JP2001254095A - Detergent composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide detergent compositions which excel in foaming and detergency, less irritate the skin, the hair and the like and, in addition, excel in a moistening effect after use and has high safety. SOLUTION: The detergent compositions comprise a compound represented by formula (1) (wherein R1 and R2 are each a 6-24C alkyl or alkenyl; R3 is H, 1-4C alkyl, alkenyl or hydroxyalkyl; R4 is 1-6C OH or alkylene which may contain -0-; and n is 0 or 1).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a detergent composition, and more particularly, to a foaming composition, excellent in detergency, less irritating to skin, hair, etc., and excellent in moist feeling after use. The present invention also relates to a cleaning composition having high safety.

[0002]

BACKGROUND OF THE INVENTION Detergent compositions such as detergents for clothing, detergents for tableware and vegetables, shampoos, facial cleansers, body soaps and the like have not only a finished feeling after use but also rich foaming. It tends to be required, and in addition to a surfactant as a main base material, a foam-enhancing agent that acts as a foam stabilizer is incorporated.

[0003] In general, fatty acid monoethanolamide, fatty acid diethanolamide, alkyldimethylamine oxide, higher alcohols and the like are used as foaming agents. It is hard to say that it is sufficiently satisfactory, and there is a demand for further improvement of these properties in a detergent composition.

[0004] The present invention has been made in order to meet the above-mentioned demands, and has as its object to provide a detergent composition which has good foaming, good detergency, excellent finish feeling, and high usability and safety. .

[0005]

Means for Solving the Problems and Embodiments of the Invention The present inventors have conducted intensive studies to achieve the above object, and as a result, have found that compounds represented by the following general formulas (1) to (4) or sulfuric acid thereof Foaming, detergency, by blending one or more of the
The inventor has found that they have excellent usability and safety, and have accomplished the present invention.

[0006]

Embedded image (Wherein, R ¹ and R ² each represent a straight-chain or branched alkyl or alkenyl group having 6 to 24 carbon atoms, R ^{3 represents a} hydrogen atom, a straight-chain or branched alkyl group or alkenyl group having 1 to 4 carbon atoms) Or a hydroxyalkyl group, R ⁴ : carbon number 1
To 6 hydroxyl groups or an alkylene group which may contain an ether bond, R ⁵ : a single bond or 1 to 2 carbon atoms
An alkyl group having 1 to 6 carbon atoms which may be substituted by an alkyl group of 4 or may contain an ether bond; R ⁶ and R ⁷ each have 6 to 24 carbon atoms which may contain an ether bond;
A linear or branched alkyl or alkenyl group of R
⁸ : a hydroxyl group having 1 to 10 carbon atoms or an alkylene group optionally containing an ether bond, n: 0 or 1
When n is 0, m is 1 to 6, and when n is 1, m is 1. )

According to the present invention, the compound represented by the above formulas (1) to (4), which is the two-chain two-hydrophilic surfactant, or its sulfated or phosphoric oxide is blended as a foaming agent. More preferably, by combining these surfactants with a surfactant selected from an anionic surfactant, a nonionic surfactant, an amphoteric surfactant and a cationic surfactant, foaming and detergency are achieved. Highly safe, less irritating to skin, hair, etc., excellent in moist feeling after use, foaming, detergency and safety are more satisfactory than conventional detergent compositions The resulting detergent composition can be obtained.

Hereinafter, the present invention will be described in more detail. The cleaning composition of the present invention comprises a compound represented by the following general formulas (1) to (4) or a sulfated or phosphated ( (Hereinafter, simply referred to as a derivative).

[0009]

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In the above general formulas (1) to (4),
R ¹ and R ² each represent a linear or branched alkyl or alkenyl group, and have 6 to 24, preferably 8 carbon atoms.
~ 18. R ³ is a hydrogen atom, a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 1 to 4 carbon atoms, particularly preferably a hydrogen atom, a methyl group or a hydroxyethyl group.

R ⁴ is a hydroxyl group having 1 to 6 carbon atoms or an alkylene group which may contain an ether bond, for example, — (CH ₂ ) ₂ —, — (CH ₂ ) ₃ —, —C ₂
H ₄ —O—C ₂ H ₄ — and —CH ₂ CH (OH) CH ₂ — are preferred. R ⁵ is a single bond or an alkylene group having 1 to 6 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms, and may contain an ether bond, for example, a methylene group, an ethylene group, a propylene group, butylene, -C ₂ H ₄
—O—C ₂ H ₄ — and the like are preferred. R ⁶ and R ⁷ each represent a linear or branched alkyl group or alkenyl group which may contain an ether bond, and have 6 to 24 carbon atoms.
Preferably 8 to 18 alkyl groups, alkenyl groups and alkyloxymethyl groups are preferred. R ⁸ has 1 to 10 carbon atoms
Or an alkylene group which may contain an ether bond.

The method for producing the compounds of the general formulas (1) to (4) and derivatives thereof of the present invention is not particularly limited, but any of them can be produced by combining known production methods. In the following, R ^{1 to} R ⁸ are the same groups as described above.

