JP3441222B2 - Detergent composition - Google Patents

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a detergent composition, and more particularly to a detergent composition which is less irritating to the skin and the like, has an excellent foaming property and has a creamy foam quality.

[0002]

2. Description of the Related Art Conventionally, the problems to be solved by the invention
As a surfactant for detergents, alkyl sulfate ester salt, polyoxyethylene alkyl sulfate ester salt, alkylbenzene sulfonate, α, which has the characteristics of high foamability
-Anionic surfactants such as olefin sulfonates are widely used. However, all of these anionic surfactants have skin irritation to varying degrees, but when they are continuously used, they have a problem of roughening the skin.

On the other hand, alkyl saccharide-based surfactants, sulfosuccinic acid-based surfactants, ethercarboxylic acid-based surfactants, amide ethercarboxylic acid-based surfactants, etc. are known as mild surfactants. Has been. However, although alkyl saccharide-based surfactants have high foaming properties, they have strong creases during cleaning and rinsing, and therefore are used in combination with conditioning agents such as cationic polymers (JP-A-2-42013). Although it has been proposed, it is not technically easy to add a large amount to shampoo or the like. In addition, sulfosuccinic acid-based surfactants have poor foaming properties by themselves, and a method in which they are used in combination with other surfactants (Japanese Patent Laid-Open No. 2-218797) has been proposed. Often used in combination.
Furthermore, commercially available ether carboxylic acid type surfactants and amido ether carboxylic acid type surfactants also have poor foaming properties, and are used only as auxiliary surfactants in detergents that require high foaming properties. ing.

This amide ether carboxylic acid type surfactant is commercially available from Chem Y of Germany under the trade name of "Akipo".
In addition to the raw material amide ether, impurities derived from the raw material polyoxyethylene glyceryl ether,
It contains polyoxyethylene glyceryl ether carboxylic acid, inorganic salts and the like.

[0005] As a technique known so far regarding application of an amide ether carboxylic acid type surfactant to a detergent, amide ether carboxylic acid, polyoxyethylene alkyl sulfuric acid ester, fatty acid diethanol amide, higher alcohol alkylene oxide are known. Detergent combined with adduct, acyl sarcosinate, etc. (European Patent No. 102118), a method of using amide ether carboxylic acid type surfactant and polyoxyethylene alkyl sulfate ester in combination (European Patent No. 215504) ), A foam bath in which amide ether carboxylic acid starting from fats and oils is combined with lauryl sulfate ester, lauryl ether sulfate ester, alkyl ether carboxylic acid, quaternary compound obtained by reacting lauric acid with glycidyl trimethyl ammonium chloride, etc. Agents, shampoo agents, shower agents and the like (JP-B 63-291996, JP-EP 2
19893), detergents containing amide ether carboxylic acid or alkyl ether carboxylic acid salt containing soap as a main component (US Pat. No. 4,865,757), and the like.

However, none of these detergents is still satisfactory in terms of foamability. Therefore, it has been desired to develop a detergent having a low irritation on the skin and the like and a high foaming property.

[0007]

Under the above circumstances, the inventors of the present invention have investigated a detergent containing amide ether carboxylic acid, and as a result, have found that polyoxyethylene glyceryl ether and polyoxyethylene glyceryl which are impurities derived from raw materials. It was found that the foaming property was inferior with a substance containing a large amount of ether carboxylic acid or a pure amide ether carboxylic acid itself. And as a result of further study, if the amide ether derivative mixture containing amide ether in a specific ratio and the content of the glycerin derivative is a certain ratio or less, and a specific anionic surfactant are used in combination, it can be applied to the skin and the like. The present invention has been completed by finding that a detergent having a low irritation, a high foaming property and a creamy foam quality can be obtained.

That is, the present invention relates to a detergent composition containing the following components (A) and (B). (A) an amide ether carboxylic acid represented by the general formula (1) or a salt thereof and an amide ether represented by the general formula (2),
(1) :( 2) = 93: 7 to 85:15 in total 50 by weight ratio in solid content
An amide ether derivative mixture containing at least 5% by weight and containing less than 5% by weight of solid content of the glycerin derivative represented by the general formula (3).

