JPH09208990A - Detergent composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new chalate compound high in water solubility, excellent in a chelating performance and useful for detergent compositions excellent in washability. SOLUTION: A compound of formula I [each M is independently H, an alkali metal, etc., R<1> is a group of formula I (R<4> is H), a group of formula III, a group of formula IV; R<2> is H, hydroxyl group; R<3> is H, a group of formula V], e.g. N-(carboxymethyl), N-(1,2-dicarboxy-2-hydroxyethyl)aspartic acid 5-sodium salt. The compound of formula I can be produced by reacting a corresponding amine or amino acid or its salt with epoxysuccinic acid.

Description

Detailed Description of the Invention

[0001]

The present invention relates to a detergent composition and a novel chelating compound. More specifically,
The present invention relates to a detergent composition having excellent detergency, which contains a phosphorus-free chelate compound having excellent chelate performance, and a novel chelate compound used in the detergent composition.

[0002]

2. Description of the Related Art Builders used in detergents improve the washing effect of surfactants and soaps by capturing calcium ions and magnesium ions in water and softening them. be able to. Conventionally, sodium tripolyphosphate has been mainly used as a builder for detergents. Sodium tripolyphosphate has a very good performance as a builder for detergents, such as chelating performance.However, since it contains phosphorus, the wastewater after washing containing the same is discharged as it is, resulting in eutrophication of rivers and lakes. Cause. For this reason, builders other than sodium tripolyphosphate have been developed.

At present, the use of zeolite, which is a crystalline sodium aluminosilicate of the type 4A, achieves phosphorus-free, and with various devised compositions, a performance comparable to that of conventional phosphorus-containing detergents is obtained. Has been reached.
However, since zeolite is insoluble in water, it is disadvantageous in terms of ion exchange capacity for lowering hardness as compared with a water-soluble chelating agent from the viewpoint of a solid-liquid interface. Organic polycarboxylates are already known as water-soluble chelating agents, but their performance, economy, and biodegradability are insufficient, and zeolites are not suitable for magnesium in water or transition metals. It is only blended as

Accordingly, an object of the present invention is to provide a detergent composition having excellent detergency which contains a phosphorus-free builder which is economically inexpensive to synthesize, has high water solubility and is excellent in chelating performance. It is in. Another object of the present invention is to provide a phosphorus-free novel chelate compound having excellent chelate performance.

[0005]

Means for Solving the Problems As a result of intensive studies, the present inventors have found that a detergent composition containing a specific chelate compound can solve the above-mentioned problems, and have completed the present invention. That is, the present invention provides a detergent composition containing a chelate compound represented by the following general formula (I).

[0006]

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[Wherein M is a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium or a basic amino acid group, and a plurality of M may be the same or different.

[0008]

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(However, R ⁴ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and M represents the above-mentioned meaning.) R ² : a hydrogen atom or a hydroxyl group.

R ³ : hydrogen atom, alkyl group having 1 to 4 carbon atoms, —CH ₂ —COOM or

[0011]

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(Where M is as defined above). Further, the present invention provides the following formulas (I-1-1) and (I-1-
2), (I-2-1), (I-2-2), (I-4-
The present invention provides a novel chelate compound represented by 1), (I-5-1) or (I-5-2).

[0013]

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[0014]

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(In the formula, M has the above-mentioned meaning.)

[0016]

Embodiments of the present invention will be described below in detail.

The chelate compound represented by the general formula (I) used in the present invention has excellent chelating ability and has extremely high water solubility, so that there is no fear of sticking to a washing machine, and a liquid cleaning agent or powder cleaning agent is used. It can be preferably used as a builder of agents.

In the general formula (I), M represents a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium or a basic amino acid group, but a hydrogen atom or an alkali metal such as Na or K is preferable, and Na is particularly preferable. preferable.

R ¹ represents the above group,

[0020]

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(Wherein M has the above-mentioned meaning) is preferred. R ³ represents the above group, but is a hydrogen atom or

[0022]

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(Wherein M has the above-mentioned meaning) is preferred.

Examples of the chelate compound represented by the general formula (I) include compounds represented by the following formulas, and one kind or a mixture of two or more kinds thereof can be used.

[0025]

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[0026]

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(In the formula, M has the above-mentioned meaning.) Among these chelate compounds, the following formula (I-1-
One or more compounds selected from the compounds represented by 1) to (I-5-2) are preferable.