Specifically, when n = 1 in the compound of the general formula (1), a diamine of the following formula (5) is reacted with a 2-fold molar amount of epichlorohydrin of the following formula (6),
The compound represented by the following formula (7) is produced by subjecting the compound to alcoholysis or hydrolysis or further hydroxyalkylation, and a two-fold molar amount of the compound represented by the following formula (7): RCOOX (R is the same as R ¹ , R ² ). Similar groups,
X is a group selected from a halogen atom such as a chlorine atom and a bromine atom, a lower alkyl group, and the like), and the product is purified by column chromatography.

[0014]

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In the compound of the general formula (1), n =
In the case of 0, the diamine of the following formula (5) is dihydroxyethylated with twice the molar amount of ethylene oxide of the following formula (8) to obtain a compound of the following formula (9), and if necessary, etherified with an alkyl halide. After obtaining the compound represented by the following formula (10), the compound can be obtained by reacting the compound with a 2-fold molar amount of a fatty acid halide or ester, and purifying the product by column chromatography.

[0016]

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When n = 1 in the compound of the general formula (2), the N, N'-dialkyldiamine of the following formula (11) is diamide-formed with a 2-fold molar amount of glyceric acid of the following formula (12) to give the following: A compound represented by the formula (13) is obtained;
After etherification if necessary, the product can be obtained by purifying the product by column chromatography.

[0018]

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In the compound of the general formula (2), n
In the case of = 0, a diamide of the following formula (15) is produced by reacting a diamine of the following formula (11) with twice the molar amount of a hydroxy acid of the following formula (14) or a cyclic ester (lactone) thereof (Japanese Patent Laid-Open No. 10-310788, etc.), etherification as required, and purification of the product by column chromatography.

[0020]

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In the compound of the general formula (3), when n = 1, an amine of the following formula (16) is reacted with an epichlorohydrin of the following formula (6) in the same manner as in the case of the general formula (1). , By alcoholysis or hydrolysis or further hydroxyalkylation to obtain the following formula (17)
Can be obtained by reacting this compound with １ ／ mole of dicarboxylic acid halide, ester or anhydride and purifying the product by column chromatography.

[0022]

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In the compound of the general formula (3), when n = 0, similarly to the case of the general formula (1), the following formula (16)
Is hydroxyethylated with an equimolar amount of an ethylene oxide of the following formula (8) to give a compound of the following formula (18). If necessary, the compound is etherified with an alkyl halide. It can be obtained by reacting a dicarboxylic acid halide, ester or anhydride in a two-fold molar amount and purifying the product by column chromatography.

[0024]

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In the compound of the general formula (4), when R ⁶ and R ⁷ contain an ether group, a 2-fold molar amount of the following formula (1)
9) The reaction of the alkyl glycidyl ether of the following formula (20) with the diol of the following formula (20) or the reaction of the diglycidyl ether of the following formula (22) with twice as much alcohol to produce an ether diol of the following formula (21) As in the case of the general formulas (1) to (3), the compound can be produced by a reaction between epichlorohydrin when n = 1 and ethylene oxide when n = 0 (Massan, Oil Chemistry, 44 , 54).
3 (1995) and JP-A-11-80783.

[0026]

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In the compound of the general formula (4), R
^{When 6} and R ⁷ do not contain an ether group, the following formula (2)
It can be produced in the same manner from 3) an alkyl epoxide and a diol represented by the following formula (20) (see DE 44441363).

[0028]

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The compounds represented by the general formulas (1) to (4) and the derivatives thereof can be easily dissolved in water, especially when they are added to a liquid detergent composition. It is also possible to mix some of the hydroxyl groups of the above as sulfated or phosphoric acid esters. At this time, the degree of substitution of the hydroxyl group in the molecule with a sulfate group or a phosphate group is preferably 80% or less, particularly preferably 3 to 70%.

The compounding amount of one or more selected from the compounds of the above formulas (1) to (4) and derivatives thereof is 0.1 to 80% (% by mass, hereinafter the same) of the whole composition, especially 1 to
50% is preferred. If the amount is too small, a satisfactory compounding effect may not be obtained, and if it is too large, the solubility may be deteriorated.

The cleaning composition of the present invention is a compound selected from the compounds represented by the above general formulas (1) to (4) and derivatives thereof.
It is preferable to combine a surfactant or two or more surfactants together with a surfactant. By blending the surfactant, an excellent foam-enhancing effect and an effect of improving the feeling after use can be exhibited.

In this case, as the surfactant, conventionally known anionic surfactants, nonionic surfactants, amphoteric surfactants, and cationic surfactants can be used. Specific examples of the surfactant are shown below.

Anionic surfactants: alkyl sulfates, polyoxyethylene alkyl sulfates, higher fatty acid salts, alkyl sulfonates, α-olefin sulfonates, α-
Sulfo fatty acid salt, alkylbenzene sulfonate, monoalkyl phosphate, polyoxyethylene alkyl phosphate, alkyl or hydroxyalkyl ether carboxylate, fatty acid amide ether carboxylate, fatty acid amide ether sulfate, N-alkylamide alkanol Acyl amino acid salts such as sulfates, N-alkyl amide alkanol carboxylate, acyl sarcosine, acyl methyl taurate, fatty acid monoglyceride sulfate, alkyl glyceryl ether sulfate, acyl isethionate, acyl glutamate, acyl aspartate and the like And secondary amide type N-acyl amino acid salts, acyl-β-alanine salts, polyoxyethylene sulfosuccinate alkyl monoester disalts, and the like.

