JPH11246474A - Sugar ether carboxylic acid compound, anionic surfactant and detergent composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a sugar ether carboxylic acid compound having excellent anionic surface activity as a detergent component. SOLUTION: A sugar ether carboxylic acid compound represented by the following general formula (1). Embedded image (R: an alkyl group, an alkenyl group or a hydroxyalkyl group having an average of 6 to 30 carbon atoms; A: an alkylene group having 2 and / or 3 carbon atoms; S: a sugar residue having 4 to 8 carbon atoms , M: an average number of moles of 0 to 10; n: an average number of condensation of 1 to 6; M: hydrogen or a salt-forming cation)

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION The present invention relates to a method for producing foams which is excellent in foaming even in hard water of high hardness, is hypoallergenic to skin and hair, and has a feeling of sliminess upon rinsing and a feeling of remaining on skin. The present invention relates to a sugar ether carboxylic acid compound having an anionic surface activity, which is useful as a detergent component having an excellent feeling in use, such as a small amount of anionic surfactant, an anionic surfactant comprising the same, and a detergent composition using the same.

[0002]

2. Description of the Related Art Soap has been awarded as a surfactant for detergents for washing the body and hands. Soaps have the characteristics that they have excellent biodegradability, low irritation to the skin, and excellent use feeling such as a refreshing feeling during rinsing.However, when the pH of the aqueous solution is high and the hair is washed, Not only does it become rough, but in seawater or hard water with high hardness, it undergoes a metathesis reaction with a polyvalent metal salt to produce a fatty acid metal salt, and produces scum, which is a mixture of it and dirt, which is not aesthetically pleasing There is a problem that. Therefore, in order to suppress the generation of those scum, α-sulfofatty acid salt,
Alternatively, it is known to use in combination with a surfactant such as a fatty acid alkanolamide. However, in order to suppress the generation of scum, it is necessary to use a large amount of those surfactants, and as a result, not only a slimy feeling occurs at the time of use, but also a refreshing feeling at the time of rinsing is lost. In addition, in the case of infinite dilution at the time of rinsing, there is a problem that generation of scum cannot be suppressed. Therefore, the combined use of surfactants does not provide a drastic solution, and it is necessary to change the chemical structure of the surfactants in order to solve those problems.
There has been a demand for the development of a surfactant having a new chemical structure that can be used in the neutral region and solves the above-mentioned problems.

[0003]

DISCLOSURE OF THE INVENTION The present invention provides good bubbling even in hard water of high hardness, little irritation to the skin and hair, a feeling of sliminess upon rinsing, a feeling of residue on the skin, etc. It is an object of the present invention to provide a sugar ether carboxylic acid compound having a good feel upon use and having excellent anionic surfactant as a detergent component, an anionic surfactant comprising the same, and a detergent composition containing the same.

[0004]

According to the present invention, there is provided a sugar ether carboxylic acid compound represented by the following general formula (1).

Embedded image (Wherein, R represents an alkyl group, alkenyl group or hydroxyalkyl group having an average of 6 to 30 carbon atoms; A: represents an alkylene group having 2 and / or 3 carbon atoms; S: a sugar residue having 4 to 8 carbon atoms; Represents a group; m: represents an average number of moles of 0 to 10; n: represents an average number of condensations of 1 to 6; M: represents hydrogen or a salt-forming cation) For example, an anionic surfactant comprising the sugar ether carboxylic acid compound and a detergent composition containing at least one thereof are provided.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION In the general formula (1), R represents an alkyl group, alkenyl group or hydroxyalkyl group having an average carbon number of 6 to 30. These alkyl groups and alkenyl groups include linear and branched ones. The optimal carbon chain length is from 10 to 24 carbon atoms in terms of foaming power and detergency. Such groups include decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, octadecenyl, undecyl, 2-hexyldecyl, 2-octylundecyl, 2-decyltetradecyl, 2-decyltetradecyl, Examples thereof include a hydroxydecyl group, a 2-hydroxydodecyl group, a 2-hydroxytetradecyl group, a 2-hydroxyhexadecyl group, and a 2-hydroxyoctadecyl group, which can be used alone or in combination.

