JP7389687B2 - Surfactant compositions and cleaning compositions - Google Patents

Description

The present invention relates to surfactant compositions and cleaning compositions.

Traditionally, ether carboxylic acid type anionic surfactants have been formulated as hair and body cleansing agents. In particular, ether carboxylic acid type anionic surfactants with a narrow addition molar distribution of alkylene oxide are hypoallergenic and stable at low temperatures. It is known to have excellent properties (Patent Documents 1 to 3).
Furthermore, it is known that ether carboxylic acid type anionic surfactants having a specific distribution have good rinsability and high sebum cleansing properties (Patent Document 4).

Japanese Unexamined Patent Publication No. 61-021199 Japanese Patent Application Publication No. 02-175799 Japanese Patent Application Publication No. 2001-207189 Japanese Patent Application Publication No. 2012-072399

However, although these detergent compositions have excellent foaming properties, rinsing properties, and sebum cleansing properties, they have insufficient foam stability and low viscosity when used as hair or body detergents, making them difficult to clean by hand. In order to create a viscosity that makes it difficult to flow when applied, it is necessary to incorporate a large amount of thickener, and adding a large amount of thickener can reduce the amount of foam and worsen the quality and appearance stability of the foam. There were issues such as:

The present inventor has arrived at the present invention as a result of intensive studies to solve the above problems. That is, the present invention provides an ether carboxylic acid (salt) (A) represented by the general formula (1), an alkylene oxide adduct (B) of an alcohol represented by the general formula (2), and the general formula (3). These are a surfactant composition containing an alcohol (C) represented by: and a cleaning composition containing the surfactant composition.
R ¹ O-(A ¹ O) _m -R ² -COOM (1)
[In the general formula (1), R ¹ is a linear or branched aliphatic hydrocarbon group having 8 to 22 carbon atoms, R ² is an alkylene group having 1 to 3 carbon atoms, and A ¹ is each independently a carbon number It is an alkylene group of 2 to 4, m represents a number of 1 to 20, and M represents a hydrogen ion, an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
R ³ O-(A ² O) _n -H (2)
[In general formula (2), R ³ is a linear or branched aliphatic hydrocarbon group having 8 to 22 carbon atoms,
Each of A ² independently represents an alkylene group having 2 to 4 carbon atoms, and n represents a number of 1 to 20. ]
R ⁴ O-H (3)
[In the general formula (3), R ⁴ is a linear or branched aliphatic hydrocarbon group having 8 to 22 carbon atoms. ]

The surfactant composition of the present invention and the cleaning agent composition containing the same have excellent foaming properties and foam stability, and have the effect of being able to impart an appropriate viscosity to the cleaning agent when incorporated into a cleaning agent. .

The surfactant composition of the present invention comprises an ether carboxylic acid (salt) (A) represented by the general formula (1), an alkylene oxide adduct (B) of an alcohol represented by the general formula (2), and a general It contains alcohol (C) represented by formula (3).

R ¹ O-(A ¹ O) _m -R ² -COOM (1)

In the above general formula (1), R ¹ is a linear or branched aliphatic hydrocarbon group having 8 to 22 carbon atoms. Examples of straight chain or branched aliphatic hydrocarbon groups having 8 to 22 carbon atoms include octyl group, nonyl group, decyl group, undecyl group, lauryl group, tridecyl group, myristyl group, pentadecyl group, cetyl group, heptadecyl group, Octadecyl group, nonadecyl group, icosyl group, henicosyl group, docosyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonadecenyl group , icosenyl group, icosenyl group, docosenyl group, octadienyl group, nonadienyl group, decadienyl group, undecadienyl group, dodecadienyl group, tridecadienyl group, tetradecadienyl group, pentadecadienyl group, hexadecadienyl group, heptadecadienyl group group, octadecadienyl group, nonadecadienyl group, icosadienyl group, henicosadienyl group, docosadienyl group, octadecatrienyl group, icosatrienyl group, icosatetraenyl group, icosapentenyl group, docosahexaenyl group, iso Examples include stearyl group and tetramethylhexadecenyl group (phytyl group).