[0009]

[Chemical 2]

(Wherein R ¹ represents a linear or branched alkyl or alkenyl group having 5 to 23 carbon atoms or a phenyl group substituted with such an alkyl group, R ² represents a hydrogen atom,-( CH ₂ CH ₂ O) _n CH ₂ COOM,-(CH ₂ CH ₂ O) _m H or an alkyl group having 1 to 3 carbon atoms, M is a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium, an alkanolamine Or a basic amino acid, n and m may be the same or different and each represents a number of 1 to 20, R ³ is a hydrogen atom, — (CH ₂ CH ₂ O) _m H or an alkyl group having 1 to 3 carbon atoms. represents a group, R ⁴ is a hydrogen _{atom, - (CH 2 CH 2 O} ) n CH 2 COOM or - (CH ₂ CH
₂ O) _m H is shown. R ¹ , M, n and m in the general formulas (1), (2) and (3) may be the same or different. ) (B) alkyl sulfosuccinic acid ester, polyoxyalkylene alkyl ether sulfosuccinic acid ester, polyoxyalkylene fatty acid amide ether sulfuric acid, monoglyceride sulfuric acid, α-olefin sulfonic acid, acylated isethionic acid, alkyl glyceryl ether sulfonic acid,
Anionic surfactant selected from acylated glutamic acid, alkanesulfonic acid, and salts thereof

In the amide ether derivative mixture which is the component (A) used in the present invention, in the general formula (1) or (2),
R ¹ is an alkyl group or an alkenyl group having 7 to 17 carbon atoms, or a phenyl group substituted with such an alkyl group, for example, a heptyl group, a nonyl group, an undecyl group,
A dodecyl group, a tridecyl group, a pentadecyl group, a heptadecyl group, a heptadecenyl group and the like are particularly preferably an alkyl group having 11 to 13 carbon atoms, R 2 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n and m are Is 1
The number is preferably -15, more preferably 1-10, and especially 2-7. Examples of M include sodium, potassium, magnesium, calcium, monoethanolamine, diethanolamine, triethanolamine, arginine, lysine and the like.

Specific preferred examples of the amide ether carboxylic acid or its salt (1) in the component (A) include capric acid monoethanolamide polyoxyethylene ether acetic acid (n = 1 to 15) and lauric acid monoethanolamide poly. Oxyethylene ether acetic acid (n = 1 to 15),
Myristic acid monoethanolamide polyoxyethylene ether acetic acid (n = 1 to 15), palmitic acid monoethanolamide polyoxyethylene ether acetic acid (n = 1 to 1)
15), stearic acid monoethanolamide polyoxyethylene ether acetic acid (n = 1 to 15), oleic acid monoethanolamide polyoxyethylene ether acetic acid (n =
1-20), behenic acid monoethanolamide polyoxyethylene ether acetic acid (n = 1-20), lauric acid-N-
Methyl ethanolamide polyoxyethylene ether acetic acid (n = 1 to 15), myristic acid-N-methyl ethanolamide polyoxyethylene ether acetic acid (n = 1 to 1)
5), palmitic acid-N-methylethanolamide polyoxyethylene ether acetic acid (n = 1 to 15), stearic acid-N-methylethanolamide polyoxyethylene ether acetic acid (n = 1 to 15), lauric acid isopropanolamide poly Oxyethylene ether acetic acid (n = 1 to 1
5), myristic acid isopropanolamide polyoxyethylene ether acetic acid (n = 1 to 15), palmitic acid isopropanolamide polyoxyethylene ether acetic acid (n = 1 to 15), stearic acid isopropanolamide polyoxyethylene ether acetic acid (n = 1) 15), lauric acid diethanolamide polyoxyethylene ether acetic acid (n = 1 to 15), myristic acid diethanolamide polyoxyethylene ether acetic acid (n = 1 to 15), palmitic acid diethanolamide polyoxyethylene ether acetic acid (n = 1-15), stearic acid diethanolamide polyoxyethylene ether acetic acid (n = 1-15), etc.
Or more preferable specific examples thereof are lauric acid monoethanolamide polyoxyethylene ether acetic acid (n = 1 to 10), myristic acid monoethanolamide polyoxyethylene ether acetic acid (n = 1 to 10),
Palmitic acid monoethanolamide polyoxyethylene ether acetic acid (n = 1 to 10), stearic acid monoethanolamide polyoxyethylene ether acetic acid (n = 1 to 10)
10) and the like or salts thereof, and particularly preferred specific examples thereof are lauric acid monoethanolamide polyoxyethylene ether acetic acid (n = 2 to 7) and myristic acid monoethanolamide polyoxyethylene ether acetic acid (n = 2 to 2). 7).