[0028]

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[0029]

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(In the formula, M has the above-mentioned meaning.) Among these compounds, the compounds represented by formulas (I-1-1) and (I-
1-2), (I-3-1), and the compounds represented by (I-3-2) are preferable, and formulas (I-1-1) and (I-1) are more preferable.
The compound represented by -2) is preferable.

Among these compounds, the above formula (I-1-
1), (I-1-2), (I-2-1), (I-2-
2), (I-4-1), (I-5-1) or (I-5-
The compound represented by 2) is a novel compound.

The chelate compound represented by the general formula (I) can be produced by the following production methods 1 and 2.

Production Method 1 Among the chelate compounds represented by the general formula (I), compounds in which R ² is a hydroxyl group, or R ² is a hydrogen atom and R ³ is

[0034]

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The compound (M has the above-mentioned meaning) can be produced by reacting the corresponding amine or amino acid or salt thereof with epoxysuccinate. The amine and amino acid (salt) used here are compounds that are industrially available or can be easily produced by known production methods, and examples thereof include monoethanolamine, β-alanine, aspartic acid, iminodisuccinic acid, and N. -Hydroxyethylglycine, N-hydroxyethylaspartic acid, N-hydroxyiminodisuccinic acid, N-carboxyethylglycine, N-carboxymethylaspartic acid, N-carboxyethylaspartic acid or salts thereof may be mentioned.

The reaction molar ratio of the amine or amino acid (salt) and the epoxy succinate is preferably epoxy succinate / (amine or amino acid (salt)) = 0.5 to 10.0, and 0.8 to
5.0 is more preferred. The reaction temperature is preferably from 50 to 150 ° C, more preferably from 60 to 90 ° C. As the reaction solvent, water, a water-soluble organic solvent (eg, methanol, ethanol, tetrahydrofuran) or a mixture thereof is used. The reaction is preferably performed by adjusting the pH of the reaction product to 7 to 13, preferably 8 to 11.

A specific reaction formula is shown below.

[0038]

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(In the formula, M has the above-mentioned meaning.) That is, N-carboxyethylaspartic acid (salt) (I
By reacting I) with epoxysuccinate (III), a chelate compound represented by the above formula (I-1-1) can be obtained. Further, by reacting β-alanine (IV) with epoxysuccinate (III), the above formula (I-1
A chelate compound represented by -2) is obtained.

By reacting N-hydroxyethylaspartic acid (salt) (V) with epoxysuccinate (III), a chelate compound represented by the above formula (I-2-1) can be obtained. Also, monoethanolamine (VI)
By reacting with the epoxysuccinate (III), the chelate compound represented by the above formula (I-2-2) is obtained.

N-carboxyethylglycine (salt) (VI
By reacting I) with epoxysuccinate (III), the chelate compound represented by the above formula (I-3-2) can be obtained. By reacting N-carboxymethylaspartic acid (salt) (VIII) with epoxysuccinate (III), a chelate compound represented by the above formula (I-4-2) can be obtained. N-hydroxyethylglycine (IX)
The chelate compound represented by the above formula (I-5-2) can be obtained by reacting with the epoxysuccinate (III).

Production method 2 Among the chelate compounds represented by the general formula (I), compounds other than the compound produced by the above production method 1, that is, R ² is a hydrogen atom, R ³ is a hydrogen atom, and the number of carbon atoms is The compound having 1 to 4 alkyl groups or --CH ₂ COOM (M has the above-mentioned meaning) can be produced from the corresponding amine or amino acid (salt) and maleic acid. The amine and amino acid (salt) used here are compounds that are industrially available or can be easily produced by a known production method, and examples thereof include monoethanolamine, glycine, β-alanine,
Aspartic acid, N-hydroxyethylglycine, N-
Examples thereof include carboxyethylglycine, N-carboxymethylaspartic acid, N-carboxyethylaspartic acid and salts thereof.

The reaction molar ratio of amine or amino acid (salt) and maleic acid is preferably maleic acid / (amine or amino acid (salt)) = 0.5 to 10.0, more preferably 0.8 to 5.0. The reaction temperature is preferably 50 to 150 ° C, 60 to 150 ° C.
120 ° C. is more preferable. As the reaction solvent, water, a water-soluble organic solvent (eg, methanol, ethanol, tetrahydrofuran) or a mixture thereof is used. PH of reactant
Is preferably adjusted to 7 to 13, preferably 8 to 11, and reacted.

A specific reaction formula is shown below.