The salts of these anionic surfactants include alkali metal salts, alkaline earth metal salts, ammonium salts, amine salts, amino alcohol salts and the like. In addition, it is preferable that the alkyl group or the acyl group of the various compounds described above usually contains 10 to 24 carbon atoms.

Nonionic surfactants: higher alcohol ethoxylate, sucrose fatty acid ester, alkyl (poly) glucoside, alkyl glyceryl ether, polyglycerin fatty acid ester, fatty acid diethanolamide, fatty acid 2,3-dihydroxypropylamide, fatty acid polyoxyethylene Examples include amides, alkylamine oxides, alkylamidoamine oxides, polyoxyethylene fatty acid esters, methyl or ethyl glycoside fatty acid esters, and acylglucamides.

Amphoteric surfactants include carboxybetaines, sulfobetaines, phosphobetaines, amidoamino acids, imidazolinium betaines, alkyliminodicarboxylate surfactants and the like.

Cationic surfactant; mono- or di-alkyl quaternary ammonium salt, mono- or di-alkyl quaternary ammonium salt containing (poly) ether group, ester group or amide group, or hydrochloride, sulfate, organic acid salt thereof And the like.

In the present invention, it is preferable to use a surfactant which is mild to the skin, hair, etc., as another surfactant.

In the present invention, it is more preferable that one or more kinds of foaming agents selected from the compounds of the above formulas (1) to (4) and their derivatives are used in combination with the above surfactant. It is preferable, and thereby, it is possible to exhibit a more excellent foam increasing effect and an effect of improving the feeling after use.

The amount of the surfactant is preferably 1 to 99%, particularly 5 to 90% of the total composition. If the amount is too small, a satisfactory effect may not be obtained.

Further, in this case, the compounding ratio of the compound of the above formulas (1) to (4) or the derivative thereof and the surfactant is as follows:
The compounding amount of the compound of the above formulas (1) to (4) or the derivative thereof is 1 to 60%, especially 1 to 60% based on the total amount of the surfactant.
A range of 50% is preferable. Formulas (1) to (4) above
If the content of the compound or its derivative is too small, a synergistic effect may not be obtained, and if the content is too large, the solubility may be reduced.

In the present invention, a water-soluble polymer compound can be blended as an optional component. The water-soluble polymer compound is not particularly limited as long as it is a water-soluble polymer compound.
Any of synthetic ones, for example, pectin, carrageenan, guar gum, locust bean gum, gelatin, xanthan gum, carboxyvinyl polymer, carboxymethylhydroxyethylcellulose, hydroxyethylcellulose, hydroxypropylmethylcellulose, alginate, starch, polyvinyl alcohol,
Polyacrylate, polymethylacrylate, polyethylene glycol, cationic modified cellulose ether derivative, cationic polyvinylpyrrolidone derivative, cationic polyacrylic acid derivative, cationic polyamide derivative, polydimethyldiallylammonium chloride, chloride Copolymers of dimethyldiallylammonium and acrylamide, cationized polymers such as alkyl polyethyleneimine, and the like can be mentioned.

The amount of the water-soluble polymer compound is preferably 0.01 to 20%, more preferably 0.05 to 10% of the whole composition.

The cleaning composition of the present invention may further contain an antibacterial agent. The antibacterial agent is not particularly limited, but a preferred example is 1-hydroxy-2-
Pyridone and / or a salt thereof [eg, 1-hydroxy-
4-methyl-6- (2,4,4-trimethylpentyl)
-2- (1H) -pyridone monoethanolamine salt; pyroctone olamine], a salt of 2-mercaptopyridine-N-oxide [eg, a zinc salt of 2,2-dithio-bis- (pyridine-N-oxide)] Abbreviations: zinc pyrithione (Z-PT)], trichlorocarbanide, triclosan, mono- or dialkyl or monoalkylbenzyl quaternary ammonium salts, alkyldiaminoethylglycine hydrochloride, salicylic acid, paraoxybenzoates,
Examples thereof include polyols having antibacterial activity.

In the present invention, one or more of these antibacterial agents can be combined and compounded, and the compounding amount is preferably 0.02 to 5%, particularly preferably 0.1 to 2% of the whole composition. . If the amount of the antibacterial agent is too small, the antidandruff effect, deodorant effect, sterilization / bactericidal effect, etc. may be insufficient.If the amount is too large, no further improvement is observed, and there is a fear of adverse effects such as skin irritation. May be done.

The detergent composition of the present invention can also contain a water-swellable clay mineral. As water-swellable clay minerals,
Natural or synthetic montmorillonite, beidellite,
Examples include smectites such as nontronite, saponite, hectorite, sauconite, and stevensite, and swelling mica. The amount of these water-swellable clay minerals varies depending on the dosage form, but is preferably 0.01% based on the total amount of the composition.
-10%, more preferably 0.1-5%.