Preferred specific examples of the amide ether (2) in the component (A) include, for example, capric acid monoethanolamide polyoxyethylene ether (n = 1 to 15) and lauric acid monoethanolamide polyoxyethylene ether (n = 1-15), myristic acid monoethanolamide polyoxyethylene ether (n = 1-15), palmitic acid monoethanolamide polyoxyethylene ether (n = 1-15), stearic acid monoethanolamide polyoxyethylene ether (n = 1 to 15), oleic acid monoethanolamide polyoxyethylene ether (n = 1 to 20), behenic acid monoethanolamide polyoxyethylene ether (n = 1 to 20), lauric acid-
N-methylethanolamide polyoxyethylene ether (n = 1 to 15), myristic acid-N-methylethanolamide polyoxyethylene ether (n = 1 to 15), palmitic acid-N-methylethanolamide polyoxyethylene ether ( n = 1 to 15), stearic acid-N-methylethanolamide polyoxyethylene ether (n = 1)
~ 15), lauric acid isopropanolamide polyoxyethylene ether (n = 1 to 15), myristic acid isopropanolamide polyoxyethylene ether (n = 1)
~ 15), palmitic acid isopropanolamide polyoxyethylene ether (n = 1 to 15), stearic acid isopropanolamide polyoxyethylene ether (n =
1 to 15), lauric acid diethanolamide polyoxyethylene ether (n = 1 to 15), myristic acid diethanolamide polyoxyethylene ether (n = 1 to 1)
5), palmitic acid diethanolamide polyoxyethylene ether (n = 1 to 15), stearic acid diethanolamide polyoxyethylene ether (n = 1 to 15) and the like are more preferable specific examples. Oxyethylene ether (n = 1 to 1
0), myristic acid monoethanolamide polyoxyethylene ether (n = 1 to 10), palmitic acid monoethanolamide polyoxyethylene ether (n = 1 to 1)
0), stearic acid monoethanolamide polyoxyethylene ether (n = 1 to 10) and the like. Particularly preferred specific examples include lauric acid monoethanolamide polyoxyethylene ether (n = 2 to 7) and myristic acid monoester. Examples include ethanolamide polyoxyethylene ether (n = 2 to 7).

The total content of the amide ether carboxylic acid or its salt (1) and the amide ether (2) in the amide ether derivative mixture of the component (A) is 50% by weight or more in the solid content of the component (A). Must be above 60% by weight,
It is preferably 70% by weight or more, and particularly preferably 80% by weight or more. If the total content of these is less than 50% by weight in the solid content, the foaming property is poor, which is not preferable.

The weight ratio of the amide ether carboxylic acid or its salt (1) and the amide ether (2) contained in the component (A) is (1) :( 2) = 93: 7 to 85:15 . Need to be
It A If the ratio of Midoeteru (2) is less than the said range inferior to cause <br/> foaming, also creaking strong at the time and rinsing bubbled exceeds the range is not preferable.

Further, the content of the glycerin derivative (3) in the component (A) is required to be 5% by weight or less, and particularly 3% by weight or less, in the solid content of the component (A). It is preferably not included. When the content of the glycerin derivative (3) exceeds 5% by weight in the solid content, the foamability is remarkably reduced, which is not preferable. Further, the content of the inorganic salt such as sodium chloride, which is an impurity other than the glycerin derivative (3) in the component (A), is preferably low.