[0045]

[Chemical 21]

(In the formula, M has the above-mentioned meaning.) That is, by reacting N-carboxyethylglycine (salt) (VII) with maleic acid (salt) (X), the above formula (I- A chelate compound represented by 3-1) is obtained. Further, the chelate compound represented by the above formula (I-4-1) can be obtained by reacting glycine (XI) with maleic acid (salt) (X). Further, by reacting N-hydroxyethylglycine (IX) with maleic acid (salt) (X), a chelate compound represented by the above formula (I-5-1) can be obtained.

The chelate compound represented by the general formula (I) in the present invention is blended in the detergent composition in an appropriate amount within the range where the desired effect is obtained, but is preferably 0.5 to 40% by weight, more preferably Is mixed in an amount of 1 to 30% by weight. 0.5% by weight of the chelating compound represented by the general formula (I)
With the above, the effect of the builder is sufficiently obtained,
Excellent cleaning performance is obtained. When the content is 40% by weight or less, other components such as a surfactant can be appropriately blended, and sufficient cleaning performance can be obtained.

The detergent composition of the present invention contains a chelate compound represented by the general formula (I) (hereinafter referred to as component (a)) as a builder, and a surfactant (hereinafter referred to as component (b)) and A detergent builder other than the component (a) (hereinafter referred to as the component (c)) can be blended if necessary.

The surfactant as the component (b) may be any of those generally used in detergents, such as anionic surfactants, nonionic surfactants, amphoteric surfactants and cationic surfactants. And so on.

The nonionic surface active agent and the anionic surface active agent used in the present invention are those usually added to detergents and have a mud detergency in the presence of hardness components (Ca, Mg, etc.). A good one is desirable. Specifically, polyoxyethylene alkyl ether having 8 to 22 carbon atoms in the alkyl group, polyoxyethylene alkylphenyl ether,
Higher fatty acid alkanolamide or its alkylene oxide adduct, sucrose fatty acid ester, alkyl and alkenyl glucoside, fatty acid glycerin monoester or its alkylene oxide adduct, alkylamine oxide, alkyl sulfate, olefin sulfonate, alkane sulfonate, alkyl And alkenyl ether sulfates, α-sulfofatty acid salts or ester salts, alkyl phosphate esters or salts thereof, alkyl benzene sulfonates, and mixtures of one or more of these. Examples of the amphoteric surfactant include amino acid surfactants and N-acyl amino acid surfactants, and examples of the cationic surfactant include quaternary ammonium salts. Among these surfactants, preferred are polyoxyethylene alkyl ethers having 8 to 22 carbon atoms in the alkyl group, alkyl sulfates, and alkylbenzene sulfonates. The component (b) is incorporated in the cleaning composition of the present invention in an amount of 5 to 60% by weight, preferably 5 to 40% by weight.

Further, as the detergent builder of the component (c),
Those known as builders for ordinary detergents can be used, and specifically, carbonates such as soda ash, sulfates, sulfites, silicates, and crystals described in JP-B-64-41116 and others. Layered silicates, aluminosilicates such as zeolite A, X and P type, inorganic builders such as tripolyphosphate, pyrophosphate and orthophosphate, polyacrylates, polymaleates, acrylic acid and maleic acid Examples thereof include salts of copolymers and organic builders such as polyglyoxylate, citrate, oxydisuccinate, and nitrilotriacetate described in JP-A-54-52196. Further, an organic chelating agent such as EDTA can be added. The component (c) may be incorporated in the detergent composition of the present invention in an amount of 0 to 94% by weight, preferably 5 to 80% by weight, more preferably 20 to 70% by weight.

In addition, an enzyme may be added to the detergent composition of the present invention, and specific examples thereof include protease, cellulase, amylase and lipase. Other minor components include ordinary fragrances, foam suppressants such as silica and silicone, a biphenyl-type optical brightener or a stilbene-type optical brightener or a fluorescent brightener using them in combination,
An anti-caking agent, a rinse aid and the like can be added.

A bleaching agent composition can be added to the detergent composition of the present invention. The bleach composition comprises sodium percarbonate, sodium perborate, preferably sodium percarbonate and various bleach activators.

The detergent composition of the present invention may be in the form of liquid, powder or granules, and it may be impregnated in a generally known production method such as spray drying method, spray mix method, crushing granulation method or inorganic builder-containing beads. It can be produced by a method for producing, a method for producing a high-density granular detergent, a method for producing a tablet-type, a flake-like, a bar-like detergent, a batch-type mixing method, a continuous-type mixing method, or the like.

