JPH09137190A - Detergent composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a detergent compsn. which is excellent in foaming properties, gives light foams, and exhibits quick foam breaking by incorporating a specific amide ether deriv. mixture and an N-alkylamidoalkanolsulfuric ester or its salt into the same. SOLUTION: This compsn. contains an amide ether deriv. mixture which contains 50wt.% or higher (based on the solid content of the mixture) component comprising an amide ether carboxylic acid represented by formula I or its salt and an amide ether represented by formula II in a wt. ratio of (99:1)-(10:90) and 5wt.% or lower (based on the solid content of the mixture) glycerin deriv. represented by formula III [wherein R<1> is a 5-23C alkyl; R<2> and R<3> are each H or a 1-3C alkyl; M is H or an alkali or an alkaline earth metal; R<4> is H or (CH2 CH2 O)m H; and (n) and (m) are each 1-20] and an N- alkylamidoalkanolsulfuric ester or its salt represented by formula IV (wherein R<5> is a 6-22C alkyl; R<6> is H or methyl; R<7> is a 1-5C alkylene; R<8> O is a 2-3C oxyalkylene; Ma is Na, Ca, or ammonium; and l is 0-20).

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 having excellent foaming properties, light foam quality, and quick foam breakage.

[0002]

2. Description of the Related Art
Alkyl sulfate, polyoxyethylene alkyl sulfate, alkyl benzene sulfonate, α,
-Anionic surfactants such as olefin sulfonates are widely used. However, these anionic surfactants have varying degrees of skin irritation, and there is a problem that the skin becomes rough when used continuously.

On the other hand, as surfactants having low irritation, alkyl saccharide surfactants, sulfosuccinic surfactants, ether carboxylic acid surfactants, amide ether carboxylic acid surfactants and the like are known. Have been. However, although alkyl saccharide-based surfactants have high foaming properties, they have strong blemishes during washing and rinsing, and are therefore used in combination with a conditioning agent such as a cationic polymer (Japanese Patent Laid-Open No. 2-42013). Although it has been proposed, it is not technically easy to mix a large amount into a shampoo or the like. In addition, sulfosuccinic surfactants alone have poor foaming properties, and a method of using them 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-based surfactants and amide ether carboxylic acid-based surfactants also have poor foaming properties, and are used only as auxiliary surfactants in detergents that require high foaming properties. ing.

[0004] This amide ether carboxylic acid type surfactant is commercially available from Chem Y in Germany under the trade name of "Akipo".
In addition to the raw material amide ether, polyoxyethylene glyceryl ether, which is an impurity derived from the raw material,
Polyoxyethylene glyceryl ether carboxylic acid, inorganic salts and the like are included.

[0005] Techniques which have heretofore been known for application of amide ether carboxylic acid surfactants to detergents include amide ether carboxylic acids, polyoxyethylene alkyl sulfates, fatty acid diethanolamides, higher alcohol alkylene oxides. Detergent in which an adduct, acyl sarcosinate and the like are combined (European Patent No. 102118), and a method in which an amide ether carboxylic acid surfactant is used in combination with a polyoxyethylene alkyl sulfate (European Patent No. 215504) ), A foam bath in which an amide ether carboxylic acid starting from an oil or fat is combined with lauryl sulfate, lauryl ether sulfate, alkyl ether carboxylic acid, or a quaternary product obtained by reacting lauric acid with glycidyltrimethylammonium chloride. Agents, shampoo agents, shower agents and the like (JP-B 63-291996, JP-EP 2
No. 19893), and a detergent containing soap as a main component and an amide ether carboxylic acid or an alkyl ether carboxylate (US Pat. No. 4,865,575).

[0006] However, none of these detergents has been satisfactory in terms of foaming properties. Therefore, there has been a demand for the development of a cleaning agent having low irritation on the skin and the like, excellent safety, high foaming properties, light foam quality, and quick foam breakage.

[0007]

Under these circumstances, the present inventors have studied a cleaning agent containing amide ether carboxylic acid and found that impurities such as polyoxyethylene glyceryl ether and polyoxyethylene glyceryl derived from raw materials were used. It was found that a foam containing a large amount of ether carboxylic acid or pure amide ether carboxylic acid itself had poor foaming properties. 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. It was found that a detergent that is hypoallergenic and safe, has a high foaming property, is light in foam quality, and has a quick foam break,
The present invention has been completed.