The method for producing the amide ether derivative mixture which is the component (A) is not particularly limited, and it can be produced directly by reacting a part of the amide ether, and the amide ether can be directly converted into the amide ether carboxylic acid. It can also be added afterwards. As a method for synthesizing an amide ether derivative mixture, a method of producing an alkanolamide from a fatty acid lower alcohol ester such as a fatty acid methyl ester as a starting material, a method of producing an alkanolamide from a fat and oil as a starting material, and a method of producing an alkanolamide from a fatty acid as a starting material Methods and the like. Among them, the method of producing a fatty acid lower alcohol ester such as fatty acid methyl ester as a starting material is preferable because it is less colored and does not substantially contain the glycerin derivative as an impurity. Other methods, for example, starting from an oil / fat having a coconut oil fatty acid composition as a starting material, and in the case of a method of directly alkoxylating and carboxymethylating an alkanolamide, a large amount of a glycerin derivative derived from an oil / fat is produced and the compound (1)
Also, the yield of (2) will be low, which is not preferable in practice.
Further, in the case of a method in which a fatty acid is used as a starting material and reacted with an alkanolamine to form an alkanolamide, coloring is remarkable because the amidation reaction is at a high temperature, which is not preferable.
The ratio of the amide ether carboxylic acid (1) and the amide ether (2) in the amide ether derivative mixture of the component (A) is a molar ratio or a mixing method when the amide ether (2) is reacted with an alkali monohaloacetic acid salt or the like. It can be adjusted by selecting the reaction conditions of.

These components (A) can be used alone or in combination of two or more. The amount of the component (A) in the detergent composition of the present invention is not particularly limited, but is preferably 3% by weight or more, and particularly preferably 5% by weight or more from the viewpoint of foaming property.

The anionic surfactant which is the component (B) used in the present invention is an alkyl sulfosuccinic acid ester, polyoxyalkylene alkyl ether sulfosuccinic acid ester, polyoxyalkylene alkyl amide ether sulfuric acid, monoglyceride sulfuric acid ester, α-olefin sulfone. Acids, acylated isethionic acids, alkyl glyceryl ether sulfonic acids, acylated glutamic acids and alkane sulfonic acids, and salts thereof, more specifically, for example, the following (B-1) ~ (B -8).

(B-1) Alkylsulfosuccinic acid ester or polyoxyalkylene alkyl ether sulfosuccinic acid ester represented by the general formula (4) or a salt thereof.

[0021]

[Chemical 3]

[Wherein M ¹ is a hydrogen atom, an alkali metal,
R ⁵ represents an alkaline earth metal, ammonium or alkanolamine, R ⁵ represents a linear or branched alkyl group or alkenyl group having 8 to 24 carbon atoms, and p R ^{6 s} may be the same or different and each is a hydrogen atom or A methyl group is shown, and p is a number from 0 to 20. ]

(B-2) Polyoxyalkylene fatty acid amide ether sulfuric acid represented by the general formula (5) or a salt thereof

[0024]

[Chemical 4]

[R ⁶ , M ¹ and p have the same meanings as described above, R ⁷ represents a linear or branched alkyl group or alkenyl group having ⁷ to 23 carbon atoms, and R ⁸ represents hydrogen atom or carbon number. 1 to 5 alkyl groups are shown. ]

(B-3) Monoglyceride sulfuric acid having a linear or branched, saturated or unsaturated fatty acid group having 8 to 24 carbon atoms, or a salt thereof with an alkali metal, alkaline earth metal, ammonium or alkanolamine

(B-4) α-Olefin sulfonic acid obtained by sulfonating a linear or branched α-olefin having 8 to 24 carbon atoms, or a salt thereof with an alkali metal, alkaline earth metal, ammonium or alkanolamine.

(B-5) Acylated isethionic acid having a linear or branched, saturated or unsaturated acyl group having 8 to 24 carbon atoms, or a salt thereof with an alkali metal, alkaline earth metal, ammonium or alkanolamine.