When the detergent composition of the present invention is made into a powder or granular composition, its production method is not particularly limited, and a conventionally known method can be used. It is preferable to use an aqueous slurry of -80% by weight, preferably 35-60% by weight, and spray-dry the slurry to obtain spray-dried particles, especially those obtained by granulating the spray-dried particles to have a high bulk density. Also, a method of adding an alkali agent such as an alkali metal hydroxide to an unneutralized material, directly neutralizing and mixing, kneading with other washing builders (neck), cooling after mixing, and pulverizing. You may. For high bulk density,
JP-A-61-69897, JP-A-61-6989
No. 9, JP-A-61-69900, and EP-A-513824A. For direct neutralization, refer to JP-A-60-72999. it can. Also, the obtained detergent particles are preferably coated with a water-insoluble substance such as zeolite.

When the detergent composition of the present invention is a powder or granular composition, the average particle size is preferably 200 to 1000 μm in order to obtain preferable powder properties, and the bulk density in this case is 0.5 to 1000 μm. 1.0g / cm ³ , preferably 0.6-0.9g
/ Cm ³ .

[0057]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Production Examples of the chelate compound of the present invention and Examples of detergents.
The present invention is not limited to these production examples and examples. The percentages in the examples are on a weight basis unless otherwise specified.

Production Example 1 66.5 L-aspartic acid was added to a 1-liter four-necked flask.
g, NaOH 30.0 g, and water 136.4 g were charged and the temperature was raised to 50 ° C.
At the same temperature, 139.8 g of 34% monochloroacetic acid aqueous solution and 110 g of 40% aqueous NaOH solution were added dropwise at the same time so as to keep the pH of the reaction solution at 9.5. After aging at the same temperature for 3 hours, 35% hydrochloric acid was added to adjust the pH of the reaction solution to 1.5. After the water was distilled off, the residue was purified with hydrous methanol to obtain 168 g of N-carboxymethylaspartic acid.

Next, in a 500 ml four-necked flask, the N
-Carboxymethyl aspartic acid 40.0 g, epoxysuccinic acid monosodium salt 57.5 g, 41% NaOH aqueous solution 35.0 g, water 150
g, and aged at 80 ° C. for 20 hours. As a result, 24.1%
N- (carboxymethyl) _, N- represented by the following formula
279.0 g of an aqueous solution containing 5 sodium (1,2-dicarboxy-2-hydroxyethyl) aspartic acid (diastereo mixture) was obtained. A part of the obtained aqueous solution was freeze-dried and the NMR spectrum was measured. The results are shown below (D ₂
O solvent).

[0060]

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[0061] Production Example 2 β-alanine 66.9 g, epoxysuccinic acid monosodium salt 120.0 g, 41% NaOH aqueous solution 14 in a 1-liter four-necked flask.
The mixture was charged with 4.9 g and water (300 g) and aged at 60 ° C. for 15 hours. As a result, 630 g of an aqueous solution containing 33.5% trisodium N-carboxyethylhydroxyaspartate was obtained.

512.0 g of the 33.5% N-carboxyethylhydroxyaspartic acid trisodium aqueous solution obtained here was charged into a 1-liter four-necked flask, and 143.0 g of epoxysuccinic acid monosodium salt and 41% NaOH 85.0 g were added, After adjusting the pH of the reaction solution to 11, it was aged at 90 ° C. for 24 hours. as a result,
Aqueous solution containing 29.7% of N- (2-carboxyethyl), N- (1,2-dicarboxy-2-hydroxyethyl), 3-hydroxyaspartic acid pentasodium salt (diastereo mixture) represented by the following formula 738.8 g was obtained.
The result of freeze-drying a part of the obtained aqueous solution and measuring the NMR spectrum is shown below (D ₂ O solvent).

[0063]

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[0064] Production Example 3 Maleic acid 116 g, water 2 in a 1-liter four-necked flask
Charge 00g, 40% NaOH 300g, β-alanine 89g, 95
Aged at ℃ for 12 hours. As a result, 704.0 g of a 36.3% sodium N-carboxyethylaspartate aqueous solution was obtained.

