecyl)oxy)isodecyl)oxy)potassium acetate, 2-((2-((2-hydroxyundecyl)oxy)undecyl)oxy)potassium acetate, 2-( Potassium (2-((2-hydroxyisododecyl)oxy)isododecyl)oxy)acetate, potassium (2-((2-hydroxytetrazyl)oxy)tetrazyl)oxy)acetate, potassium (2-((2-hydroxyisotetrazyl)oxy)isotetrazyl)oxy)acetate, potassium (2-((2-hydroxytetradecyl)oxy)tetradecyl)oxy)acetate, potassium (2-((2-hydroxyisotetradecyl)oxy)isotetradecyl)oxy)acetate, potassium (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, 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetate, 2-((1-((1-hydroxyisododecyl-2-yl)oxy)isododecyl-2-yl)oxy)acetate, 2-((1-((1-hydroxytetrazyl-2-yl)oxy)tetrazyl-2-yl)oxy)acetate, 2-((1-((1-hydroxyisotetrazyl-2-yl)oxy)isotetrazyl-2-yl)oxy)acetate, 2-((1-((1-hydroxytetradecyl-2-yl)oxy)tetradecyl-2-yl)oxy)acetate, 2-((1-((1-hydroxytetradecyl-2-yl)oxy)tetradecyl-2-yl)oxy)acetate,2-((1-((1-hydroxyisotetradecyl-2-yl)oxy)isotetradecyl-2-yl)oxy)potassium acetate, 2-((2-((1-hydroxydecyl-2-yl)oxy)decyl)oxy)potassium acetate, 2-((2-((1-hydroxyisodecyl-2-yl)oxy)isodecyl)oxy)potassium acetate, 2-((2-((1-hydroxyundecyl-2-yl)oxy)undecyl)oxy)potassium acetate, 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)potassium acetate, 2-( Potassium acetate of the following types: (2-((1-hydroxyisododecyl-2-yl)oxy)isododecyl)oxy)acetate, (2-((2-((1-hydroxytetrazyl-2-yl)oxy)tetrazyl)oxy)acetate, (2-((2-((1-hydroxyisotetrazyl-2-yl)oxy)isotetrazyl)oxy)acetate, (2-((2-((1-hydroxyisotetradecyl-2-yl)oxy)tetradecyl)oxy)acetate, (2-((2-((1-hydroxyisotetradecyl-2-yl)oxy)isotetradecyl)oxy)acetate, etc.)

[0081] Specific examples of alkyl hydroxy ether acetates (B) of general formula (2) as triethanolamine salts include 2-((1-((2-hydroxydecyl)oxy)decyl-2-yl)oxy)triethanolamine acetate, 2-((1-((2-hydroxyisodecyl)oxy)isodecyl-2-yl)oxy)triethanolamine acetate, 2-((1-((2-hydroxyundecyl)oxy)undecyl-2-yl)oxy)triethanolamine acetate, 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)triethanolamine acetate, 2-((1-((2-hydroxyisododecyl)oxy)isododecyl-2-yl)oxy)triethanolamine acetate, 2-((1-((2-hydroxyisododecyl)oxy)isododecyl-2-yl)oxy)triethanolamine acetate, 2-((1-((2-hydroxytetrazyl)oxy)tetrazyl ... -2-yl)oxy)triethanolammonium acetate, 2-((1-((2-hydroxyisotetrazyl)oxy)isotetrazyl-2-yl)oxy)triethanolammonium acetate, 2-((1-((2-hydroxytetradecyl)oxy)tetradecyl-2-yl)oxy)triethanolammonium acetate, 2-((1-((2-hydroxyisotetradecyl)oxy)isotetradecyl-2-yl)oxy)triethanolammonium acetate, 2-((2-hydroxydecyl)oxy)decyl)oxy)triethanolammonium acetate, 2-((2-hydroxyisodecyl)oxy)isodecyl)oxy)triethanolammonium acetate, 2-((2-hydroxyundecyl)oxy)undecyl)oxy)triethanolammonium acetate, 2-((2-hydroxydodecane) 2-((2-hydroxyisododecyl)oxy)oxy)triethanolammonium acetate, 2-((2-((2-hydroxyisododecyl)oxy)oxy)triethanolammonium acetate, 2-((2-((2-hydroxytetrazyl)oxy)tetrazyl)oxy)triethanolammonium acetate, 2-((2-((2-hydroxyisotetrazyl)oxy)isotetrazyl)oxy)triethanolammonium acetate, 2-((2-((2-hydroxytetradecyl)oxy)tetradecyl)oxy)triethanolammonium acetate, 2-((1-((1-hydroxydecyl-2-yl)oxy)decyl-2-yl)oxy)triethanolammonium acetate, 2-((1-(1- Hydroxyisodecyl-2-yl)oxy)isodecyl-2-yl)oxy)triethanol ammonium acetate, 2-((1-((1-hydroxyundecyl-2-yl)oxy)undecyl-2-yl)oxy)triethanol ammonium acetate, 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)triethanol ammonium acetate, 2-((1-((1-hydroxyisododecyl-2-yl)oxy)isododecyl-2-yl)oxy)triethanol ammonium acetate, 2-((1-((1-hydroxytetrazyl-2-yl)oxy)tetrazyl-2-yl)oxy)triethanol ammonium acetate, 2-((1-((1-hydroxyisotetrazyl-2-yl)oxy)isotetrazyl-2-yl)oxy)triethanol ammonium acetate,2-((1-((1-hydroxytetradecyl-2-yl)oxy)tetradecyl-2-yl)oxy)triethanolammonium acetate, 2-((1-((1-hydroxyisotetradecyl-2-yl)oxy)isotetradecyl-2-yl)oxy)triethanolammonium acetate, 2-((2-((1-hydroxydecyl-2-yl)oxy)decyl)oxy)triethanolammonium acetate, 2-((2-((1-hydroxyisodecyl-2-yl)oxy)isodecyl)oxy)triethanolammonium acetate, 2-((2-((1-hydroxyundecyl-2-yl)oxy)undecyl)oxy)triethanolammonium acetate, 2-((2-((1-hydroxydodecyl-2-yl)) Triethanolamine acetate, 2-((2-((1-hydroxyisododecyl-2-yl)oxy)isododecyl)oxy)acetate, 2-((2-((1-hydroxytetrazyl-2-yl)oxy)tetrazyl)oxy)acetate, 2-((2-((1-hydroxyisotetrazyl-2-yl)oxy)isotetrazyl)oxy)acetate, 2-((2-((1-hydroxytetradecyl-2-yl)oxy)tetradecyl)oxy)acetate, and 2-((2-((1-hydroxyisotetradecyl-2-yl)oxy)tetradecyl)oxy)acetate, etc.

[0082] Of these, one can be used alone, or two or more can be used together.

[0083] As for the alkyl hydroxy ether acetate and its salt (B) represented by general formula (2), from the perspective of moisturizing the skin after cleansing, the alkyl hydroxy ether acetate salt represented by general formula (2) is preferred, and more preferably 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetic acid sodium salt, 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetic acid sodium salt, 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetic acid sodium salt, 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) Potassium acetate, 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)triethanolammonium acetate, 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)triethanolammonium acetate, and 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)triethanolammonium acetate, particularly preferably 2-((1-((2-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)triethanolammonium acetate, 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, with the most preferred being sodium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate.

[0084] The following example illustrates the relationship between the compound names of alkyl hydroxy ether acetic acid and its salt (B) and the structures in general formula (2).

[0085] For sodium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate, in general formula (2), R 2 2-Hydroxydodecyl, X 1 For hydrogen atoms, X 2 decyl, M 2 R represents a sodium atom. 2 It is a structure obtained by substitution of the hydrogen atom bonded to the carbon atom at position 1 of 2-dodecanool with the oxygen atom of the ether bond.