From the viewpoint of foaming properties, ^R1 is preferably an aliphatic hydrocarbon group having 10 to 16 carbon atoms containing saturated or unsaturated bonds, and more preferably an aliphatic hydrocarbon group having 12 to 14 carbon atoms containing only saturated bonds. It is a hydrocarbon group.

In the above general formula (1), R ² is an alkylene group having 1 to 3 carbon atoms, and examples of the alkylene group having 1 to 3 carbon atoms include a methylene group, an ethylene group, and a propylene group.
Among ^R2 , methylene group is preferred from the viewpoint of viscosity during blending.

In the above general formula (1), each A ¹ O independently represents an oxyalkylene group having 2 to 4 carbon atoms. Specific examples thereof include an oxyethylene group (hereinafter abbreviated as EO), an oxypropylene group (hereinafter abbreviated as PO), and an oxybutylene group (hereinafter abbreviated as BO). Among these, from the viewpoint of foaming properties, EO and PO are preferred, and EO is more preferred.

In the above general formula (1), m represents a number from 1 to 20, and is preferably a number from 1 to 5 from the viewpoint of foaming property.

M in the above general formula (1) represents a hydrogen ion, an alkali metal ion, an ammonium ion, or an organic ammonium ion.
Examples of alkali metal ions include sodium ions and potassium ions.
Examples of organic ammonium ions include tetramethylammonium ion, tetraethylammonium ion, tetrapropylammonium ion, and tetrabutylammonium ion.
Among these, from the viewpoint of foaming properties, alkali metal ions and ammonium ions are preferred, and alkali metal ions are more preferred.

Examples of the ether carboxylic acid (salt) (A) represented by the general formula (1) of the present invention include polyoxyethylene (EO3) lauryl ether acetic acid, polyoxyethylene (EO3) potassium lauryl ether acetate, polyoxyethylene ( EO3) Sodium lauryl ether acetate, polyoxyethylene (EO5) sodium lauryl ether acetate, polyoxyethylene (EO4) tridecyl ether acetic acid, polyoxyethylene (EO3) sodium tridecyl ether acetate, polyoxyethylene (EO7) tridecyl ether Examples include sodium acetate, polyoxyethylene (EO11) sodium lauryl ether acetate, and polyoxyethylene (EO3) myristyl ether sodium acetate.
Among these, from the viewpoint of foaming properties, polyoxyethylene (EO3) potassium lauryl ether acetate, polyoxyethylene (EO3) sodium lauryl ether acetate, polyoxyethylene (EO3) sodium tridecyl ether acetate, and polyoxyethylene (EO3) Myristyl ether sodium acetate.

R ³ O-(A ² O) _n -H (2)

The above general formula (2) represents an alkylene oxide adduct of alcohol.
In the general formula (2), R ³ is a linear or branched aliphatic hydrocarbon group having 8 to 22 carbon atoms, and the groups exemplified for R ¹ above can be used.
Among these, from the viewpoint of foaming properties, aliphatic hydrocarbon groups having 10 to 16 carbon atoms containing saturated or unsaturated bonds are preferred, and aliphatic hydrocarbon groups having 12 to 14 carbon atoms containing unsaturated bonds are more preferable. It is a hydrocarbon group.

In the above general formula (2), each A ² O independently represents an oxyalkylene group having 2 to 4 carbon atoms. Specific examples thereof include an oxyethylene group (hereinafter abbreviated as EO), an oxypropylene group (hereinafter abbreviated as PO), and an oxybutylene group (hereinafter abbreviated as BO). Among these, from the viewpoint of viscosity during blending, EO and PO are preferred, and EO is more preferred.

In the above general formula (2), n represents a number from 1 to 20, and is preferably a number from 1 to 5 from the viewpoint of viscosity during blending.

Examples of the alkylene oxide adduct (B) of alcohol represented by general formula (2) include polyoxyethylene octyl ether, polyoxyethylene decyl ether, polyoxyethylene lauryl ether, polyoxyethylene tridecyl ether, and Examples include ethylene myristyl ether, polyoxyethylene pentadecyl ether, polyoxyethylene cetyl ether, polyoxyethylene heptadecyl ether, polyoxyethylene octadecyl ether, and polyoxyethylene isostearyl ether.
Among these, polyoxyethylene decyl ether, polyoxyethylene lauryl ether, polyoxyethylene myristyl ether, and polyoxyethylene cetyl ether are preferred from the viewpoint of foaming properties.

