JPH107635A - N-alkylamide ether carboxylic acid or its salt, production thereof and detergent composition containing the acid or its salt - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound useful as a surfactant excellent in water solubility, foaming properties, cleaning power, resistance hard water and mild to hair and skin. SOLUTION: This compound is shown by formula I R<1> is a 8-22C alkyl or alkenyl; R<2> is H, a 1-18C alkyl, (AO)a (BO)b H, etc.; R<3> is H or methyl; A and B are each a 2-4C alkylene; M is H, an alkali metal, etc.; (n) is 1-6; (a) and (b) are each 0-20; a+b is 0-20} or its salt. The compound is obtained by reacting an amide ether alcohol of formula II (R<2> ' is H, a 1-18C alkyl, etc.) with an unsaturated compound of formula III (X is CN or COOR<4> ; R<4> is H or an alkyl) in the presence of a basic catalyst to form an amide ether alcohol derivative of formula IV (R<2> ' is H, a 1-18C alkyl, etc.) and hydrolyzing the derivative with a basic or an acidic substance.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a water-soluble, foamed,
The present invention relates to a novel N-alkylamide ether carboxylic acid or a salt thereof, which is excellent in hard water resistance and detergency, is mild on hair and skin, is useful as a detergent, a method for producing the same, and a detergent composition containing the same. .

[0002]

2. Description of the Related Art Among the surfactants, anionic surfactants are widely used as components of detergents generally used in the industrial field and at home. This anionic surfactant has various structures, but recently, an anionic surfactant having good water solubility, good detergency and good foaming, and mild on the skin and hair has been desired. Among the studies corresponding to these, amide ether carboxylic acids that are mild to the skin and a method for producing the same are disclosed in Japanese Patent Publication No. 8-311.
No. 4 discloses this.

[0003] However, these amide ether carboxylic acids are obtained by adding ethylene oxide to fatty acid monoethanolamide and carboxyalkylating it with a monohaloalkanoic acid such as monohaloacetic acid.
Those having an RCONH- group are not preferred because a fatty acid ester of fatty acid monoethanolamide having poor water solubility is formed during the reaction between fatty acid and monoethanolamine and during the addition reaction of ethylene oxide. .

[0004]

DISCLOSURE OF THE INVENTION The present invention has no problem at the time of production, has excellent water solubility even at low temperatures, has good detergency and foaming, and is useful as a mild surfactant for skin and hair. An object of the present invention is to provide a novel N-alkylamide ether carboxylic acid or a salt thereof, a method for producing the same, and a detergent composition containing the same.

[0005]

According to the present invention, there is provided an N-alkylamidoethercarboxylic acid having an amide group and an ether group in a molecule represented by the following general formula (1) or a salt thereof.

Embedded image 中 wherein R ¹ ; a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms R ² ; a hydrogen atom or a linear or branched alkyl or alkenyl group having 1 to 18 carbon atoms, (AO ) a (BO) b
H, or (AO) a (BO) bCH ₂ CHR ³ COOM R ³ ; hydrogen atom or methyl group A, B; same or different linear or branched alkylene group having 2 to 4 carbon atoms M; hydrogen atom, alkali Metal, monovalent alkaline earth metal, ammonium or organic ammonium n; integer of 1 to 6 a, b; number of 0 to 20 each a + b; number of 0 to 20} According to the present invention, General formula (2)

Embedded image 中 wherein, R ¹ ; a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms R ² ′; a hydrogen atom or a linear or branched alkyl or alkenyl group having 1 to 18 carbon atoms, ( AO) a (BO) b
H, A, B; the same or different linear or branched alkylene groups having 2 to 4 carbon atoms; n; integers from 1 to 6; a, b; numbers from 0 to 20; a + b; numbers from 0 to 20; Amide ether alcohol represented by the following general formula (3)

Embedded image (Wherein, R ³ : hydrogen atom or methyl group X: CN or COOR ⁴ R ⁴ : hydrogen atom or lower alkyl group) is reacted with an unsaturated compound represented by the following formula: General formula (4)

Embedded image Wherein R ² ″ is a hydrogen atom or a linear or branched alkyl or alkenyl group having 1 to 18 carbon atoms, (A
O) a (BO) bOH, (AO) a (BO) bCH ₂ CHR ³ XR ¹ , R ³ , A, B, M, X, n, a, b; amide represented by｝ as defined above The following general formula (1) characterized in that an ether alcohol derivative is formed and then hydrolyzed with a basic substance or an acidic substance.