A is an alkylene group having 2 and / or 3 carbon atoms. Thus, AO is ethylene oxide or propylene oxide or a mixture thereof. m is the average number of moles of the alkylene oxide added,
Is the number of From the above, the RO (AO) m group represents a polyoxyalkylene alkyl ether group, a polyoxyalkylene alkenyl ether group, or a polyoxyalkylene hydroxyalkyl ether group.

[0007] S represents a sugar residue having 4 to 8 carbon atoms. Such sugar residues include those obtained by removing two hydroxyl groups from sugars such as sugar alcohols, monosaccharides, and disaccharides. As those sugars, glucose, galactose,
Xylose, lactose, mannose, talose, rhamnose, arabinose, glucosylmannose, lyxose, allose, altrose, growth, idose, ribose, erythrose, threose, psicose, fructose, sorbose, tagatose, pentulose, tetroses, sucrose, maltose, isomaltose ,
Cellobiose, lactose, trehalose, kojibiose, sophorose, nigerose, laminaribiose, isomaltose, gentiobiose, melibiose, blanteobiose, turanose, vicianose, agarobiose, silaviose, rutinose, primemeprose,
Xylobiose, lojmenaviose, erythritol,
Mesoerythritol, maltitol, lactitol, D
-Threitol, D-arabinitol, ribitol, xylitol, sorbitol, galactitol, D-mannitol, allitol, higher alditol and the like. n is the average number of condensation of those sugars, and is a number of 1 to 6. Preferably, it is a number of 1 to 3 in terms of foaming power and detergency.

The carboxyl group, which is a terminal hydrophilic group, is a lactic acid residue obtained by removing hydrogen from the hydroxyl group of lactic acid. The counter ion M of the carboxyl group is hydrogen or a salt-forming cation.
Salt-forming cations include ions of alkali metals such as sodium, potassium and lithium; ions of alkaline earth metals such as calcium and magnesium; ammonium ions; organic ammonium ions derived from organic amines and the like. As the organic ammonium ion, it is preferable to use one derived from an alkanolamine (such as mono-, di- or tri-ethanolamine, n- or iso-propanolamine). Two or more of these cations can be used in combination.

The compound represented by the general formula (1) (anionic surfactant) according to the present invention can be prepared by combining known methods. For example, Japanese Patent Application Laid-Open No. 9-95478, Nakamura et al., Proceedings of the Symposium on Oil Chemistry, 32nd, P14 (1993), 31st, P152
(1992), that is, a method of condensing a saccharide and an alkyl halide in the presence of a basic catalyst, and a method of condensing a saccharide with an alkyl sulfate or a higher alcohol in the presence of an acidic catalyst. After an alkyl sugar ether, which is a known substance, is prepared by a method or the like, subsequently, the anionic surfactant of the present invention can be produced by reacting with a monohalogenopropionic acid or a salt thereof by a conventional method.

When the lipophilic group is a hydroxyalkyl group, a hydroxyalkyl sugar ether formed by reacting an epoxy alkane and a saccharide in the presence of a basic catalyst is used as a raw material, and the hydroxyalkyl sugar ether is added thereto in the presence of a basic catalyst. , Monohalogenopropionic acid or a salt thereof.

In the reaction of a saccharide with an alkyl halide, an alkyl sulfate, a higher alcohol or an epoxy alkane, the alkyl group is obtained as a mixture of isomers introduced into the primary and secondary alcohols of the saccharide. Although any of the alkyl sugar ether carboxylic acid compounds can be used as a surfactant, the foaming power in the presence of oily dirt is preferably those in which they are ether-bonded to a primary alcohol. The primary alcohol ether lactate of these saccharides is, as shown in the reaction example of the alkylxylitol ether lactate of the following formula, ketalized the saccharide in advance by a conventional method to leave only the primary alcohol, alkylate the saccharide, and further remove it. It can be prepared by ketalization and etherification with a monohalogen propionic acid or a salt thereof.

[0012]

Embedded image (In the above formula, R ¹ and R ² represent a lower alkyl group.)

The ketalization and deketalization reactions proceed almost quantitatively in the presence of an acidic catalyst. As the acidic catalyst, inorganic acids such as sulfuric acid, hydrochloric acid and phosphoric acid, and organic acids such as paratoluenesulfonic acid and benzenesulfonic acid are used.
As the lower ketone used in the ketalization reaction, those having a lower alkyl group are preferable from the viewpoint of separation and purification after the reaction, and examples thereof include acetone and methyl ethyl ketone. The lower alcohol used in the deketalization reaction includes methanol, ethanol, normal or isopropanol, normal or isobutanol, and the like.