The ether carboxylic acid (salt) (A) represented by the general formula (1) in the present invention can be produced by a known method, for example, through the following steps (1) to (4). Can be manufactured.
Step (1): Adding an alkylene oxide having 2 to 4 carbon atoms to the alcohol (a1) represented by the general formula R ¹ OH [R ¹ is the same as the group in the general formula (1)] to form the alcohol (a1). Step of obtaining alkylene oxide adduct (a2).
Step (2): A step of carboxyalkylating the above (a2) with an alkali metal halogenated carboxylic acid salt or the like in the presence of a caustic alkali.
Step (3): A step of making the inside of the reaction system acidic, washing with water and separating, removing by-produced alkali metal halide salts, and purifying to obtain an acid-type ether carboxylic acid type surfactant.
Step (4): Neutralizing using an alkaline substance to obtain an ether carboxylic acid type surfactant containing at least a portion of the salt type ether carboxylic acid type surfactant.

The reaction conditions for step (1) are as follows: (a1) is charged with a catalyst and a solvent if necessary, and after nitrogen substitution, an alkylene oxide having 2 to 4 carbon atoms is heated at -0.8 to 5 MPa and 80 to 200°C. Examples include a method in which a predetermined amount of alkylene oxide is introduced under pressure, and then ripening is carried out at 80 to 200° C. until the pressure in the reaction system reaches equilibrium.
Examples of the above-mentioned catalysts include alkali catalysts, Lewis acid catalysts, perhalogen acids or salts thereof, sulfuric acid or salts thereof, phosphoric acid or salts thereof, and nitric acid or salts thereof.
Examples of the alkali catalyst include hydroxides of alkali metals and alkaline earth metals, specifically lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, magnesium hydroxide, calcium hydroxide, and hydroxide. Examples include barium. Among these, potassium hydroxide and cesium hydroxide are preferred.
Examples of Lewis acid catalysts include tin tetrachloride, antimony pentachloride, iron trichloride, and boron trifluoride.

The amount of catalyst to be used is preferably 0.001 to 1 per 100 parts by weight of the above-mentioned (a1) and the alkylene oxide having 2 to 4 carbon atoms to be added to (a1), from the viewpoint of reaction rate and economy. Parts by weight, more preferably 0.003 to 0.8 parts by weight, most preferably 0.005 to 0.5 parts by weight.
Further, as for the catalyst, solvent, amount of catalyst used, etc., those described in JP-A No. 2001-011489 can also be applied.

Examples of the caustic alkali in step (2) include sodium hydroxide and potassium hydroxide. The properties of the caustic alkali include aqueous solution, powder, granule, and flake. From the viewpoint of reaction efficiency and safety, granules are preferred among these.

Examples of the alkali metal halogenated carboxylic acid salt in step (2) include sodium monochloroacetate, potassium monochloroacetate, sodium monobromoacetate, potassium monobromoacetate, and the like.

In step (2), a solvent may be used. Examples of the solvent include benzene, toluene, xylene, hexane, and cyclohexane, but toluene is preferred from the viewpoint of high reaction efficiency and ease of removal after the reaction. When a solvent is used, the preferred solvent concentration is 5 to 130% by weight based on the total weight of all raw materials other than the solvent used in step (2).

The acids that can be used in step (3) are preferably mineral acids such as hydrochloric acid and sulfuric acid.
By adding an acid to form an acid-type ether carboxylic acid, it becomes easier to separate the aqueous solution of the salt by-produced during the reaction. The equivalent amount of acid charged is preferably 1.0 to 1.5 equivalents of the equivalent of caustic alkali in step (2). Further, water may be added as appropriate to facilitate washing and liquid separation.

Examples of the alkaline substance that can be used in step (4) include lithium hydroxide, sodium hydroxide, potassium hydroxide, ammonia, organic amines, basic amino acids, and quaternary ammonium hydroxide.