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) = 99: 1 to 1: 9 in a weight ratio of 50
An amide ether derivative mixture containing at least 5% by weight of a glycerin derivative represented by the general formula (3) and not more than 5% by weight of the solid content.

[0009]

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(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 alkanol ammonium Or a group consisting of a basic amino acid and one hydrogen atom, 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, R ⁴ is a hydrogen atom,
Indicates (CH ₂ CH ₂ O) _n CH ₂ COOM or-(CH ₂ CH ₂ O) _m H. General formula
R ¹ , M, n and m in (1), (2) and (3) may be the same or different. ) (B) N-alkylamide alkanol sulfuric acid ester represented by the general formula (4) or a salt thereof

[0011]

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(In the formula, R ⁵ represents a linear or branched alkyl or alkenyl group having ⁶ to 22 carbon atoms, R ⁶ represents a linear or branched alkyl group having 1 to 22 carbon atoms, or 2 carbon atoms. ~ 22 is a linear or branched alkenyl group or a hydrogen atom, R ⁷ is a linear or branched alkylene group having 1 to 5 carbon atoms, and R ⁸ O is an oxyalkylene group having 2 or 3 carbon atoms. , 1 is the average number of moles of the oxyalkylene group added, and is a number between 0 and 20, and Ma is a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium,
Alkanol ammonium having 2 to 9 carbon atoms, alkyl ammonium having 1 to 22 carbon atoms, alkenyl ammonium having 2 to 22 carbon atoms, alkyl having 1 to 18 carbon atoms, or alkenyl-substituted pyridinium having 2 to 18 carbon atoms or basic A group consisting of an amino acid and one hydrogen atom is shown. )

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION Component (A) used in the present invention
In the amide ether derivative mixture
R in (2)¹As an alkyl group having 7 to 17 carbon atoms
Substituted with an alkenyl group or such an alkyl group.
Phenyl groups such as heptyl, nonyl, unde
Sil group, dodecyl group, tridecyl group, pentadecyl group,
Heptadecyl group, heptadecenyl group, etc., especially 11 to 11 carbon atoms
13 alkyl groups are preferred, R ^TwoAs a hydrogen atom or
Is preferably an alkyl group having 1 to 3 carbon atoms, and n and m
As for the number, 1-15, more preferably 1-10, especially 2-7 is preferable.
As M, for example, sodium, potassium, magne
Sium, calcium, monoethanolamine, dietano
Amine, triethanolamine, arginine, lysine
And the like.

Preferred examples of the amide ether carboxylic acid or the salt thereof (1) in the component (A) include, for example, monoethanolamide capric acid polyoxyethylene ether acetic acid (n = 1 to 15) and monoethanolamide polylaurate. 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-
Methylethanolamide polyoxyethylene ether acetic acid (n = 1 to 15), myristic acid-N-methylethanolamide 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), isopropanolamide polyoxyethylene ether acetic acid myristic acid (n = 1 to 15), isopropanolamide polyoxyethylene ether acetic acid palmitate (n = 1 to 15), isopropanolamide polyoxyethylene ether acetic acid stearic 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),
Or a salt thereof, as more preferred specific examples, 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 1)
10) and the like and salts thereof. Particularly preferred specific examples 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 examples of the amide ether (2) in the component (A) include, for example, monoethanolamide polyoxyethylene ether of capric acid (n = 1 to 15) and monoethanolamide polyoxyethylene ether of lauric acid (n = 1 to 15), myristic acid monoethanolamide polyoxyethylene ether (n = 1 to 15), palmitic acid monoethanolamide polyoxyethylene ether (n = 1 to 15), stearic acid monoethanolamide polyoxyethylene ether (n = 1-15), oleic acid monoethanolamide polyoxyethylene ether (n = 1-20), behenic acid monoethanolamide polyoxyethylene ether (n = 1-20), 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), isopropanolamide polyoxyethylene ether palmitate (n = 1 to 15), isopropanolamide polyoxyethylene ether stearic acid (n =
1-15), 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, and particularly preferred specific examples are lauric acid monoethanolamide polyoxyethylene ether (n = 2 to 7) and myristic acid Ethanolamide polyoxyethylene ether (n = 2 to 7) may be mentioned.