(B-6) Alkyl glyceryl ether sulfonic acid having a linear or branched alkyl group or alkenyl group having 8 to 24 carbon atoms or an alkylene oxide adduct thereof, or an alkali metal, an alkaline earth metal or ammonium. Or its salt with alkanolamine

(B-7) Acylated glutamic acid having a linear or branched, saturated or unsaturated acyl group having 8 to 24 carbon atoms, or a salt thereof with an alkali metal, alkaline earth metal, ammonium or alkanolamine.

(B-8) Primary or secondary alkane sulfonic acid having a linear or branched, saturated or unsaturated alkyl group or alkenyl group having 8 to 24 carbon atoms, or an alkali metal or alkaline earth metal , Ammonium or its salts with alkanolamines

Of these components (B), alkyl sulfosuccinic acid ester, polyoxyalkylene alkyl ether sulfosuccinic acid ester, polyoxyalkylene fatty acid amide ether sulfuric acid, monoglyceride sulfuric acid, α-olefin sulfonic acid, acylated glutamic acid or alkane sulfonic acid or Those salts are preferred.

These components (B) can be used alone or in combination of two or more. The amount of the component (B) in the detergent composition of the present invention is not particularly limited, but is preferably 0.1 to 45% by weight, particularly preferably 0.5 to 20% by weight. If the blending amount of the component (B) is less than 0.1% by weight, the creaminess of the foam quality is poor, and if the blending amount exceeds 45% by weight, the foaming power is lowered, which is not preferable.

The mixing ratio of the component (A) and the component (B) in the detergent composition of the present invention is not particularly limited, but from the viewpoint of foaming power, the component (A) is It is preferable to add more than the component (B).

The detergent composition of the present invention has a pH of 2 to 10, more preferably pH 4 to 8, and especially pH 4 to 7 due to the known acidic or alkaline agents used in conventional detergent compositions.
Is preferably adjusted to pH (pH measurement condition: effective 5% by weight aqueous solution).

In addition to the above-mentioned essential components, the detergent composition of the present invention contains anionic surfactants other than amide ether carboxylic acid, nonionic surfactants and amphoteric surfactants, as long as the effects of the present invention are not impaired. , Various components such as a cationic surfactant and a conditioning component can be blended.

Examples of such anionic surfactants include fatty acid salts, polyoxyalkylene alkyl ether acetate salts,
Examples thereof include alkyl sulfates, polyoxyalkylene alkyl ether sulfates, sulfosuccinamate surfactants, alkyl phosphates, polyoxyalkylene alkyl ether phosphates, and the like, and nonionic surfactants include alkyl polyglucosides. , Sucrose fatty acid esters, polyglycerin fatty acid esters, polyoxyalkylene alkyl ethers, fatty acid alkanolamides, alkylamine oxides, fatty acid polyhydric alcohol esters, etc., and cationic surfactants include linear or branched mono or Examples thereof include di-long-chain alkyl quaternary ammonium salts, mono- or di-long-chain alkyl tertiary amines, and the like, and as amphoteric surfactants, amide amino acid-based surfactants, carbobetaine-based surfactants, sulfobetaine-based surfactants. Activator, a Desulfobetaine-based surfactants, imidazolinium betaine-based surfactants, amino acid-based betaine surfactants, phosphobetaine-based surfactants, and the like, the conditioning components, higher alcohols, silicones, silicone derivatives, lanolin, Examples thereof include squalene, hydrocarbons, protein derivatives, oil agents such as fatty acid esters of polyethylene glycol, cationized cellulose, cationized guar gum, and cationized polymers such as Marcoat 550 (manufactured by Merck).