The alkylene oxide adduct (B) of alcohol represented by general formula (2) in the present invention can be produced by a known method.
For example, an alcohol (a3) represented by the general formula R ³ OH [R ³ is the same as the group in general formula (2)] is charged into a pressurized reaction vessel, and an alcohol having 2 to 4 carbon atoms is added to a pressurized reaction vessel without a catalyst or in the presence of a catalyst. An example is a method in which alkylene oxide is added dropwise and the reaction is carried out in one step or in multiple steps. Examples of the alkylene oxide having 2 to 4 carbon atoms include EO, PO and BO, among which one type or two or more types can be used in combination.
The reaction temperature is preferably 60 to 200°C, more preferably 70 to 140°C. The reaction pressure is preferably 0.001 to 0.5 MPa. The reaction time is preferably 2 to 24 hours, more preferably 3 to 10 hours.
Examples of the catalyst include alkali catalysts (sodium hydroxide, potassium hydroxide, etc.). The amount of the catalyst used is preferably 0.01 to 5% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the above-mentioned (a3) and the alkylene oxide having 2 to 4 carbon atoms to be added to (a3). It is 0.5% by weight.
After the reaction is complete, the catalyst may be left in (B) as it is, or it may be treated with a method such as removing it by adsorption and filtration using an adsorbent, or inactivating the catalyst by neutralizing it with an acid. You can.

R ⁴ O-H (3)

The above general formula (3) is a monohydric alcohol.
R ⁴ in the general formula (3) is a linear or branched aliphatic hydrocarbon group having 8 to 22 carbon atoms, and the groups exemplified for R ¹ above can be used.
Among these, from the viewpoint of foaming properties, aliphatic hydrocarbon groups having 10 to 16 carbon atoms containing saturated or unsaturated bonds are preferred, and aliphatic hydrocarbon groups having 12 to 14 carbon atoms containing unsaturated bonds are more preferable. It is a hydrocarbon group.

Examples of the alcohol (C) represented by the general formula (3) include octinol, decanol, undecanol, lauryl alcohol, tridecyl alcohol, myristyl alcohol, pentadecyl alcohol, cetyl alcohol, heptadecyl alcohol, octadecyl alcohol, nonadecyl alcohol, and Examples include isostearyl alcohol.
Among these, from the viewpoint of foaming properties, decanol, lauryl alcohol, myristyl alcohol and cetyl alcohol are preferred.

The content of (A) is preferably 78 to 98% by weight based on the total weight of (A), (B), and (C) from the viewpoint of foaming properties.

The weight ratio (B)/(C) of the above (B) and the above (C) is preferably 30/70 to 99/1, more preferably 40/60 to 99/1, from the viewpoint of viscosity at the time of blending. It's 90/10.

The surfactant composition of the present invention may further contain water.

When the surfactant composition of the present invention contains water, the content of (A) is determined from the viewpoint of foaming property with respect to the total weight of (A), (B), (C), and water. It is preferably 20 to 35% by weight, more preferably 23 to 30% by weight.

The total content of (B) and (C) is determined based on the total weight of (A), (B), (C), and water in the cleaning composition containing the surfactant composition of the present invention. From the viewpoint of viscosity and foam stability, the amount is preferably 0.4 to 8% by weight, more preferably 0.6 to 4% by weight.

From the viewpoint of the viscosity and foam stability of the cleaning composition of the present invention, the water content is preferably 57 to 79.6 based on the total weight of (A), (B), (C), and water. % by weight, more preferably 66 to 74.4% by weight.

The properties of the cleaning composition of the present invention are not particularly limited, but include liquid and paste. Among these, liquid forms are preferred from the viewpoint of ease of handling.

The cleaning composition of the present invention includes not only the above-mentioned surfactant composition, but also an alcohol having 1 to 6 carbon atoms, an amphoteric surfactant, a cationic surfactant, an anionic surfactant other than (A), ( Nonionic surfactants other than B), thickeners, gelling agents, medicinal agents, anti-inflammatory agents, antibacterial agents, preservatives, ultraviolet absorbers, antioxidants, conditioning agents, emollients, silicones, pearlizing agents, It is preferable to contain one or more selected from the group consisting of a chelating agent, a pH adjuster, a pigment, and a fragrance.

Examples of the amphoteric surfactant include amino acid type amphoteric surfactants, carbobetaine type amphoteric surfactants, and sulfobetaine type amphoteric surfactants.