The cleaning composition of the present invention may contain known auxiliary components to be added to the cleaning agent as long as the object of the present invention is not impaired. Examples of such auxiliary components include organic and inorganic builders, humectants, ethylenediaminetetraacetic acid derivatives, chelating agents such as citric acid, highly polymerized methylpolysiloxane, and dimethylsiloxane / methyl (polyoxyethylene) siloxane copolymer. Silicones, preservatives, anti-inflammatory agents, antioxidants, ultraviolet absorbers, dye transfer inhibitors, water-soluble polymer compounds, water-soluble inorganic substances, organic and inorganic compounds used for pH adjustment, conditioning agents, pearlescent agents, Dyes, fragrances, enzymes, bleaches and the like can be mentioned.

The cleaning composition of the present invention is prepared in various forms such as liquid, cream, granule, tablet, etc., and in various dosage forms by a usual method, and is used for skin, hair, tableware, clothing and the like. Available.

[0049]

EFFECT OF THE INVENTION The detergent composition of the present invention, by blending the above-mentioned foaming agent, foams, has excellent detergency, is less irritating to skin and hair, and has a moist feeling after use. It is excellent in safety and can be widely used for skin, hair, tableware, clothing and so on.

[0050]

EXAMPLES Hereinafter, the present invention will be described specifically with reference to Synthesis Examples, Examples and Comparative Examples, but the present invention is not limited to the following Examples. In the following,% is% by mass.
It is.

In each of the following examples, (1) to (4)
The structural formulas of the compounds (Sample 1-1 to Sample 4-5) are shown below.

[0052]

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[0053]

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[0054]

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[0055]

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[0056]

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Synthesis Example 1 In a 200 ml four-necked flask equipped with a stirrer, thermometer, and condenser, 3.85 g of N,
N'-bis (2-hydroxyethyl) -3-oxabendilendiamine was dissolved in 20 ml of water, and 8.0 g of decanoic acid chloride was added dropwise while maintaining the pH at around 9 with sodium hydroxide. After the completion of the dropwise addition, the mixture was further stirred for 2 hours. After evaporating the solvent and drying, the residue was purified by a silica gel column to obtain 8.3 g of a product (sample 1-4) (83% yield).

[Synthesis Example 2] In a 200 ml four-necked flask equipped with a stirrer, a thermometer, and a condenser, 14.3 g of dichloroethyl ether and 50 ml of n-propyl alcohol were put. 42.6 g of tetradecylamine were slowly added dropwise. After the completion of the dropwise addition, the mixture was refluxed for 8 hours. After the solvent was distilled off, the residue was washed with an alkali, and the unreacted material was distilled off under reduced pressure to obtain 43.6 g of N, N'-ditetradecyl-bis-aminoethyl ether (yield: 88).
%). In a 300 ml four-necked flask, 24.8 g of N,
N′-ditetradecyl-bis-aminoethyl ether and 11 g of ethyl glycolate and 2 g of sodium methylate (28% methanol solution) were added, and the mixture was gradually heated to remove methanol and ethanol, and further stirred at 90 ° C. for 5 hours. Matured. After completion of the reaction, 100 ml of ethyl ether was added, washed with water, dried, and topped with ether.
23.2 g of bisamide alcohol was obtained (yield 76
%). 6.1 g of this product and 0.05 g of potassium hydroxide were charged into an autoclave equipped with a press-fitting tube, heated to 90 ° C. under a nitrogen atmosphere, dehydrated under reduced pressure, and then gradually charged with 0.9 g of ethylene oxide. After completion of the injection, aging was carried out for 3 hours, the product was dissolved in ethanol, the catalyst was neutralized and filtered with phosphoric acid, ethanol was removed, and the product was purified with a silica gel column, and 3.6 g of the product (sample 2-4) was removed. ) Was obtained (yield 52%).

[Synthesis Example 3] 9.1 g of 2,3-dihydroxypropylamine, 80 ml of ethanol, and 2.5 g of sodium hydrogen carbonate were charged into a 200-ml round-bottom flask equipped with a stirrer, a condenser, and a dropping funnel. Then, the mixture was heated to reflux at 80 ° C. while stirring to obtain 1-bromodecane 5.5.
3 g was added dropwise using a dropping funnel. After reacting under heating and refluxing for 6 to 8 hours until the generation of carbon dioxide ceased, the resulting precipitate of sodium bromide was filtered. Ethanol was distilled off under reduced pressure, and the residue was dissolved in 30 ml of toluene, and washed with ion-exchanged water. The organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain 5.1 g of a crude product. The crude product was purified by a silica gel column to obtain 4.9 g of N- (2,3-dihydroxypropyl) dodecylamine (85% yield). 2.3 g of N- (2,3-dihydroxypropyl) dodecylamine was charged into a 20 ml round bottom flask, and heated to 120 ° C. under a nitrogen stream while stirring. To this, 0.66 g of dimethyl malonate was added and reacted for 8 to 12 hours, and the obtained crude product was purified by a silica gel column to obtain 1.4 g of a product (sample 3-1). Rate 53%).