208.7 g of this aqueous solution, 41% NaOH aqueous solution 41.0
g, 147.0 g of water were charged into a 1-liter four-necked flask,
69.5 g of monosodium epoxysuccinate was added. 36 at 80 ° C
As a result of aging for a time, an aqueous solution containing 23.5% of N- (2-carboxyethyl), N- (1,2-dicarboxy-2-hydroxyethyl) aspartic acid 5 sodium (diastereo mixture) represented by the following formula: 466 g Got The result of freeze-drying a part of the obtained aqueous solution and measuring the NMR spectrum is shown below (D ₂ O solvent).

[0066]

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[0067] Production Example 4 Maleic acid 116 g, water 2 in a 1-liter four-necked flask
00 g and 40% NaOH 200 g were charged, and ethanolamine 61.0 g was added dropwise at room temperature over 1 hour. The temperature was raised to 80 ° C. and aged for 6 hours. As a result, 576.0 g of a 36.4% disodium N-hydroxyethylaspartate aqueous solution was obtained.

303.8 g of this aqueous solution, 48.8% 41% NaOH aqueous solution
g, 100.0g of water into a 1 liter 4-neck flask,
115.6 g of mono sodium salt of epoxysuccinic acid was added. At 80 ℃
As a result of aging for 36 hours, an aqueous solution containing 21.6% of N- (1,2-dicarboxy-2-hydroxyethyl), N- (2-hydroxyethyl) aspartic acid tetrasodium represented by the following formula (diastereo mixture). 567.8 g were obtained. The result of freeze-drying a part of the obtained aqueous solution and measuring the NMR spectrum is shown below (D ₂ O solvent).

[0069]

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[0070] Production Example 5 A 1-liter four-necked flask was charged with 118 g of hydroxyethylglycine, 200 g of water and 200 g of 40% NaOH, and 154.0 g of monosodium epoxysuccinate salt was added. As a result of aging at 80 ° C. for 36 hours, 672.8 g of an aqueous solution containing 41.4% of N-carboxymethyl, N- (2-hydroxyethyl), and trisodium 3-hydroxyaspartate represented by the following formula
I got The result of freeze-drying a part of the obtained aqueous solution and measuring the NMR spectrum is shown below (D ₂ O solvent).

[0071]

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[0072] Production Example 6 A 1-liter four-necked flask was charged with 119 g of hydroxyethylglycine, 200 g of water and 300 g of 40% NaOH, and 116 g of maleic acid was added. As a result of aging at 90 ° C. for 18 hours, 35.2% of N-carboxymethyl, N- (2-hydroxyethyl) and trisodium aspartate represented by the following formula were obtained.
733.8 g of an aqueous solution containing it was obtained. The result of freeze-drying a part of the obtained aqueous solution and measuring the NMR spectrum is shown below (D ₂ O solvent).

[0073]

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[0074] Production Example 7 Monoethanolamine 61 was added to a 2-liter four-necked flask.
g, 200 g of water, and 300 g of 40% NaOH were charged, and 459 g of monosodium epoxysuccinate was added. As a result of aging at 80 ° C. for 50 hours, N- (1,2-dicarboxy-2 represented by the following formula:
-Hydroxyethyl), N- (2-hydroxyethyl), 3-hydroxyaspartic acid tetrasodium (1018 g) containing 24.1% of an aqueous solution containing 24.1% was obtained.
The result of freeze-drying a part of the obtained aqueous solution and measuring the NMR spectrum is shown below (D ₂ O solvent).

[0075]

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[0076] Production Example 8 L-aspartic acid 66.5 was added to a 1-liter four-necked flask.
g, NaOH 30.0 g, and water 136.4 g were charged and the temperature was raised to 50 ° C.
At the same temperature, 139.8 g of 34% monochloroacetic acid aqueous solution and 110 g of 40% aqueous NaOH solution were added dropwise at the same time so as to keep the pH of the reaction solution at 9.5. After aging at the same temperature for 3 hours, 35% hydrochloric acid was added to adjust the pH of the reaction solution to 1.5. After the water was distilled off, the residue was purified with hydrous methanol to obtain 168 g of N-carboxymethylaspartic acid.

Next, in a 500 ml four-necked flask, the N
-Carboxymethyl aspartic acid 40.0 g, maleic acid
Charge 25.5 g, 40% NaOH aqueous solution 84 g, water 100.5 g, 80
It was aged at ℃ for 24 hours. As a result, 248 g of an aqueous solution containing 25.0% of sodium 5-N-carboxymethyliminodisuccinate represented by the following formula (diastereo mixture) was obtained.
The result of freeze-drying a part of the obtained aqueous solution and measuring the NMR spectrum is shown below (D ₂ O solvent).