The halogen element used in the alkyl halide is chlorine, bromine or iodine. Preferably, it is chlorine or bromine in view of economy and reactivity.

Examples of the monohalogenopropionic acid or a salt thereof include α-chloropropionic acid, α-bromopropionic acid and a salt thereof. Preferably, α-chloropropionic acid and a salt thereof are used from the viewpoint of economy and reactivity. The reaction between monohalogenopropionic acid or a salt thereof and an alkyl sugar ether or a hydroxyalkyl sugar ether is carried out by heating a mixture of a monohalogenopropionate and the alkyl sugar ether and gradually applying a basic catalyst aqueous solution under reduced pressure. Heating the mixture of both raw materials and the solid basic catalyst, reacting the mixture under reduced pressure, heating the alkyl sugar ether, and gradually reducing the monohalogenopropionic acid or its aqueous solution and the basic catalyst aqueous solution under reduced pressure. Any method can be used, such as a method of reacting under appropriate conditions.

A monohalogenopropionic acid or a salt thereof,
In the reaction with an alkyl sugar ether or a hydroxyalkyl sugar ether, monohalogenopropionic acid,
Alternatively, a salt thereof is condensed with a primary alcohol and a secondary alcohol of the sugar ether to form a lactic acid ether salt, and any of them can be used as a surfactant.

Examples of the basic catalyst include alkali metal alkoxides, alkali hydroxides and alkali carbonates.
It is selected from the reaction method and the like. Preferably, sodium hydroxide or potassium hydroxide is used from the viewpoint of economy and handling. The use amount of these basic catalysts is from equimolar to 1.5-fold mol based on monohalogenopropionic acid. The pH during the reaction is preferably kept at 7 to 13 in view of the reaction rate and the hydrolysis of the amide group.

This reaction can be carried out without a solvent.
In order to reduce the viscosity of the product in the latter half of the reaction and smoothly proceed the reaction by distilling off water, hexane, toluene, xylene, chloroform, carbon tetrachloride, dioxane, tetrahydrofuran should be used from the beginning or the latter half of the reaction. , Dimethylformamide, dimethylacetamide and the like. The amount used is suitably 1.0 to 5.0 in weight ratio to the alkyl sugar ether.

Since the alkyl sugar ether acts as a nonionic surfactant, it is also desirable that part of the alkyl sugar ether remains in the reaction product in the above reaction. Therefore, the reaction molar ratio of the monohalogenopropionic acid or a salt thereof to the alkyl sugar ether is selected in view of the amount of the alkyl sugar ether remaining as unreacted and their reactivity. From the viewpoint of further improving the foaming power and further reducing the irritancy to the skin, it is preferable to leave the alkyl sugar ether. For this purpose, the reaction mole of monohalogenopropionic acid or its salt with respect to the alkyl sugar ether is preferably The smaller is better, and the larger is better in order to obtain a sufficient reaction rate. In general, the reaction molar ratio is 0.1.
It is 1 to 2.0, preferably 0.2 to 1.5. When the reaction molar ratio is large, 2 moles of monohalogenopropionic acid reacts with 1 mole of alkyl sugar ether,
Products with improved solubility can also be obtained.

The reaction temperature is from 50 to 120 ° C., especially from 60 to 120 ° C.
It is preferable to carry out in the range of 100 ° C. Reaction temperature is 50 ° C
If the temperature is lower than 120 ° C., the reaction rate is low. If the temperature is higher than 120 ° C., the product is colored, which is not preferable. The reaction time varies depending on the reaction method and the reaction reagent, but is 1 to 10 hours, preferably 2 hours.
~ 6 hours.

The reaction product (anionic surfactant) obtained as described above includes an unreacted alkyl sugar ether or polyoxyalkylene alkyl sugar ether, a reaction by-product higher alcohol, dihydroxyalkane. , Lactates and inorganic salts. This reaction product can be used as it is as an anionic surfactant having excellent bubble power by simply adjusting the pH.However, when using a high-purity product such as a surfactant for a liquid detergent, a solvent is required. It can also be purified using a known purification method such as extraction and silica gel column chromatography.