Embedded image (Wherein, R ¹ , R ² , R ³ , A, B, M, n, a, b; as defined above), an N-alkylamide ether having an amide group and an ether group in the molecule A method for producing a carboxylic acid or a salt thereof is provided. Furthermore, according to the present invention, there is provided a detergent composition comprising the N-alkylamide ether carboxylic acid or a salt thereof.

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION In the N-alkylamide ether carboxylic acid and its salt of the present invention, the compound represented by the general formula (1)
In the formula, R ¹ represents a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms, preferably ¹ to 22 carbon atoms.
0 to 18 alkyl groups or alkenyl groups. Specific examples of R ¹ include, but are not limited to, a lauryl group, a coconut alkyl group, a myristyl group, a cetyl group, a stearyl group, an oleyl group, a tallow alkyl group, and a hardened tallow alkyl group.

In the general formula (1), R ² represents a hydrogen atom or a linear or branched alkyl or alkenyl group having 1 to 18 carbon atoms, or (AO) a (BO) bH, or
(AO) a (BO) b represents CH ₂ CHR ³ COOM, preferably a hydrogen atom, a methyl group, an ethyl group, or a C 12
To 18 alkyl groups or alkenyl groups. In the general formula (1), R ³ is a hydrogen atom or a methyl group.

In the general formula (1), A and B represent the same or different linear or branched alkylene groups having 2 to 4 carbon atoms, and are preferably ethylene and propylene groups.

In the general formula (1), M represents a hydrogen atom, an alkali metal, monovalent alkaline earth metal, ammonium or organic ammonium, preferably a hydrogen atom, sodium, potassium, ammonium, Triethanolamine, calcium and magnesium.

Further, in the general formula (1), n is 1 to
6 represents an integer, preferably 1 to 3. a and b are
Each represents a number of 0 to 20, preferably 0 to 10.
A + b represents a number of 0 to 20, and preferably 1 to 15.

The N-alkyl amide ether carboxylic acid or its salt (1) and the starting amide ether alcohol (2) of the present invention are produced, for example, by the methods shown in Table 1 below.

[Table 1] (Wherein, R ¹ , R ² , R ² ′, R ² ″, R ³ , A, B,
M, Y, n, a, and b are as described above, and R ² ″ is a hydrogen atom or a linear or branched alkyl or alkenyl group having 1 to 18 carbon atoms.

Next, raw materials and intermediates in the method for producing the N-alkylamidoethercarboxylic acid or a salt thereof of the present invention will be described. Examples of the aliphatic amine represented by the general formula (5) include the following. Primary amines: octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, oleylamine, octadecenylamine and the like. Secondary amines: octylmethylamine, decylmethylamine, dodecylmethylamine, tetradecylmethylamine, dioctylamine, didecylamine, didodecylamine and the like. Of these, preferred aliphatic amines include dodecylamine, tetradecylamine, hexadecylamine and the like.

The following are examples of the cyclic lactone represented by the general formula (6). β-propiolactone, γ-butyrolactone, δ-valerolactone, ε-
Caprolactone and the like. The following are examples of the ε-hydroxyalkanoic acid or its ester represented by the general formula (7). Glycolic acid, β-hydroxypropionic acid, γ-hydroxybutyric acid, δ-hydroxypentanoic acid, ε-hydroxyhexanoic acid, and their methyl, ethyl, propyl, and butyl esters. Of these, preferred are methyl glycolate, ethyl glycolate, methyl ε-hydroxyhexanoate and the like.

Further, examples of the alkylene oxide include the following. Ethylene oxide, propylene oxide, butylene oxide and the like.

Further, the unsaturated compound represented by the general formula (3) is acrylonitrile, methacrylonitrile, acrylic acid, methacrylic acid, or their lower alkyl esters. Ethyl esters are preferred.