[0086] For sodium 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetate, in general formula (2), R 2 2-Hydroxydodecyl, X 1 For decyl, X 2 For hydrogen atoms, M 2 R represents a sodium atom. 2 It is a structure obtained by substitution of the hydrogen atom bonded to the carbon atom at position 1 of 2-dodecanool with the oxygen atom of the ether bond.

[0087] For sodium 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetate, in general formula (2), R 2 Hydroxydodecyl, X 1 For hydrogen atoms, X 2 decyl, M 2 R represents a sodium atom. 2 It is a structure obtained by substitution of the hydrogen atom bonded to the carbon atom at position 2 of 1-dodecanool with the oxygen atom of the ether bond. It should be noted that R... 2 The compound is described as "1-hydroxydodecyl-2-yl" in the above compound name, but R in this invention... 2 The carbon atom numbered 1 is not the carbon atom at position 1 in the compound name mentioned above, but refers to the carbon atom with position R. 2 The oxygen atom of the bonded ether bond is bonded to the carbon atom. That is, the carbon atom equivalent to the carbon atom at position 2 of 1-dodecanoic acid becomes R in this invention. 2 The carbon atom with position number 1.

[0088] For sodium 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetate, in general formula (2), R 2 Hydroxydodecyl, X 1 For decyl, X 2 For hydrogen atoms, M 2 R represents a sodium atom. 2 It is a structure obtained by substitution of the hydrogen atom bonded to the carbon atom at position 2 of 1-dodecanool with the oxygen atom of the ether bond. It should be noted that R... 2 The compound is described as "1-hydroxydodecyl-2-yl" in the above compound name, but in this invention, R 2 The carbon atom numbered 1 does not refer to the carbon atom at position 1 in the compound name mentioned above, but rather to the carbon atom associated with R. 2 The oxygen atom of the bonded ether bond is bonded to the carbon atom. That is, the carbon atom equivalent to the carbon atom at position 2 of 1-dodecanoic acid becomes R in this invention. 2 The carbon atom with position number 1.

[0089] The method for manufacturing alkyl hydroxy ether acetic acid and its salt (B) represented by general formula (2) is as follows.

[0090] First, 1,2-diols with 10 to 14 carbon atoms undergo intermolecular dehydration condensation to obtain a dimer of 1,2-diol. Relative to 1 mole of the obtained 1,2-diol dimer, 1.04 moles of sodium monochloroacetate are added, and the mixture is reacted via an SN2 reaction at a preferably 30–80°C, more preferably 50–80°C, to obtain an aqueous solution containing crude alkyl hydroxy ether acetate. Hydrochloric acid is then added to obtain an aqueous surfactant containing alkyl hydroxy ether acetate (B).

[0091] Next, the obtained aqueous surfactant containing alkyl ether hydroxyacetic acid (B) is neutralized by alkaline compounds such as sodium hydroxide, potassium hydroxide, and triethanolamine, thereby obtaining an aqueous surfactant containing alkyl hydroxy ether acetate (B).

[0092] An aqueous solution of a surfactant containing alkyl hydroxy ether acetic acid or its salt (B) can be used directly in the manufacture of the surfactant composition of the present invention; the aqueous solution of the surfactant can also be desolventized using known methods such as an evaporator, and the resulting powder containing alkyl hydroxy ether acetic acid or its salt (B) can be used in the manufacture of the surfactant composition; or the aqueous solution of a surfactant containing alkyl hydroxy ether acetic acid or its salt (B) can be mixed with the powder containing alkyl hydroxy ether acetic acid or its salt (B) for the manufacture of the surfactant composition.

[0093] The molecular structure of alkyl hydroxy ether acetate (B) can be determined by NMR spectroscopy, and the types of cations constituting alkyl hydroxy ether acetate (B) can be determined by ICP analysis and NMR spectroscopy. ICP analysis and NMR spectroscopy are the same as those described above in the methods for determining the types of cations constituting alkyl hydroxy ether acetate using ICP analysis and NMR spectroscopy.

[0094] In addition, the contents of alkyl hydroxy ether acetic acid and its salt (B) can be determined by HPLC using the methods described in the HPLC-based quantitative analysis method for alkyl hydroxy ether acetic acid (salt) (B) described later.

[0095] <HPLC-based quantitative analysis method for alkyl hydroxy ether acetic acid (salt) (B)>

[0096] R of alkyl hydroxy ether acetic acid (salt) (B) 2 Alkyl groups with 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] Under the HPLC measurement conditions described below, the sample solution and calibration curve solutions 4 to 6 are analyzed. 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 carried out 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 this application contains alkyl hydroxy ether acetic acid (salt) (A) and alkyl hydroxy ether acetic acid (salt) (B), and the total weight ratio of alkyl hydroxy ether acetic acid and its salt (B) is 0.05 to 1% by weight relative to the total weight of alkyl hydroxy ether acetic acid and its salt (A).

[0108] In a surfactant composition, if the total weight ratio of alkyl hydroxy ether acetic acid and its salt (B) relative to the total weight of alkyl hydroxy ether acetic acid and its salt (A) is less than 0.05% by weight, the moisturizing effect on the skin after washing is insufficient; if the total weight ratio of alkyl hydroxy ether acetic acid and its salt (B) relative to the total weight of alkyl hydroxy ether acetic acid and its salt (A) is greater than 1% by weight, the foaming during washing is insufficient.

[0109] In the surfactant composition of the first invention of this application, from the perspective of moisturizing properties, the total weight ratio of alkyl hydroxy ether acetic acid and its salt (B) relative to the total weight of 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.

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

[0111] In the surfactant composition of the first invention of this application, from the viewpoint of storage stability, the total weight ratio of alkyl hydroxy ether acetic acid and its salt (B) relative to the total weight of the surfactant composition 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.

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

[0113] The surfactant compositions of the present invention may further include optional other components, preferably water.

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

[0115] Water included in the surfactant composition may be directly included as a reaction solvent in the manufacture of alkyl hydroxy ether acetic acid or its salt (A) and alkyl hydroxy ether acetic acid or its salt (B), or ordinary water, purified water, hard water, soft water, natural water, deep sea water, hot spring water, electrolyzed alkaline ionized water, electrolyzed acidic ionized water, ion-exchange water, and clustered water may be used in a manner that reaches a specified weight ratio and mixed with alkyl hydroxy ether acetic acid and its salt (A) and alkyl hydroxy ether acetic acid and its salt (B).

[0116] In addition, the surfactant composition of the first invention of this application may also include a portion of the amphoteric surfactants, anionic surfactants (hereinafter referred to as other anionic surfactants) other than alkyl hydroxy ether acetic acid and its salts (A) and alkyl hydroxy ether acetic acid and its salts (B) contained in the cleaning agents described later, cationic surfactants, nonionic surfactants, water, oily components, solvents, humectants, chelating agents, conditioning agents, thickeners, whitening agents, pH adjusters, cooling agents, colorants, ultraviolet scattering agents, ultraviolet absorbing agents, preservatives, and antioxidants contained in the cleaning agents described later.

[0117] In addition, the surfactant composition may also contain unreacted materials and residues of reaction catalysts from the synthesis of alkyl hydroxy ether acetic acid or its salt (A) and alkyl hydroxy ether acetic acid or its salt (B).

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

[0119] The content of alkyl hydroxy ether acetic acid and its salt (A) contained in the surfactant composition can be determined by HPLC. The HPLC determination method and conditions are the same as the HPLC-based quantitative analysis method for alkyl hydroxy ether acetic acid (salt) (A) described above.

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

[0121] The surfactant composition of the first invention of this application has excellent foaming properties and storage stability, and is therefore a preferred raw material for use as a cleaning agent.

[0122] Cleaning Agent

[0123] The cleaning agent of the second invention of this application is a cleaning agent containing the surfactant composition of the first invention of this application, which is a cleaning agent containing alkyl hydroxy ether acetic acid (salt) (A) and alkyl hydroxy ether acetic acid (salt) (B) as essential components of the surfactant composition.

[0124] It should be noted that the cleaning agent in this application refers to a cleaning agent for hair or skin (shampoo, facial cleanser, shower gel, solid soap, cleansing milk, and liquid soap, etc.).