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). Need to be more than 60% by weight
It is preferably at least 70% by weight, particularly preferably at least 80% by weight. If the total content of these components is less than 50% by weight of the solid content, the foaming properties are 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) = 99: 1 to 10:90. It is necessary that the ratio be in the range of 95: 5 to 60:40, particularly 92: 8 to 70:30. If the ratio of the amide ether (2) is less than the above range (less than 1% by weight), the foaming property is poor, and if it exceeds the above range (more than 90% by weight), the whisking and rinsing are strong, Not preferred.

Further, the content of the glycerin derivative (3) in the component (A) must be 5% by weight or less in the solid content of the component (A), and 3% by weight or less, particularly substantially Preferably, it is not included. When the content of the glycerin derivative (3) exceeds 5% by weight in the solid content, the foaming property is remarkably reduced, which is not preferable. It is preferable that 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 small.

The method for producing the amide ether derivative mixture as the component (A) is not particularly limited, and it can be directly produced by reacting a part of the amide ether. It can be added later. 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 or oil as a starting material, and an alkanolamide from a fatty acid Methods and the like. Among them, a method of producing a fatty acid lower alcohol ester such as a fatty acid methyl ester as a starting material is preferable because the coloring is less and the glycerin derivative which is an impurity is not substantially contained. In the case of other methods, for example, a method in which a fat or oil having a coconut oil fatty acid composition is used as a starting material and directly converted into an alkanolamide and then subjected to alkoxylation and carboxymethylation, a large amount of a glycerin derivative derived from the fat or oil is produced and the compound (1)
And (2) are not practically preferable because the yield is low.
In the case of a method in which a fatty acid is reacted with an alkanolamine as a starting material to form an alkanolamide, the coloration is remarkable due to the high temperature of the amidation reaction, which is not preferable.
The ratio of the amide ether carboxylic acid (1) to the amide ether (2) in the amide ether derivative mixture of the component (A) is determined by the molar ratio and the mixing method when the amide ether (2) is reacted with an alkali monohaloacetate or the like. Can be adjusted by selecting the reaction conditions.

These components (A) can be used alone or in combination of two or more. The content of the component (A) in the detergent composition of the present invention is not particularly limited, but is preferably 1% by weight or more, particularly preferably 5% by weight or more from the viewpoint of foaming property.

The component (B) used in the present invention, N-a
As rukylamido alkanol sulfate or its salt
In the general formula (4), R^FiveHas 6 to 22 carbon atoms
The straight-chain or branched-chain alkyl group of
From the viewpoint, it is preferably a linear alkyl group having 8 to 18 carbon atoms.
Is more preferable. R^FiveExamples of the alkyl group of
Hexyl group, octyl group, decyl group, dodecyl group, tet
Radecyl group, hexadecyl group, octadecyl group, isos
Examples of the aryl group include a thearyl group, an eicosyl group, and a docosyl group, and R
^FiveAn octadecenyl group is an example of the alkenyl group of
I can do it. R⁶Examples of the alkyl group of are a methyl group,
Ethyl group, propyl group, butyl group and R ^FiveShown as an example of
And an alkyl group represented by R⁶Alkenyl
Examples of groups include octadecenyl groups. this
Of these, a hydrogen atom or a methyl group is preferable, and a hydrogen atom is particularly preferable.
Is preferred from the viewpoints of foaming property, safety and chemical stability.
R⁷Is a straight-chain or branched chain alkyl group having 1 to 5 carbon atoms.
It is preferably a alkylene group, specifically methylene.
Group, pentamethylene group (pentylene group), 2-methylbutane
Tylene group is mentioned, and methylene group is the foaming property of surfactant.
And particularly preferable in terms of chemical stability. R⁸As O
Is -CH_TwoCH_TwoO- (oxyethylene group) or -CH_TwoCH (CH_Three) O-
(Oxypropylene group) is preferred, and oxyalkylene
The group is a mixture of two or more oxyalkylene groups
Is also good. As l, a number between 0 and 10 is preferable, and
Preferably it is 0. As for Ma, the foamability of the surfactant
From the point, ammonium, sodium, potassium, magne
Sium, calcium or alkanol having 2 to 9 total carbon atoms
Ammonium is preferred, ammonium, sodium,
Calcium or triethanol ammonium is especially preferred
New