Next, the reaction conditions of each step in the production method of the present invention will be described. <A fatty amine represented by the general formula (5) and a general formula (6)
Reaction with cyclic lactone represented by the formula> Raw material usage ratio;
Double molar (preferably 1.0 to 1.3 molar) solvent; no solvent may be used, but a solvent may be used. Solvents include benzene, toluene, xylene, dibutyl ether and the like. Reaction temperature; 10 to 180 ° C (preferably 30 to 130 ° C)
C) Reaction time; 1 to 20 hours (preferably 3 to 10 hours)

<Reaction of fatty amine represented by general formula (5) with ω-hydroxyalkanoic acid or ester thereof represented by general formula (7)> Ratio of raw materials used: ω-hydroxyalkanoic acid to fatty amine Or 1 to 2 moles of the ester thereof (preferably,
(1.0 to 1.3 times mol) Solvent: No solvent may be used, but a solvent may be used in some cases. Solvents include benzene, toluene, xylene, dibutyl ether and the like. Reaction temperature; 40 to 180 ° C (preferably 60 to 140 ° C)
° C) Reaction time; 1 to 20 hours (preferably 3 to 10 hours)

<Addition reaction of alkylene oxide to amide alcohol represented by general formula (8)> General formula (8)
In the presence of an acidic or basic catalyst, one or two kinds of alkylene oxides are simultaneously or sequentially added to the amide alcohol represented by the formula (1). Catalyst; acidic or basic catalyst Examples of the basic catalyst include alkali metal hydroxides, alkali metal carbonates, alkali metal alcoholates, amines and the like. Examples of the acid catalyst include boron trifluoride and magnesium oxide. Preferably, potassium hydroxide, sodium hydroxide and the like are used. Reaction temperature; 10 to 180 ° C Reaction mole number: 20 mol or less (preferably 0.5 to 10 mol) ethylene oxide 20 mol or less (preferably 0 to 5) propylene oxide
Mol) Butylene oxide 20 mol or less (preferably 0 to 2 mol) After the reaction, the product may be neutralized or desalted.

<Reaction of Amide Alcohol (8) or Amide Ether Alcohol (2) with Acrylonitrile or Methacrylonitrile (3)> Ratio of Raw Materials Used: 1 to 2 parts of acrylonitrile or methacrylonitrile per amide alcohol or amide ether alcohol. Times mole (preferably 1.0 to 1.3 times mole) Catalyst; Basic catalyst Alcohol (C ₁ ) of alkali metal and alkaline earth metal
To C ₃ ), hydroxides, carbonates; solvents; no solvent may be used, but a solvent may be used. Benzene, toluene, xylene, dibutyl ether, etc. Reaction temperature; 40 to 180 ° C (preferably 80 to 140
C) Reaction time; 1 to 20 hours (preferably 3 to 10 hours) During the reaction, it is preferable to add a small amount of a polymerization inhibitor such as hydroquinone.

<Hydrolysis reaction of amide ether nitrile (of 4)>
Hydrolysis is carried out in the presence of 3 times (preferably 1.0 to 1.2 times) of a basic substance or an acidic substance. Basic substance; hydroxide or carbonate of alkali metal or alkaline earth metal (preferably, 20% sodium hydroxide or potassium hydroxide) Acidic substance; hydrochloric acid, sulfuric acid, etc. Reaction temperature; ~ 90
C) Reaction time; 1 to 100 hours (preferably 3 to 24 hours) The aqueous solution of propionate having an amide group and an ether group obtained by hydrolysis is acidified (pH 1) with an acidic substance (hydrochloric acid, sulfuric acid, etc.). To 4), and the resulting compound is converted into the acid of (1) or a salt with a desired basic substance.