[0078]

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[0079] Examples 1 to 9 and Comparative Example 1 A powdery detergent composition was produced by crushing and granulating particles obtained by spray-drying a slurry having the composition shown in Table 1 using a high-speed mixer. The cleaning performance of the obtained cleaning composition on artificially stained cloth was evaluated by the following method. The results are shown in Table 1.

<Evaluation method of cleaning performance> (1) Preparation of sebum soiling contaminated cloth (artificial soiling cloth) Model sebum soiling 2 consisting of 10 cm × 10 cm cotton cloth with the following composition
g was evenly applied to prepare a sebum soiled cloth.・ Model sebum dirt composition Cottonseed oil 60% Cholesterol 10% Oleic acid 10% Palmitic acid 10% Liquid and solid paraffin 10% (2) Preparation of mud soiled cloth (artificial soiled cloth) After drying for 4 hours at 150 ° C, a 150-mesh (100 µm) pass is ground at 120 ° C ± 5 ° C.
After drying for 2 hours, disperse about 150 g in 1 liter of perclene, contact a # 2023 cloth with this liquid, brush, remove the dispersion, and remove excess adhered dirt.
A mud-dirt-contaminated cloth was created.

(3) Washing conditions and evaluation method In 1 liter of an aqueous detergent solution for evaluation, 10 cm prepared as described above was used.
Five pieces of cotton sebum stained cloth or mud stained cloth of × 10 cm were put and washed at 100 rpm with a tergotometer. The washing conditions are as follows.・ Washing conditions Washing time 10 minutes Washing agent concentration 0.083% Water hardness 4 ° DH Water temperature 20 ° C Rinsing Tap water 5 minutes Washing power is the self-recording color at 460nm of the original cloth before and after cleaning. The cleaning rate (%) was determined by the following equation, and the average of the measured values of the five sheets was shown as the cleaning power.

[0082]

[Equation 1]

[0083]

[Table 1]

Note) * 1 LAS: straight chain alkylbenzene sulfonate sodium (C
_{12 ~C 13)} * 2 AS: alkyl sulfate sodium (C ₁₄ ~C ₁₅₎ * 3 Non-ionic surface active agents: polyoxyethylene alkyl ether (C ₁₂ ~C _13, ethylene oxide average addition molar number of 10)

[0085]

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[0086]

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Examples 10 to 16 and Comparative Example 2 Liquid detergent compositions having the compositions shown in Table 2 were produced by batch compounding using a propeller shaft agitator. With respect to the obtained cleaning composition, the cleaning performance against the artificially contaminated cloth was evaluated in the same manner as in Example 1, except that the cleaning concentration alone was 0.133% among the cleaning conditions. Table 2 shows the results.

[0088]

[Table 2]

Note) * 1: The same compounds as in Table 1 were used as the compounds A to G.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Hiromitsu Hayashi 1334 Minato Minato, Wakayama City, Wakayama Kao Research Institute

Claims (5)

[Claims] 1. A cleaning composition comprising a chelate compound represented by the following general formula (I). Embedded image [Wherein, M represents a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium or a basic amino acid group, and a plurality of Ms may be the same or different. Embedded image (Wherein, R ⁴ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, M represents the meaning of the.) R ^2: represents a hydrogen atom or a hydroxyl group. R ³ : hydrogen atom, alkyl group having 1 to 4 carbon atoms, —CH ₂ —COOM
Or (Where M represents the same meaning as described above). ] 2. The chelate compound represented by the general formula (I) is one or more compounds selected from compounds represented by the following formulas (I-1-1) to (I-5-2). The cleaning composition according to claim 1. Embedded image Embedded image (In the formula, M has the meaning described above.) 3. The detergent composition according to claim 1, wherein the content of the chelate compound represented by the general formula (I) in the detergent composition is 0.5 to 40% by weight. 4. (a) 1 to 30% by weight of a chelate compound represented by the above general formula (I) (b) 5 to 60% by weight of a surfactant (c) a detergent builder 0 to 94 other than the component (a). The cleaning composition according to any one of claims 1 to 3, wherein the cleaning composition contains 10% by weight. 5. The following formulas (I-1-1) and (I-1-)
2), (I-2-1), (I-2-2), (I-4-
1), a novel chelate compound represented by (I-5-1) or (I-5-2). [Chemical 6] Embedded image (In the formula, M has the above-mentioned meaning.)