[0125] From the perspective of cleansing power against sebum and moisturizing properties after cleansing, in the cleansing agent of the second invention of this application, the surfactant composition of the first invention of this application preferably contains 0.1 to 10.0% by weight, more preferably 1.0 to 3.0% by weight, relative to the total weight of the cleansing agent.

[0126] In the cleaning agent of the second invention of this application, from the perspective of moisturizing properties, the total weight ratio of alkyl hydroxy ether acetic acid and its salt (B) relative to the total weight of 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 perspective of cleaning power, the total weight ratio of alkyl hydroxy ether acetic acid and its salt (A) and alkyl hydroxy ether acetic acid and its salt (B) contained in the cleaning agent of the second invention of this application is preferably 0.00175 to 1.75% by weight, more preferably 0.175 to 1.05% by weight.

[0128] The content of alkyl hydroxy ether acetic acid and its salt (A) in the cleaning agent can be determined by HPLC. The HPLC determination method and conditions are the same as the HPLC-based quantitative analysis method for alkyl hydroxy ether acetic acid (salt) (A) described above.

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

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

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

[0132] The cleaning agent of the second invention of this application may contain optional other ingredients. Examples of optional other ingredients include amphoteric surfactants, other anionic surfactants, cationic surfactants, nonionic surfactants, water, oily components, solvents, humectants, chelating agents, conditioning agents, thickeners, whitening agents, pH adjusters, cooling agents, colorants, ultraviolet scattering agents, ultraviolet absorbing agents, preservatives, and antioxidants, as well as other known cosmetic ingredients.

[0133] Examples of amphoteric surfactants include alkyl dimethyl acetate betaine, fatty acid amyl propyl betaine, alkyl imidazoline betaine, sulfobetaine-type amphoteric surfactants, and amphoteric amino acid-based surfactants.

[0134] Examples of alkyl dimethylacetic acid betaine include lauryl dimethylaminoacetic acid betaine (also known as lauryl betaine), myristyl dimethylaminoacetic acid betaine (also known as myristyl betaine), and stearyl dimethylaminoacetic acid betaine (also known as stearyl betaine).

[0135] Examples of fatty aminopropyl betaines include lauryl aminopropyl betaine, myristoyl aminopropyl betaine, isostearic acid aminopropyl betaine, and cocoamidopropyl betaine.

[0136] Examples of alkyl imidazoline betaines include 2-cocoa fatty acid-N-hydroxyethyl-N-hydroxyethyl imidazoline betaine, sodium N-lauroyl-N'-carboxymethyl-N'-hydroxyethyl ethylenediamine (also known as sodium lauroyl amphoteric acetate) and sodium N-cocoa fatty acid acyl-N'-carboxymethyl-N'-hydroxyethyl ethylenediamine (also known as sodium cocoyl amphoteric acetate).

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

[0138] Examples of amphoteric amino acid surfactants include sodium lauryl aspartate, sodium myristyl aspartate, sodium lauryl-β-aminopropionate, and sodium lauroyl methyl-β-alanine (also known as lauroyl methyl alanine Na).

[0139] Other anionic surfactants include ether carboxylic acids or their salts (hereinafter referred to as ether carboxylic acids or their salts), sulfate esters, sulfonates, phosphate esters, fatty acid salts, and acylated amino acid salts, excluding alkyl hydroxy ether acetic acid and its salts (A) and alkyl hydroxy ether acetic acid and its salts (B).

[0140] Examples of ether carboxylates or their salts include polyoxyethylene (average degree of polymerization 4) lauryl ether carboxylate sodium [alias: polyoxyethylene (average degree of polymerization 4) lauryl ether acetate sodium, lauryl alcohol polyether-4 carboxylate Na], polyoxyethylene (average degree of polymerization 6) lauryl ether carboxylate sodium [alias: lauryl alcohol polyether-6 carboxylate Na], polyoxyethylene (average degree of polymerization 4) tridecyl ether carboxylate sodium [alias: tridecyl alcohol polyether-4 carboxylate Na], and polyoxyethylene (average degree of polymerization 7) tridecyl ether carboxylate sodium [alias: tridecyl alcohol polyether-7 carboxylate Na].

[0141] Examples of sulfate esters include sodium lauryl sulfate (also known as Na lauryl sulfate), sodium lauryl ether sulfate (also known as Na lauryl alcohol polyether-2 sulfate), sodium lauryl ether sulfate (also known as Na lauryl alcohol polyether-3 sulfate), triethanolamine lauryl ether sulfate (also known as TEA lauryl alcohol polyether-3 sulfate), sodium coconut oil fatty acid monoethanolamide sulfate (also known as PEG-3 coconut oil fatty acid amide MEA sulfate), and sodium alkyl (carbon number 12-13) ether sulfate (also known as (C12,C13) alkanol polyether (Pareth)-3 sulfate).

[0142] Examples of sulfonates include sodium olefin (C14-16) sulfonate [also known as: olefin (C14-16) sulfonate Na], sodium dodecylbenzene sulfonate [also known as: dodecylbenzene sulfonate Na], disodium lauryl sulfosuccinate (average degree of polymerization 2) sulfonated succinate [also known as: lauryl sulfosuccinate 2Na], disodium lauryl sulfosuccinate [also known as: lauryl sulfosuccinate 2Na], and disodium lauroyl sulfosuccinate (average degree of polymerization 5) sulfonated succinate.

[0143] Examples of phosphate salts include sodium lauryl phosphate (also known as lauryl phosphate Na) and sodium polyoxyethylene lauryl ether phosphate (also known as tris(lauryl alcohol polyether-4) phosphate).

[0144] Examples of fatty acid salts include salts of myristic acid (sodium myristicate, potassium myristicate, triethanolamine myristicate, etc.), salts of lauric acid (sodium laurate, potassium laurate, triethanolamine laurate, etc.), salts of stearic acid (sodium stearate, triethanolamine stearate, etc.), and salts of palmitic acid (sodium palmitate, sodium palmitate, and triethanolamine palmitate, etc.).

[0145] Examples of acylated amino acid salts include potassium N-cocoa fatty acid acylglycine (also known as cocoa acylglycine K), sodium N-cocoa fatty acid methyl taurate (also known as cocoa acyl methyl taurate Na), sodium N-cocoa fatty acid sarcosine (also known as cocoa acyl sarcosine Na), sodium N-lauroyl sarcosine (also known as lauroyl sarcosine Na), N-cocoa fatty acid sarcosine triethanolamine (also known as acyl glutamate TEA), N-cocoa fatty acid acyl-L-glutamate triethanolamine (also known as cocoa acyl glutamate TEA), sodium N-cocoa fatty acid acyl-L-glutamate (also known as cocoa acyl glutamate Na), and lauroyl-L-glutamate triethanolamine (also known as lauroyl glutamate TEA).

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

[0147] Examples of quaternary ammonium salts include stearyltrimethylammonium chloride, behenyltrimethylammonium chloride, distearate dimethylammonium chloride, and ethyl lanolin sulfate fatty acid aminopropyl ethyl dimethylammonium chloride.

[0148] Examples of amine salts include diethylaminoethylamide stearate (also known as stearamide ethyl diethylamine lactate) and dimethylaminoethylamide behenate (also known as behenamide propyl dimethylamine lactate).

[0149] Examples of nonionic surfactants include alkylene oxide (2-8 carbon atoms) adducts of alcohols with 4-24 carbon atoms, esters or ethers of fatty acids with 8-24 carbon atoms polymerized with alcohols or alkylene oxide (2-8 carbon atoms), alkylene oxide adducts of higher fatty acid esters of poly(2-10) alcohols, glycerol fatty acid esters, polyglycerol fatty acid esters, and fatty acid alkanolamides.