<Reaction of Amide Alcohol (8) or Amide Ether Alcohol (2) with Acrylic Acid or Methacrylic Acid or Their Esters (3)> Ratio of Raw Materials Used: Acrylic acid or meta to fatty amide ether alcohol Acrylic acid or an ester thereof is 1 to 2 moles (preferably 1.0 to 1.3 moles) Catalyst; Basic Catalyst Alcohol (C ₁ ) of an alkali metal or alkaline earth metal
To C ₃ ), hydroxide, carbonate solvent; no solvent may be used, but a solvent may be used. Benzene, toluene, xylene, dibutyl ether, etc. Reaction temperature; 40 to 180 ° C (preferably 80 to 140
C) Reaction time; 1 to 20 hours (preferably 3 to 10 hours) During the reaction, it is preferable to add a small amount of a polymerization inhibitor such as hydroquinone.

<Amide ether carboxylic acid ester (4
Hydrolysis reaction>) Hydrolysis is carried out in the presence of a basic substance or an acidic substance in an amount of 1.0 to 3 times (preferably 1.0 to 1.2 times) the mol of amide ether carboxylic acid. Basic substance; hydroxide or carbonate of alkali metal or alkaline earth metal (preferably, 20% caustic soda or caustic potash) Acidic substance; hydrochloric acid, sulfuric acid, etc. Reaction temperature; 50-100 ° C (preferably 60-90)
C) Reaction time: 1 to 30 hours (preferably 2 to 20 hours) An aqueous solution of a carboxylate having an amide group and an ether group obtained by hydrolysis is converted into an acidic substance (hydrochloric acid, sulfuric acid, etc.).
To make it acidic (pH 1 to 4) to obtain the acid (1) or a salt with a desired basic substance.

The N-alkylamidoethercarboxylic acid or salt thereof of the present invention thus obtained is excellent in hard water resistance, good in foaming, and mild on skin and hair. A detergent composition containing the same, a detergent for clothing,
Effective for dishwashing vegetable detergent, shampoo, body shampoo, etc.

The case where the N-alkylamidoethercarboxylic acid or its salt is used as a detergent will be described below. [Cleaning composition] The cleaning composition of the present invention contains the N-alkylamide ether carboxylic acid represented by the general formula (1) or a salt thereof in an amount of 0.5 to 70% by weight (preferably 3 to
(50% by weight). At this time, another surfactant can be used in combination with the N-alkylamide ether carboxylic acid or a salt thereof.

The following are surfactants that can be used in combination. [Surfactants that can be used in combination] Can be used with all anionic surfactants, nonionic surfactants, amphoteric surfactants, and cationic surfactants. It is preferably used in combination with a surfactant. Preferred surfactants for use in combination are shown below. Anionic surfactants: alkyl sulfates, polyoxyethylene alkyl sulfates or fatty acid salts, alkyl benzene sulfonates, alkyl sulfonates, α-olefin sulfonates, α-sulfo fatty acid esters, monoalkyl phosphate esters, alkyl Or hydroxyalkyl ether carboxylate, alkyl amide ether sulfate, acyl sarcosinate, acyl tauride,
Nonionic surfactants such as fatty acid monoglyceride sulfates, acylamino acids, and secondary amide N-acylamino acids; higher alcohol ethoxylates;
Sucrose fatty acid ester, alkyl polyglucoside, polyglycerin fatty acid ester, fatty acid diethanolamide,
Cationic surfactants such as alkylamine oxides, alkylamidoamine oxides, polyoxyethylene fatty acid esters, methyl or ethyl glucoside fatty acid esters; mono- or di-alkyl quaternary ammonium salts, mono- or di-alkyl quaternary ammonium salts containing ether or ester groups, Or their hydrochlorides, sulfates, organic acid salts, etc., amphoteric surfactants; carboxybetaines, sulfobetaines, phosphobetaines, amidoamino acids, imidazolinium betaines, etc.

The cleaning composition of the present invention may further contain, if necessary, known auxiliary components to be added to the cleaning composition. Such auxiliary components include builders,
Humectants, viscosity modifiers, preservatives, anti-inflammatory agents, antioxidants,
Examples include ultraviolet absorbers, sequestering agents, bactericides, water-soluble polymer compounds, water-soluble inorganic substances, organic and inorganic compounds used for pH control, pearlescent agents, pigments, fragrances, enzymes and the like.

[0027]

EXAMPLES The present invention will be described below more specifically based on examples.