[Synthesis Example 4] 5.4 g of 1,8-bis (dodecyloxymethyl) -3,6-dioxaoctane-
1,8-diol and 0.1 g of potassium hydroxide were charged into an autoclave equipped with a gas injection tube, and charged in a nitrogen atmosphere.
After heat dehydration at 30 ° C., 0.9 g of ethylene oxide was gradually injected. After completion of the injection, aging was carried out for another 2 hours. After completion of the reaction, the product was dissolved in ethanol, neutralized with phosphoric acid, and filtered. After removing ethanol, the obtained crude product was purified by silica gel column chromatography, and 4.3
g of product (Sample 4-5) was obtained (68% yield).

Examples 1 to 21 and Comparative Examples 1 to 3
Using the sample or the surfactant shown in No. 3, each component and purified water were blended so that the total amount becomes 100% as shown in the following composition to prepare a detergent composition, and each composition was evaluated by the following method.
The results are shown in Tables 1 to 3. Detergent composition; sample or surfactant shown in Tables 1 to 3 4% POE (3) Sodium dodecyl sulfate 6 Sodium dodecyl sulfate 2 Sodium lauroylmethyltaurine 3 Sodium tetradecene sulfonate 2 Sodium paraffin sulfonate 1 POE (4 ) Sodium dodecyl ether acetate 2 POE (3) Sodium lauric amide ether acetate 2 Amidopropyl betaine laurate 2 POE (11) Dodecyl ether 1 Dodecyl glyceryl ether 1 Purified water Balance 100.0%

(1) Foaming property of composition A 20% aqueous solution (25 ° C.) of a 6% aqueous solution of the detergent composition was added to 100
The sample was collected in a ml Epton tube, 0.2 g of liquid lanolin was added as artificial soil, shaken 20 times for 10 seconds, and the foam volume after 1 minute was measured. The evaluation was described as follows according to the measured foam volume. ：: foam volume is 60 ml or more △: foam volume is 50 ml to less than 60 ml ×: foam volume is less than 50 ml

(2) Detergency 4 g of soybean oil and 6 g of tallow were dissolved in 60 ml of chloroform, and 0.1 g of oil red was added and mixed well to prepare a dirty solution. A glass plate is immersed in this solution to contaminate it, and air-dried at 25 ° C. for 30 minutes to remove chloroform to obtain a dirt piece (dirt amount: 18 to 22 mg / sheet). Six of these pieces of dirt were added to 700 ml of a 0.15% detergent composition at 25 ° C., washed for 3 minutes at a rotation speed of 250 rpm, air-dried, weighed, and the oil removal rate after washing was calculated. And detergency.

(3) Moist feeling of hair As a standard sample, sodium polyoxyethylene lauryl ether sulfate (average number of moles of polyoxyethylene added:
3 mol): 15%, coconut oil fatty acid diethanolamide:
5%, anhydrous sodium sulfate: 1%, cationized cellulose: 0.5%, citric acid / monohydrate: appropriate amount (pH 6.0 adjusted amount) and purified water: balance were prepared. The hair was divided into left and right, 3 g of the standard sample was applied to one side, and 3 g of the test sample was applied to the other side. The hair was washed, and the moist feeling was evaluated by the ten subjects as follows, and the scores of the ten subjects were calculated. And the following symbols.

(4) Moistness of Hand Skin After Drying Hands and arms were washed by 10 subjects and evaluated. The evaluation was performed by calculating the average of the scores according to the following criteria, and indicated by the following symbols.

From the results of Tables 1 to 3, the above formulas (1) to (1)
Detergent composition not containing compound (4) (Comparative Example)
Is inferior in any of foaming, detergency, finish feeling, and usability, whereas the detergent composition containing the compound of the above formulas (1) to (4) (Example) has foaming power, It was confirmed to be excellent in all of the detergency, the moist feeling of the hair, and the moisture of the hand skin after drying.

[0067]

[Table 1]

[0068]

[Table 2]

[0069]

[Table 3]

Example 22 The shampoo composition shown below had good foaming properties and the hair after washing was moist. POE (3) sodium lauryl ether sulfate 13% sodium lauryl glyceryl sulfate 2 sodium lauryl sulfate 2 sodium lauryl aminopropionate 3 sample (2-1) 1 sample (2-4) 3 lauryl dimethylamine oxide 1 glycerin fatty acid ester 1 hydroxyethyl cellulose Reference Signs List 1 cationized cellulose 0.2 pyrocton olamine 0.5 highly polymerized dimethyl silicone 3 montmorillonite 1 glycine 0.2 glycerin 1 butylene glycol 0.5 sodium benzoate 1 methyl paraben 0.2 dye 0.002 fragrance 0.5 citric acid 0.5 purified water balance meter 100.0%

Example 23 The shampoo composition shown below had good foaming properties and the hair after washing was moist. Sodium lauroylmethyltaurine 7% sodium glycolic acid N-laurylamide sulfate 4 sodium dodecyl ether carboxylate 3 dodecylamidopropyl betaine 6 sample (1-2) 3 dimethyldiallylammonium chloride / acrylamide copolymer 0.2 benzalkonium chloride 0 0.2 Sodium citrate 0.5 Paraben 0.2 Methyl isothiazoline on / methyl chloroisothiazoline on 0.02 Ethylene glycol distearate 2 Citric acid 0.2 Purified water Balance meter 100.0%