[0150] Examples of epoxide alkane (carbon number 2-8) adducts of alcohols with 4-24 carbon atoms include polyoxyethylene (average degree of polymerization 10) polyoxypropylene (average degree of polymerization 7) butyl ether [alias: PPG-7 butanol polyether-10], polyoxyethylene (average degree of polymerization 20) lauryl ether [alias: lauryl alcohol polyether-20], polyoxyethylene (average degree of polymerization 20) oleyl ether [alias: oleyl alcohol polyether-20], polyoxyethylene (average degree of polymerization 12) polyoxypropylene (average degree of polymerization 2) cetyl ether [alias: PPG-2 cetyl alcohol polyether-12], and mixtures of polyoxyethylene cetearyl ether and polyoxyethylene oleyl ether [alias: cetoleth-5].

[0151] Examples of esters or ethers that are polymers of fatty acids with 8 to 24 carbon atoms with alcohols or epoxides (2 to 8 carbon atoms) include glyceryl monostearate, glyceryl monocaprylate, glyceryl monomyristate, glyceryl monooleate, and ethylene glycol monostearate. Sorbitan monolaurate (also known as sorbitan monolaurate), sorbitan monopalmitate (also known as sorbitan palmitate), sorbitan monostearate (also known as sorbitan monostearate), sorbitan monooleate (also known as sorbitan monooleate), sorbitan monooleate (also known as sorbitan monooleate), sorbitan monooleate (also known as sorbitan monooleate), sorbitan monooleate (also known as PEG-6 sorbitan oleate), sorbitan monooleate (also known as PEG-6 sorbitan oleate), sorbitan monooleate (also known as sorbitan monooleate) (average degree of polymerization 6), sorbitan monooleate (average degree of polymerization 20) (also known as 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 polyethylene oxide (average degree of polymerization 60) hydrogenated castor oil [alias: PEG-60 hydrogenated castor oil], etc.

[0152] Examples of epoxide alkane adducts of higher fatty acid esters of poly(2- to 10-membered) alcohols include: ethylene oxide (average degree of polymerization 6) addition polymers of glycerides of caprylic and capric acids [alias: PEG-6 (caprylic / 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-6 sorbitan oleate], and polyoxyethylene monooleate (average degree of polymerization 3) sorbitan ester [alias: PEG-6 sorbitan oleate], etc. PEG-3 sorbitan oleate, PEG-40 sorbitan oleate, PEG-6 sorbitan stearate, PEG-160 sorbitan triisostearate, and PEG-120 dioleoyl methyl glucoside, etc.

[0153] Examples of polyglycerol fatty acid esters include monooleate decaglycerol ester [also known as: polyglycerol oleate-10], monolaurate decaglycerol ester [also known as: polyglycerol laurate-10], isostearate decaglycerol ester [also known as: polyglycerol isostearate-10], disostearate polyglycerol ester [also known as: polyglycerol disostearate-10], stearate polyglycerol ester [also known as: polyglycerol stearate-10], polyricinoleate hexaglycerol ester [also known as: polyricinoleate-6], and monoisostearate diglycerol ester [also known as: polyglycerol isostearate-2], etc.

[0154] Examples of fatty acid alkyl alcohol amides include coconut oil fatty acid monoethanolamide (also known as cocamidoyl MEA), coconut oil fatty acid N-methylethanolamide (also known as cocamidoyl methyl MEA), and coconut oil fatty acid diethanolamide (also known as cocamidoyl DEA).

[0155] As for water, examples include ordinary water, purified water, as well as hard water, soft water, natural water, deep ocean water, hot spring water, electrolyzed alkaline ionized water, electrolyzed acidic ionized water, ion-exchange water, and clustered water.

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

[0157] Examples of liquid oils include avocado oil, camellia oil, turtle 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, flaxseed oil, safflower oil, cottonseed oil, soybean oil, peanut oil, tea seed oil, lemongrass oil, rice bran oil, jojoba oil, rice germ oil, tri(2-ethylhexanoic acid) glycerides [also known as triethylhexanoic acid glycerides], and triisopalmitoyl glycerides [also known as triisopalmitin], etc.

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

[0159] Examples of hydrocarbon oils 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-hexamethyltetracos-2,6,10,14,18,22-hexaene (also known as squalene), petrolatum, paraffin wax, hydrogenated polyisobutylene, ceresin, 2,6,10,14-tetramethylpentadecane, pure ceresin wax, and microcrystalline wax.

[0160] Examples of synthetic ester oils include isopropyl myristate, cetyl ethylhexanoate, octyl dodecyl myristate, cetyl palmitate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyl decyl ethylhexanoate, cetyl lactate, myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesterol hydroxystearate, and glycol diethylhexanoate. Neopentyl glycol didecanoate, triesters of caprylic and capric acids with glycerol [alias: tri(caprylic / capric acid)glycerol ester], hydroxystearic acid, hydroxystearic acid, stearic acid, and hexaesters of rosin acid with dipentaerythritol [alias: hexa(hydroxystearic acid / stearic acid / rosin acid) dipentaerythritol ester], diisostearyl malate, glyceryl diisostearate, trimethylolpropane tri(2-ethylhexanoate), trimethylolpropane triethylhexanoate, pentaerythritol... Tetraethylhexanoate, Trimethylolpropane Triisostearate, Ethylhexyl Palmitate, Trimyristin, Methyl Castor Oil, Oleic Acid, Diisobutyl Adipate, Lauroyl Glutamate Ester with Phytosterol and Octyldodecyl Alcohol, Diheptyl Undecyl Adipate, Ethyl Lauroyl Glutamate Di(Phytosterol / Octylactone) Ester, Diheptyl Undecyl Adipate, Ethyl Laurate Esters, diethylhexyl sebacate, isocetyl myristate, hexyl decyl palmitate, dihexyl decyl adipate, diisopropyl sebacate, diethylhexyl succinate, triethyl citrate, polyoxyethylene (average degree of polymerization 3) trimethylolpropane triisostearate [also known as PEG-3 trimethylolpropane triisostearate], triisostearate diglyceride [also known as polyglycerol-2 triisostearate], and sucrose tetraisostearate, etc.

[0161] Examples of silicone oils include chain polysiloxanes, cyclic polysiloxanes, and modified polysiloxanes (such as amino-modified polysiloxanes, polyether-modified polysiloxanes, alkyl-modified polysiloxanes, and fluorine-modified polysiloxanes).

[0162] Examples of chain-like polysiloxanes include methylphenyl polysiloxane (also known as diphenyl polydimethylsiloxane), octyl polymethylsiloxane, polydimethylsiloxane, dimethyl polysiloxane crosslinked with divinyl dimethyl polysiloxane (also known as (polydimethylsiloxane / vinyl polydimethylsiloxane) crosslinked polymer), and dimethyl polysiloxane copolymer crosslinked with phenyl vinyl dimethyl polysiloxane (also known as (polydimethylsiloxane / phenyl vinyl polydimethylsiloxane) crosslinked polymer).

[0163] Examples of cyclic polysiloxanes include decamethylcyclopentasiloxane (also known as cyclopentasiloxane) and dodecylcyclohexasiloxane (also known as cyclohexasiloxane).

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

[0165] Examples of solvents include ethanol, isoprene glycol, modified alcohols, dipropylene glycol (DPG), 1,2-hexanediol, isododecane, isopropanol, butyl acetate, diethylene glycol monoethyl ether (ethoxydiethylene), and propylene glycol (PG).

[0166] Examples of moisturizers include glycerin, 1,3-butanediol (also known as BG), hydrogenated rapeseed oil 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 chelating agents include ethylenediaminetetraacetic acid (EDTA), disodium EDTA, sodium polyphosphate, disodium pyrophosphate, gluconic acid, sodium gluconate, and ascorbic acid.