In addition, other components usually used in detergent compositions, for example, water-soluble polymers such as methyl cellulose, hydroxyethyl cellulose, carboxyvinyl polymer, and polysaccharides such as xanthan gum; polyoxyalkylene sorbitan ester, polyoxyethylene glycol. Viscosity modifiers such as distearate and ethanol; Chelating agents such as ethylenediaminetetraacetic acid (EDTA) and phosphonates; Preservatives such as methylparaben and butylparaben; Nutritional components such as vitamins and their precursors, lecithin, gelatin, etc. Animal and plant extracts or derivatives thereof; polymer fine powders such as nylon and polyethylene; anti-inflammatory agents such as potassium glycyrrhizinate; fungicides and anti-dandruff agents such as triclosan, trichlorocarban, octopirox, zinc pyrithione;
An antioxidant such as dibutylhydroxytoluene; a pearling agent, an ultraviolet absorber, a pH adjusting agent, a dye, a fragrance, etc. may be added, if necessary, within a range that does not impair the effects of the present invention.

The detergent composition of the present invention can be applied to detergents for skin and hair, as well as detergents for various purposes such as detergents for dishes, detergents for clothes and foam baths.
In this case, the total amount of the component (A) and other surfactants added, as the surfactant in the entire composition,
The solid dosage form is preferably 30% by weight or more, the paste dosage form is 20% by weight or more, and the liquid dosage form is preferably 10% by weight or more.

[0040]

The present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.

Synthesis Example 1 Synthesis of amide ether carboxylate containing amide ether: Of methyl laurate 214.4 g (1 mol), monoethanolamine 61.7 g (1.02 mol) and sodium methoxide
88.2 g of ethylene oxide was added to the product obtained by heating 15.3 g of a 30 wt% methanol solution at 90 ° C. and 50 mmHg for 5 hours.
(2 mol) was introduced at 100 to 110 ° C. and a gauge pressure of 0 to 3.5 atm. 331 g of the reaction mixture was heated to 70-75 ° C and 174.8 g (1.5 mol) of sodium monochloroacetate (SMCA) and 65.2 g of solid sodium hydroxide were added over 4 hours. SM
CA and sodium hydroxide were divided into 5 parts and added at the start of the reaction and at 1, 2, 3, and 4 hours after the start of the reaction. After the addition at the 4th hour, the mixture was aged for 1 hour. Next, the reaction temperature was adjusted to 85 ° C., 5.3 g of water was added, and the mixture was aged for another 1 hour.
g was obtained. To this reaction mixture was added 500 g of water, and the mixture was added at 90 ° C to 36 g.
% Aqueous solution of hydrochloric acid was added to adjust the pH to 2.8, and the mixture was stirred for 1 hour and then allowed to stand for 1 hour for layer separation to obtain 545 g of an acid type product.
This acid type compound was adjusted to pH 7 with 30% aqueous sodium hydroxide solution.
Then, water was added to form a transparent solution to obtain an amide ether derivative mixture 2 shown in Table 1.

Synthesis Examples 2 to 6 Synthesis of Amido Ether Carboxylate Containing Amido Ether: In the same manner as in Synthesis Example 1, amide ether derivative mixtures 1, 3, 5 and 6 shown in Table 1 were obtained. In addition, without conversion to the acid form and purification, use a 30% aqueous sodium hydroxide solution after the reaction.
Table 1 is the same as Synthesis Example 1 except that the pH is kept at 7.
The amide ether derivative mixture 4 shown in was obtained.

Synthesis Example 7 Synthesis of Amido Ether Carboxylate Containing Amido Ether: The acid type product obtained in Synthesis Example 1 was neutralized to pH 6 to 7 with a 30% aqueous magnesium hydroxide suspension, and water was added. The mixture was added to give a clear solution, and the amide ether derivative mixture 10 shown in Table 1 was obtained.