The component (B) used in the present invention, N-a
Preference is given to rukylamido alkanol sulfate or its salts.
Suitable examples are those belonging to the following groups A to E. A. R in general formula (4)^FiveIs a straight chain having 6 to 22 carbon atoms or
Branched chain alkyl group, R ⁶Is a hydrogen atom or methyl
Group, preferably hydrogen atom, R⁷Is a straight chain having 1 to 5 carbon atoms
Or a branched alkylene group, R⁸O is Oechi
Ren group or oxypropylene group, l is between 0 and 10
Number, Ma, ammonium, sodium, potassium, ma
Gnesium, calcium or alkano having 2 to 9 total carbons
Those that are ammonium chloride. B. R in general formula (4)^FiveIs a straight-chain alkyl having 8 to 18 carbon atoms
Group, R⁶Is a hydrogen atom or a methyl group, R⁷But the carbon number
1-5 straight chain alkylene groups, l is 0, Ma is ammoniu
Mu, sodium, potassium, magnesium, calcium
Or that which is triethanol ammonium. C. R in general formula (4)^FiveIs a straight-chain alkyl having 8 to 18 carbon atoms
Group, R⁶Is a hydrogen atom, R⁷Is a straight or branched chain having 1 to 5 carbon atoms
Branched alkylene group, l is 0, Ma is ammonium,
Thorium or triethanol ammonium. D. R in general formula (4)^FiveIs a straight-chain alkyl having 8 to 18 carbon atoms
Group, R⁶Is a hydrogen atom, R⁷But methylene group, pentamethyl
Group or 2-methylbutylene group, preferably methylene
Group, l is 0, Ma is ammonium, sodium, kaliu
Aluminum, magnesium, calcium or triethanolamine
What is monium. E. FIG. R in general formula (4)^FiveIs a straight-chain alkyl having 8 to 18 carbon atoms
Group, R⁶Is a hydrogen atom, R⁷Is a methylene group, l is 0, Ma is
Ammonium, sodium, potassium, magnesium, calcium
What is lucium or triethanol ammonium.

Further, as a more preferable example of the component (B), CH ₃ (CH ₂ ) ₁₁ NHCOCH ₂ OSO ₃ NH ₄ , CH ₃ (CH ₂ ) ₁₁ NHCO (CH ₂ ) ₅
OSO ₃ NH ₄ ,, CH ₃ (CH ₂ ) ₉ NHCOCH ₂ OSO ₃ NH ₄ ,, CH ₃ (CH ₂ ) ₁₁ N (CH ₃ ) C
OCH ₂ OSO ₃ Na, CH ₃ (CH ₂ ) ₁₁ NHCOCH ₂ OSO ₃ Na, CH ₃ (CH ₂ ) ₁₁ NHCO
(CH ₂ ) ₂ OSO ₃ Na, CH ₃ (CH ₂ ) ₁₁ NHCO (CH ₂ ) ₃ OSO ₃ Na, CH ₃ (CH ₂ )
₁₁ NHCO (CH ₂ ) ₄ OSO ₃ Na, CH ₃ (CH ₂ ) ₁₁ NHCO (CH ₂ ) ₅ OSO ₃ Na, CH ₃
(CH ₂ ) ₁₁ NHCOCH ₂ CH (CH ₃ ) CH ₂ CH ₂ OSO ₃ Na, CH ₃ (CH ₂ ) ₁₁ NHCOCH
₂ CH (CH ₃ ) CH ₂ CH ₂ OSO ₃ K, CH ₃ (CH ₂ ) ₁₃ NHCO (CH ₂ ) ₃ OSO ₃ Na, CH
₃ (CH ₂ ) ₁₃ NHCO (CH ₂ ) ₃ OSO ₃ NH ₄ , CH ₃ (CH ₂ ) ₁₃ NHCO (CH ₂ ) ₄ OSO
₃ NH ₄ , CH ₃ (CH ₂ ) ₉ NHCO (CH ₂ ) ₃ OSO ₃ Na, CH ₃ (CH ₂ ) ₉ NHCO (CH ₂ )
₃ OSO ₃ HN (CH ₂ CH ₂ OH) ₃ , CH ₃ (CH ₂ ) ₉ NHCO (CH ₂ ) ₃ OSO ₃ H ₂ N (CH ₂ C
H ₂ OH) ₂ , CH ₃ (CH ₂ ) ₉ NHCO (CH ₂ ) ₃ OSO ₃ H ₃ NCH ₂ CH ₂ OH, CH ₃ (C
H ₂ ) ₉ NHCO (CH ₂ ) ₅ OSO ₃ Na, CH ₃ (CH ₂ ) ₇ NHCO (CH ₂ ) ₄ OSO ₃ Na, CH
₃ (CH ₂ ) ₁₁ N (CH ₃ ) CO (CH ₂ ) ₃ OSO ₃ Na, CH ₃ (CH ₂ ) ₁₃ N (CH ₃ ) CO (CH
₂ ) ₄ OSO ₃ Na, CH ₃ (CH ₂ ) ₁₁ NHCO (CH ₂ ) ₃ OCH ₂ CH ₂ OSO ₃ Na, CH ₃ (C
H ₂ ) ₁₁ NHCO (CH ₂ ) ₄ OCH ₂ CH (CH ₃ ) OSO ₃ Na, CH ₃ (CH ₂ ) ₁₁ NHCOCH
₂ OSO ₃ K, [CH ₃ (CH ₂ ) ₁₁ NHCOCH ₂ OSO ₃ ] ₂ Ca and CH ₃ (CH ₂ ) ₉ NHCO
(CH ₂ ) ₄ O (CH ₂ CH ₂ O) ₅ SO ₃ Na.