[0168] Examples of conditioning agents include polymers of quaternary ammonium salts obtained by adding glycidyltrimethylammonium chloride to hydroxyethyl cellulose [alias: polyquaternary ammonium salt-10], polymers of quaternary ammonium salts obtained by adding acrylamide and dimethyl diallyl ammonium chloride [alias: polyquaternary ammonium salt-7], copolymers of dimethyl diallyl ammonium chloride and acrylic acid [alias: polyquaternary ammonium salt-22], copolymers of vinyl acetate and vinylpyrrolidone [alias: (VP / VA) copolymer], quaternary ammonium salts obtained by adding glycidyltrimethylammonium chloride to guar gum [alias: guar hydroxypropyltrimethylammonium chloride], polyethylene glycol 20000 [alias: PEG-400], sodium polyacrylate [alias: polyacrylate Na], and hydroxyethyl cellulose and D-panthenol [alias: panthenol], etc.

[0169] Examples of thickeners include guar gum, xanthan gum, starch, behenol, stearyl alcohol, cetearyl alcohol, cetyl alcohol, myristyl alcohol, carboxyvinyl polymers (also known as carbomer), hydroxypropyl methylcellulose, polyvinyl alcohol, sodium polyacrylate (also known as polyacrylate Na), sodium salts of substances grafted onto starch (also known as Na-grafted starch), lithium distearate (also known as distearate dimethylammonium lithium montmorillonite), talc, N-methylethanolamide of coconut oil fatty acids (also known as cocamidomethyl MEA), and copolymers of ethylene glycol distearate and alkyl methacrylate (C10-30) crosspolymers (also known as (acrylate / alkyl methacrylate (C10-30))).

[0170] Examples of skin-whitening agents include tranexamic acid, arbutin, and hydroquinone.

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

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

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

[0174] Examples of ultraviolet scattering agents include titanium dioxide and zinc oxide.

[0175] Examples of UV absorbers include ethylhexyl methoxycinnamate, the ester of dimethyl-p-aminobenzoic acid and 2-ethylhexanol [also known as dimethyl-PABA-ethylhexyl ester], and tert-butylmethoxydibenzoylmethane.

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

[0177] Examples of antioxidants include vitamin E (also known as tocopherol), butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), dipotassium glycyrrhizate (also known as glycyrrhizic acid 2K), ascorbate 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 this 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 components, solvent, and humectant are preferably 50% or less by weight, and more preferably 10% or less by weight, respectively.

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

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

[0182] As a method for manufacturing the cleaning agent of the second invention of this application, it can be manufactured by mixing a surfactant composition and optional other ingredients using a known mixer.

[0183] Examples of mixers used in manufacturing the cleaning agent of the second invention of this application include Henschel mixers, ball mills, jet mills, kneaders, planetary mixers, sand mills, ultrafine mills, screw mixers, dispersion mixers, and homogenizers, with dispersion mixers being preferred.

[0184] The cleaning agent of the second invention of this application is preferably in solid, liquid or paste form at 25°C, and is further preferably in liquid form from the perspective of ease of handling.

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

[0186] It should be noted that, in the following description, the active ingredient refers to the component after water has been removed from the raw materials of each component.

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

[0188] Based on the total weight of the shampoo, the active ingredient may contain 3.0–10.0 wt% sodium lauryl ether sulfate (average degree of polymerization 2). Based on the total weight of the shampoo, the active ingredient may contain 1.0–5.0 wt% sodium lauryl ether acetate (average degree of polymerization 4). Based on the total weight of the shampoo, the active ingredient may contain 3.0–10.0 wt% sodium N-cocoacid acyl-L-glutamate. Based on the total weight of the shampoo, the active ingredient may contain 1.0–5.0 wt% sodium N-lauroyl sarcosinate. Based on the total weight of the shampoo, the active ingredient may contain 1.0–10.0 wt% sodium olefin (C14-16) sulfonate.

[0189] As an amphoteric surfactant, it is preferably at least one selected from the group consisting of cocamidopropyl betaine and 2-cocoa fatty acid-N-hydroxyethyl-N-hydroxyethyl imidazoline betaine.

[0190] The shampoo may contain 1.0 to 5.0% by weight of cocamidopropyl betaine, calculated as an active ingredient based on the total weight of the shampoo. The shampoo may also contain 1.0 to 5.0% by weight of 2-cocoa fatty acid-N-hydroxyethyl-N-hydroxyethyl imidazoline betaine, calculated as an active ingredient based on the total weight of the shampoo.

[0191] As a moisturizer, it is preferably at least one selected from the group consisting of 1,3-butanediol and glycerin.

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

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

[0194] The shampoo may contain 0.1 to 1.0 wt% of polyquaternium-22, calculated as an active ingredient based on the total weight of the shampoo. The shampoo may contain 0.05 to 0.5 wt% of polyquaternium-7, calculated as an active ingredient based on the total weight of the shampoo. The shampoo may contain 0.1 to 1.0 wt% of polyquaternium-10, calculated as an active ingredient based on the total weight of the shampoo.

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

[0196] Based on the total weight of the shampoo, the active ingredient may contain 0.1 to 1.0% by weight of polydimethylsiloxane.

[0197] EDTA-2Na is preferred as a chelating agent.

[0198] Based on the total weight of the shampoo, the active ingredient may contain 0.05 to 0.5% by weight of EDTA-2Na.

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

[0200] Based on the total weight of the shampoo, the active ingredient may contain 1.0 to 5.0% by weight of coconut oil fatty acid N-methylethanolamide.

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

[0202] Based on the total weight of the shampoo, the active ingredient may contain 1.0 to 5.0% by weight of PEG-160 sorbitan triisostearate.

[0203] Menthol is preferred as a cooling agent.

[0204] Based on the total weight of the shampoo, the active ingredient may contain 0.5 to 3.0% menthol.

[0205] Citric acid is preferred as a pH adjuster.

[0206] Based on the total weight of the shampoo, the active ingredient may contain 0.05 to 0.5% citric acid.

[0207] When the cleaning agent of the present invention is a shampoo, the following composition can be cited as a preferred composition of each component when converted into effective ingredients.

[0208] Alkyl hydroxy ether acetic acid (salt) (A): 0.15–1.30% by weight

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

[0210] Other anionic surfactants: 3.0–20.0% by weight

[0211] Amphoteric surfactants: 1.0–5.0% by weight

[0212] Moisturizer: 1.0–5.0% by weight

[0213] Conditioner: 0.1–1.0% by weight

[0214] Oily components: 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 surfactants: 1.0–5.0% by weight

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

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

[0220] When the cleaning agent of the present invention is a facial cleanser for a pump-type foamer, the facial cleanser for a pump-type foamer preferably contains, for example, the following ingredients.

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

[0222] In pump-type foaming facial cleansers, based on the total weight of the cleanser, the active ingredient may contain 1.0 to 10.0% by weight of lauroyl-L-glutamic acid triethanolamine. In pump-type foaming facial cleansers, based on the total weight of the cleanser, the active ingredient may contain 0.5 to 3.0% by weight of olefin (C14-16) sulfonate.

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

[0224] In pump-foaming facial cleansers, based on the total weight of the pump-foaming facial cleanser, the active ingredient may contain 0.5 to 3.0% by weight of cocamidopropyl betaine.

[0225] Polyquaternium-7 is preferred as a conditioning agent.

[0226] In pump-type foaming facial cleansers, based on the total weight of the pump-type foaming facial cleanser, the active ingredient may contain 0.05 to 0.5% by weight of polyquaternium-7.

[0227] When the cleaning agent of the present invention is a facial cleanser for a pump-type foamer, the following composition can be cited as a preferred composition of each component when calculated based on the effective ingredients.

[0228] Alkyl hydroxy ether acetic acid (salt) (A): 0.20–1.00% by weight

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

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

[0231] Amphoteric surfactants: 0.5–3.0% by weight

[0232] Conditioner: 0.05–0.5% by weight

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

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

[0235] Based on the total weight of the cream-based facial cleanser, the active ingredient may contain 1.0–3.0% by weight of N-cocoacid acyl-L-glutamate sodium salt, calculated as an effective ingredient. Based on the total weight of the cream-based facial cleanser, the active ingredient may contain 5.0–20.0% by weight of N-cocoacid acyl-glycinate potassium, calculated as an effective ingredient. Based on the total weight of the cream-based facial cleanser, the active ingredient may contain 0.5–5.0% by weight of lauric acid salt, calculated as an effective ingredient. Based on the total weight of the cream-based facial cleanser, the active ingredient may contain 0.5–20.0% by weight of stearic acid salt, calculated as an effective ingredient. Based on the total weight of the cream-based facial cleanser, the active ingredient may contain 5.0–20.0% by weight of palmitic acid salt.