Example 1 A stirrer, reflux condenser, nitrogen blowing tube, dropping funnel,
185 g in a 1 liter four-necked flask equipped with a thermometer
(1.0 mol) of dodecylamine and heated to 70 ° C. while blowing in nitrogen to obtain 86 g (1.0 mol) of γ-
When butyrolactone was gradually added from a dropping funnel, the temperature rose due to heat generation. Therefore, the dropping was performed while maintaining the temperature at 80 to 90 ° C. After completion of the dropping, aging was performed at 90 ° C. for further 7 hours. After cooling the reaction mixture, 500 ml of ethyl ether was added to separate the ether phase, and the mixture was washed twice with ion-exchanged water.
The ether was distilled off to obtain 249 g (0.92 mol) of N-dotesyl-γ-hydroxybutyroamide.
108 g (0.4 mol) of this product and 4 g of 20% caustic soda (0.02 mol) were placed in a 500 ml autoclave, and stirred at 90 ° C. under reduced pressure (80 mmHg) for 1 hour.
88 g (2.0 mol) while maintaining at 100 to 110 ° C.
Of ethylene oxide over 30 minutes.
After completion of the press-in, the mixture was aged for about 1 hour. From the increase in the weight of the reaction product, the number of moles of ethylene oxide added was about 4.9 mol. In a 500 ml four-necked flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 146 g (0.3 mol) of this product and 10 g of 20% caustic soda (0.05 mol) were added. After heating and the reaction solution became transparent, it was cooled to 80 ° C., a small amount of hydroquinone was added, and 26.5 g (0.5 mol) of acrylonitrile was added dropwise while maintaining the temperature at 80 ° C. After completion of the dropwise addition, the mixture was aged at the same temperature for 1 hour, and unreacted acrylonitrile was distilled off under reduced pressure to obtain a cyanoethylated product. 100 ml of ion-exchanged water is added to the cyanoethylated product, and 0.5 mol of concentrated hydrochloric acid is further added. After heating at 100 ° C. for 7 hours, stirring is stopped and the mixture is allowed to stand for separation. This was further washed twice with warm ion-exchanged water to obtain 136 g (0.24 mol) of a product (yield from a 2.4 mol adduct of ethylene oxide of N-dotesyl-γ-hydroxybutyroamide). Rate 81
%). Carboxylic acid in 1725 cm ^-1 in the infrared absorption spectrum, an amide group 1635 cm ^-1, absorption of ether group in 1,120 cm ^-1 were observed. This product was neutralized with caustic soda to prepare a 30% aqueous solution. The cmc (critical micelle concentration) of the sodium salt was 1.6 g / l. The product was well soluble in water, foamed well, and remained unchanged even in hard water.

Example 2 A stirrer, reflux condenser, nitrogen blowing tube, dropping funnel,
185 g in a 1 liter four-necked flask equipped with a thermometer
(1.0 mol) of dodecylamine is charged, and 72 g (1.0 mol) of β-propiolactone is gradually added from a dropping funnel while blowing nitrogen. Since the temperature rises due to heat generation, dropping was performed while maintaining the temperature at 40 ° C. or lower. After completion of the dropwise addition, aging was performed at 50 ° C. for further 4 hours. After cooling the reaction mixture, 500 ml of ethyl ether was added to separate the ether phase, and the mixture was washed twice with ion-exchanged water. The ether was distilled off to obtain 221 g (0.86 mol) of N-dodecyl-β-hydroxypropioamide. This product 12
8 g (0.5 mol) and 4 g of 20% caustic soda (0.
02 mol) in a 500 ml autoclave and stirred at 90 ° C. for 1 hour under reduced pressure (80 mmHg).
While maintaining the temperature at 0 ° C., 93 g (2.1 mol) of ethylene oxide is gradually injected over 30 minutes. After press-fitting,
Aged for about 1 hour. From the increase in the weight of the reaction product, the number of moles of ethylene oxide added was about 4.1 mol. 5 equipped with stirrer, reflux condenser, dropping funnel and thermometer
175 g of this product (0.
4 mol) and 16 g of 20% caustic soda (0.08 mol) were added, and the mixture was heated to 100 ° C., and after the reaction solution became transparent, cooled to 60 ° C. and a small amount of hydroquinone was added.
Subsequently, 26.5 g (0.5 mol) of acrylonitrile was added dropwise while maintaining the temperature at 60 ° C. After the completion of dropping, at 90 ° C 5
After aging for an hour, unreacted acrylonitrile was distilled off under reduced pressure to obtain a cyanoethylated product. 100 ml of ion-exchanged water was added to the cyanoethylated product, and concentrated hydrochloric acid (0.5%) was added.
(Equivalent to 1 mol), and heated at 100 ° C. for 5 hours. This was further washed twice with ion-exchanged water to obtain 159 g (0.31 mol) of a product (yield from the adduct of 4.1 mol of ethylene oxide with N-dodecyl-β-hydroxypropioamide: 78). %). In the infrared absorption spectrum, a carboxylic acid group at 1725 cm ^-1 and 163
5 cm ^-1 in the amide group, the absorption of ether group in 1,120 cm ^-1 were observed. Neutralize this product with caustic soda,
A 30% aqueous solution was used. cmc was 1.4 g / l. The product was well soluble in water, foamed well, and remained unchanged even in hard water.