Example 24 The shampoo composition shown below had good foaming properties and the hair after washing was moist. POE (3) sodium lauryl ether sulfate 4% lauroylmethyl-β-alanine triethanolamine salt 5 cocoylglutamic acid triethanolamine salt 5 laurylamide propyl betaine 5 dodecylaminopropionic acid 1 POE hydrogenated castor oil (40) 2 sample (3- 6) 1 decylglyceryl glucoside 1 glycerin laurate 3 polydimethylsiloxane (100,000 cst) 4 cetyl isooctanoate 3 wax 1 cationized cellulose 0.4 pyrocton olamine 0.5 hydrolyzed protein 0.2 ethanol 3 dipropylene Glycol 0.5 Sodium chloride 1 Sodium benzoate 0.3 Paraben 0.2 Dibutylhydroxytoluene 0.05 Fragrance 0.4 Citric acid 1.5 Purified water Balance meter 100.0%

Example 25 The shampoo composition shown below had good foaming properties and the hair after washing was moist. POE (3) sodium lauryl ether sulfate 3% POE (4) sodium laurate ester sulfate 2 sodium alkyl glyceryl ether sulfate 4 laurylamide propyl betaine 2 dodecylaminopropionic acid 4 sample (4-4) 2 monoethanolamide laurate 2 set Stearyl alcohol 2 cationized guar gum 0.3 dimethyldiallylammonium chloride / acrylamide copolymer 0.2 dimethyldiallylammonium chloride / acrylamide / acrylic acid copolymer 0.2 pyroctone olamine 0.5 sodium sulfate 1 sodium benzoate 0 5.5 Dibutylhydroxytoluene trace amount ethylene glycol distearate 1 Dye 0.02 Fragrance 0.4 Citric acid 0.3 Purified water Balance meter 100.0%

Example 26 The shampoo composition shown below had good foaming properties and the hair after washing was moist. Lauroyltaurine sodium 5% Lauroyl-β-alanine triethanolamine 7 Lauroylglutamate triethanolamine 4 POE (4) Lauric acid amide ether acetate triethanolamine 1 Dodecylamidopropyl betaine 3 POE hydrogenated castor oil 2 Sample (3-2) 4 Glycerin laurate 1 wax 1 cationized guar gum 0.6 dimethyldiallylammonium chloride / acrylamide / acrylic acid copolymer 0.3 pyrocton olamine 0.5 glycine 0.5 sodium benzoate 0.5 dibutylhydroxytoluene trace amount of distearin Ethylene glycol 1 Perfume 0.2 Citric acid 0.8 Purified water Balance meter 100.0%

Example 27 The shampoo composition shown below had good foaming properties and cleansing properties, and the hair after washing was moist. POE (2.5) sodium tridecyl ether sulfate 10% sodium C14-α-olefin sulfonate 5 sodium paraffin sulfonate 1 amidopropyl betaine laurate 2 dodecyl carboxyethyl hydroxyethyl betaine 1 POE (15) dodecyl ether 3 POE cured castor Oil (40) 3 sample (4-2) 2 dodecylglycerin ether 2 dimethylsiloxane 2 cetyl isooctanoate 1 liquid paraffin 1 dimethyldiallylammonium chloride / acrylamide copolymer 0.3 hydrolyzed protein 0.5 ethanol 2 sodium chloride 0. 5 Sodium citrate 0.2 Paraben 0.2 Methyl isothiazoline on / methyl chloroisothiazoline on 0.03 Dibutyl hydroxytoluene Trace amount of ethyl stearate Glycolic 2 Citric acid 0.8 Purified water Balance Total 100.0%

Example 28 The following shampoo composition had good foaming properties and foam quality, and the hair after washing was moist. Coconut fatty acid N-methylethanolamide triethanolamine sulfate 8% C12-15 alkyl POE (3) sodium sulfate 10 Sample (4-1) 3 Coconut fatty acid amidopropyl dimethylamine oxide 2 Coconut fatty acid amidopropyl dimethylamino hydroxypropanesulfonic acid 1 Cationized cellulose 0.4 ethanol 3 citric acid qs sodium hydroxide qs perfume 0.5 dye qs purified water balance meter 100.0%

Example 29 The shampoo composition shown below had good foaming properties and foam quality, and was excellent in conditioning effect. POE (3) dodecanoic acid amide ether triethanolamine acetate 8% POE (3) dodecanoic acid amide 1 coconut fatty acid amide butylguanidine glycolate 3 coconut alkyl imidazilium betaine 2 sample (2-3) 2 propylene glycol 3 Perfume 0.5 Dye Suitable amount Purified water Balance meter 100.0%

Example 30 The following body soap composition had creamy foam and moisturized skin after use. Potassium laurate 10% Potassium myristate 10 Potassium N-lauroyl-N-methyl-β-alanine 2 Monopotassium N-lauroyl-glutamate 2 Coconut oil fatty acid diethanolamide 1 Sample (1-1) 1 Sample (1-3) 2 Propylene glycol 6 Hydroxypropyl methylcellulose 0.5 Ethylene glycol distearate 1 Polystyrene polymer (n = 300) 0.1 Tetrasodium tetrasodium edetate 0.2 Vegetable squalane 1 Callophyllis violacea water extract 0.5 Potassium chloride 0 .1 Piroctone olamine 0.2 Benclay 1 Potassium hydroxide Trace fragrance Trace purified water Balance meter 100.0%