The method for producing the N-alkylamidoalkanol sulfuric acid ester or its salt which is the component (B) of the present invention is as follows:
The method described in JP-A-7-267917 can be mentioned.

These components (B) can be used alone or in combination of two or more. The content of the component (B) in the detergent composition of the present invention is not particularly limited, but is preferably 1 to 50% by weight, particularly 1 to 35% by weight. If the blending amount of the component (B) is less than 1% by weight, the foaming power is inferior, and if the blending amount exceeds 50% by weight, the foam quality is heavy and the finger passage is deteriorated, which is not preferable.

Further, the mixing ratio of the component (A) and the component (B) in the cleaning composition of the present invention is not particularly limited.

The detergent composition of the present invention has a pH of 2 to 10, more preferably pH 4 to 8, and especially pH 5 to 8 due to the known acidic or alkaline chemicals used in conventional detergent compositions.
(PH measurement conditions: 5% by weight aqueous solution of active ingredient).

The detergent composition of the present invention contains, in addition to the above-mentioned essential components, anions other than amide ether carboxylic acid or a salt thereof and N-alkylamide alkanol sulfuric acid ester or a salt thereof, as long as the effects of the present invention are not impaired. Various components such as surfactants, nonionic surfactants, amphoteric surfactants, cationic surfactants and conditioning components can be added.

Examples of such anionic surfactants include fatty acid salts, polyoxyalkylene alkyl ether acetates,
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 methylcellulose, hydroxyethylcellulose, carboxyvinyl polymer, 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 pearlizing agent, an ultraviolet absorber, a pH adjuster, a coloring matter, a fragrance, and the like can be blended as needed within a range not to impair the effects of the present invention.

The cleaning composition of the present invention can be applied to various purposes such as cleaning agents for skin and hair, as well as cleaning agents for dishes, cleaning agents for clothes, foam baths and the like.
In this case, the sum of the component (A) and other surfactants, the total amount of surfactants in the entire composition,
The solid dosage form is preferably 25% by weight or more, the paste dosage form is preferably 15% by weight or more, and the liquid dosage form is preferably 5% by weight or more.

[0032]

EFFECT OF THE INVENTION The detergent composition of the present invention has excellent foaming properties, light foam quality, and quick foam breakage.

[0033]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the invention is limited thereto.