[0236] It should be noted that in this specification, when other anionic surfactants contain fatty acid salts, it is assumed that all fatty acids are formed into 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 an amphoteric surfactant, cocamidopropyl betaine is preferred.

[0238] Based on the total weight of the cream-based facial cleanser, the active ingredient may contain 0.5 to 3.0% by weight of cocamidopropyl betaine.

[0239] Glycerin is preferred as a moisturizer.

[0240] Cream-based facial cleansers may contain 5.0 to 20.0% by weight of glycerin, based on the total weight of the cream-based facial cleanser and converted into active ingredients.

[0241] Polyquaternium-7 is preferred as a conditioning agent.

[0242] In cream-based facial cleansers, based on the total weight of the cream-based facial cleanser, the effective ingredient content can be 0.01 to 0.10% by weight of polyquaternium-7.

[0243] Vitamin E is the preferred antioxidant.

[0244] Based on the total weight of the cream-based facial cleanser, it can contain 0.05 to 0.30% by weight of vitamin E as an active ingredient.

[0245] As a thickener, it is preferably at least one selected from the group consisting of coconut oil fatty acid N-methylethanolamide and ethylene distearate.

[0246] Cream-based facial cleansers may contain 1.0–3.0% by weight of N-methylethanolamide of coconut oil fatty acids, calculated based on the total weight of the cream-based facial cleanser and its active ingredients. Also, cream-based facial cleansers may contain 1.0–3.0% by weight of polyethylene distearate, calculated based on the total weight of the cream-based facial cleanser and its active ingredients.

[0247] PEG-190 distearate is preferred as a nonionic surfactant.

[0248] Cream-based facial cleansers may contain 3.0 to 10.0% by weight of PEG-190 distearate, based on the total weight of the cream-based facial cleanser and converted into active ingredients.

[0249] Potassium hydroxide is preferred as a pH adjuster.

[0250] In cream-based facial cleansers, based on the total weight of the cream-based facial cleanser and converted into active ingredients, it can contain 3.0 to 10.0% by weight of potassium hydroxide.

[0251] When the cleansing agent of the present invention is a cream-like facial cleanser, the following composition can be cited as a preferred composition of each component when calculated based on the effective ingredients.

[0252] Alkyl hydroxy ether acetic acid (salt) (A): 0.015–1.5% by weight

[0253] Alkyl hydroxy ether acetic acid (salt) (B): 0.000005–0.003% by weight

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

[0255] Amphoteric surfactants: 0.5–3.0% by weight

[0256] Moisturizer: 5.0–20.0% by weight

[0257] Conditioner: 0.01–0.10% by weight

[0258] Antioxidant: 0.05–0.30% by weight

[0259] Thickener: 1.0–10.0% by weight

[0260] Nonionic surfactants: 3.0–10.0% by weight

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

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

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

[0264] The total weight percentage of alkyl hydroxy ether acetic acid and its salt (B) is based on a total weight of 0.05 to 1% of alkyl hydroxy ether acetic acid and its salt (A).

[0265] R 1 -CH(OH)-CH2-OCH2COOM 1 (1)

[0266] [In the formula, R] 1 M represents an alkyl group with 8 to 12 carbon atoms. 1 This represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolamine.

[0267] R 2 -O-CH(X 1 )CH(X 2 )-OCH2COOM 2 (2)

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

[0269] R 2 A hydroxyalkyl group is formed by replacing any one hydrogen atom bonded to the carbon atom at position 1 of an alkyl group with 10 to 14 carbon atoms with a hydroxyl group.

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

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

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

[0273] Example

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

[0275] <Manufacturing Example 1>

[0276] Add 50g of 1,2-dodecanediol [manufactured by Fujifilm and Wako Pure Chemical Industries, Ltd.], 10g of toluene [manufactured by Fujifilm and Wako Pure Chemical Industries, Ltd.], and 30g of sodium monochloroacetate [manufactured by Denak Corporation] to a 1L four-necked flask equipped with a stirrer, reflux cooler, dropping funnel, and thermometer. After nitrogen purging, heat to 50°C, and slowly add 10g of granular sodium hydroxide [manufactured by Tosoh Corporation] over 5 hours with stirring, followed by aging for 3 hours.

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

[0278] 1g of powder 1 containing surfactant was sampled, and the molecular structure of the surfactant and the types of cations constituting the surfactant in powder 1 were determined by ICP and NMR. The content of surfactant in powder 1 containing surfactant was further determined by the HPLC-based quantitative analysis method described later.

[0279] Powder 1 containing surfactant is a powder containing 40% by weight sodium decyl hydroxy ether acetate as an alkyl hydroxy ether acetate (salt) (A).

[0280] <HPLC-based quantitative analysis method for the content of alkyl hydroxy ether acetic acid (salt) (A)>

[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 1,2-dodecanediol peak appearing at a retention time of 11.7 - 12.2 minutes, the alkyl hydroxy ether acetate (salt) (A) peak appearing at a retention time of 13.4 - 14.7 minutes, and the undecanoic acid peak appearing at a retention time of 12.1 - 19.6 minutes in the obtained HPLC spectra, 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 a 35% hydrochloric acid aqueous 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] A sample was taken from the surfactant aqueous solution 1, and the molecular structure of the surfactant contained in the surfactant aqueous solution 1 and the types of cations constituting the surfactant were determined using the same method as in Manufacturing Example 1. Furthermore, the content of the surfactant contained in the surfactant aqueous solution 1 was 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 decyl hydroxy ether acetic acid as an alkyl hydroxy ether acetic acid (salt) (A).

[0294] <Manufacturing Example 3>

[0295] Add 33.3g of surfactant aqueous solution 1 prepared in Manufacturing Example 2, 16.5g of deionized water and 6g of triethanolamine [manufactured by Tokyo Chemical Industry Co., Ltd.] to a 50mL beaker, heat to 70°C and stir for 60 minutes to obtain 55.8g of surfactant aqueous solution 2.

[0296] A sample was taken from the surfactant aqueous solution 2, and the molecular structure of the surfactant contained in the surfactant aqueous solution 2 and the types of cations constituting the surfactant were determined using the same method as in Manufacturing Example 1. The content of the surfactant contained in the surfactant aqueous solution 2 was further determined using the same method as in Manufacturing Example 1.

[0297] Surfactant aqueous solution 2 is an aqueous solution containing 27.3% by weight of decyl hydroxy ether acetate triethanolamine as alkyl hydroxy ether acetate (salt) (A).

[0298] <Manufacturing Example 4>

[0299] Add 33.3g of surfactant aqueous solution 1 prepared in Manufacturing Example 2, 17.5g of deionized water, and potassium hydroxide [manufactured by Fujifilm and Kohden Chemical Co., Ltd.] to a 50mL beaker, heat to 70°C and stir for 60 minutes to obtain 52.8g of surfactant aqueous solution 3.

[0300] A sample was taken from the surfactant aqueous solution 3, and the molecular structure of the surfactant contained in the surfactant aqueous solution 3 and the types of cations constituting the surfactant were determined using the same method as in Manufacturing Example 1. The content of the surfactant contained in the surfactant aqueous solution 3 was further determined using the same method as in Manufacturing Example 1.

[0301] Surfactant aqueous solution 3 is an aqueous solution containing 28.9% by weight of potassium decyl hydroxy ether acetate as alkyl hydroxy ether acetate (salt) (A).

[0302] <Manufacturing 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 nitrogen replacement, 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] After that, the temperature was raised to 120°C, and the solvent of toluene was removed, thereby obtaining 380 g of Intermediate 1 containing a dehydration condensate of 1,2-dodecanediol.