Example 3 108 g of N-dodecyl-γ-hydroxybutyroamide obtained in Example 1 was placed in a 500 ml autoclave.
(0.4 mol) and 4 g of 20% caustic soda, and the mixture was stirred at 90 ° C. for 1 hour under reduced pressure (80 mmHg).
While maintaining the temperature at 20 ° C., 57 g (1.3 mol) of ethylene oxide is gradually injected over 30 minutes. After completion of the press-in, the mixture was aged for about 2 hours. Due to the weight increase of the reaction product,
The number of moles of ethylene oxide added was about 3.1 mol. This product 108 was placed in a 500 ml four-necked flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer.
g (0.3 mol) and 8 g of 20% caustic soda,
After heating to 100 ° C. and the reaction solution becoming transparent, it was cooled to 80 ° C., and a small amount of hydroquinone was added.
(0.4 mol) of methyl acrylate was added dropwise at 80 ° C. After completion of the dropwise addition, the mixture was aged at the same temperature for 5 hours, and unreacted methyl acrylate was distilled off under reduced pressure. To this product was added 100 ml of ion-exchanged water,
After adding a molar equivalent and heating at 100 ° C. for 7 hours, the stirring is stopped and the mixture is allowed to stand for separation. This is further washed with warm ion exchange water,
104 g of product were obtained (72% yield from a 3.1 mol adduct of ethylene oxide of N-dotesyl-γ-hydroxybutyroamide). 1725 in the infrared absorption spectrum
cm ^-1 to a carboxylic acid group, an amide group 1635 cm ^-1, 1
Absorption of an ether group was observed at 120 cm ^-1 . This product was neutralized with caustic soda to obtain a 30% aqueous solution. The cmc (critical micelle concentration) of the sodium salt is 1.4 g /
l. The product was well soluble in water, foamed well, and remained unchanged even in hard water.

Comparative Example An aqueous solution of a compound corresponding to the amide ether carboxylic acid salt described in JP-B-8-3114 was prepared as a comparative example.

The following tests were performed on the aqueous solutions of Examples 1 to 7 and Comparative Example, and the performance was evaluated. The results are shown in Table 1. [Test Example] 1) Low-temperature stability test A 10% surfactant solution was prepared and placed in a refrigerator at -5 ° C.
After storage for a week, the state of the solution was visually observed. 2) Foaming test A foaming test was carried out according to JIS K3362 by diluting with water adjusted to 5 ° C. (German hardness) so that the amount of surfactant becomes 0.2%. 3) Rinsing properties Hands were washed with a 0.5% surfactant solution, and the feel of rinsing with tap water was evaluated. ：: good Δ: slightly poor ×: poor The results are shown in Table 2.

[0033]

[Table 2]

Formulation Example 1 Shampoo composition% by weight Product obtained in Example 1 (solid basis) polyoxyethylene (EO 3) lauryl ether disodium sulfosuccinate 3 lauroyl diethanolamide 4 lauryl dimethylamine oxide 0.5 Cationized Cellulose 0.1 Sodium Benzoate 0.3 Dye Appropriate Fragrance Appropriate Citric Acid Appropriate Purified Water Balance This shampoo was rich in lather and had a good feel during use.