Synthesis Example 1 Synthesis of amide ether carboxylate containing amide ether: 214.4 g of methyl laurate
(1 mol), 61.7 g (1.02 mol) of monoethanolamine
And sodium methoxide 30% by weight methanol solution 1
5.3 g was heated at 90 ° C. and 50 mmHg for 5 hours, and 88.2 g (2 mol) of ethylene oxide was added to 100 to 110 g of the product obtained.
C and a pressure of 0 to 3.5 atm. 331 g of reaction mixture
Is heated to 70-75 ℃, sodium monochloroacetate (SMC
A) 174.8 g (1.5 mol) and solid sodium hydroxide 65.2
g was added over 4 hours. SMCA and sodium hydroxide are divided into 5 parts at the start of the reaction and 1, 2, 3, 4 after the start of the reaction.
Added at time. After the addition at the 4th hour, the mixture was aged for 1 hour. Next, the reaction temperature was raised to 85 ° C., 5.3 g of water was added, and the mixture was aged for 1 hour to obtain 592 g of a reaction mixture. To this reaction mixture was added 500 g of water, and at 90 ° C., a 36% hydrochloric acid aqueous solution was added.
The mixture was adjusted to H2.8, stirred for 1 hour, and then allowed to stand for 1 hour for layer separation to obtain 545 g of an acid type product. 30% of this acid type compound
The pH was adjusted to 7 with an aqueous sodium hydroxide solution, and water was added to form a transparent solution, whereby an amide ether derivative mixture 2 shown in Table 1 was obtained.

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 shown in Table 1 were used.
And 6 were obtained. Further, the amide ether derivative mixture 4 shown in Table 1 was obtained in the same manner as in Synthesis Example 1 except that the acid form was not converted and purified, and the pH was kept at 7 with a 30% sodium hydroxide aqueous solution after the reaction.

Synthesis Example 7 Synthesis of amide ether carboxylate containing amide 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 Carboxylic Acid Sodium Salt from which Amido Ether was Removed: In the same manner as in Synthesis Example 1, a carboxymethylation reaction mixture was obtained, and then ethanol was added thereto to precipitate a solid. After filtration, ethanol was added to the filtered product for washing to remove amide ether. Further, the mixture was made into an acid form in the same manner as in Synthesis Example 1 and then neutralized with sodium hydroxide to obtain an amide ether derivative mixture 7
I got

Comparative Synthesis Example 2 Synthesis of Amido Ether Carboxylic Acid Sodium Salt Containing Amido Ether: Up to amide ether was obtained in the same manner as in Synthesis Example 1, and the molar ratio of SMCA to amide ether and solid sodium hydroxide was varied. The reaction was carried out under the condition of 0.05, and then the same treatment was carried out to obtain an amide ether derivative mixture 8.

Comparative Synthesis Example 3 Synthesis of Amido Ether Carboxylate Containing Glycerin Derivative: Purified Coconut Oil 510.6 g
(2.2 mol) was melted at 35 ° C. Then, 138.8 g (2.3 mol) of monoethanolamine and 5.1 g of a 30 wt% methanol solution of sodium methoxide were heated at 70 ° C for 2 hours at 105 ° C.
The product obtained by heating at 60 ° C. for 6 hours was charged with 298 g (6.75 mol) of ethylene oxide at 100 to 110 ° C. and a gauge pressure of 0 to 3.5.
It was introduced at atmospheric pressure over 30 minutes. 675 g of reaction mixture 70-75
After heating to 0 ° C., 281.7 g (2.41 mol) of SMCA and 105.1 g of solid sodium hydroxide were added over 4 hours. SMCA 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 g of water was added, and the mixture was aged for 1 hour to obtain 1039 g of a reaction mixture. 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.

[0040]

[Table 1]

Example 1 A detergent composition having the composition shown in Table 2 was prepared, and the foaming amount, foam quality and foam breakage were evaluated for each. Table 2 shows the results. The blending weight% shown in Table 2 is
It is the value of the effective component of the activator (solid content of amide ether carboxylates). The pH was adjusted with an aqueous sodium hydroxide solution and citric acid.

<Evaluation Method> The amount of foam, the quality of foam, and the speed of foam breakage were measured with 20 g (15 cm) of hair of a healthy Japanese woman and cleaning agent 1
g was applied, and the mixture was foamed for 1 minute and evaluated by 20 professional panelists according to the following evaluation criteria. The results are shown in Table 2 based on the average score of 20 subjects according to the following criteria.