[0305] Sampling was carried out 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] <Analysis method of 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 according to the following calculation formula.

[0311] Content (wt%) of the dimer of 1,2-dodecanediol contained in Intermediate 1 = (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] <Manufacturing Example 6>

[0319] Add 386g of intermediate 1, 77g of toluene [manufactured by Fujifilm and Wako Pure Chemical Industries, Ltd.], and 121.2g of sodium monochloroacetate [manufactured by Denak Corporation] to a 1L four-necked flask equipped with a stirrer, reflux cooler, dropping funnel, and thermometer. After nitrogen purging, heat to 50°C, and slowly add 40.4g of granular sodium hydroxide [manufactured by Tosoh Corporation] over 5 hours with stirring, followed by 3 hours of curing.

[0320] 211 g of ion-exchanged water was added to the reacted solution at 50 °C, the temperature was raised to 75 °C, and 110 g of 38% hydrochloric acid aqueous solution [manufactured by Toa Synthetic Co., Ltd.] was added. The mixture was stirred for 30 minutes, then transferred to a separatory funnel, allowed to stand for 30 minutes, and separated to remove the lower layer. The remaining supernatant was transferred to a 1 L four-necked flask equipped with a stirrer, reflux cooler, and thermometer, and 86 g of ion-exchanged water was added. The mixture was stirred for 30 minutes. After mixing, the mixture was transferred to a separatory funnel, allowed to stand for 30 minutes, and then the lower layer was removed. 10 g of sodium hydroxide was added to the remaining supernatant, and the mixture was evaporated at 75 °C under reduced pressure until the gauge pressure reached 2.7 kPa using a rotary evaporator. The volatile components were removed by maintaining this temperature and pressure for 7 hours, yielding 400 g of powder 2 containing surfactant.

[0321] 1g of the surfactant-containing powder 2 was sampled, and the molecular structure of the surfactant and the types of cations constituting the surfactant were determined by ICP and NMR. The content of the surfactant in the surfactant-containing powder 2 was further determined by the HPLC-based quantitative analysis method described later.

[0322] Powder 2 containing surfactant is a powder containing a total of 40% by 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] <HPLC-based quantitative analysis method for the content of alkyl hydroxy ether acetic acid (salt) (B)>

[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 that appears at a retention time of 9.0 - 9.52 minutes, the peak of alkyl hydroxy ether acetate (B) that appears at a retention time of 12.5 - 13.0 minutes, and the peak of undecanoic acid that appears 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 prepared 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] A sample was taken from the surfactant aqueous solution 4, and the molecular structure of the surfactant contained in the surfactant aqueous solution 4 and the types of cations constituting the surfactant were determined using the same method as in Manufacturing Example 6. Furthermore, the content of the surfactant contained in the surfactant aqueous solution 4 was determined using the same method as in Manufacturing Example 6.

[0336] The surfactant aqueous solution 4 is an aqueous solution containing a total of 30% by weight 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] <Manufacturing Example 8>

[0338] Add 33.3g of the surfactant aqueous solution 4 prepared in Manufacturing Example 7, 13.5g of ion-exchanged water, and 3.9g of triethanolamine [manufactured by Tokyo Chemical Industry Co., Ltd.] to a 50mL beaker, heat to 70°C and stir for 60 minutes to obtain 50.7g of surfactant aqueous solution 5.

[0339] A sample was taken from the surfactant aqueous solution 5, and the molecular structure of the surfactant contained in the surfactant aqueous solution 5 and the types of cations constituting the surfactant were determined using the same method as in Manufacturing Example 6. The content of the surfactant contained in the surfactant aqueous solution 5 was further determined using the same method as in Manufacturing Example 6.

[0340] The surfactant aqueous solution 5 is an aqueous solution containing a total of 27.3% by weight of 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetic acid triethanolammonium, 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)acetic acid triethanolammonium, 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 as alkyl hydroxy ether acetic acid (salt) (B).

[0341] <Manufacturing Example 9>

[0342] Add 33.3g of the surfactant aqueous solution 4 prepared in Manufacturing Example 7 and 1.3g of potassium hydroxide [manufactured by Fujifilm and Kohden Chemical Co., Ltd.] to a 50mL beaker, heat to 70°C and stir for 60 minutes to obtain 24.6g of surfactant aqueous solution 6.

[0343] A sample was taken from the surfactant aqueous solution 6, and the molecular structure of the surfactant contained in the surfactant aqueous solution 6 and the types of cations constituting the surfactant were determined using the same method as in Manufacturing Example 6. Furthermore, the content of the surfactant contained in the surfactant aqueous solution 6 was determined using the same method as in Manufacturing Example 6.

[0344] The surfactant aqueous solution 6 is an aqueous solution containing a total of 28.9% by 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 1-5 and Comparative Examples 1-3>

[0346] The surfactant-containing powders 1 and 2 obtained in manufacturing examples 1 and 6, and the surfactant aqueous solutions 1 to 6 obtained in manufacturing examples 2 to 4 and 7 to 9, were mixed in the proportions shown in Table 1 to prepare surfactant compositions 1 to 5 of the present invention and surfactant compositions 1' to 3' for comparison.

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

[0349] <Maintaining Stability>

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

[0351] (Evaluation criteria for preservation stability)

[0352] 〇: On day 90, the appearance was clear, and no cloudiness or separation was observed.

[0353] ×: Cloudiness or separation observed on day 90.

[0354]

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

[0356] Surfactant compositions 1 to 5 and comparative surfactant compositions 1' to 3' were mixed with other optional ingredients described later in proportions as shown in Tables 2 to 5 to prepare the cleaning agents (shampoos, pump foamers, and creams) of the present invention in Examples 6 to 14, and the comparative cleaning agents (shampoos) in Comparative Examples 4 to 5.

[0357] It should be noted that the figures in parentheses in Tables 2-5 are converted into the proportions of the components (sometimes called active ingredients) remaining after water is removed from each raw material.

[0358] <Sebum residue after shampoo use>

[0359] Ten judges, both male and female, thoroughly wetted their hair with hot water at 40°C, then washed their hair with 5g of the cleaning agent (shampoo) from Example 6. After rinsing with hot water at 40°C, they randomly wiped five areas of their scalp with kitchen paper towels (1cm×1cm) soaked in ethanol one hour later.

[0360] Soak the wiped kitchen paper towel in a screw tube (screw tube No. 6, manufactured by Maruemu Co., Ltd.) containing 1 mL of methanol. Shake by hand for 5 minutes to extract the components obtained from wiping with the kitchen paper towel into the methanol to prepare a sample solution.

[0361] Methanol solutions containing triolein 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 using GC under the conditions described later.

[0363] Based on the relationship between the concentration of trioleic acid glyceride in the calibration curve sample and the peak area of ​​the GC spectrum obtained using trioleic acid glyceride, a calibration curve was constructed using the least squares method. The amount of trioleic acid glyceride in methanol was then quantified based on the calibration curve and the peak area of ​​the GC spectrum of the component extracted into methanol.

[0364] Trioleic acid glycerides are one of the main components of sebum. The lower the concentration of trioleic acid glycerides extracted into methanol, the lower the amount of sebum residue after shampooing. Therefore, the concentration of trioleic acid glycerides in methanol is quantified as the amount of sebum residue (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] <Sebum residue amount after using the facial cleanser for pump-type foaming device and cream-type facial cleanser>

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

[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 manually for 5 minutes to extract the components wiped with the kitchen paper towel into methanol to prepare a sample solution.

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

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

[0383] The cleansing agents (cream-like facial cleansers) of Examples 13-14 were also evaluated using the same method, and the results are shown in Table 5.

[0384] Oily skin after using shampoo

[0385] Ten judges, both male and female, thoroughly wetted their hair with 40°C hot water, then washed it with 5g of the cleaning agent (shampoo) from Example 6, rinsed it with 40°C hot water, and dried it with a hairdryer. The hair was then left to rest for two hours at 25°C and 40% relative humidity. Afterwards, the shine of five random hairline points was measured using a Gloss Meter [trade name: MJ-GM26 Gloss Checker, Satotech Co., Ltd.]. A lower shine value indicated better control of oil production.