Examples of amino acid type amphoteric surfactants include alkylaminopropionate salts (sodium lauryl aminopropionate, etc.).
Carbobetaine-type amphoteric surfactants include alkyl dimethyl acetate betaines (stearyl dimethylamino acetate betaine and lauryl dimethyl amino acetate betaine, etc.), alkylamido acetic acid betaines {coconut oil fatty acid amidopropyl betaine, lauric acid amidopropyl betaine, etc.} and alkyl Examples include dihydroxyalkyl betaine (lauryl dihydroxyethyl betaine, etc.).
Examples of the sulfobetaine-type amphoteric surfactants include alkyldimethylhydroxysulfobetaines (lauryldimethylhydroxysulfobetaine, etc.), alkylamidohydroxysulfobetaines (laurylamidepropylhydroxysulfobetaine, etc.), and the like.

Examples of the cationic surfactant include quaternary ammonium salt type and amine salt type.

Examples of anionic surfactants other than (A) include carboxylates other than (A), sulfate ester salts, higher alkyl ether sulfate salts, sulfated oils, sulfated fatty acid esters, sulfated olefins, sulfonates, and Examples include phosphate ester salts.

Examples of nonionic surfactants other than (B) include alkylene oxide-added nonionic surfactants [higher alcohols (aliphatic alcohols having 23 or more carbon atoms), alkylphenols (10 to 24 carbon atoms) or higher amines (8 carbon atoms). ~18) with alkylene oxide added, or with the hydroxyl group further alkyl etherified with an alkylating agent, polyoxyalkylene glycol reacted with higher fatty acids (12 to 24 carbon atoms), or; diol or Higher fatty acids (8 to 24 carbon atoms) are obtained by adding alkylene oxide to esterified products obtained by reacting higher fatty acids (12 to 24 carbon atoms) with hydroxyl group-containing compounds such as tri- to octahydric polyhydric alcohols. amide with alkylene oxide added, polyhydric alcohol (the above), alkyl (carbon number 8-60) ether with alkylene oxide added], and polyhydric alcohol (carbon number 3-20) type. Nonionic surfactants [polyhydric alcohol fatty acid (8 to 60 carbon atoms) ester, polyhydric alcohol alkyl (8 to 60 carbon atoms) ether, fatty acid (8 to 60 carbon atoms) alkanolamide (e.g., coconut oil fatty acid monoethanol) amide)] and the like.

Thickeners, gelling agents, medicinal agents, anti-inflammatory agents, antibacterial agents, preservatives, ultraviolet absorbers, antioxidants, and fragrances include "Cosmetics Science" by Takeo Tamura, Japan Hair Science Association, 1976. Polymer compounds as gelling agents as described on pages 204 to 211 of the issue, disinfectants and preservatives as described on pages 185 to 196, ultraviolet absorbers as described on pages 177 to 183, antioxidants as described on pages 199 to 203, p 145 Examples include the coloring agents described on pages 150 to 176, and the fragrances described on pages 150 to 176.
Emollients include, for example, carnauba wax, beeswax, mineral oil, tonsil oil, castor oil, sesame oil, hydrogenated polyisobutene, and butylene glycol dicaprylate (commercially available as Myglyol® from Sasol). Mixtures may be mentioned.
Conditioning agents include cationized cellulose with a weight average molecular weight of 5 million to 5 million, cationized guar gum, silicones, polyethylene glycol, sodium polyacrylate, hydroxyethyl cellulose, protein derivatives, ceramides, pseudoceramides, carbon atoms 16 to 40. fatty acids and panthenol.
Examples of the chelating agent include ethylenediaminetetraacetic acid, polyphosphoric acid, pyrophosphoric acid, gluconic acid, ascorbic acid, and salts thereof.
Examples of the pH adjusting agent include potassium carbonate, sodium hydrogen carbonate, ammonium hydrogen carbonate, lactic acid, succinic acid, and citric acid.
Examples of the dye include Blue No. 1, Blue No. 2, Green No. 3, and Red No. 1.

The present invention will be further explained below with reference to Examples and Comparative Examples, but the present invention is not limited thereto. Hereinafter, unless otherwise specified, % means % by weight and parts means parts by weight.