The anionic surfactant of the present invention can be used in combination with existing anionic surfactants, nonionic surfactants, amphoteric surfactants and the like. In this case, the anionic surfactant is used in combination for the purpose of further improving the detergency and foaming power. Specific examples thereof include alkyl sulfates, polyoxyethylene alkyl sulfates, α-sulfofatty acid ester salts, α-olefin sulfonates,
Alkyl or hydroxyalkyl ether carboxylate, N-acylated taurine, N-acylated methyltaurine, N-acylated glycine, N-acylated aspartic acid, N-acylated sarcosine, N-acylated glutamic acid, higher fatty acid salt Alkyl benzene sulfonate, alkyl sulfonate, monoalkyl phosphate, alkyl amide ether sulfate, fatty acid monoglyceride sulfate, alkyl iminodicarboxylate, secondary amide type N-acyl amino acid salt, alkyl tartaric acid salt, Malic acid alkylamide, citric acid alkylamide and the like can be mentioned.

Nonionic surfactants, like anionic surfactants, are also used for the purpose of further reducing irritation to the skin and hair, in addition to detergency and foaming power.
Specific examples thereof include alkyl alcohol ethers, polyoxyethylene alkyl sugar ethers, hydroxyalkyl sugar ethers, and polyoxyethylene hydroxyalkyl sugar ethers which are precursors of the anionic surfactant of the present invention, as well as higher alcohol ethoxylates. , Higher alcohol ethoxypropoxylate, nonylphenol ethoxylate, fatty acid alkanolamide, sucrose fatty acid ester, alkyl (poly) glycoside, polyglycerin fatty acid ester, fatty acid 2,3-dihydroxypropylamide, fatty acid polyoxyethylene amide, alkylamine oxide, alkyl Amidoamine oxide, polyoxyethylene fatty acid ester, methyl or ethyl glycoside, fatty acid ester, acyl glucamide and the like can be mentioned.

The amphoteric surfactant is used in combination for the purpose of further improving foaming power and mildness on the skin.
Specific examples thereof include amide amino acid type amphoteric surfactants, long-chain alkyl dimethyl carboxymethyl betaines,
Examples include sulfobetaine, imidazolium betaine, glycine-type and alanine-type amphoteric surfactants, carboxybetaine, sulfobetaine, phosphobetaine, amide amino acids, and imidazolinium betaine-based surfactants.

When the anionic surfactant (A) represented by the general formula (1) is used by mixing with the existing surfactant (B), the mixing ratio (A) / (B) is , 98/2 to 10/90 by weight, preferably 80/20 to 30 /
70. If the mixing ratio is smaller than this, the characteristics of the anionic surfactant of the present invention cannot be sufficiently exhibited. The amount of the anionic surfactant of the present invention incorporated into the detergent composition varies depending on the dosage form of the detergent.
It is preferably 0.5 to 50% by weight, 1 to 70% by weight in the case of a paste, and 1 to 80% by weight in the case of a solid.

The pH when the detergent is dissolved in water varies depending on the type and use of the active agent to be blended, but the preferred range is pH for shampoos, body shampoos and kitchen detergents.
5 to 8, preferably 7 to 11 for clothes detergent, pH
When the pH is less than 4.9 and the pH is 11.1 or more, it is not preferable from the viewpoints of irritation to the skin and damage to the washing.

In the cleaning composition of the present invention, known auxiliary components to be added to the cleaning agent can be added, if necessary. Such auxiliary components include builders, humectants, viscosity modifiers, preservatives, anti-inflammatory agents, antioxidants, ultraviolet absorbers, sequestering agents, migration inhibitors, bactericides, water-soluble polymers Examples include compounds, water-soluble inorganic salts, organic and inorganic compounds used for pH adjustment, pearlescent agents, pigments, enzymes, bleaching agents and the like.

[0028]

According to the present invention, even in high-hardness hard water, foaming is good, it is less irritating to the skin and hair, and it has a feeling of sliminess upon rinsing and persistence on the skin. There is provided a novel anionic surfactant which is excellent in use feeling and useful as a cleaning component, for example, in a small amount. Therefore, the detergent composition containing the surfactant of the present invention can be widely used as a body shampoo, a hand soap, a shampoo, a dishwashing vegetable detergent, a residential detergent, and the like.