<Reference> (1) Foaming amount A. Evaluation Very good lather ... score 4 Good lather ... score 3 lather but slightly lack ... score 2 poor lather ... score 1 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 ・ ・ ・ ×

(2) Foam quality A. Evaluation: The foam quality is very light and slips well .... Score 4 The foam quality is light and well slips ..... Score 3 The foam quality is slightly heavy and does not slip. Score 2 The foam quality is heavy 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) Out of foam A. Evaluation Very fast defoaming ... score 4 Fast defoaming ... score 3 Slowly defoaming ... score 2 Slow defoaming ... score 1 B. Judgment Average score 3.5 to 4.0 ・ ・ ・ ◎ Average score 2.5 to 3.4 ・ ・ ・ ○ Average score 1.5 to 2.4 ・ ・ ・ △ Average score 1.0 to 1.4 ・ ・ ・ ×

[0046]

[Table 2]

Example 2 (shampoo composition)

[0048]

[Table 3] (% by weight) Amide ether derivative mixture 3 14 N-dodecyl-1-sulfoxyacetamide Na 10 Lauric acid monoethanolamide 3 Perfume 0.2 Citric acid Adequate amount Sodium hydroxide Adequate amount Ion-exchanged water Balance 100

Example 3 (body shampoo composition)

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(Table 4) (wt%) Amide ether derivative mixture 6 10 N-dodecyl-1-sulfoxyacetamide Na 10 glycerin fatty acid ester (Sunsoft No760, Taiyo Kagaku) 5 Perfume 0.2 Citric acid Adequate amount Sodium hydroxide Adequate amount Ion exchange water balance 100

Example 4 (shampoo composition)

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[Table 5] (wt%) amide ether derivative mixture 4 10 N-dodecyl-1-sulfoxyacetamide K 7 dodecyl polyglucoside 5 lauric acid monoethanolamide 3 perfume 0.2 citric acid proper amount sodium hydroxide proper amount ion exchanged water balance 100

Example 5 (shampoo composition)

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[Table 6] (% by weight) Amide ether derivative mixture 4 10 N-dodecyl-1-sulfoxyacetamide Na 10 Ammonium lauryl sulfate 3 Lauryl amine oxide 2 Perfume 0.2 Citric acid Adequate amount Sodium hydroxide Adequate amount Exchanged water balance 100

Example 6 (dishwashing agent)

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[Table 7] (% by weight) Amide ether derivative mixture 1 15 N-dodecyl-1-sulfoxyacetamide K 5 Lauryl glyceryl ether sulfonate Na 5 Ethanol 2 Fragrance 0.2 Citric acid Adequate amount Sodium hydroxide Adequate amount Exchanged water balance 100

Example 7 (conditioning shampoo composition)

[0058]

(% By weight) Amide ether derivative mixture 3 8 Amide ether derivative mixture 10 5 N-dodecyl-1-sulfoxyacetamide Na 5 dodecyl polyglucoside 2 Palm oil fatty acid amide propyldimethylamino acetic acid betaine 2 Hydrolyzed collagen 0.2. 5 Cationized guar gum (Jaguar C-13-S, manufactured by Celanese Stein Hall) 0.4 Dimethyl polysiloxane (2 million CS) 0.2 Monostearyl trimethyl ammonium chloride 0.2 Ethanol 2 Perfume 0.2 Quent Acid Suitable amount Sodium hydroxide Suitable amount Ion exchange water Balance 100

Example 8 (body shampoo composition)

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(% By weight) Amide ether derivative mixture 2 3 Amide ether derivative mixture 10 5 N-dodecyl-1-sulfoxyacetamide 1 / 2Ca 5 dodecyl polyglucoside 2 sodium α-olefin sulfonate 3 N-lauroyl-N ′ -Carboxymethyl-N '-(2-hydroxyethyl) ethylenediamine Na 2 propylene glycol 2 Perfume 0.2 Citric acid proper amount sodium hydroxide proper amount ion exchanged water balance 100

Example 9 (dishwashing detergent composition)

[0062]