Example 31 The following body soap composition had creamy foam and moisturized skin after use. Potassium laurate 10% potassium myristate 10 N-lauroyl-N-methyl-β-alanine potassium 2 N-lauroyl-aspartate monopotassium 2 sample (3-4) 2 lauric acid-2,3-dihydroxypropylamide 2 propylene Glycol 6 hydroxypropylmethylcellulose 0.5 ethylene glycol distearate 1 cationized cellulose 0.1 polystyrene polymer (n = 300) 0.1 edetate tetrasodium tetrahydrate 0.2 vegetable squalane 0.5 dimethylpolysiloxane ( 100cs) 0.5 Potassium chloride 0.1 Cyclipirox olamine 0.2 Benclay 1 Potassium hydroxide Trace amount Fragrance Trace amount purified water Balance meter 100.0%

Example 32 The following body soap composition had creamy foam and moisturized skin after use. Potassium laurate 10% Potassium myristate 10 Potassium N-lauroyl-β-alanine 2 N-Lauroyl-monopotassium glutamate 2 Sample (4-5) 2 N-Lauryl glycerate 2 Propylene glycol 6 Hydroxypropyl methylcellulose 0.5 Distearin Ethylene glycol 1 cationized cellulose 0.1 polystyrene polymer (n = 300) 0.1 edetate tetrasodium tetrahydrate 0.2 vegetable squalane 1 Callophyllis violacea water extract 1.0 potassium chloride 0.1 cyclicol Cus olamine / Vegum T complex 0.2 Potassium hydroxide Trace amount Fragrance Trace amount purified water Balance meter 100.0%

Example 33 The following body soap composition had creamy foam and moisturized skin after use. Potassium laurate 6% Potassium myristate 5 Monopotassium tridecyl phosphate 10 Monoisopropanolamide myristate 2 Amidopropyl dimethylamine oxide laurate 3 Sample (1-5) 2 Propylene glycol 6 Ethanol 3 Ethylene glycol distearate 3 Dibutylhydroxytoluene 0 .05 Vegetable squalane 1 Potassium chloride 0.1 Cycripirox olamine / Vegum T complex 0.2 Potassium hydroxide Trace amount Fragrance Trace amount purified water Balance meter 100.0%

Example 34 The following body soap composition had a creamy lather and had good lather removal, and the skin after use was moist. Ethyl-6-O-6-ethylnonanoyl glucoside 10% POE (3) Coconut fatty acid monoethanolamide Sodium ether propionate 5 POE (3) Coconut fatty acid monoethanolamide 1 Sample (2-5) 3 Hydroxyethyl cellulose 0.5 Citric acid qs Sodium hydroxide qs Fragrance 0.4 Purified water Balance meter 100.0%

Example 35 The following body shampoo composition had creamy foam and the skin after use was smooth. N-dodecyl glycolic acid amide sulfate 10% potassium laurate 5 potassium myristate 5 potassium N-lauroyl-N-methyl-β-alanine 2 potassium monopotassium N-lauroyl-glutamate 2 sample (1-1) 3 lauryl dimethylamine oxide 1 Bentonite 1 Propylene glycol 6 Hydroxypropyl methylcellulose 0.5 Ethylene glycol distearate 1 MAA / BuA / MMA copolymer 1.5 Polystyrene polymer (n = 300) 0.1 Tetrasodium edetate tetrahydrate 0.2 Plant sex squalane 1 Callophyllis violacea water extract 0.5 dimethyl polysiloxane (100 cs) 0.5 potassium chloride 0.1 piroctone olamine 0.2 Benkure monopotassium trace perfume trace rectification hydroxide Water making balance meter 100.0%

Example 36 The following medicated hand soap composition had good foaming properties and foam quality, and also had a good hand feel after use. Potassium laurate 0.5% Potassium myristate 10 N-Lauroyl-N-methyl-β-alanine potassium 2 N-Lauroyl-glutamate monopotassium 2 Sample (1-4) 3 Coconut fatty acid monoethanolamide 1 Amidopropyldimethyl laurate Amine oxide 2 glycerin 5 propylene glycol 6 hydroxyethanediphosphonic acid 0.1 edetate tetrasodium tetrahydrate 0.2 vegetable squalane 1 dimethylpolysiloxane (100 cp) 0.5 potassium chloride 0.1 triclosan / Benkeley SL complex 1 Potassium hydroxide trace fragrance trace purified water balance meter 100.0%

Example 37 The following medicated hand soap composition had good foaming properties and foam quality, and also had a good hand feel after use. Potassium laurate 10% potassium myristate 10 N-lauroyl-N-methyl-β-alanine potassium 2 N-lauroyl-monopotassium glutamate 2 sample (1-3) 1 sample (4-3) 4 dodecylglyceryl ether 2 lauryldimethyl Amine oxide 1 Glycerin 5 Propylene glycol 6 Hydroxypropylcellulose 0.5 Ethylene glycol distearate 1 Hydroxyethanediphosphonic acid 0.1 Tetrasodium tetrasodium tetrahydrate 0.2 Vegetable squalane 0.5 Callophyllis heanophylla water extract 0. 5 Potassium chloride 0.1 Triclosan 0.2 Benclay 0.8 Potassium hydroxide Trace fragrance Trace purified water Balance meter 100.0%