Comparative Synthesis Example 1 Synthesis of Amido Ether Carboxylate Containing Glycerin Derivative: Purified coconut oil 510.6 g (2.2 mol) was dissolved at 35 ° C. Next, 138.8 g (2.3 mol) of monoethanolamine and 5.1 g of a 30 wt% methanol solution of sodium methoxide were added to 70 parts.
298 g (6.75 mol) of ethylene oxide was added to the product obtained by heating at 105 ° C. for 2 hours and at 105 ° C. for 6 hours to 100 to 11
It was introduced at 0 ° C. and a gauge pressure of 0 to 3.5 atm over 30 minutes. 675 g of the reaction mixture was heated to 70 to 75 ° C. and 281.7 g of SMCA (2.41
Mol) and 105.1 g of solid sodium hydroxide were added over 4 hours. SMCA and sodium hydroxide were divided into 5 portions and added at the start of the reaction and at 1, 2, 3, and 4 hours after the start of the reaction. After the addition at the 4th hour, the mixture was aged for 1 hour. Next, the reaction temperature is set to 85 ° C., 5 g of water is added, and the mixture is aged for 1 hour,
1039 g of reaction mixture was obtained. To this reaction mixture, 500 g of water was added, and a 36% hydrochloric acid aqueous solution was added at 50 ° C. to adjust the pH to 7, and the mixture was diluted with water until a transparent solution was obtained to obtain an amide ether derivative mixture 9 shown in Table 1.

[0045]

[Table 1]

Example 1 A detergent composition having the composition shown in Table 2 was prepared, and the foaming amount, foam quality and skin irritation of each was evaluated. The results are shown in Table 2. In addition, the blending weight% shown in Table 2 is a value of the effective component of the activator (the amide ether carboxylates are solid components). The pH was adjusted with an aqueous sodium hydroxide solution and citric acid.

<Evaluation Method> The foaming amount and foam quality were as follows: 1 g of the cleaning agent was applied to 20 g (15 cm) of hair of a healthy Japanese woman,
It was bubbled for minutes and evaluated by 20 professional panelists according to the following evaluation criteria. The results are shown in Table 2 from the average score of 20 persons according to the following criteria. For skin irritation, each cleaning composition was applied to the healthy skin of 5 guinea pigs 4 times, and the reaction of the 4th time was evaluated according to the following evaluation criteria. The results are shown in Table 2 from the average score of 5 animals according to the following criteria.

<Standard> (1) foaming amount A. Evaluation Very good lather ... score 4 Good lather ... score 3 Foaming but slightly lacking ... Score 2 Poor bubbling ・ ・ ・ ・ Score 1 B. Judgment Average score 3.5-4.0 ・ ・ ・ ◎ Average score 2.5-3.4 ・ ・ ・ ○ Average score 1.5-2.4 ... △ Average score 1.0-1.4 ... ×

[0049] (2) foam quality A. Evaluation The foam quality is creamy and slides very well ... Score 4 The quality of the foam is creamy and slips .... Score 3 The quality of the foam is rather coarse and it does not slip easily ... score 2 The foam quality is rough and does not slip .... Score 1 B. Judgment Average score 3.5-4.0 ・ ・ ・ ◎ Average score 2.5-3.4 ・ ・ ・ ○ Average score 1.5-2.4 ... △ Average score 1.0-1.4 ... ×

(3) Skin irritation A. Evaluation No irritation (no reaction was observed) ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ Score 5 Slight irritation (slight erythema was observed) ・ ・ ・ ・ ・ Score 4 Weak irritation (clear erythema was observed)・ ・ ・ ・ ・ ・ ・ ・ Score 3 Moderate irritability (clear erythema with edema) ・ ・ ・ ・ ・ ・ Score 2 Strong stimulus (clear erythema with necrosis or asphyxia) ・ Score 1 B. Judgment average score 3.5 to 5.0 ・ ・ ・ ○ Average score 2.5 to 3.4 ・ ・ ・ △ Average score 1.0 to 2.4 ・ ・ ・ ×

[0051]

[Table 2]

[0052]

[0053]

[0054]

[0055]

Example 2 A dishwashing detergent having the following composition and having a pH of 6.4 was prepared. It was hypoallergenic to the skin, and was excellent in detergency, foaming property, foam quality, and hand feel after washing.

[Table 3]                                                   (weight%) Amide ether derivative mixture 1 15 Sodium lauryl glyceryl ether sulfonate 5 Ethanol 2 Fragrance 0.2 Citric acid Sodium hydroxide suitable amount Ion exchange water balance

[0057]

Example 3 A body shampoo of pH 7.0 having the following composition was prepared. This product was hypoallergenic to the skin and was excellent in foamability and foam quality.