[0029]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail based on embodiments. Synthesis Example 1: Synthesis of dodecyl xylitol ether 100 equipped with a stirrer, a Liebig condenser, and a thermometer
100 g of xylitol in a 0 ml four-necked flask
(0.657 mol), methyl ethyl ketone 189.6
g (2.630 mol), sulfuric acid 1 g and hexane 200
The reaction mixture was refluxed at a reaction temperature of 85 ° C. to remove by-produced water. After reacting for 10 hours, 2.6 g of sodium bicarbonate was added, the catalyst was neutralized, and the mixture was filtered and the solvent was distilled off to obtain a xylitol ketalized product. Subsequently, sodium dodecyl sulfate powder 1 was added to the xylitol ketalized product.
89.5 g (0.657 mol) and 34.2 g of sodium hydroxide powder were added, and after substitution with nitrogen, the mixture was stirred at 150 ° C. for 10 hours to perform alkyl etherification. After the reaction was completed, 9.7 g of sulfuric acid was added to neutralize the mixture, and then 100 ml of isopropanol was added.
g and 1 g of sulfuric acid, and a solvolysis reaction was carried out at 70 ° C. for 3 hours under pressure. After completion of the reaction, the product was neutralized, filtered and the solvent was distilled off to obtain dodecylxylitol ether 19
1.4 g (90.9% yield) was obtained.

Synthesis Example 2: Synthesis of dodecyl mesoerythritol ether 100 equipped with stirrer, Liebig condenser and thermometer
In a 0 ml four-necked flask, mesoerythritol 6.0 was added.
g (49.1 mmol) and dimethylformamide 60
0 ml was charged and heated to 110 ° C. 3.0 g (27.0 mmol) of potassium butoxide was added to the solution, and the inside of the reactor was purged with nitrogen and then stirred for 20 minutes. Subsequently, 6.1 g (24.6 mmol) of dodecyl bromide was added, and 1
The reaction was performed at 20 ° C. for 48 hours. After completion of the reaction, cooling,
After filtration, the solvent was distilled off from the obtained filtrate to obtain a crude product of dodecyl mesoerythritol ether. Subsequently, the crude product was purified using column chromatography to obtain the dodecyl mesoerythritol ether product.
0 g was obtained (primary ether / secondary ether ratio: 47/5).
3, 91% yield).

Synthesis Example 3: Synthesis of decyl glycoside 100 equipped with a stirrer, a Liebig condenser and a thermometer
In a 0 ml four-necked flask, 400 g of decyl alcohol
(2.53 mol), 91 g of anhydrous glucose (0.53 mol)
mol) and 1.5 g of p-toluenesulfonic acid, the inside of the reactor was replaced with nitrogen, and the temperature was raised to 105 ° C and 25 m
Dehydration condensation was performed for 6 hours under the condition of mHg. After cooling,
Unreacted glucose precipitated after neutralizing the catalyst with an aqueous NaOH solution was separated by filtration and distilled under reduced pressure to obtain 135 g of decylglucoside (having a glucose condensation degree of 1.3).

Example 1: Synthesis of sodium dodecyl xylitol ether lactate 5 equipped with a vacuum stirrer, a Liebig condenser and a thermometer
In a 00 ml four-necked flask, 100 g (0.312 mol) of dodecylxylitol ether prepared in Synthesis Example 1 was added.
l) and 61.1 g of sodium monochloropropionate
(0.468 mol), 80 ° C, 25 mmHg
Under stirring conditions, a 40% aqueous NaOH solution 47.7 was stirred.
g (0.477 mol) was added dropwise over 2 hours to remove distilled water. Subsequently, 150 ml of dioxane was added, and the mixture was reacted and aged for 1.5 hours under the same conditions while distilling off water and dioxane. Dissolve the product in pure water,
Sodium dodecyl xylitol ether lactate 26.0
378.0 g of a 30% aqueous solution (76% yield, by liquid phase chromatography) was obtained.

Example 2 Synthesis of Sodium Dodecyl Mesoerythritol Ether Lactate In Example 1, dodecyl mesoerythritol ether purified in Example 2 was used in place of dodecyl xyltol ether, and dodecyl mesoerythritol ether was used. A 29% aqueous solution of sodium mesoerythritol ether lactate (yield: 80%, quantification method was based on Example 1) was obtained.