<Example 1>
Into a stainless steel autoclave equipped with stirring and temperature control functions, 158 parts (1 mol) of decanol manufactured by Fuji Film Wako Pure Chemical Industries, Ltd. and 0.5 part of a 28% methanol solution of sodium methylate were charged, mixed, and then the system The gas phase inside was replaced with nitrogen. Thereafter, methanol removal was performed at 120° C. for 2 hours under reduced pressure (2.6 KPa). Next, 132 parts (3 mol) of EO was introduced at 150° C. so that the gauge pressure was 0.1 to 0.3 MPa. The time required for addition polymerization of EO was 3 hours. Thereafter, 217.5 parts (0.75 mol) of the above product and 116.5 parts (1.0 mol) of sodium monochloroacetate were charged into a glass reaction vessel equipped with stirring and temperature control functions, and the temperature was raised to 50°C. While maintaining the pressure, the degree of vacuum was gradually increased to 10 KPa. Thereafter, 45.2 parts (1.13 mol) of granular sodium hydroxide was added over 2 hours while dehydrating under reduced pressure, and the mixture was further aged for 6 hours. 350 parts of water was added, acidified with 133 parts of 35% hydrochloric acid, stirred for 30 minutes, left to stand for 3 hours, and the liquid was separated and the lower liquid containing by-product salts was discarded. A surfactant composition (X1) was obtained by adding 337 parts of water at 70° C. and gradually adding 62 parts (0.75 mol) of a 48.5% aqueous sodium hydroxide solution for neutralization. The composition of (X1) is polyoxyethylene (average number of added moles of EO = 3 moles), sodium tridecyl ether acetate (A1) is 29% by weight based on the total weight of (X1), polyoxyethylene decyl ether (B1 ) was adjusted to 0.5% by weight and decanol (C1) was adjusted to 0.4% by weight by adding water.

<Example 2>
In Production Example 1, surfactant composition (X2) was prepared under the same conditions except that decanol was changed to 186 parts (1 mol) of lauryl alcohol manufactured by Fuji Film Wako Pure Chemical Industries, Ltd. and 337 parts of water was changed to 384 parts. Obtained. The composition of (X2) is that polyoxyethylene (EO3) lauryl ether sodium acetate (A2) is 29% by weight based on the total weight of (X2), polyoxyethylene lauryl ether (B2) is 0.5% by weight, and lauryl ether is 0.5% by weight. Alcohol (C1) was 0.4% by weight.

<Example 3>
In Production Example 1, the surfactant composition (X3) was prepared under the same conditions except that decanol was changed to 214 parts (1 mol) of myristyl alcohol manufactured by Fuji Film Wako Pure Chemical Industries, Ltd. and 337 parts of water was changed to 431 parts. Obtained. The composition of (X3) is that polyoxyethylene (EO3) myristyl ether sodium acetate (A3) is 29% by weight based on the total weight of (X3), polyoxyethylene myristyl ether (B3) is 0.5% by weight, and myristyl ether (B3) is 0.5% by weight. Alcohol (C3) was 0.4% by weight.

<Manufacture example 1>
186 parts (1 mole) of lauryl alcohol manufactured by Fuji Film Wako Pure Chemical Industries, Ltd. and 0.1 part of potassium hydroxide were placed in a stainless steel autoclave equipped with stirring and temperature control functions, and after mixing, the air in the system was removed. The phase was purged with nitrogen. Next, 220 parts (5 mol) of EO was introduced at 170° C. so that the gauge pressure was 0.1 to 0.3 MPa. The time required for addition polymerization of EO was 5 hours. Thereafter, it was cooled to 50°C, 0.1 part of citric acid was added and mixed, the pH was adjusted to about 7.0, 93% by weight of polyoxyethylene lauryl ether (B2) and 7% by weight of lauryl alcohol (C2). A mixture (D1) was obtained.

<Manufacture example 2>
In Production Example 4, 93 weight of polyoxyethylene myristyl ether (B3) was produced under the same conditions except that 186 parts (1 mol) of lauryl alcohol was changed to 214 parts (1 mol) of myristyl alcohol manufactured by Fuji Film Wako Pure Chemical Industries, Ltd. A mixture (D2) of 7% by weight of myristyl alcohol (C3) and 7% by weight of myristyl alcohol (C3) was obtained.