Formulation Example 2 Shampoo composition% by weight Product obtained in Example 2 10 (in terms of solids) Polyoxyethylene (EO 3) sodium lauryl sulfate 10 Lauroyl diethanolamide 3 Cetyl trimethyl ammonium chloride 1 Cationized cellulose 0. 3 Sodium benzoate 0.3 Dye, Dye proper amount Citric acid proper amount Purified water balance This shampoo was rich in lather and had a good feel after use.

Formulation Example 3 Detergent composition for tableware and vegetables 16% by weight of product obtained in Example 1 (in terms of solids) Polyoxyethylene (EO 3) sodium lauryl sulfate 5 lauryl dimethylamine oxide 3 denatured ethanol 5 sodium benzoate 0.5 Dyes, flavors proper amount Citric acid proper amount tap water balance This dishwashing vegetable detergent has good foaming and good rinsing properties.

Formulation Example 4 Body shampoo composition Product obtained in Example 3 15% by weight (in terms of solids) Triethanolamine myristate 10 Amidopropyl betaine laurate 3 Propylene glycol 5 Dye, flavor appropriate amount Citric acid appropriate amount Triethanol Amine Suitable amount Purified water balance This body shampoo had good foaming and good skin and hair feel after use.

[0038]

Industrial Applicability The N-alkylamide ether carboxylic acids and salts thereof of the present invention are novel compounds, are excellent in foaming, hard water resistance, detergency, mild on hair and skin,
It is a very excellent compound as a surfactant. And
The detergent composition containing the compound is effective for a detergent for clothing, a dishwashing vegetable detergent, a shampoo, a body shampoo and the like. Further, the compound can be industrially advantageously produced by the production method of the present invention.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification number Agency reference number FI Technical display location C11D 1/72 C11D 1/72

Claims (3)

[Claims] 1. An N-alkylamide ether carboxylic acid having an amide group and an ether group in a molecule represented by the following general formula (1) or a salt thereof. Embedded image 中 wherein R ¹ ; a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms R ² ; a hydrogen atom or a linear or branched alkyl or alkenyl group having 1 to 18 carbon atoms, (AO ) a (BO) b
H, or (AO) a (BO) bCH ₂ CHR ³ COOM R ³ ; hydrogen atom or methyl group A, B; same or different linear or branched alkylene group having 2 to 4 carbon atoms M; hydrogen atom, alkali Metal, monovalent alkaline earth metal, ammonium, or organic ammonium n; an integer of 1 to 6 a, b; a number of 0 to 20 each a + b; a number of 0 to 20} 2. The following general formula (2): 中 wherein, R ¹ ; a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms R ² ′; a hydrogen atom or a linear or branched alkyl or alkenyl group having 1 to 18 carbon atoms, ( AO) a (BO) b
HR ³ ; hydrogen atom or methyl group A, B; same or different linear or branched alkylene group having 2 to 4 carbon atoms n; integer of 1 to 6 a, b; number of 0 to 20 each a + b; An amide ether alcohol represented by the following formula (2): (Wherein, R ³ : hydrogen atom or methyl group X: CN or COOR ⁴ R ⁴ : hydrogen atom or lower alkyl group) is reacted with an unsaturated compound represented by the following formula: General formula (4) Wherein R ² ″ is a hydrogen atom or a linear or branched alkyl or alkenyl group having 1 to 18 carbon atoms, (A
O) a (BO) bOH, (AO) a (BO) bCH ₂ CHR ³ XR ¹ , R ³ , A, B, M, X, n, a, b; amide represented by｝ as defined above An ether alcohol derivative is formed, and then hydrolyzed with a basic substance or an acidic substance. (Wherein, R ¹ , R ² , R ³ , A, B, M, n, a, b; as defined above), an N-alkyl ether carboxy having an amide group and an ether group in the molecule. A method for producing an acid or a salt thereof. 3. A detergent composition comprising the N-alkylamide ether carboxylic acid according to claim 1 or a salt thereof.