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

[0387] Oily skin after using pump-type foaming facial cleansers and cream-based facial cleansers.

[0388] Ten judges, both male and female, thoroughly wetted their faces with 40°C hot water, then washed their faces with 1g of the cleanser from Example 12 (a pump-type foaming facial cleanser), rinsed with 40°C hot water, and patted dry with a towel for 10 seconds. The faces were then left to rest quietly for 2 hours at 25°C and 40% relative humidity. Afterwards, the gloss of five random areas on the forehead was measured using a Gloss Meter [trade name: MJ-GM26 Gloss Checker Satotech {Sato Shoji Co., Ltd.}]. Lower gloss values ​​indicated greater control over oil production.

[0389] The cleansing agents (cream-like facial cleansers) of Examples 13-14 were also evaluated using the same method, and the results are shown in Table 5.

[0390] <Hair volume retention after shampoo use>

[0391] Twenty female judges with hair lengths of 30cm or more thoroughly wetted their hair with 40°C hot water, then washed it with 5g of the cleansing agent (shampoo) from Example 6, rinsed it with 40°C hot water, and dried it with a hairdryer. Immediately after drying, they spent the time in a room with a temperature of 25°C and a relative humidity of 40%. The vertical height of the highest point of the hair from the roots at the top of the head was measured 10 minutes after drying and 2 hours after drying. The difference between the two times was used as the retention of hair volume. The smaller the difference between 10 minutes and 2 hours, the better the hair volume was maintained.

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

[0393] <Skin's moisturizing effect after using shampoo>

[0394] Twenty Japanese men and women aged 20 to 50 thoroughly wet their hair with hot water at 40°C, then washed their scalp with 1g of the cleaning agent (shampoo) from Example 6, rinsed thoroughly with hot water at 40°C, and dried their hair with a hairdryer for 5 minutes. This process was repeated once a day.

[0395] On the 14th day after starting use, 2 hours after scalp washing, the keratin moisture content of 3 random scalp points was measured using a skin moisture meter [product name: Corneometor CM825 {Courage+Khazaka manufactured}], and the average value was calculated.

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

[0397] <Skin moisturization after using pump-type foaming facial cleansers and cream-based facial cleansers>

[0398] Twenty Japanese men and women aged 20 to 50 thoroughly wet their faces with hot water at 40°C, then washed their faces with 1g of the cleanser (pump-type foaming facial cleanser) from Example 12, rinsed thoroughly with hot water at 40°C, and patted their faces dry with a towel for 10 seconds. This process was repeated once a day.

[0399] On the 14th day after starting use, two hours after washing my face, I randomly measured the keratin content of three spots on my forehead using a skin moisture meter [product name: Corneometor CM825 {Courage+Khazaka manufactured}] and calculated the average value.

[0400] The cleansing agents (cream-like facial cleansers) of Examples 13-14 were also evaluated using the same method, and the results are shown in Table 5.

[0401] [Table 2]

[0402]

[0403] [Table 3]

[0404]

[0405] [Table 4]

[0406]

[0407] [Table 5]

[0408]

[0409] It should be noted that the following ingredients are used as optional other ingredients listed in Tables 2 to 5.

[0410] <Optional other ingredients>

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

[0412] • 28% by weight aqueous solution of polyoxyethylene (average degree of polymerization 4) sodium lauryl ether acetate [Trade name: Beaulight LCA-25N {manufactured by Sanyo Chemical Industry Co., Ltd.}]

[0413] • 29% by weight aqueous solution of N-cocoacid fatty acid acyl-L-glutamate sodium [Trade name: Plantapon AminoSCG-L {manufactured by BASF (Plantapon is a registered trademark of Cognis IP Management GmbH)}]

[0414] • 30% by weight 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] • Sodium N-lauroyl sarcosinate 30% by weight aqueous solution [Trade name: Soypon SLE {manufactured by Kawaken Fine Chemicals Co., Ltd. (Soypon is a registered trademark of Kawaken Fine Chemicals Co., Ltd.)}]

[0416] • N-Coconut Fatty Acid Acylglycine Potassium [Trade Name: Amilite GCK-11 {Manufactured by Ajinomoto HealthySupply Co., Ltd. (Amilite is a registered trademark of Ajinomoto Co., Ltd.)}]

[0417] • 37% by weight aqueous solution of Na sulfonic acid in olefins (C14-16) [Trade name: Lipolan LJ-441 {manufactured by LION Corporation (Lipolan is a registered trademark of LION Specialty Chemicals Co., Ltd.)}]

[0418] • 30% by weight aqueous solution of cocamidopropyl betaine [Trade name: Lebon HC-30W {manufactured by Sanyo Chemical Industry Co., Ltd.}]

[0419] · 43% by weight aqueous solution of 2-cocoa fatty acid-N-hydroxyethyl-N-hydroxyethylimidazoline betaine [Trade name: Lebon CIB {manufactured by Sanyo Chemical Industry Co., Ltd.}]

[0420] · Lauric acid [Trade name: NAA-122 {Manufactured by Nippon Yuko Co., Ltd. (NAA is a registered trademark of Nippon Yuko Co., Ltd.)}]

[0421] Stearic acid [Trade name: NAA-172 {Manufactured by Nippon Yu Co., Ltd.}]

[0422] Palmitic acid [Trade name: NAA-160 {Manufactured by Nippon Oil Co., Ltd.}]

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

[0424] • Glycerin [Product Name: Cosmetic Concentrated Glycerin {Manufactured by Kao Corporation}]

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

[0426] • Polyquaternium-7 (9% by weight aqueous solution) [Trade name: MERQUAT550 (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 [Brand Name: D-α-Tocopherol {Manufactured by Tokyo Chemical Industry Co., Ltd.}]

[0430] •EDTA-2Na [Trade name: 2NA (EDTA·2Na) {Manufactured by Dojin Chemical Research & Development Co., Ltd.}]

[0431] • Coconut oil 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 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 shown in Tables 2-5, the cleaning agents of Examples 6-14, compared with the cleaning agents of Comparative Examples 4-5, have less sebum residue and less oil production on the skin, and the hair has a better sense of volume and the skin has better moisturizing properties.

[0439] Industrial applicability

[0440] Cleaning agents using the surfactant composition of this application are suitable for shampoos, facial cleansers, etc., due to their excellent sebum residue, low skin oil production, hair volume, and skin moisturizing properties. Furthermore, they have the potential to be used as household cleaning agents (laundry detergents, dishwashing detergents, etc.) and industrial cleaning agents (cleaning agents for metals, precision parts, etc.).

Claims

1. A surfactant composition comprising: The alkyl hydroxy ether acetic acid (salt) represented by the following general formula (1) and, The alkyl hydroxy ether acetic acid (salt) (B) represented by the following general formula (2) The total weight percentage of alkyl hydroxy ether acetic acid and its salt (B) relative to the total weight of alkyl hydroxy ether acetic acid and its salt (A) is 0.05% to 1% by weight. R 1 -CH(OH)-CH2-OCH2COOM 1 (1) In equation (1), R 1 M represents an alkyl group with 8 to 12 carbon atoms. 1 Represents hydrogen atoms, sodium atoms, potassium atoms, or triethanolamine. R 2 -O-CH(X 1 )CH(X 2 )-OCH2COOM 2 (2) In equation (2), X 1 and X 2 One of them is a hydrogen atom, and the other is an alkyl group with 8 to 12 carbon atoms. R 2 A hydroxyalkyl group is formed by replacing any one hydrogen atom bonded to the carbon atom at position 1 of an alkyl group with 10 to 14 carbon atoms with a hydroxyl group. X 1 or X 2 When the alkyl group representing 8 to 12 carbon atoms has n carbon atoms, R 2 The number of carbon atoms is n+2. M 2 It represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolamine.

2. A cleaning agent comprising the surfactant composition of claim 1.

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