[Table 4]                                                 (weight%) Amide ether derivative mixture 2 3 Amide ether derivative mixture 10 5 Sodium α-olefin sulfonate   [After sulfonation of Dialen 124 (manufactured by Mitsubishi Kasei)    Neutralized] 3 Dodecyl polyglucoside 3 N-lauroyl-N′-carboxymethyl-N′-    (2-hydroxyethyl) ethylenediamine Na 2 Propylene glycol 2 Fragrance 0.4 Citric acid Sodium hydroxide suitable amount Ion exchange water balance

[0059]

[0060]

[0061]

EFFECTS OF THE INVENTION The detergent composition of the present invention has little irritation to the skin and the like, has excellent foaming properties, and has a creamy foam quality.

─────────────────────────────────────────────────── --- Continuation of the front page (56) References JP-A-5-156281 (JP, A) JP-A-2-175799 (JP, A) JP-A-6-1997 (JP, A) JP-A-58- 7495 (JP, A) JP 63-291996 (JP, A) JP 6-16534 (JP, A) JP 60-261536 (JP, A) European Patent Application Publication 102118 (EP, A 1) (58) Fields investigated (Int.Cl. ⁷ , DB name) C11D 1/00-17/08 A61K 7/00 A61K 7/075 A61K 7/50

Claims (6)

(57) [Claims] 1. The following components (A) and (B) are added to (A) :( B) = 95: 5.
Detergent composition containing at a weight ratio of 5 to 95 : (A) an amide ether carboxylic acid represented by the general formula (1) or a salt thereof and an amide ether represented by the general formula (2),
(1) :( 2) = 93: 7 to 85:15 in total 50 by weight ratio in solid content
Amide ether derivative mixture containing at least 5% by weight and containing 5% by weight or less of the glycerin derivative represented by the general formula (3) in the solid content. (In the formula, R ¹ represents a linear or branched alkyl group or alkenyl group having 5 to 23 carbon atoms or a phenyl group substituted with such an alkyl group, R ² represents a hydrogen atom,-(C
H ₂ CH ₂ O) _n CH ₂ COOM,-(CH ₂ CH ₂ O) _m H or an alkyl group having 1 to 3 carbon atoms, M is a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium, an alkanolamine Or a basic amino acid, n and m may be the same or different and each represents a number of 1 to 20, R ³ is a hydrogen atom, — (CH ₂ CH _2
2 O) _m H or an alkyl group having 1 to 3 carbon atoms, R ⁴ represents a hydrogen atom,-(CH ₂ CH ₂ O) _n CH ₂ COOM or-(CH ₂ CH ₂ O) _m H. R ¹ , M, n and m in the general formulas (1), (2) and (3) may be the same or different. ) (B) alkyl sulfosuccinic acid ester, polyoxyalkylene alkyl ether sulfosuccinic acid ester, polyoxyalkylene fatty acid amide ether sulfuric acid, monoglyceride sulfuric acid, α-olefin sulfonic acid, acylated isethionic acid, alkyl glyceryl ether sulfonic acid,
Anionic surfactant selected from acylated glutamic acid, alkanesulfonic acid, and salts thereof. 2. In the general formulas (1) and (2), R ¹ is a linear or branched alkyl group or alkenyl group having 7 to 17 carbon atoms or a phenyl group substituted with such an alkyl group. , R ² is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n and m are each a number of 1 to 10. Wherein component (A), represented by the general formula (1) or an amide ether carboxylic acid salts thereof and Formula amides ether represented by (2), solid content in the total of 60 wt% The cleaning composition according to claim 1 or 2, which is an amide ether derivative mixture containing the glycerin derivative represented by the general formula (3) in an amount of 3% by weight or less based on the solid content. 4. The cleaning composition according to claim 3, wherein the component (A) is an amide ether derivative mixture which does not substantially contain the glycerin derivative represented by the general formula (3). 5. The cleaning composition according to any one of claims 1 to 4, wherein the component (A) is made from a fatty acid alkanolamide synthesized from a fatty acid lower alcohol ester. 6. The detergent composition according to claim 1, which has a pH of 4 to 7.