Example 3 Synthesis of Sodium Lactyl Decyl Glycoside Ether In Example 1, the decyl glycoside prepared in Synthesis Example 3 was used in place of dodecyl xyl tol ether,
According to Example 1, a 30% aqueous solution of sodium decyl glycoside ether lactate (yield 83%, quantitative method was based on Example 1) was obtained.

Examples 4 to 6 and Comparative Examples 1 to 2 The foaming power and feeling in use of the compounds obtained in Examples 1 to 3 were evaluated as follows. Table 1 shows the results. Table 1 also shows the results for sodium laurate or sodium polyoxyethylene (P = 3) lauryl ether sulfate for comparison.

1) Foaming power Using artificial hardened water adjusted to a hardness of 8 ° DH using CaCl ₂ , mixed soil as a soil component was added to a 1.9% by weight aqueous solution of a surfactant concentration adjusted to pH 7.0. Stain (lanolin /
Paraffin / triolein / tristearin = 90/4
/ 4/2) Prepare 20 ml of a solution containing 0.2% by weight, put into a 100 ml stoppered Epton tube, shake at room temperature 20 times for 10 seconds, and measure the foam volume 30 seconds after that did. The evaluation was performed using the following criteria in comparison with the amount of bubbles of sodium lauryl ether sulfate. ：: Foam is equivalent ○: Slight foam ×: Foam is low 2) Feeling of use A 5-ml panelists adjusted the pH of the surfactant to 0.5% by weight and prepared a 100% aqueous solution with a surfactant concentration of 100ml with a lid. Put in a bottle, shake it 10 times at 40 ° C,
The face was washed with the foamed sample solution, and the sensory evaluation was performed on the refreshing feeling after washing. Calculate the average value of the panelists,
The case where the average value was 2.5 or more was evaluated as (○), the case where the average value was 2.4 to 1.5 was evaluated as (△), and the case where the average value was 1.4 or less was evaluated as (x).
In addition, the following criteria were used for evaluation. 3: excellent 2: normal 1: poor Evaluation methods used in the examples are as follows.

[0037]

[Table 1]

Next, examples of specific formulations using the anionic surfactant of the present invention as a detergent component will be shown.

Example 7 Body soap (% by weight) Compound of Example 1 10 Lauroyl glutamate Na 7 Coconut fatty acid diethanolamide 3 Ethylene glycol fatty acid ester 3 Ethanol 3 Propylene glycol 5 Dye, perfume Appropriate amount Purified water balance This body soap is skin There was little irritation, and there was abundant foaming during use, and there was little residual feeling on the skin during rinsing, and the feel during use was good.

Example 8 Shampoo composition (% by weight) Compound of Example 1 8 N-Lauroylmethyltaurine Na 4 Coconut fatty acid diethanolamide 2 Alkylimidozolinium betaine 2 Propylene glycol 5 Dye, perfume Appropriate amount Purified water balance It had low irritation to the skin and good foaming, and the skin after rinsing was refreshed and had a good feel upon use.

Example 9 Shampoo composition (% by weight) Compound of Example 3 10 Lauroyl N-methyltaurine Na 6 2-decyltetradecyltrimethylammonium chloride 0.2 Citric acid qs Perfume, dye qs Purified water balance It was hypoallergenic to the skin, foamed well, and had good hair feel after shampooing.

Example 10 Detergent composition for tableware and vegetables (% by weight) Compound of Example 3 12 Polyoxyethylene lauryl alcohol (P = 10) 13 Amidopropyltrimethylamine oxide laurate 3 Ethanol 5 Flavor, dye Suitable amount Purified water Balance This dishwashing vegetable detergent is hypoallergenic to the skin,
The detergency and foaming were good, and the feel upon use was also good.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification symbol FI C11D 1/06 C11D 1/06

Claims (3)

[Claims] 1. A sugar ether carboxylic acid compound represented by the following general formula (1). Embedded image (Wherein, R represents an alkyl group, alkenyl group or hydroxyalkyl group having an average of 6 to 30 carbon atoms; A: represents an alkylene group having 2 and / or 3 carbon atoms; S: a sugar residue having 4 to 8 carbon atoms; M: represents a number of 0 to 10 by an average number of moles added; n: represents a number of 1 to 6 by an average number of condensation; M: represents hydrogen or a salt-forming cation) 2. An anionic surfactant comprising the sugar ether carboxylic acid compound of claim 1. 3. A detergent composition comprising at least one anionic surfactant according to claim 2.