Example 38 A dishwashing detergent having the following composition was prepared. This product was excellent in detergency, foaming properties, and hand feeling after washing. POE (3) sodium lauryl ether sulfate 10% sodium coconut β-alanine 5 sodium alkylbenzene sulfonate 5 sample (3-3) 3 50% sulfate of sample (2-2) 4 sodium benzoate 4 sodium salicylate 4 toluene sulfonic acid Sodium 3 Ethanol 5 Purified water Balance meter 100.0%

Example 39 A dishwashing detergent having the following composition was prepared. This product was excellent in detergency, foaming properties, and hand feeling after washing. POE (2) Sodium lauryl ether sulfate 12% 3- (N, N-dimethylamino) sodium tetradecanesulfonate 5 Sodium tetradecenesulfonate 1 Alkyloyl (C8 / C10 = 1/1) methyl glucoside 8 Sodium laurate 0.5 Sample (3-5) 3 sodium dodecyl polyoxyethylene (3) ether acetate 6 sodium N-lauroyl-N-methyl-β-alanine 2 ethanol 5 magnesium chloride 1 citric acid qs sodium hydroxide qs perfume qs ion-exchange water balance meter 100.0%

Example 40 A dishwashing detergent having the following composition was prepared. This product was excellent in detergency, foaming properties, and hand feeling after washing. Magnesium dodecylbenzenesulfonate 15% POE (3) Sodium tridecyl ether sulfate 5 POE (11) Dodecyl ether 3 Sample (3-1) 4 Disodium ethylenediaminetetraacetate 0.1 Ethanol 5 Polyethylene glycol (# 200) 2 Benzoic acid Sodium 0.5 Perfume 0.2 Dye Appropriate amount Purified water Balance meter 100.0%

Example 41 The dishwashing composition shown below had good foaming properties and the hands after washing the hair were moist. N-lauryl-β-alanine 5% sodium N-laurylglycine 10 sodium dodecylbenzenesulfonate 3 POE (3) sodium laurylethoxysulfate 5 sample (2-2) 6 ethanol 8 polyethylene glycol (# 1000) 4 purified water balance meter 100.0%

Example 42 The light detergent composition for clothing shown below had good foaming properties, and the hand skin after washing was moist. Sodium α-olefin sulfonate from tetradecene-1 10% sec-alcohol ethoxylate (sophthalanol 85) 17 Sample (2-4) 3 Urea 10 Ethanol 1 Disodium ethylenediaminetetraacetate 0.1 Ammonium chloride 1 Fragrance 0.2 Dye Appropriate amount Triethanolamine 1 Purified water Balance meter 100.0%

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Shinmi On 1-3-7 Honjo, Sumida-ku, Tokyo F-term in Lion Corporation (reference) 4C083 AB032 AB332 AB352 AB442 AC012 AC022 AC092 AC102 AC112 AC122 AC172 AC182 AC242 AC302 AC312 AC352 AC392 AC422 AC432 AC482 AC482 AC532 AC562 AC582 AC641 AC642 AC662 AC692 AC712 AC742 AC761 AC782 AC792 AC812 AC852 AC862 AC902 AD022 AD042 AD132 AD152 AD282 AD392 AD412 CC23 CC38 DD23 DD31 EE06 EE10 4H003 AB05 AB13 AB13 AB13 AB23 AB13 AB13 AB13 AC15 AD02 AD04 DA01 DA02 DA17 EA27 EB04 EB05 EB07 EB08 EB13 EB21 EB37 EB42 ED02 FA02 FA18 FA21 FA33

Claims (2)

[Claims] 1. A detergent composition comprising a compound represented by the following general formulas (1) to (4) or one or more selected from sulfates and phosphates thereof. . Embedded image (Wherein, R ¹ and R ² each represent a straight-chain or branched alkyl or alkenyl group having 6 to 24 carbon atoms, R ^{3 represents a} hydrogen atom, a straight-chain or branched alkyl group or alkenyl group having 1 to 4 carbon atoms) Or a hydroxyalkyl group, R ⁴ : carbon number 1
To 6 hydroxyl groups or an alkylene group which may contain an ether bond, R ⁵ : a single bond or 1 to 2 carbon atoms
An alkylene group having 1 to 6 carbon atoms which may be substituted with an alkyl group of 4 or may contain an ether bond; R ⁶ and R ⁷ each have 6 to 24 carbon atoms which may contain an ether bond;
A linear or branched alkyl or alkenyl group of R
⁸ : a hydroxyl group having 1 to 10 carbon atoms or an alkylene group optionally containing an ether bond, n: 0 or 1
When n is 0, m is 1 to 6, and when n is 1, m is 1. ) 2. The cleaning composition according to claim 1, comprising a surfactant selected from an anionic surfactant, a nonionic surfactant, an amphoteric surfactant and a cationic surfactant.