<Manufacture example 3>
In Production Example 4, polyoxyethylene cetyl ether (B4) 93 A mixture (D3) of 7% by weight of cetyl alcohol (C4) was obtained.

<Examples 4 to 12 and Comparative Examples 1 to 4>
(X1) to (X3) obtained in Examples 1 to 3 above, (D1) to (D3) obtained in Production Examples 1 to 3, (C2) to (C4) which are the following various alcohols, and water Surfactant compositions (X4) to (X12) and (X'1) to (X'4) were prepared by blending them in the amounts shown in Table 1 or Table 2.
(C2) Lauryl alcohol (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.)
(C3) Myristyl alcohol (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.)
(C4) Cetyl alcohol (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.) (X4) contains 2.2% by weight of (D3) based on the total weight of (X1) and (X1) as shown in Table 1. This is a surfactant composition obtained by blending the two in a weight ratio.
(X5) is a surfactant obtained by blending (X2) and (D1) in a weight ratio of 2.2% by weight based on the total weight of (X2) as shown in Table 1. It is a composition.
(X6) is a surfactant obtained by blending (X3) and (D2) in a weight ratio of 2.2% by weight based on the total weight of (X3) as shown in Table 1. It is a composition.
(X7) is a surfactant composition obtained by blending (X2) and 16% by weight of water based on the total weight of (X2) so that the weight ratio is as shown in Table 1. .
(X8) is a surfactant composition obtained by blending (X3) and 16% by weight of water based on the total weight of (X3) so that the weight ratio is as shown in Table 1. .
(X9) is (X7), (D1) of 1.1% by weight based on the total weight of (X7), and (D2) of 1.1% by weight based on the total weight of (X7), This is a surfactant composition obtained by blending 2.2% by weight of (D3) with respect to the total weight of (X7) at the weight ratio shown in Table 1.
(X10) is (X8), (D1) of 3.3% by weight based on the total weight of (X8), and (C4) of 3% by weight based on the total weight of (X8) in Table 1 This is a surfactant composition obtained by blending in the weight ratio described in .
(X11) is a surfactant composition obtained by blending (X2) and 38% by weight of water based on the total weight of (X2) at the weight ratio shown in Table 1. be.
(X12) is a surfactant composition obtained by adding (X2), (D1), (C2), and water to achieve the weight ratio shown in Table 1.
(X'1) is a surfactant composition obtained by distilling (B2) and (C2) from X2 under reduced pressure and then adding water.
(X'2) is a surfactant composition obtained by blending X1 and water at the weight ratio shown in Table 2.
(X'3) is a surfactant composition obtained by adding (X2), (D1), (C2), and water so that the weight ratios shown in Table 2 are obtained.
(X'4) is a surfactant composition obtained by adding (X3), (D1), (C4), and water to achieve the weight ratio shown in Table 2.

<Examples 13 to 24 and Comparative Examples 5 to 8>
Regarding the above various surfactant compositions (X1) to (X12) and (X'1) to (X'4), coconut oil fatty acid amidopropyl betaine (manufactured by Sanyo Chemical Industries, Ltd., Levon HC-30W), coconut oil Oil fatty acid monoethanolamide (manufactured by Sanyo Chemical Industries, Ltd., Profan AB-20), polyoxyethylene (60) cetostearyl hydroxymyristyrene ether (manufactured by Lion Specialty Chemicals Co., Ltd., Elphakos GT 282S), citric acid Acid, benzoic acid, salicylic acid and water were blended at 60° C. according to the parts shown in Table 3 or Table 4. After stirring uniformly, the above composition was cooled to 40°C or less, and the pH was adjusted to 6.0 by adding sodium hydroxide to prepare cleaning compositions (Y1) to (Y12) and comparative cleaning compositions. (Y'1) to (Y'4) were produced and various evaluations were performed.

<Foaming property evaluation>
The above various surfactant compositions (X1) to (X12) and (X'1) to (X'4) were diluted 100 times with tap water, and the pH was adjusted to 7.0 with citric acid. Also, (Y1) to (Y1
2) and cleaning compositions (Y'1) to (Y'4) were diluted 50 times with tap water, and 200 mL of each aqueous solution was mixed using a juice mixer (MX-390GM) manufactured by Toshiba Corporation. Immediately after stirring at 25° C. for 30 seconds, the foam height was read and judged according to the following criteria, and the results are listed in Tables 1 to 4.