(% By weight) Amide ether derivative mixture 47 N-dodecyl-1-sulfoxyacetamide Na 3 N-dodecyl-1-sulfoxyacetamide K 3 monoglyceride sulfate Na (sulfate neutralization of coconut oil fatty acid monoglyceride 4 Polyoxyethylene (3) Lauryl ether sulfate Na 4 Lauryl dimethylamine oxide 3 Dodecyl polyglucoside 2 Ethanol 2 Magnesium chloride 0.3 Perfume 0.2 Citric acid Adequate amount Sodium hydroxide Adequate amount Exchanged water balance 100

Example 10 (dishwashing detergent composition)

[0064]

[Table 11] (wt%) Amide ether derivative mixture 38 N-dodecyl-1-sulfoxyacetamide 1 / 2Ca 4 N-dodecyl-1-sulfoxyacetamide Na 3 Alkanesulfonic acid Na (Hostafa SAS60, Hoechst) 5 Coconut oil fatty acid amide propyldimethylamino acetic acid betaine 3 Magnesium chloride 0.05 Ethanol 2 Perfume 0.2 Citric acid proper amount sodium hydroxide proper amount ion exchanged water balance 100

The detergent compositions of Examples 2 to 10 are all excellent in foaming property, lightness of foam quality, and defoaming.
The composition of (1) had an excellent feel on the hands after washing or on the hair.

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Claims (8)

[Claims] 1. A cleaning composition comprising 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) = 99: 1 to 10:90 by weight in solid content in total of 50
An amide ether derivative mixture containing at least 5% by weight and the content of the glycerin derivative represented by the general formula (3) is at most 5% by weight in the solid content. (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,-(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, alkali metal, alkaline earth metal, ammonium, alkanol ammonium Or a group consisting of a basic amino acid and one hydrogen atom,
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 a carbon number of 1 to
3 represents an alkyl 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. General formula (1), (2) and (3)
R ¹ , M, n and m in each other may be the same or different. ) (B) N-alkylamide alkanol sulfuric acid ester represented by the general formula (4) or a salt thereof: (In the formula, R ⁵ represents a linear or branched alkyl group or alkenyl group having ⁶ to 22 carbon atoms, and R ⁶ represents 1 to 22 carbon atoms.
Represents a linear or branched alkyl group, a linear or branched alkenyl group having 2 to 22 carbon atoms or a hydrogen atom,
R ⁷ represents a linear or branched alkylene group having 1 to 5 carbon atoms, R ⁸ O represents an oxyalkylene group having 2 or 3 carbon atoms, l represents the average number of added moles of the oxyalkylene group, and 0 Is a number between 20 and 20, Ma is hydrogen atom, alkali metal, alkaline earth metal, ammonium, total carbon number 2 to
9 alkanol ammonium, alkyl ammonium having 1 to 22 carbon atoms, alkenyl ammonium having 2 to 22 carbon atoms, alkyl having 1 to 18 carbon atoms or 2 to 18 carbon atoms
Represents a group consisting of the alkenyl-substituted pyridinium or the basic amino acid and one hydrogen atom. ) 2. In the general formulas (1) and (2), R ¹ is a linear or branched alkyl or alkenyl group having 7 to 17 carbon atoms or a phenyl group substituted with such an alkyl group. And 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. (3) Component (A) is 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) = 95 : A total of 60% by weight or more in solid content in a weight ratio of 5 to 60:40, and a general formula
3. The cleaning composition according to claim 1, wherein the composition is an amide ether derivative mixture in which the content of the glycerin derivative represented by (3) is 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 of a fatty acid alkanolamide synthesized from a fatty acid lower alcohol ester. 6. In the general formula (4), R ⁵ has 6 to 22 carbon atoms.
A linear or branched alkyl group, R ⁶ is a hydrogen atom or a methyl group, R ⁷ is a linear or branched alkylene group having 1 to 5 carbon atoms, R ⁸ O is an oxyethylene group or an oxypropylene group, n Is a number between 0 and 10, Ma is ammonium, sodium, potassium, magnesium, calcium, or an alkanolammonium having a total carbon number of 2 to 9. 6. The cleaning composition according to claim 1. 7. The component (A) is 1 to 50% by weight, and the component (B) is 1 to 50% by weight, based on the detergent composition.
The cleaning composition according to any one of claims 1 to 6. 8. The cleaning composition according to claim 1, which has a pH of 5-8.