[Judgment criteria]
◎; 135 mm or more ○; 120 mm or more and less than 135 mm △; 105 mm or more and less than 120 mm ×; less than 105 mm

<Foam stability evaluation>
Stir various aqueous solutions prepared in the same manner as in the above foaming evaluation at 25°C for 30 seconds, read the foam height immediately after and after 5 minutes of standing, and calculate the difference in foam height using the following criteria: The results were determined and listed in Tables 1 to 4.

[Judgment criteria]
◎; Difference in foam height is less than 5 mm ○; Difference in foam height is 5 mm or more and less than 10 mm △; Difference in foam height is 10 mm or more and less than 20 mm ×; Difference in foam height is 20 mm or more

<Viscosity during blending>
The viscosity of cleaning compositions (Y1) to (Y12) and comparative cleaning compositions (Y'1) to (Y'4) one day after blending at 25°C was measured using a B-type viscometer. It was judged based on the following criteria.

[Judgment criteria]
◎; 4000 mPa・s or more and less than 8000 mPa・s ○; 1000 mPa・s or more and less than 4000 mPa・s △; 500 mPa・s or more and less than 1000 mPa・s or 4000 mPa・s or more and less than 8000 mPa・s ×; less than 500 mPa・s or 8000 mPa・s or more

The present invention relates to a surfactant composition and a cleaning composition. A cleansing composition containing the above-mentioned surfactant composition has suitable appearance stability, foaming property, and foam stability, and can impart an appropriate viscosity to the formulation when blended into a cleansing agent, so that it is suitable for hair removal. It is suitable as a cleansing agent for the skin or as a cleansing agent for the skin. It can also be used as a household cleaning agent (clothing detergent, dishwashing detergent, etc.) and an industrial cleaning agent (cleaning agent for metals, precision parts, etc.).

Claims (5)

Ether carboxylic acid (salt) (A) represented by general formula (1), alkylene oxide adduct of alcohol represented by general formula (2) (B), and alcohol represented by general formula (3) (C) A surfactant composition containing,
The surfactant composition further contains water, and the content of (A) is 20 to 25% by weight based on the total weight of (A), (B), (C), and water, (B), and A surfactant composition having a total content of (C) of 0.4 to 8% by weight and a water content of 67 to 79.6% by weight .
R ¹ O-(A ¹ O) _m -R ² -COOM (1)
[In the general formula (1), R ¹ is a linear or branched aliphatic hydrocarbon group having 8 to 22 carbon atoms, R ² is an alkylene group having 1 to 3 carbon atoms, and A ¹ is each independently a carbon number It is an alkylene group of 2 to 4, m represents a number of 1 to 20, and M represents a hydrogen ion, an alkali metal ion, an ammonium ion, or an organic ammonium ion. ]
R ³ O-(A ² O) _n -H (2)
[In general formula (2), R ³ is a linear or branched aliphatic hydrocarbon group having 8 to 22 carbon atoms, A ² is each independently an alkylene group having 2 to 4 carbon atoms, and n is 1 Represents the number ~20. ]
R ⁴ O-H (3)
[In the general formula (3), R ⁴ is a linear or branched aliphatic hydrocarbon group having 8 to 22 carbon atoms. ] The surfactant composition according to claim 1, wherein A ¹ in general formula (1) is an ethylene group and R ² is a methylene group. The surfactant composition according to claim 1 or 2, wherein the content of (A) based on the total weight of (A), (B), and (C) is 78 to 98% by weight. The surfactant composition according to any one of claims 1 to 3 , wherein the weight ratio (B)/(C) of the (B) and the (C) is from 30/70 to 99/1. Alcohol having 1 to 6 carbon atoms, amphoteric surfactant, cationic surfactant, anionic surfactant other than (A), nonionic surfactant other than (B), thickener, gelling agent, medicinal agent , anti-inflammatory agents, antibacterial agents, preservatives, ultraviolet absorbers, antioxidants, conditioning agents, emollients, silicones, pearlizing agents, chelating agents, pH adjusting agents, pigments, and fragrances. and a cleaning composition comprising the surfactant composition according to any one of claims 1 to 4 .